U.S. patent application number 14/044158 was filed with the patent office on 2014-06-19 for compositions and methods for improving rebaudioside x solubility.
The applicant listed for this patent is Venkata Sai Prakash Chaturvedula, Gil Ma, Avetik Markosyan, Indra Prakash. Invention is credited to Venkata Sai Prakash Chaturvedula, Gil Ma, Avetik Markosyan, Indra Prakash.
Application Number | 20140171519 14/044158 |
Document ID | / |
Family ID | 50931623 |
Filed Date | 2014-06-19 |
United States Patent
Application |
20140171519 |
Kind Code |
A1 |
Prakash; Indra ; et
al. |
June 19, 2014 |
COMPOSITIONS AND METHODS FOR IMPROVING REBAUDIOSIDE X
SOLUBILITY
Abstract
Polymorphic and amorphous forms of Rebaudioside X and methods
for preparing the same are provided herein. Also provided herein
are Rebaudioside X complexes and methods for preparing the same.
Sweetener compositions and sweetened compositions comprising
Rebaudioside X forms and Rebaudioside X complexes are described, as
well as and methods of their preparation. Methods of improving the
flavor and/or temporal profile of sweetenable compositions, such as
beverages, are also provided herein.
Inventors: |
Prakash; Indra; (Alpharetta,
GA) ; Markosyan; Avetik; (Kuala Lumpur, MY) ;
Chaturvedula; Venkata Sai Prakash; (Mission Viejo, CA)
; Ma; Gil; (Atlanta, GA) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Prakash; Indra
Markosyan; Avetik
Chaturvedula; Venkata Sai Prakash
Ma; Gil |
Alpharetta
Kuala Lumpur
Mission Viejo
Atlanta |
GA
CA
GA |
US
MY
US
US |
|
|
Family ID: |
50931623 |
Appl. No.: |
14/044158 |
Filed: |
October 2, 2013 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
PCT/US12/70564 |
Dec 19, 2012 |
|
|
|
14044158 |
|
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Current U.S.
Class: |
514/777 ; 264/12;
426/548; 426/61; 426/650; 426/656; 426/658; 426/71; 426/72;
536/18.1 |
Current CPC
Class: |
C07H 15/256 20130101;
A61K 47/26 20130101; A23V 2002/00 20130101; A61Q 11/00 20130101;
C08B 37/0009 20130101; C07C 31/24 20130101; A23L 27/33 20160801;
C07H 15/24 20130101; C08B 37/0015 20130101; A61K 8/602 20130101;
A23L 27/36 20160801; A23V 2002/00 20130101; A23V 2250/262
20130101 |
Class at
Publication: |
514/777 ;
426/658; 426/650; 426/548; 426/656; 426/61; 426/71; 426/72;
536/18.1; 264/12 |
International
Class: |
C07H 15/24 20060101
C07H015/24; A61K 47/36 20060101 A61K047/36; A23L 1/236 20060101
A23L001/236 |
Claims
1.-10. (canceled)
11. Amorphous Rebaudioside X.
12. The amorphous Rebaudioside X of claim 11, wherein the amorphous
Rebaudioside X has a water solubility greater than about 0.3%.
13. The amorphous Rebaudioside X of claim 11, wherein the amorphous
Rebaudioside X has a particle size less than 200 nm.
14. A sweetener composition comprising amorphous Rebaudioside
X.
15. The sweetener composition of claim 14, wherein amorphous
Rebaudioside X is present in an effective amount to provide a
sucrose equivalence of greater than about 10% in a sweetened
composition.
16. The sweetener composition of claim 14, further comprising at
least one additional sweetener.
17. The sweetener composition of claim 14, further comprising at
least one additive selected from the group consisting of
carbohydrates, polyols, amino acids and their corresponding salts,
poly-amino acids and their corresponding salts, sugar acids and
their corresponding salts, nucleotides, organic acids, inorganic
acids, organic salts including organic acid salts and organic base
salts, inorganic salts, bitter compounds, flavorants and flavoring
ingredients, astringent compounds, proteins or protein
hydrolysates, surfactants, emulsifiers, flavonoids, alcohols,
polymers and combinations thereof.
18. The sweetener composition of claim 14, further comprising at
least one functional ingredient selected from the group consisting
of saponins, antioxidants, dietary fiber sources, fatty acids,
vitamins, glucosamine, minerals, preservatives, hydration agents,
probiotics, prebiotics, weight management agents, osteoporosis
management agents, phytoestrogens, long chain primary aliphatic
saturated alcohols, phytosterols and combinations thereof.
19. A tabletop sweetener composition comprising amorphous
Rebaudioside X.
20.-62. (canceled)
63. The amorphous Rebaudioside X of claim 11, wherein the amorphous
Rebaudioside X is in substantially pure form.
64. The sweetener composition of claim 14, wherein Rebaudioside X
is provided as a component of a partially purified Stevia extract
or a mixture of steviol glycosides.
65. The sweetener composition of claim 64, wherein Rebaudioside X
is provided as a component of a partially purified Stevia extract,
wherein the Stevia extract comprises Rebaudioside X in an amount
greater than about 80% by weight on a dry basis.
66. The sweetener composition of claim 64, wherein Rebaudioside X
is provided as a component of a steviol glycoside mixture, wherein
the steviol glycoside mixture comprises from about 5% to about 99%
Rebaudioside X on a dry basis.
67. The sweetener composition of claim 14, wherein amorphous
Rebaudioside X is the sole sweetener.
68. The amorphous Rebaudioside X of claim 11 prepared by: (i)
heating a mixture comprising solvent and Rebaudioside X; (ii)
cooling the mixture; and (iii) removing the solvent from the
mixture.
69. The amorphous Rebaudioside X of claim 68, wherein the
Rebaudioside X in (i) comprises Form A Rebaudioside X and/or
Material E Rebaudioside X.
70. The amorphous Rebaudioside X of claim 68, wherein the solvent
comprises water, ethanol, methanol or a combination thereof.
71. The amorphous Rebaudioside X of claim 70, wherein the solvent
is water.
72. The amorphous Rebaudioside X of claim 71, wherein the mixture
is heated to about reflux.
73. The amorphous Rebaudioside X of claim 70, wherein the solvent
is ethanol.
74. The amorphous Rebaudioside X of claim 73, wherein the mixture
is heated to about reflux.
75. The amorphous Rebaudioside X of claim 70, wherein the solvent
is methanol.
76. The amorphous Rebaudioside X of claim 75, wherein the mixture
is heated to about reflux.
77. The amorphous Rebaudioside X of claim 68, wherein the resultant
mixture of (i) is cooled to room temperature.
78. The amorphous Rebaudioside X of claim 68, wherein the solvent
is removed by a method selected from decantation, centrifugation,
filtration, evaporation, vacuum or spray-drying.
79. The amorphous Rebaudioside X of claim 79, wherein the solvent
is removed by spray-drying.
Description
CROSS REFERENCE TO RELATED APPLICATIONS
[0001] This application is a continuation of International
Application No. PCT/US2012/070564, filed Dec. 19, 2012.
FIELD OF THE INVENTION
[0002] The present invention relates generally to crystalline forms
and amorphous Rebaudioside X and methods of preparing the same. The
present invention also relates to Rebaudioside X complexes and
methods of preparing the same. Certain forms of Rebaudioside X and
the Rebaudioside X complexes are advantageous compared to other
forms of Rebaudioside X because of improved aqueous solubility. The
present invention also encompasses sweetener compositions and
sweetened compositions comprising amorphous Rebaudioside X and
Rebaudioside X complexes in addition to methods for preparing the
same.
BACKGROUND OF THE INVENTION
[0003] Stevia is the common name for Stevia rebaudiana (Bertoni), a
perennial shrub of the Asteracae (Compositae) family native to
Brazil and Paraguay. The plant's leaves, the aqueous extract of the
leaves, and purified stevioglycosides have been developed as
sweeteners desirable as both non-caloric and natural in origin.
Specific steviol glycosides that can be isolated from Stevia
rebaudiana include Stevioside, Rebaudioside A, Rebaudioside C,
Dulcoside A, Rubusoside, steviolbioside, Rebaudioside B,
Rebaudioside D and Rebaudioside F.
[0004] More recently, Rebaudioside X,
13-[(2-O-.beta.-D-glucopyranosyl-3-O-.beta.-D-glucopyranosyl-.beta.-D-glu-
copyranosyl)oxy]ent kaur-16-en-19-oic
acid-[(2-O-.beta.-D-glucopyranosyl-3-O-.beta.-D-glucopyranosyl-.beta.-D-g-
lucopyranosyl)ester] was isolated from Stevia rebaudiana and
characterized:
##STR00001##
[0005] Rebaudioside X can be obtained from Stevia rebaudiana, and
is present in minute quantities, about 1%-2% by weight.
Rebaudioside X obtained from Stevia rebaudiana has poor aqueous
solubility and dissolution qualities in beverage formulations.
Accordingly, there remains a need to develop Rebaudioside X and
Rebaudioside X compositions with improved aqueous solubility.
SUMMARY OF THE INVENTION
[0006] In one embodiment, the present invention provides Form A
Rebaudioside X, a variable hydrate/solvate. In a particular
embodiment, Form A Rebaudioside X can be characterized by the X-ray
diffraction pattern of FIG. 1 when prepared by ambient temperature
slurrying of x-ray amorphous Rebaudioside X in a 1:1 mixture of
methanol and water.
[0007] The present invention also provides a method for preparing
Form A Rebaudioside X. In one embodiment, a method for preparing
Form A Rebaudioside X comprises (i) combining Rebaudioside X and an
aqueous alcoholic solvent to provide a mixture; and (ii) stirring
the mixture at approximately room temperature to provide Form A
Rebaudioside X. In some embodiments, the aqueous alcoholic solvent
is water and methanol.
[0008] The present invention provides a method for preparing
amorphous Rebaudioside X from comprising (i) heating a mixture
comprising solvent and Rebaudioside X, (ii) cooling the mixture and
(iii) removing the solvent from the mixture to provide amorphous
Rebaudioside X. The Rebaudioside X can be Form A or Material E
Rebaudioside X. The solvent can be any suitable solvent, such as,
for example, water, methanol and/or ethanol. In a particular
embodiment, the solvent is water. In another embodiment, the
solvent is ethanol. In another particular embodiment, the mixture
is heated to reflux. In another particular embodiment, the solvent
is removed by evaporation or spray-drying.
[0009] Amorphous Rebaudioside X is characterized by a X-ray
diffraction pattern of FIG. 4. In a particular embodiment,
amorphous Rebaudioside X is substantially pure, i.e. about 90% pure
relative to other forms of Rebaudioside X. In other embodiments,
amorphous Rebaudioside X is greater than about 95% or 98% pure
relative to other forms of Rebaudioside X. In yet other
embodiments, amorphous Rebaudioside X is provided in the absence of
other forms of Rebaudioside X.
[0010] Amorphous Rebaudioside X has improved solubility properties
compared to other forms of Rebaudioside X, including Form A
Rebaudioside X. In one embodiment, amorphous Rebaudioside X has an
aqueous solubility greater than about 0.3%.
[0011] In a still further embodiment, the present invention is a
sweetener composition comprising amorphous Rebaudioside X. In one
embodiment, amorphous Rebaudioside X can be the sole sweetener in a
sweetener composition. In other embodiments, a sweetener
composition comprises amorphous Rebaudioside X, wherein the
amorphous Rebaudioside X is provided as part of partially purified
Stevia extract or part of a mixture of steviol glycosides (i.e. a
composition comprising amorphous Rebaudioside X).
[0012] The present invention also provides for methods of preparing
Form B Rebaudioside X. In one embodiment, a method for preparing
Form B Rebaudioside X comprises (i) heating a mixture of amorphous
Rebaudioside X and a solvent, (ii) cooling the mixture and (iii)
removing the solvent from the mixture to provide Form B
Rebaudioside X. In one embodiment, the solvent is ethanol. In
another embodiment, the mixture is heated to a temperature between
about 30.degree. C. and 100.degree. C. Form B Rebaudioside X can be
characterized by the X-ray diffraction pattern shown in FIGS. 7A
and 7B when generated by slurrying in ethanol at 40.degree. C.
[0013] In another aspect of the invention, Rebaudioside X complexes
are provided. The Rebaudioside complexes have improved aqueous
solubility over Form A Rebaudioside X. The complexes are prepared
by certain methods that provide compositions with increased aqueous
solubility.
[0014] In one embodiment, Rebaudioside X complexes comprising
Rebaudioside X and at least one polyol are provided. Such
compositions can be prepared by (i) heating a mixture comprising
solvent, Rebaudioside X and at least one polyol; (ii) cooling the
mixture; and (iii) removing the solvent from the mixture to provide
a Rebaudioside X complex. In a particular embodiment, the at least
one polyol is erythritol. In another embodiment, the weight ratio
of Rebaudioside X to erythritol is from about 1:1 to about
1:20.
[0015] In another embodiment, Rebaudioside X complexes comprising
Rebaudioside X and at maltodextrin are provided. Such compositions
can be prepared by (i) heating a mixture comprising solvent,
Rebaudioside X and maltodextrin; (ii) cooling the mixture; and
(iii) removing the solvent from the mixture to provide a
Rebaudioside X complex. In a particular embodiment, the weight
ratio of Rebaudioside X to maltodextrin is from about 1:1 to about
1:20.
[0016] In still another embodiment, Rebaudioside X complexes
comprising Rebaudioside X and at least one cyclodextrin are
provided. Such compositions can be prepared by (i) heating a
mixture comprising solvent, Rebaudioside X and at least one
cyclodextrin; (ii) cooling the mixture and (iii) removing the
solvent from the mixture to provide a Rebaudioside X complex. In a
particular embodiment, the at least one cyclodextrin is selected
from the group consisting of .alpha.-cyclodextrin,
.beta.-cyclodextrin, .gamma.-cyclodextrin, or a derivative thereof.
In a more particular embodiment, the at least one cyclodextrin is
.gamma.-cyclodextrin. In still another embodiment, the weight ratio
of Rebaudioside X to the at least one cyclodextrin is from about
1:1 to about 1:20.
[0017] Amorphous Rebaudioside X, Rebaudioside X complexes or
compositions comprising the same can be used in a sweetener
composition. In one embodiment, the sweetener compositions of the
present invention can also contain one or more additional
sweeteners, including, for example, natural sweeteners, high
potency sweeteners, carbohydrate sweeteners, synthetic sweeteners
and combinations thereof.
[0018] The present invention also provides methods for preparing
sweetener compositing comprising combining amorphous Rebaudioside X
or a composition comprising amorphous Rebaudioside X with at least
one sweetener and/or additive and/or functional ingredient.
[0019] The present invention also provides methods for preparing
sweetener compositing comprising combining Rebaudioside X complexes
or a composition comprising a Rebaudioside X complex with at least
one sweetener and/or additive and/or functional ingredient
[0020] The sweetener compositions of the present invention can also
contain one or more additives including, for example,
carbohydrates, polyols, amino acids and their corresponding salts,
poly-amino acids and their corresponding salts, sugar acids and
their corresponding salts, nucleotides, organic acids, inorganic
acids, organic salts including organic acid salts and organic base
salts, inorganic salts, bitter compounds, flavorants and flavoring
ingredients, astringent compounds, proteins or protein
hydrolysates, surfactants, emulsifiers, flavonoids, alcohols,
polymers and combinations thereof.
[0021] The sweetener compositions of the present invention can also
contain one or more functional ingredients, such as, for example,
saponins, antioxidants, dietary fiber sources, fatty acids,
vitamins, glucosamine, minerals, preservatives, hydration agents,
probiotics, prebiotics, weight management agents, osteoporosis
management agents, phytoestrogens, long chain primary aliphatic
saturated alcohols, phytosterols and combinations thereof.
[0022] In yet another embodiment, the present invention is a
tabletop sweetener composition comprising amorphous Rebaudioside X
or a sweetener composition comprising amorphous Rebaudioside X. In
another embodiment, the present invention is a tabletop sweetener
composition comprising a Rebaudioside X complex or a sweetener
composition comprising a Rebaudioside X complex. The tabletop
composition can further include at least one bulking agent,
additive, anti-caking agent, functional ingredient and combinations
thereof.
[0023] In another embodiment, the present invention includes
sweetened compositions comprising a sweetenable composition and
amorphous Rebaudioside X or a sweetener composition comprising
Rebaudioside X. In one embodiment, the sweetened composition
comprises a sweetenable composition and amorphous Rebaudioside X.
In another embodiment, the sweetened composition comprises a
sweetenable composition and a sweetener composition comprising
amorphous Rebaudioside X. The sweetened compositions of the present
invention can optionally include additives, sweeteners, functional
ingredients and combinations thereof.
[0024] The present invention also includes sweetened compositions
comprising a sweetenable composition and a Rebaudioside X complex
or a sweetener composition comprising a Rebaudioside X complex. In
one embodiment, a sweetened composition comprises a sweetenable
composition and a Rebaudioside X complex. In another embodiment, a
sweetened composition comprises a sweetenable composition and a
sweetener composition comprising a Rebaudioside X complex. The
sweetened compositions of the present invention can optionally
include additives, sweeteners, functional ingredients and
combinations thereof.
[0025] The sweetenable composition may be unsweetened or sweetened.
Sweetenable compositions are substances that are desirable to
sweeten, including ingested substances and substances that are
contacted with the mouth but not eaten or swallowed such as, for
example, pharmaceutical compositions, edible gel mixes and
compositions, dental compositions, foodstuffs, beverages and
beverage products.
[0026] In one embodiment, the present invention provides a method
for preparing a sweetened composition comprising combining a
sweetenable composition with amorphous Rebaudioside X or a
sweetener composition comprising amorphous Rebaudioside X.
[0027] In another embodiment, the present invention provides a
method for preparing a sweetened composition comprising combining a
sweetenable composition with a Rebaudioside X complex or a
sweetener composition comprising a Rebaudioside X complex.
[0028] In a particular embodiment, the sweetenable composition or
sweetened composition is a beverage. In one embodiment, the
sweetenable composition is a beverage comprising a liquid matrix.
The liquid matrix may be, for example, deionized water, distilled
water, degassed water, reverse osmosis water, carbon-treated water,
purified water, demineralized water, phosphoric acid, phosphate
buffer, citric acid, citrate buffer or carbon-treated water.
[0029] In one embodiment, the present invention provides a method
for preparing a beverage comprising combining an unsweetened or
sweetened beverage with amorphous Rebaudioside X or a sweetener
composition comprising amorphous Rebaudioside X. In another
embodiment, the present invention provides a method for preparing a
beverage product comprising combining an unsweetened or sweetened
beverage product with amorphous Rebaudioside X or a sweetener
composition comprising amorphous Rebaudioside X.
[0030] In another embodiment, the present invention is a method for
preparing a beverage by combining an unsweetened or sweetened
beverage with a Rebaudioside X complex or a sweetener composition
comprising a Rebaudioside X complex. In another embodiment, the
present invention is a method for preparing a beverage product by
combining an unsweetened or sweetened beverage product with a
Rebaudioside X complex or a sweetener composition comprising a
Rebaudioside X complex.
[0031] Sweetened compositions retain the identity of the
sweetenable composition upon addition of amorphous Rebaudioside X,
a Rebaudioside X complex or the sweetener compositions of the
present invention, such that the sweetened composition may also be,
for example, pharmaceutical compositions, edible gel mixes and
compositions, dental compositions, foodstuffs, beverages and
beverage products. In one embodiment, the sweetened composition is
a beverage comprising amorphous Rebaudioside X. In another
embodiment, the sweetened composition is a beverage comprising a
sweetener composition of the present invention. Full-calorie,
mid-calorie, low-calorie and zero-calorie beverages containing
amorphous Rebaudioside X, a Rebaudioside X complex or the sweetener
compositions of the present invention are encompassed by the
present invention.
[0032] In a still further embodiment, the present invention is a
method for imparting a more sugar-like temporal profile, flavor
profile, or both to a sweetenable composition by combining a
sweetenable composition with amorphous Rebaudioside X or the
sweetener compositions of the present invention. The method can
further include the addition of other sweeteners, additives,
functional ingredients and combinations thereof.
BRIEF DESCRIPTION OF THE FIGURES
[0033] FIG. 1: illustrates the X-ray diffraction pattern of Form A
Rebaudioside X collected with Cu-K.alpha. radiation (the wavelength
used to calculate d-spacings was 1.541874 .ANG., a weighted average
of the Cu-K.sub..alpha.1 and Cu-K.sub..alpha.2 wavelengths).
Material for this trace was prepared via 1:1 methanol:water (v/v)
slurry held at ambient temperature overnight.
[0034] FIG. 2: illustrates the X-ray diffraction pattern of Form A
Rebaudioside X collected with Cu-K.alpha. radiation Cu-K.alpha.
radiation (the wavelength used to calculate d-spacings was 1.541874
.ANG., a weighted average of the Cu-K.sub..alpha.1 and
Cu-K.sub..alpha.2 wavelengths). Material for the top trace was
prepared via 1:1 isopropanol:water (v/v) held at ambient
temperature overnight. Material for the second trace was prepared
via 1:1 methanol water (v/v) held at ambient temperature overnight.
Material for the third trace was prepared via water slurry at
ambient temperature for 3 days. Material for the fourth trace was
analyzed after isolation of Rebaudioside X from Stevia extract
without further preparation. Material for the fifth trace was
vacuum dried at ambient temperature for 2 days.
[0035] FIG. 3: illustrates the Dynamic Vapor Soprtion (DVS)
isotherm of Form A Rebaudioside X.
[0036] FIG. 4: illustrates the X-ray diffraction pattern of
amorphous Rebaudioside X collected with Cu-K.alpha. radiation (the
wavelength used to calculate d-spacings was 1.541874 .ANG., a
weighted average of the Cu-K.sub..alpha.1 and Cu-K.sub..alpha.2
wavelengths). Material for the top trace was prepared via the
process described herein wherein the solvent was water. Material
for the bottom trace was prepared via the process described herein
wherein the solvent is ethanol.
[0037] FIG. 5: illustrates the Differential Scanning Calorimetry
(DSC) thermogram of amorphous Rebaudioside X obtained by heating at
2.degree. C./min.
[0038] FIG. 6: illustrates the Dynamic Vapor Soprtion (DVS)
isotherm of amorphous Rebaudioside X.
[0039] FIGS. 7A and 7B: illustrate the X-ray diffraction pattern of
Form B Rebaudioside X collected with Cu-K.alpha. radiation
Cu-K.alpha. radiation (the wavelength used to calculate d-spacings
was 1.541874 .ANG., a weighted average of the Cu-K.sub..alpha.1 and
Cu-K.sub..alpha.2 wavelengths) when generated by slurrying in
ethanol at 40.degree. C.
[0040] FIG. 8: illustrates Differential Scanning Calorimetry (DSC)
thermogram of Material E.
[0041] FIG. 9: illustrates the Dynamic Vapor Sorption (DVS)
thermogram of Material E.
[0042] FIG. 10: illustrates the X-ray diffraction pattern of
Material E (top trace), Form A Rebaudioside X (middle trace,
prepared via 1:1 methanol:water (v/v) slurry held at ambient
temperature overnight) and Form B Rebaudioside X (bottom trace,
prepared via ethanol slurry at 40.degree. C.). Collected with
Cu-K.alpha. radiation Cu-K.alpha. radiation (the wavelength used to
calculate d-spacings was 1.541874 .ANG., a weighted average of the
Cu-K.sub..alpha.1 and Cu-K.sub..alpha.2 wavelengths).
[0043] FIG. 11A: illustrates the .sup.13C NMR spectrum of Reb X
(150 MHz, C.sub.5D.sub.5N).
[0044] FIG. 11B: provides the peaks (ppm) and heights associated
with the .sup.13C NMR spectrum of Reb X in FIG. 11A.
[0045] FIGS. 12A and 12B: illustrate the .sup.1H NMR spectrum of
Reb X (600 MHz, C.sub.5D.sub.5N).
[0046] FIG. 12C: provides the peaks (ppm) and heights associated
with the .sup.1H NMR spectrum of Reb X in FIGS. 12A and 12B.
[0047] FIG. 13: illustrates the .sup.1H-.sup.1H COSY spectrum of
Reb X (600 MHz, C.sub.5D.sub.5N).
[0048] FIG. 14: illustrates the HMBC spectrum of Reb X (600 MHz,
C.sub.5D.sub.5N).
DETAILED DESCRIPTION OF THE INVENTION
[0049] The present invention is directed to novel crystalline
polymorphic and amorphous forms of Rebaudioside X, including an
amorphous form of Rebaudioside X with increased aqueous solubility.
Compositions comprising amorphous Rebaudioside X, as well as
methods for preparing amorphous Rebaudioside X and other forms of
Rebaudioside X are also provided.
[0050] Finally, compositions comprising amorphous Rebaudioside X
are also provided. Forms of Rebaudioside X, and their respective
conversions are as follows:
Material E.revreaction.Form A.revreaction.amorphous.fwdarw.Form
B
[0051] As used herein, "amorphous" is defined as a non-crystalline
solid material.
[0052] The amorphous form of Rebaudioside X and a polymorphic form
of Rebaudioside X (e.g. Forms A and B) can be distinguished from
other forms of Rebaudioside X by X-ray diffraction patterns,
differential scanning calorimetry thermograms, the methods by which
they are made and solubility characteristics. The amorphous form of
Rebaudioside X, Form A Rebaudioside X and other polymorphic forms
of Rebaudioside X (e.g. Form B Rebaudioside X) are referred to
herein in the collective as "forms of Rebaudioside X".
[0053] As used herein, the term "substantially pure", when used in
reference to Rebaudioside X, refers to forms of Rebaudioside X
which are greater than about 90% pure by weight on a dry basis.
This means that the crystalline or amorphous form of Rebaudioside X
does not contain more than about 10% of another form. For example,
substantially pure Form A Rebaudioside X does not contain more than
about 10% of non-Form A Rebaudioside X. In another example,
substantially pure amorphous Rebaudioside X does not contain more
than about 10% of non-amorphous Rebaudioside X.
[0054] Form A Rebaudioside X
[0055] The Form A Rebaudioside X polymorph, a variable
hydrate/solvate, can be characterized, for example, by the X-ray
diffraction pattern shown in FIG. 1, when generated by ambient
temperature slurrying of x-ray amorphous Rebaudioside X in a 1:1
mixture of methanol and water. The angular positions (two theta) of
the prominent X-ray diffraction peaks are as follows (Table 1) when
generated by ambient temperature slurrying of x-ray amorphous
Rebaudioside X in a 1:1 mixture of methanol and water:
TABLE-US-00001 TABLE 1 Form A Rebaudioside X Prominent XPRD
.degree.2.THETA. d space (.ANG.) Intensity (%) 3.76 .+-. 0.20
23.489 .+-. 1.319 67 6.50 .+-. 0.20 13.594 .+-. 0.431 58 6.62 .+-.
0.20 13.354 .+-. 0.416 89 6.79 .+-. 0.20 13.025 .+-. 0.395 100 9.93
.+-. 0.20 8.909 .+-. 0.183 36 12.33 .+-. 0.20 7.176 .+-. 0.118 40
12.45 .+-. 0.20 7.109 .+-. 0.116 49 13.69 .+-. 0.20 6.469 .+-.
0.095 44 14.06 .+-. 0.20 6.301 .+-. 0.090 50 15.44 .+-. 0.20 5.738
.+-. 0.075 37 16.25 .+-. 0.20 5.456 .+-. 0.068 46 16.80 .+-. 0.20
5.278 .+-. 0.063 66 20.44 .+-. 0.20 4.345 .+-. 0.042 48
[0056] One of skill in the art will recognize that XRPD patterns of
Form A Rebaudioside X produced under different conditions may
display peak shifts from those of FIG. 1, consistent with the
variable solvent/water content of the material.
[0057] Form A exists as a solvate/hydrate, with approximately 9
moles of water and 16 moles of methanol per one mole of
Rebaudioside X.
[0058] In one embodiment, the invention is Form A Rebaudioside X in
substantially pure form.
[0059] In other embodiments, Form A Rebaudioside X is greater than
about 91%, 92%, 93%, 94%, 95%, 96%, 97% or 98% pure with respect to
other forms of Rebaudioside X.
[0060] In another embodiment, Form A Rebaudioside X is provided in
the absence of other forms of Rebaudioside X, i.e. 100% pure Form A
Rebaudioside X with respect to other forms of Rebaudioside X.
[0061] In one embodiment, a method for preparing Form A
Rebaudioside X comprises: [0062] (i) combining Rebaudioside X and
an aqueous alcoholic solvent to provide a mixture; and [0063] (iii)
stirring the mixture at approximately room temperature to provide
Form A Rebaudioside X.
[0064] In particular embodiment, the form of Rebaudioside X used in
(i) is X-ray amorphous Rebaudioside X. In another particular
embodiment, the form of Rebaudioside X used in (i) is Material E
Rebaudioside X. As used herein, "Material E", when used in
reference to Rebaudioside X, refers to composition comprising
Rebaudioside X that appears similar to Form A Rebaudioside X by
XRPD, but is severely disordered and could not be indexed. The
"material" may contain one or more polymorphic and/or amorphous
forms of Rebaudioside X.
[0065] In one embodiment, Rebaudioside X prepared by the following
process can be used in (i): two kg of Stevia rebaudiana Bertoni
plant leaves were dried at 45.degree. C. to an 8.0% moisture
content and ground to 10-20 mm particles. The content of different
glycosides in the leaves was as follows: Stevioside--2.55%, Reb
A--7.78%, Reb B--0.01%, Reb C--1.04%, Reb D--0.21%, Reb F--0.14%,
Reb X--0.10% Dulcoside A--0.05%, and Steviolbioside--0.05%. The
dried material was loaded into a continuous extractor and the
extraction was carried out with 40.0 L of water at a pH of 6.5 at
40.degree. C. for 160 min. The filtrate was collected and subjected
to chemical treatment. Calcium oxide in the amount of 400 g was
added to the filtrate to adjust the pH within the range of 8.5-9.0,
and the mixture was maintained for 15 min with slow agitation.
Then, the pH was adjusted to around 3.0 by adding 600 g of
FeCl.sub.3 and the mixture was maintained for 15 min with slow
agitation. A small amount of calcium oxide was further added to
adjust the pH to 8.5-9.0 and the mixture was maintained for 30 min
with slow agitation. The precipitate was removed by filtration on a
plate-and-frame filter press using cotton cloth as the filtration
material. The slightly yellow filtrate was passed through the
column, packed with cation-exchange resin Amberlite FCP22 (H.sup.+)
and then, through the column with anion-exchange resin Amberlite
FPA53 (OH.sup.-). The flow rate in both columns was maintained at
SV=0.8 hour.sup.-1. After completion both columns were washed with
RO water to recover the steviol glycosides left in the columns and
the filtrates were combined. The portion of combined solution
containing 120 g total steviol glycosides was passed through seven
columns, wherein each column was packed with specific macroporous
polymeric adsorbent YWD-03 (Cangzhou Yuanwei, China). The first
column with the size of 1/3 of the others acted as a "catcher
column". The SV was around 1.0 hour.sup.-1. After all extract was
passed through the columns, the resin sequentially was washed with
1 volume of water, 2 volumes of 0.5% NaOH, 1 volume of water, 2
volumes of 0.5% HCl, and finally with water until the pH was 7.0.
The "catcher column" was washed separately.
[0066] Desorption of the adsorbed steviol glycosides was carried
out with 52% ethanol at SV=1.0 hour.sup.-1. Desorption of the first
"catcher column" was carried out separately and the filtrate was
not mixed with the main solution obtained from other columns.
Desorption of the last column also was carried out separately. The
quality of extract from different columns with specific macroporous
adsorbent is shown in Table 3.
TABLE-US-00002 TABLE 3 Steviol Glycoside Content Column Total
steviol glycosides, % 1 (catcher) 55.3 2 92.7 3 94.3 4 96.1 5 96.3
6 95.8 7 80.2
[0067] Eluates from second to sixth columns were combined and
treated separately. The combined solution of steviol glycosides was
mixed with 0.3% of activated carbon from the total volume of
solution. The suspension was maintained at 25.degree. C. for 30 min
with continuous agitation. Separation of carbon was carried out on
a press-filtration system. For additional decolorization the
filtrate was passed through the columns packed with cation-exchange
resin Amberlite FCP22 (H.sup.+) followed with anion-exchange resin
Amberlite FPA53 A30B (OH.sup.-). The flow rate in both columns was
around SV=0.5 hour.sup.-1. The ethanol was distilled using a vacuum
evaporator. The solids content in the final solution was around
15%. The concentrate was passed through the columns packed with
cation-exchange resin Amberlite FCP22 (H.sup.+) and anion-exchange
resin Amberlite FPA53 (OH.sup.-) with SV=0.5 hour.sup.-1. After all
the solution was passed through the columns, both resins were
washed with RO water to recover the steviol glycosides left in the
columns. The resulting refined extract was transferred to the
nano-filtration device, concentrated to around 52% of solids
content and spray dried to provide a highly purified mixture of
steviol glycosides. The yield was 99.7 g. The mixture contained
Stevioside--20.5%, Reb A--65.6%, Reb B--0.1%, Reb C--8.4%, Reb
D--0.5%, Reb F--1.1%, Reb X--0.1%, Dulcoside A--0.4%, and
Steviolbioside--0.4%.
[0068] The combined eluate from the last column, contained about
5.3 g of total steviol glycosides including 2.3 g Reb D and around
1.9 g Reb X (35.8% Reb X/TSG ratio). It was deionized and
decolorized as discussed above and then concentrated to a 33.5%
content of total solids.
[0069] The concentrate was mixed with two volumes of anhydrous
methanol and maintained at 20-22.degree. C. for 24 hours with
intensive agitation.
[0070] The resulting precipitate was separated by filtration and
washed with about two volumes of absolute methanol. The yield of
Rebaudioside X was 1.5 g with around 80% purity.
[0071] For the further purification the precipitate was suspended
in three volumes of 60% methanol and treated at 55.degree. C. for
30 min, then cooled down to 20-22.degree. C. and agitated for
another 2 hours.
[0072] The resulting precipitate was separated by filtration and
washed with about two volumes of absolute methanol and subjected to
similar treatment with a mixture of methanol and water.
[0073] The yield of Rebaudioside X was 1.2 g with 97.3% purity.
[0074] In one embodiment, the aqueous alcoholic solvent comprises
water and an alcohol selected from ethanol, methanol, isopropanol,
butanol or combinations thereof. In a particular embodiment, the
aqueous alcoholic solvent comprises water and methanol. In a more
particular embodiment, the aqueous alcoholic solvent comprises
water and methanol in a 1:1 (v/v) ratio.
[0075] The duration of stirring in (ii) can vary, but is generally
from about 15 minutes to about 2 weeks, such as, for example, about
12 hours, about 24 hours, about 2 days, about 3 days, about 4 days,
about 5 days, about 6 days, about 7 days, about 8 days, about 9
days, about 10 days, about 11 days, about 12 days, about 13 days or
about 14 days.
[0076] When Rebaudioside X is combined with the aqueous alcoholic
solvent, a slurry is generally formed.
[0077] In a more specific embodiment, a method for preparing Form A
Rebaudioside X comprises:
[0078] (i) combining amorphous Rebaudioside X and a solvent
containing water and methanol in a 1:1 (v/v) ratio to provide a
slurry; and
[0079] (ii) stirring the slurry at approximately room
temperature.
[0080] Material E Rebaudioside X can also be converted to Form A
Rebaudioside X, which can further be converted to amorphous
Rebaudioside X, if desired. In one embodiment, a method for
preparing Form A Rebaudioside X comprises:
[0081] (i) mixing material E Rebaudioside X with water to provide a
slurry;
[0082] (ii) heating the slurry to a temperature between about
40.degree. C. and about 90.degree. C.; and
[0083] (iii) removing the water from the slurry to provide Form A
Rebaudioside X.
[0084] In one embodiment, the slurry can be maintained at
temperatures between about 40.degree. C. and about 60.degree. C.
for a duration from about 1 day to about 15 days, such as, for
example, about 12 days.
[0085] Removal of the water in step (iii) can be accomplished by
any suitable method including, for example, decantation,
centrifugation, filtration, evaporation, vacuum or spray drier.
[0086] In one embodiment, Form A Rebaudioside X is in substantially
pure form. In other embodiments, Form A Rebaudioside X is greater
than about than about 91%, 92%, 93%, 94%, 95%, 96%, 97% or 98% pure
with respect to other forms of Rebaudioside X. In one embodiment, a
composition comprises Form A Rebaudioside X.
[0087] In another embodiment, Form A Rebaudioside X is provided in
the absence of other forms of Rebaudioside X, i.e. 100% pure Form A
Rebaudioside X with respect to other forms of Rebaudioside X.
[0088] Amorphous Rebaudioside X
[0089] In one embodiment, a method for preparing amorphous
Rebaudioside X comprises (i) heating a mixture comprising solvent
and Rebaudioside X, (ii) cooling the mixture and (iii) removing
solvent from the mixture to provide amorphous Rebaudioside X.
[0090] Both Form A and Material E can be converted to amorphous
Rebaudioside X by this process. In one embodiment, a method for
preparing amorphous Rebaudioside X comprises (i) heating a mixture
comprising Form A Rebaudioside X, (ii) cooling the mixture and
(iii) removing solvent from the mixture to provide amorphous
Rebaudioside X. In another embodiment, a method for preparing
amorphous Rebaudioside X comprises (i) heating a mixture comprising
Material E Rebaudioside X, (ii) cooling the mixture and (iii)
removing the solvent from the mixture to provide amorphous
Rebaudioside X.
[0091] The solvent can be any suitable solvent, such as, for
example, water, ethanol, methanol, toluene, ethyl acetate, hexane,
acetone, dioxane, tetrahydrofuran, acetonitrile, isopropanol,
diethyl ether, dichloromethane, 2-butanone, 2,2,2-trifluoroethanol
and combinations thereof. In a particular embodiment, the solvent
comprises water. In a more particular embodiment, the solvent is
water. In another embodiment, the solvent comprises ethanol. In a
more particular embodiment, the solvent is ethanol.
[0092] The temperature and duration of heating in (i) will vary
based on the quantity of Rebaudioside X and the identity of the
solvent. In embodiments where the solvent comprises, or is water,
the mixture can be heated to reflux. Suitable temperatures for
refluxing will vary based on the solvent(s) used, but may be
greater than about 100.degree. C., such as, for example, about
105.degree. C., about 110.degree. C., about 115.degree. C., about
120.degree. C., about 125.degree. C., about 130.degree. C., about
140.degree. C., or about 150.degree. C. In a particular embodiment,
the temperature is maintained between about 100.degree. C. and
about 130.degree. C., such as, for example, between about
120.degree. C. and 125.degree. C. In certain embodiments, the
temperature is raised at 1.degree. C. per minute until the desired
temperature is reached. The mixture can be maintained at the
desired temperature for any duration suitable, such as, for
example, between 5 minutes and 5 hours, between about 1 hour and
about 5 hours, between about 1 hour and about 4 hours, between
about 1 hour and about 3 hours or between about 1 hour and about 2
hours.
[0093] In embodiments where the solvent comprises, or is ethanol,
the mixture can be heated to and maintained at about reflux
temperatures. Suitable temperatures for reflux will vary based on
the solvent(s), if any, are combined with ethanol and can be
greater than or equal to about 75.degree. C., such as for example,
about 80.degree. C., about 85.degree. C., about 90.degree. C.,
about 95.degree. C., about 100.degree. C., about 105.degree. C.,
about 110.degree. C., about 115.degree. C. or about 120.degree. C.
In a particular embodiment, the temperature is maintained between
about 70.degree. C. and about 120.degree. C., such as, for example,
between about 80.degree. C. and about 85.degree. C. In certain
embodiments, the temperature is raised at 1.degree. C. per minute
until the desired temperature is reached. The mixture can be
maintained at the desired temperature for any duration suitable,
such as, for example, between 5 minutes and 5 hours, between about
1 hour and about 5 hours, between about 1 hour and about 4 hours,
between about 1 hour and about 3 hours or between about 1 hour and
about 2 hours.
[0094] The resultant mixture of (i) can be cooled to room
temperature (.about.25.degree. C.) at any rate, provided that crash
precipitation does not occur. In a particular embodiment, the
mixture is cooled at a rate of about 1.degree. C. per minute.
[0095] Removal of the solvent in (iii) can be accomplished by any
suitable method including, for example, decantation,
centrifugation, filtration, evaporation, vacuum or spray drier. The
final amorphous product should be dry, i.e. substantially free of
all solvent.
[0096] In a particular embodiment, a method for preparing amorphous
Rebaudioside X comprises: [0097] (i) heating a mixture comprising
Form A Rebaudioside X and water; [0098] (ii) cooling the mixture to
room temperature; and [0099] (iii) removing solvent from the
mixture using a spray drier to provide amorphous Rebaudioside
X.
[0100] In another particular embodiment, a method for preparing
amorphous Rebaudioside X comprises: [0101] (i) heating a mixture
comprising Material E Rebaudioside X and water; [0102] (ii) cooling
the mixture to room temperature; and [0103] (iii) removing solvent
from the mixture using a spray drier to provide amorphous
Rebaudioside X.
[0104] In a more particular embodiment, the temperature is
maintained at about 121.degree. C.
[0105] In another embodiment, a method for preparing amorphous
Rebaudioside X comprises: [0106] (i) heating a mixture comprising
Form A Rebaudioside X and ethanol to reflux; [0107] (ii) cooling
the mixture to room temperature; and [0108] (iii) removing the
solvent from the mixture via evaporation to provide amorphous
Rebaudioside X.
[0109] In another embodiment, a method for preparing amorphous
Rebaudioside X comprises: [0110] (i) heating a mixture comprising
Material E Rebaudioside X and ethanol to reflux; [0111] (ii)
cooling the mixture to room temperature; and [0112] (iii) removing
the solvent from the mixture via evaporation to provide amorphous
Rebaudioside X.
[0113] The amorphous Rebaudioside X obtained by the present methods
is characterized by the X-ray diffraction patterns illustrated in
FIG. 4.
[0114] In exemplary embodiments, amorphous Rebaudioside X has
increased aqueous solubility compared to other forms of
Rebaudioside X, e.g. Form A Rebaudioside X, Form B Rebaudioside X
or Material E Rebaudioside X. The approximate solubility of Form A
Rebaudioside X is from about 0.1 to about 0.14%. In contrast,
amorphous Rebaudioside X prepared the processes described herein
exhibit approximate aqueous solubilities greater than 0.3%, such
as, for example, 0.4%, 0.5%, 0.6%, about 0.7%, about 0.8%, about
0.9%, about 1.0%, about 2.0%, about 3.0%, about 4.0%, or about
5.0%.
[0115] Approximate solubility (%) is calculated as grams of
Rebaudioside X per 100 mL water, e.g. 31 mg of amorphous
Rebaudioside X dissolved in 1 mL water provides a solubility of
3.1%.
[0116] The approximate aqueous solubility can be determined by a
solvent addition method in which a weighed sample is treated with
aliquots of water. The mixture is generally vortexed and/or
sonicated between additions to facilitate dissolution. Complete
dissolution of the test material is determined by visual
inspection. Solubility is estimated based on the total solvent used
to provide complete dissolution.
[0117] In other embodiments, the method provides amorphous
Rebaudioside X having a greater than about 10%, about 20%, about
30%, about 40%, about 50%, about 60%, about 70%, about 80% about
90%, about 100%, about 150%, about 200%, about 250%, about 300%,
about 350%, about 400%, about 450%, about 500%, about 550% or about
600% increase in water solubility compared to Form A Rebaudioside X
water solubility.
[0118] In one embodiment, the amorphous Rebaudioside X is in
substantially pure form. In other embodiments, amorphous
Rebaudioside X is greater than about than about 91%, 92%, 93%, 94%,
95%, 96%, 97% or 98% pure with respect to other forms of
Rebaudioside X. In one embodiment, a composition comprises
amorphous Rebaudioside X.
[0119] In another embodiment, amorphous Rebaudioside X is provided
in the absence of other forms of Rebaudioside X, i.e. 100% pure
amorphous Rebaudioside X with respect to other forms of
Rebaudioside X.
[0120] Form B Rebaudioside X
[0121] A method for preparing Form B Rebaudioside A comprises:
[0122] (i) heating a mixture comprising amorphous Rebaudioside X
and a solvent; [0123] (ii) cooling the mixture; and [0124] (iii)
removing the solvent from the mixture to provide Form B
Rebaudioside X.
[0125] The solvent can be water, organic solvents (e.g. alcohols),
or a mixture thereof. Suitable solvents include, but are not
limited to, water, ethanol, methanol, toluene, ethyl acetate,
hexane, acetone, dioxane, tetrahydrofuran, acetonitrile,
isopropanol, diethyl ether, dichloromethane, 2-butanone,
2,2,2-trifluoroethanol and combinations thereof. In a particular
embodiment, the solvent is ethanol.
[0126] The mixture of (i), which can be a slurry, can be heated to
a temperature form about 30.degree. C. to about 100.degree. C.,
such as, for example, about 40.degree. C., about 50.degree. C.,
about 60.degree. C., about 70.degree. C., about 80.degree. C.,
about .degree. C. or about 100.degree. C. In a particular
embodiment, the mixture is heated to about 40.degree. C. In a more
particular embodiment, the solvent is ethanol and the mixture is
heated to about 40.degree. C.
[0127] The duration of heating can also vary. In one embodiment,
the mixture can be heated from 5 hours to about 1 week, such as,
for example, about 10 hours, about 24 hours, about 2 days, about 3
days, about 4 days, about 5 days, about 6 days or about 7 days. In
a particular embodiment, the solvent is ethanol and the mixture is
heated to about 40.degree. C. for about 5 days.
[0128] Removal of the solvent in (iii) can be accomplished by any
suitable method including, for example, decantation,
centrifugation, filtration, evaporation, vacuum or spray drier. The
angular positions (two theta) of the prominent X-ray diffraction
peaks are as follows (Table 2) when generated by slurrying in
ethanol at 40.degree. C.:
TABLE-US-00003 TABLE 2 Form B Rebaudioside X Prominent XPRD
.degree.2.THETA. d space (.ANG.) Intensity (%) 4.20 .+-. 0.20
21.058 .+-. 1.053 100 5.17 .+-. 0.20 17.108 .+-. 0.689 41 6.47 .+-.
0.20 13.664 .+-. 0.435 78 7.40 .+-. 0.20 11.939 .+-. 0.331 54 7.92
.+-. 0.20 11.159 .+-. 0.289 99 13.40 .+-. 0.20 6.606 .+-. 0.100 70
14.46 .+-. 0.20 6.127 .+-. 0.085 57 16.08 .+-. 0.20 5.513 .+-.
0.069 65 17.48 .+-. 0.20 5.073 .+-. 0.058 91 18.15 .+-. 0.20 4.888
.+-. 0.054 71
[0129] One of skill in the art will recognize that XRPD patterns of
Form B Rebaudioside X produced under different conditions may
display peak shifts from those of FIGS. 7A and 7B, consistent with
the variable solvent/water content of the material. Form B exists
as a variable solvate/hydrate.
[0130] In one embodiment, the invention is Form B Rebaudioside X in
substantially pure form.
[0131] In other embodiments, Form B Rebaudioside X is greater than
about 91%, 92%, 93%, 94%, 95%, 96%, 97% or 98% pure with respect to
other forms of Rebaudioside X.
[0132] In another embodiment, Form B Rebaudioside X is provided in
the absence of other forms of Rebaudioside X, i.e. 100% pure Form B
Rebaudioside X with respect to other forms of Rebaudioside X.
[0133] In one embodiment, Form B Rebaudioside X is in substantially
pure form. In other embodiments, Form B Rebaudioside X is greater
than about than about 91%, 92%, 93%, 94%, 95%, 96%, 97% or 98% pure
with respect to other forms of Rebaudioside X. In one embodiment, a
composition comprises Form B Rebaudioside X.
[0134] In another embodiment, Form B Rebaudioside X is provided in
the absence of other forms of Rebaudioside X, i.e. 100% pure Form B
Rebaudioside X with respect to other forms of Rebaudioside X.
[0135] Rebaudioside X Complexes
[0136] The present invention also provides certain complexes
comprises Rebaudioside X and at least one other compound that, when
prepared under appropriate conditions, provide greater aqueous
solubility than the aqueous solubility over other forms of
Rebaudioside X, including Form A Rebaudioside X. As used herein,
the term "complex" means that the Rebaudioside X and the other
compound(s) are in intimate contact with each other, such that the
complex displays different properties, e.g. increased aqueous
solubility, compared to a physical mixture (e.g. a grind) of Form A
Rebaudioside X and the other compound(s).
[0137] In one embodiment, a complex comprises Rebaudioside X and at
least one polyol prepared by (i) heating a mixture comprising
solvent, Rebaudioside X and at least one polyol, (ii) cooling the
mixture and (iii) removing the solvent from the mixture to provide
a Rebaudioside X complex. In one embodiment, the Rebaudioside X
complex has greater aqueous solubility than Form A Rebaudioside
X.
[0138] The term "polyol", as used herein, refers to a molecule that
contains more than one hydroxyl group. A polyol may be a diol,
triol, or a tetraol which contains 2, 3, and 4 hydroxyl groups
respectively. A polyol also may contain more than 4 hydroxyl
groups, such as a pentaol, hexaol, heptaol, or the like, which
contain 5, 6, or 7 hydroxyl groups, respectively. Additionally, a
polyol also may be a sugar alcohol, polyhydric alcohol, or
polyalcohol which is a reduced form of carbohydrate, wherein the
carbonyl group (aldehyde or ketone, reducing sugar) has been
reduced to a primary or secondary hydroxyl group.
[0139] Non-limiting examples of polyols in some embodiments include
erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol,
isomalt, propylene glycol, glycerol (glycerin), threitol,
galactitol, palatinose, reduced isomalto-oligosaccharides, reduced
xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced
maltose syrup, reduced glucose syrup, and sugar alcohols or any
other carbohydrates capable of being reduced.
[0140] In certain embodiments, the mixture of Rebaudioside and at
least one polyol is heated until the mixture is visibly clear by
inspection, i.e. a solution with no visible solid particulates. In
a particular embodiment, the mixture is heated to a temperature
between about 100.degree. C. and 120.degree. C. The solvent can
vary but is preferably water. In one embodiment, Rebaudioside X and
the at least one polyol may be in a weight of about 1:1 to about
1:20. In a particular embodiment, the Rebaudioside X and at least
one polyol are present in a weight ratio of about 1:1. In a
particular embodiment, freeze-drying or spray drying is used in
(iii) to remove the solvent from the mixture. The final product
should be dry, i.e. substantially free of solvent.
[0141] In a specific embodiment, a complex comprises Rebaudioside X
and erythritol, wherein the complex has greater aqueous solubility
than Form A Rebaudioside X. In certain cases, the complex also has
greater aqueous solubility compared to a physical mixture of
Rebaudioside X and erythritol.
[0142] In another specific embodiment, a method for preparing a
Rebaudioside X complex comprises:
[0143] (i) heating a mixture comprising water, Rebaudioside X and
erythritol;
[0144] (ii) cooling the mixture to approximately room temperature;
and
[0145] (iii) freeze-drying the mixture to provide a Rebaudioside X
complex.
[0146] In a particular embodiment, the weight ratio of Rebaudioside
X to erythritol is about 1:1, and the mixture in (i) is heated
until it is visibly clear. Not wishing to be bound by theory, it is
believed that the complex provides superior aqueous solubility
properties over the physical mixture of Form A Rebaudioside X and
erythritol because the erythritol present during the
heating/cooling steps may act to disrupt formation of crystalline
polymorphs of Rebaudioside X (e.g. Form A).
[0147] In one embodiment, a complex comprises Rebaudioside X and
maltodextrin prepared by (i) heating a mixture comprising solvent,
Rebaudioside X and maltodextrin, (ii) cooling the mixture and (iii)
removing the solvent from the mixture to provide a Rebaudioside X
complex. In a particular embodiment, the Rebaudioside X complex has
greater aqueous solubility than the Form A Rebaudioside X.
[0148] In certain embodiments, the mixture of Rebaudioside and
maltodextrin is heated until the mixture is visibly clear by
inspection, i.e. a solution with no visible solid particulates. In
a particular embodiment, the mixture is heated to reflux. In
another embodiment, the mixture is heated to a temperature from
about 100.degree. C. and about 120.degree. C. The solvent can vary
but is preferably water. Rebaudioside X and maltodextrin may be in
a weight ratio of about 1:1 to about 1:20. In a particular
embodiment, the weight ratio of Rebaudioside X and maltodextrin is
about 1:1. In a particular embodiment, freeze-drying or spray
drying is used in (iii) to remove the solvent from the mixture. The
final product should be dry, i.e. substantially free of
solvent.
[0149] In another specific embodiment, a complex comprises
Rebaudioside X and maltodextrin, wherein the complex has greater
aqueous solubility than Form A Rebaudioside X. In certain cases,
the complex also has greater aqueous solubility compared to a
physical mixture of Rebaudioside X and maltodextrin.
[0150] In another specific embodiment, a method for preparing a
Rebaudioside X complex comprises:
[0151] (i) heating a mixture comprising water, Rebaudioside X and
maltodextrin;
[0152] (ii) cooling the mixture to approximately room temperature;
and
[0153] (iii) freeze-drying the mixture to provide a Rebaudioside X
complex.
[0154] In a particular embodiment, the weight ratio of Rebaudioside
X to maltodextrin is about 1:1, and the mixture in (i) is heated
until it is visibly clear. Not wishing to be bound by theory, it is
believed that the complex provides superior aqueous solubility
properties over the physical mixture of Form A Rebaudioside X and
maltodextrin because the maltodextrin present during the
heating/cooling steps may act to disrupt formation of crystalline
polymorphs of Rebaudioside X (e.g. Form A).
[0155] In one embodiment, a complex comprises Rebaudioside X and at
least one cyclodextrin prepared by (i) heating a mixture comprising
solvent, Rebaudioside X and at least one cyclodextrin, (ii) cooling
the mixture and (iii) removing the solvent from the mixture to
provide a Rebaudioside X complex with greater aqueous solubility
than Form A Rebaudioside X alone.
[0156] Cyclodextrins are cyclic oligosaccharides having at least
six glucopyranose units. They generally form a toroid shape with an
interior cavity that is less hydrophilic than the cyclodextrin
exterior. They may form inclusion complexes and, as such, host
other molecules. Cyclodextrins may change the physico-chemical
properties of such other molecules, such as the solubility. As used
herein, "cyclodextrin" refers to any cyclodextrin that increases
the solubility of Rebaudioside X.
[0157] Not wishing to be bound by theory, it is believed that the
cyclodextrin and Rebaudioside A may form an inclusion complex,
which provides superior aqueous solubility compared to Form A
Rebaudioside X alone. The term "inclusion complex" is understood to
mean that Rebaudioside X and cyclodextrin are in intimate contact
with one another, such as a complete or partial association or
contact (e.g. hydrophobic interactions) between Rebaudioside X and
cyclodextrin, such that Rebaudioside X resides in a cyclodextrin
cavity.
[0158] In one embodiment, a complex comprises Rebaudioside X and at
least one cyclodextrin, wherein the aqueous solubility of the
complex is greater than the solubility of Form A Rebaudioside X
alone.
[0159] The at least one cyclodextrin can be, but is not limited to,
.alpha.-cyclodextrin, .beta.-cyclodextrin, .gamma.-cyclodextrin, or
a derivative thereof. In a particular embodiment, the at least one
cyclodextrin is .gamma.-cyclodextrin.
[0160] Commercially available cyclodextrin may be used, for
example, those sold by the companies Cyclolab Ltd., those sold
under the trade name TRAPPSOL.RTM. by CDT, Inc., those sold under
the trade name CAVAMAX.RTM. by Wacker, those sold under the
tradenames KLEPTOSE.RTM. and CRYSMEB.RTM. by Roquette, and those
sold under the tradename CAPTISOL.RTM. by CYDEX
Pharmaceuticals.
[0161] Cyclodextrin derivatives may have modified or substituted
hydroxyl groups located on the exterior or interior cavity of the
cyclodextrin. Non-limiting examples of such cyclodextrin
derivatives include alkylated cyclodextrins; hydroxyalkylated
cyclodextrins; ethylcarboxymethyl cyclodextrins; sulfonated and
sulfoalkylether cyclodextrins; cyclodextrins substituted with
ammonium groups, phosphate groups, and hydroxyl groups, and salts
thereof; fluorinated cyclodextrins; and cyclodextrins substituted
with saccharides. Derivatives are generally prepared by modifying
or substituting the hydroxyl groups located on the exterior or
interior of the cyclodextrin. The modifications may be made to
increase the aqueous solubility and stability of the inclusion
complex. Modifications may also be made to alter the physical
characteristics of the complex. Modifications of those types and
others are well known in the art.
[0162] In one embodiment, a complex comprises Rebaudioside X and
.gamma.-cyclodextrin. In some embodiments, the ratio of
Rebaudioside X to cyclodextrin ranges from about 1:1 to about 1:20.
For example, the ratio may range from about 1:1 to about 1:19, or
from about 1:1 to about 1:15 or from about 1:1 to about 1:9, or
from about 1:1 to about 1:8, or from about 1:1 to about 1:7, or
from about 1:1 to about 1:6, or from about 1:1 to about 1:5, or
from about 1:1 to about 1:4.
[0163] In one embodiment, a method of preparing a Rebaudioside X
complex comprises (i) heating a mixture comprising Rebaudioside X,
at least one cyclodextrin and water; (ii) cooling the mixture to
approximately room temperature and (iii) freeze-drying the mixture
to provide a Rebaudioside X complex.
[0164] The amount of Rebaudioside X and the at least one
cyclodextrin can vary. Generally, Rebaudioside X and the at least
one cyclodextrin are provided in a weight ratio from about 1:4 to
about 1:20. In a particular embodiment, the weight ratio of
Rebaudioside X to the at least one cyclodextrin is from about 1:1
to about 1:4, such as about 1:1, about 1:2, about 1:3 and about
1:4. In a more particular embodiment, the at least one cyclodextrin
is .gamma.-cyclodextrin, and the weight ratio of Rebaudioside X to
.gamma.-cyclodextrin is from about 1:1 to about 1:4. In an further
particular embodiment, the Rebaudioside X is substantially pure
Form A Rebaudioside X, the at least one cyclodextrin is
.gamma.-cyclodextrin, and the weight ratio of Rebaudioside X to
.gamma.-cyclodextrin is from about 1:1 to about 1:4.
[0165] The solvent in (ii) can vary. Suitable solvents include, but
are not limited to, water, methanol, ethanol or combinations
thereof. The mixture should generally be heated until all the
contents/materials are dissolved and the mixture is a clear
solution. Suitable temperatures will depend on the amount of
materials in the mixture and the identity of the solvent. In
certain embodiments, the solvent is water and the mixture is heated
to reflux. In other embodiments, the mixture is heated to a
temperature from 100.degree. C. to about 120.degree. C.
[0166] The solvent can be removed from the mixture in (iii) by any
suitable method, such as, for example, freeze-drying or spray
drying. In a particular embodiment, the solvent is removed by
freeze-drying. In an exemplary procedure, Rebaudioside X (1.0 g)
and .gamma.-cyclodextrin (4.0 g) are added to water (100 mL). The
mixture is heated until all materials are dissolved (visual
inspection for clarity). In one embodiment, the mixture is heated
to reflux. In another embodiment, the mixture is heated to a
temperature from 100.degree. C. to about 120.degree. C. The mixture
can then be cooled to room temperature and freeze-dried. The
mixture can be freeze-dried for any suitable time frame, such as,
for example, from about 1 to about 3 days.
[0167] Any form of Rebaudioside X can be used in any of the
complexes described herein, including Form A, Form B, Material E,
amorphous and mixtures thereof.
[0168] The Rebaudioside X complexes can further contain other
terpene glycosides in addition to Rebaudioside X. Suitable terpene
glycosides include, but are not limited to, rebaudioside A;
rebaudioside B; rebaudioside C; rebaudioside D; rebaudioside E;
rebaudioside F; stevioside; steviolbioside; dulcoside A;
rubusoside; steviol; steviol 13 O-.beta.-D-glycoside; suavioside A;
suavioside B; suavioside G; suavioside H; suavioside I; suavioside
J; isosteviol;
13-[(2-O-(3-O-.alpha.-D-glucopyranosyl)-.beta.-D-glucopyranosyl-3-O-.beta-
.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]kaur-16-en-18-oic
acid .beta.-D-glucopyranosyl ester;
13-[(2-O-.beta.-D-glucopyranosyl-3-O-(4-O-.alpha.-D-glucopyranosyl)-.beta-
.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]kaur-16-en-18-oic
acid .beta.-D-glucopyranosyl ester;
13-[(3-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]kaur-16-en-1-
8-oic acid .beta.-D-glucopyranosyl ester;
13-hydroxy-kaur-16-en-18-oic acid .beta.-D-glucopyranosyl ester;
13-methyl-16-oxo-17-norkauran-18-oic acid .beta.-D-glucopyranosyl
ester;
13-[(2-O-.beta.-D-glucopyranosyl-3-O-.beta.-D-glucopyranosyl-.beta.-D-glu-
copyranosyl)oxy]kaur-15-en-18-oic acid .beta.-D-glucopyranosyl
ester;
13-[(2-O-.beta.-D-glucopyranosyl-3-O-.beta.-D-glucopyranosyl-.beta.-D-glu-
copyranosyl)oxy]kaur-15-en-18-oic acid;
13-[(2-O-.beta.-D-glucopyranosyl-3-O-.beta.-D-glucopyranosyl]-.beta.-D-gl-
ucopyranosyl)oxy]-17-hydroxy-kaur-15-en-18-oic acid
.beta.-D-glucopyranosyl ester;
13-[(2-O-.beta.-D-glucopyranosyl-3-O-.beta.-D-glucopyranosyl-.beta.-D-glu-
copyranosyl)oxy]-16-hydroxy kauran-18-oic acid
.beta.-D-glucopyranosyl ester;
13-[(2-O-.beta.-D-glucopyranosyl-3-O-.beta.-D-glucopyranosyl-.beta-
.-D-glucopyranosyl)oxy]-16-hydroxy kauran-18-oic acid;
1-[13-hydroxykaur-16-en-18-oate].beta.-D-glucopyranuronic acid;
13-[(2-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]-17-hydroxy--
kaur-15-en-18-oic acid .beta.-D-glucopyranosyl ester;
13-[(2-O-.alpha.-L-rhamnopyranosyl-3-O-.beta.-D-glucopyranosyl-.beta.-D-g-
lucopyranosyl)oxy]kaur-16-en-18-oic
acid-(2-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl) ester;
13-[(2-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]-17-oxo-kaur-
-15-en-18-oic acid .beta.-D-glucopyranosyl ester;
13-[(2-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]-17-oxo-kaur-
-15-en-18-oic acid .beta.-D-glucopyranosyl ester;
13-[(2-O-(6-O-.beta.-D-glucopyranosyl)-.beta.-D-glucopyranosyl-.beta.-D-g-
lucopyranosyl)oxy]kaur-16-en-18-oic acid .beta.-D-glucopyranosyl
ester;
13-[(2-O-.beta.-D-glucopyranosyl-3-O-.beta.-D-fructofuranosyl-.beta.-D-gl-
ucopyranosyl)oxy]kaur-16-en-18-oic acid .beta.-D-glucopyranosyl
ester;
13-[(2-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]kaur-16-en-1-
8-oic
acid-(6-O-.beta.-D-xylopyranosyl-.beta.-D-glucopyranosyl)ester;
13-[(2-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]kaur-16-en-1-
8-oic
acid-(4-O-(2-O-.alpha.-D-glucopyranosyl)-.alpha.-D-glucopyranosyl-.b-
eta.-D-glucopyranosyl)ester;
13-[(2-O-.beta.-D-glucopyranosyl-3-O-.beta.-D-glucopyranosyl-.beta.-D-glu-
copyranosyl)oxy]kaur-16-en-18-oic
acid-(2-O-6-deoxy-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)ester;
13-[(2-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]kaur-15-en-1-
8-oic acid .beta.-D-glucopyranosyl ester;
13-[(2-O-.beta.-D-glucopyranosyl-3-O-.beta.-D-xylopyranosyl-.beta.-D-gluc-
opyranosyl)oxy]kaur-16-en-18-oic acid .beta.-D-glucopyranosyl
ester;
13-[(2-O-.beta.-D-xylopyranosyl-.beta.-D-glucopyranosyl)oxy]kaur-16-en-18-
-oic acid .beta.-D-glucopyranosyl ester;
13-[(3-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]kaur-16-en-1-
8-oic acid .beta.-D-glucopyranosyl ester;
13-[(2-O-6-deoxy-.beta.-D-glucopyranosyl-3-O-.beta.-D-glucopyranosyl-.bet-
a.-D-glucopyranosyl)oxy]kaur-16-en-18-oic acid
.beta.-D-glucopyranosyl ester;
13-[(2-O-6-deoxy-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)o-
xy]kaur-16-en-18-oic acid .beta.-D-glucopyranosyl ester mogroside
E; mogroside I A; mogroside I E; mogroside II A; mogroside II
A.sub.1; mogroside II B; mogroside II E; mogroside III; mogroside
III A.sub.2; mogroside IV; mogroside IV A; mogroside V; mogroside
VI; 11-oxomogroside; 11-oxomogroside I A; 11-oxomogroside I
A.sub.1; 20-hydroxy-11-oxomogroside I A.sub.1; 11-oxomogroside II
A.sub.1; 7-oxomogroside II E; 11-oxomogroside II E;
11-deoxymogroside III; 11-oxomogroside IV A; 7-oxomogroside V;
11-oxomogroside V; mogrol; 11-oxo-mogrol; siamenoside;
siamenoside-1; isomogroside; isomogroside V; and polymorphic and
amorphous forms thereof.
[0169] In at least one embodiment, the aqueous solubility of the
Rebaudioside X complexes is increased compared to the aqueous
solubility of Form A Rebaudioside X. For example, the aqueous
solubility may be range from 0.1% to 7%, for example from 0.2% to
7%, such as from 0.2% to 5%. In some embodiments, the aqueous
solubility may range from 0.5% to 7%, such as from 1% to 5%, or
from 2% to 5%, or from 3% to 5%, or from 4% to 5%.
[0170] The Rebaudioside X complexes can be used as the sweet
component (i.e. the material that provides sweetness) in a
sweetener composition. In addition, sweetened compositions, e.g.
beverages, can comprise the Rebaudioside X complexes provided
herein.
[0171] Sweetener Compositions and Methods of Making the Same
[0172] Sweetener composition, as used herein, means a composition
that contains at least one sweet component in combination with at
least one other substance. The at least one other substance may be,
for example, a functional ingredient and/or an additive. The
sweetener compositions of the present invention are dry
powders.
[0173] Sweetenable composition, as used herein, means a substance
that is desirable to sweeten, including ingested substances and
substances that are contacted with the mouth but not eaten or
swallowed. Sweetenable compositions may be unsweetened, i.e. lack
any sweetener component, or sweetened, i.e. already contain a
sweetener component.
[0174] Sweetened composition, as used herein, means substances that
contain both a sweetenable composition and a sweetener or sweetener
composition.
[0175] For example, a beverage with no sweetener component is a
type of sweetenable composition. A sweetener composition comprising
amorphous Rebaudioside X can be added to the unsweetened beverage,
thereby providing a sweetened beverage. The sweetened beverage is a
type of sweetened composition.
[0176] In another example, a beverage that contains a
non-Rebaudioside X sweetener is a type of sweetenable composition.
A sweetener composition comprising amorphous Rebaudioside X can be
added to a beverage that contains a non-Rebaudioside X sweetener,
thereby providing a sweetened beverage. The sweetened beverage is a
type of sweetened composition.
[0177] In the sweetener compositions of the forgoing embodiments,
Rebaudioside X can be any form of Rebaudioside X described herein
(e.g. Form A Rebaudioside X, amorphous Rebaudioside X, Form B
Rebaudioside X). In another embodiment, Rebaudioside X can be
provided as a Rebaudioside X complexes.
[0178] In a particular embodiment, the sweetener compositions
comprise amorphous Rebaudioside, which X can be provided in the
presence or absence of other compounds, i.e. amorphous Rebaudioside
X can be part of a composition containing one or more compounds
that are not amorphous Rebaudioside X.
[0179] In one embodiment, Rebaudioside X is provided in a
composition containing or more additional compounds. The
composition may contain Rebaudioside X in an amount greater than
about 80% by weight on a dry basis, such as, for example, greater
than about 85%, greater than about 90%, greater than about 91%,
greater than about 92%, greater than about 93%, greater than about
94%, greater than about 95%, greater than about 96%, greater than
about 97%, greater than about 98% or greater than about 99%
amorphous Rebaudioside X by weight on a dry basis.
[0180] In a particular embodiment, Rebaudioside X is provided as a
component of partially purified Stevia extract. For example, the
Stevia extract may contain Rebaudioside X in an amount greater than
about 80% by weight on a dry basis, such as, for example, greater
than about 85%, greater than about 90%, greater than about 91%,
greater than about 92%, greater than about 93%, greater than about
94%, greater than about 95%, greater than about 96%, greater than
about 97%, greater than about 98% or greater than about 99%
Rebaudioside X by weight on a dry basis.
[0181] In another particular embodiment, Rebaudioside X is provided
as a component of a steviol glycoside mixture. The identities of
steviol glycosides are known in the art and include, but are not
limited to, steviol monoside, rubososide, steviolbioside,
stevioside, Rebaudioside A, Rebaudioside B, Rebaudioside C,
Rebaudioside D, Rebaudioside E, Rebaudioside F and dulcoside A. The
steviol glycoside mixture may contain from about 5% to about 99%
Rebaudioside X by weight on a dry basis. For example, a steviol
glycoside mixture may contain greater than about 10%, greater than
about 20%, greater than about 30%, greater than about 40%, greater
than about 50%, greater than about 60%, greater than about 70%,
greater than about 80% or greater than about 90% Rebaudioside X by
weight on a dry basis. In still further embodiments, the steviol
glycoside mixture may contain greater than about 90%, for example,
greater than about 91%, greater than about 92%, greater than about
93%, greater than about 94%, greater than about 95%, greater than
about 96%, greater than about 97%, greater than about 98% or
greater than about 99% Rebaudioside X by weight on a dry basis.
[0182] It is contemplated that a composition can contain
substantial quantities of non-Rebaudioside X compounds while the
Rebaudioside X within the composition is substantially pure
amorphous Rebaudioside X, i.e. does not contain greater than about
10% non-amorphous Rebaudioside X. For example, a composition may
contain amorphous Rebaudioside X in an amount greater than about
80% by weight on a dry basis, wherein the amorphous Rebaudioside X
is substantially pure. In another example, Rebaudioside X may be
present in a Stevia extract in an amount of about 80% by weight on
a dry basis wherein the Rebaudioside X is 100% pure amorphous
Rebaudioside X with respect to other forms of Rebaudioside X.
[0183] In one embodiment, amorphous Rebaudioside X can be used as
the sole sweetener in the sweetener composition, i.e. amorphous
Rebaudioside X is the only compound present in the sweetener
composition that provides sweetness. In another embodiment,
amorphous Rebaudioside X is one of two or more sweetener compounds
present in the sweetener composition.
[0184] In another embodiment, a Rebaudioside X complex can be used
as the sole sweetener component in the sweetener composition, i.e.
the complex is the only material present in the sweetener
composition that provides sweetness. In other embodiments, other
sweetener compounds can be present in the sweetener composition in
addition to the Rebaudioside X complex.
[0185] The sweetness of a given composition is typically measured
with reference to a solution of sucrose. See generally "A
Systematic Study of Concentration-Response Relationships of
Sweeteners," G. E. DuBois, D. E. Walters, S. S. Schiffman, Z. S.
Warwick, B. J. Booth, S. D. Pecore, K. Gibes, B. T. Carr, and L. M.
Brands, in Sweeteners: Discovery, Molecular Design and
Chemoreception, D. E. Walters, F. T. Orthoefer, and G. E. DuBois,
Eds., American Chemical Society, Washington, D.C. (1991), pp
261-276.
[0186] The amount of sucrose in a reference solution may be
described in degrees Brix (.degree. Bx). One degree Brix is 1 gram
of sucrose in 100 grams of solution and represents the strength of
the solution as percentage by weight (% w/w) (strictly speaking, by
mass). In one embodiment, a sweetener composition contains
amorphous Rebaudioside X in an amount effective to provide
sweetness equivalent from about 0.50 to 14 degrees Brix of sugar
when present in a sweetened composition, such as, for example, from
about 5 to about 11 degrees Brix, from about 4 to about 7 degrees
Brix, or about 5 degrees Brix. In another embodiment, amorphous
Rebaudioside X is present in an amount effective to provide
sweetness equivalent to about 10 degrees Brix when present in a
sweetened composition.
[0187] The sweetness of a non-sucrose sweetener can also be
measured against a sucrose reference by determining the non-sucrose
sweetener's sucrose equivalence. Typically, taste panelists are
trained to detect sweetness of reference sucrose solutions
containing between 1-15% sucrose (w/v). Other non-sucrose
sweeteners are then tasted at a series of dilutions to determine
the concentration of the non-sucrose sweetener that is as sweet as
a given percent sucrose reference. For example, if a 1% solution of
a sweetener is as sweet as a 10% sucrose solution, then the
sweetener is said to be 10 times as potent as sucrose.
[0188] In one embodiment, amorphous Rebaudioside X is present in a
sweetener composition in an amount effective to provide a sucrose
equivalence of greater than about 10% (w/v) when present in a
sweetened composition, such as, for example, greater than about
11%, greater than about 12%, greater than about 13% or greater than
about 14%.
[0189] In another embodiment, a Rebaudioside X complex is present
in a sweetener composition in an amount effective to provide a
sucrose equivalence of greater than about 10% (w/v) when present in
a sweetened composition, such as, for example, greater than about
11%, greater than about 12%, greater than about 13% or greater than
about 14%.
[0190] In some embodiments, sweetener compositions contain one or
more additional sweeteners. The additional sweetener can be any
type of sweetener, for example, a natural, non-natural, or
synthetic sweetener. In at least one embodiment, the at least one
additional sweetener is chosen from natural sweeteners other than
Stevia sweeteners. In another embodiment, the at least one
additional sweetener is chosen from synthetic high potency
sweeteners.
[0191] For example, the at least one additional sweetener may be a
carbohydrate sweetener. Non-limiting examples of suitable
carbohydrate sweeteners include sucrose, fructose, glucose,
erythritol, maltitol, lactitol, sorbitol, mannitol, xylitol,
D-tagatose, trehalose, galactose, rhamnose, cyclodextrin (e.g.,
.alpha.-cyclodextrin, .beta.-cyclodextrin, and
.gamma.-cyclodextrin), ribulose, threose, arabinose, xylose,
lyxose, allose, altrose, mannose, idose, lactose, maltose, invert
sugar, isotrehalose, neotrehalose, palatinose or isomaltulose,
erythrose, deoxyribose, gulose, idose, talose, erythrulose,
xylulose, psicose, turanose, cellobiose, glucosamine, mannosamine,
fucose, fuculose, glucuronic acid, gluconic acid, glucono-lactone,
abequose, galactosamine, xylo-oligosaccharides (xylotriose,
xylobiose and the like), gentio-oligoscaccharides (gentiobiose,
gentiotriose, gentiotetraose and the like),
galacto-oligosaccharides, sorbose, ketotriose (dehydroxyacetone),
aldotriose (glyceraldehyde), nigero-oligosaccharides,
fructooligosaccharides (kestose, nystose and the like),
maltotetraose, maltotriol, tetrasaccharides,
mannan-oligosaccharides, malto-oligosaccharides (maltotriose,
maltotetraose, maltopentaose, maltohexaose, maltoheptaose and the
like), dextrins, lactulose, melibiose, raffinose, rhamnose, ribose,
isomerized liquid sugars such as high fructose corn/starch syrup
(HFCS/HFSS) (e.g., HFCS55, HFCS42, or HFCS90), coupling sugars,
soybean oligosaccharides, glucose syrup and combinations
thereof.
[0192] In other embodiments, the additional sweetener is a
carbohydrate sweetener selected from the group consisting of
glucose, fructose, sucrose and combinations thereof.
[0193] The Rebaudioside X and carbohydrate sweetener may be present
in the sweetener composition in any weight ratio, such as, for
example, from about 0.001:14 to about 1:0.01, such as, for example,
about 0.06:6. Carbohydrates are present in the sweetener
composition in an amount effective to provide a concentration from
about 100 ppm to about 140,000 ppm when present in a sweetened
composition, such as, for example, a beverage.
[0194] In yet other embodiments, the at least one additional
sweetener is a synthetic sweetener. As used herein, the phrase
"synthetic sweetener" refers to any composition which is not found
naturally in nature and characteristically has a sweetness potency
greater than sucrose, fructose, or glucose, yet has less calories.
Non-limiting examples of synthetic high-potency sweeteners suitable
for embodiments of this disclosure include sucralose, potassium
acesulfame, acesulfame acid and salts thereof, aspartame, alitame,
saccharin and salts thereof, neohesperidin dihydrochalcone,
cyclamate, cyclamic acid and salts thereof, neotame, advantame,
glucosylated steviol glycosides (GSGs) and combinations thereof.
The synthetic sweetener is present in the sweetener composition in
an amount effective to provide a concentration from about 0.3 ppm
to about 3,500 ppm when present in a sweetened composition, such
as, for example, a beverage.
[0195] In still other embodiments, the additional sweetener can be
a natural high potency sweetener. Suitable natural high potency
sweeteners include, but are not limited to, rebaudioside A,
rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E,
rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L,
rebaudioside K, rebaudioside J, rebaudioside M, rebaudioside N,
rebaudioside O, dulcoside A, dulcoside B, rubusoside, stevia,
stevioside, mogroside IV, mogroside V, Luo Han Guo sweetener,
siamenoside, monatin and its salts (monatin SS, RR, RS, SR),
curculin, glycyrrhizic acid and its salts, thaumatin, monellin,
mabinlin, brazzein, hernandulcin, phyllodulcin, glycyphyllin,
phloridzin, trilobtain, baiyunoside, osladin, polypodoside A,
pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I,
periandrin I, abrusoside A, steviolbioside and cyclocarioside I.
The natural high potency sweetener can be provided as a pure
compound or, alternatively, as part of an extract. For example,
rebaudioside A can be provided as a sole compound or as part of a
Stevia extract. The natural high potency sweetener is present in
the sweetener composition in an amount effective to provide a
concentration from about 0.1 ppm to about 3,000 ppm when present in
a sweetened composition, such as, for example, a beverage.
[0196] The sweetener compositions can be customized to obtain a
desired calorie content. In one embodiment, the sweetener
composition is "full-calorie", such that the composition imparts
the desired sweetness when added to a sweetenable composition (such
as, for example, a beverage) and the sweetened composition has
about 120 calories per 8 oz serving.
[0197] In another embodiment, the sweetener composition is
"mid-calorie", such that the composition imparts the desired
sweetness when added to a sweetenable composition (such as, for
example, as beverage) and less than about 60 calories per 8 oz
serving.
[0198] In another embodiment, the sweetener composition is
"low-calorie", such that the composition imparts the desired
sweetness when added to a sweetenable composition (such as, for
example, as beverage) and the sweetened composition has less than
about 40 calories per 8 oz serving.
[0199] In yet other embodiments, the sweetener compositions can be
"zero-calorie", such that the composition imparts the desired
sweetness when added to a sweetenable composition (such as, for
example, a beverage) and the sweetened composition has less than
about 5 calories per 8 oz. serving.
[0200] Additives
[0201] In addition to Rebaudioside X and, optionally, other
sweeteners, the sweetener compositions of the present invention can
optionally include additional additives, detailed herein below. In
some embodiments, the sweetener composition contains additives
including, but not limited to, carbohydrates, polyols, amino acids
and their corresponding salts, poly-amino acids and their
corresponding salts, sugar acids and their corresponding salts,
nucleotides, organic acids, inorganic acids, organic salts
including organic acid salts and organic base salts, inorganic
salts, bitter compounds, flavorants and flavoring ingredients,
astringent compounds, proteins or protein hydrolysates,
surfactants, emulsifiers, weighing agents, gums, antioxidants,
colorants, flavonoids, alcohols, polymers and combinations thereof.
In some embodiments, the additives act to improve the temporal and
flavor profile of the sweetener to provide a sweetener composition
with a taste similar to sucrose.
[0202] In one embodiment, the sweetener compositions comprise one
or more polyols.
[0203] In certain embodiments, the polyol is present in the
sweetener composition in an amount effective to provide a
concentration from about 100 ppm to about 250,000 ppm when present
in a sweetened composition, such as, for example, a beverage. In
other embodiments, the polyol is present in the sweetener
composition in an amount effective to provide a concentration from
about 400 ppm to about 80,000 ppm when present in a sweetened
composition, such as, for example, from about 5,000 ppm to about
40,000 ppm.
[0204] In other embodiments, Rebaudioside X and the polyol are
present in the sweetener composition in a weight ratio from about
1:1 to about 1:800, such as, for example, from about 1:4 to about
1:800, from about 1:20 to about 1:600, from about 1:50 to about
1:300 or from about 1:75 to about 1:150.
[0205] Suitable amino acid additives include, but are not limited
to, aspartic acid, arginine, glycine, glutamic acid, proline,
threonine, theanine, cysteine, cystine, alanine, valine, tyrosine,
leucine, arabinose, trans-4-hydroxyproline, isoleucine, asparagine,
serine, lysine, histidine, ornithine, methionine, carnitine,
aminobutyric acid (.alpha.-, .beta.-, and/or .delta.-isomers),
glutamine, hydroxyproline, taurine, norvaline, sarcosine, and their
salt forms such as sodium or potassium salts or acid salts. The
amino acid additives also may be in the D- or L-configuration and
in the mono-, di-, or tri-form of the same or different amino
acids. Additionally, the amino acids may be .alpha.-, .beta.-,
.gamma.- and/or .delta.-isomers if appropriate. Combinations of the
foregoing amino acids and their corresponding salts (e.g., sodium,
potassium, calcium, magnesium salts or other alkali or alkaline
earth metal salts thereof, or acid salts) also are suitable
additives in some embodiments.
[0206] The amino acids may be natural or synthetic. The amino acids
also may be modified. Modified amino acids refers to any amino acid
wherein at least one atom has been added, removed, substituted, or
combinations thereof (e.g., N-alkyl amino acid, N-acyl amino acid,
or N-methyl amino acid). Non-limiting examples of modified amino
acids include amino acid derivatives such as trimethyl glycine,
N-methyl-glycine, and N-methyl-alanine. As used herein, modified
amino acids encompass both modified and unmodified amino acids. As
used herein, amino acids also encompass both peptides and
polypeptides (e.g., dipeptides, tripeptides, tetrapeptides, and
pentapeptides) such as glutathione and L-alanyl-L-glutamine.
Suitable polyamino acid additives include poly-L-aspartic acid,
poly-L-lysine (e.g., poly-L-.alpha.-lysine or
poly-L-.epsilon.-lysine), poly-L-ornithine (e.g.,
poly-L-.alpha.-ornithine or poly-L-.epsilon.-ornithine),
poly-L-arginine, other polymeric forms of amino acids, and salt
forms thereof (e.g., calcium, potassium, sodium, or magnesium salts
such as L-glutamic acid mono sodium salt). The poly-amino acid
additives also may be in the D- or L-configuration. Additionally,
the poly-amino acids may be .alpha.-, .beta.-, .gamma.-, .delta.-,
and .epsilon.-isomers if appropriate. Combinations of the foregoing
poly-amino acids and their corresponding salts (e.g., sodium,
potassium, calcium, magnesium salts or other alkali or alkaline
earth metal salts thereof or acid salts) also are suitable
additives in some embodiments. The poly-amino acids described
herein also may comprise co-polymers of different amino acids. The
poly-amino acids may be natural or synthetic. The poly-amino acids
also may be modified, such that at least one atom has been added,
removed, substituted, or combinations thereof (e.g., N-alkyl
poly-amino acid or N-acyl poly-amino acid). As used herein,
poly-amino acids encompass both modified and unmodified poly-amino
acids. For example, modified poly-amino acids include, but are not
limited to, poly-amino acids of various molecular weights (MW),
such as poly-L-.alpha.-lysine with a MW of 1,500, MW of 6,000, MW
of 25,200, MW of 63,000, MW of 83,000, or MW of 300,000.
[0207] In particular embodiments, the amino acid is present in the
sweetener composition in an amount effective to provide a
concentration from about 10 ppm to about 50,000 ppm when present in
a sweetened composition, such as, for example, a beverage. In
another embodiment, the amino acid is present in the sweetener
composition in an amount effective to provide a concentration from
about 1,000 ppm to about 10,000 ppm when present in a sweetened
composition, such as, for example, from about 2,500 ppm to about
5,000 ppm or from about 250 ppm to about 7,500 ppm.
[0208] Suitable sugar acid additives include, but are not limited
to, aldonic, uronic, aldaric, alginic, gluconic, glucuronic,
glucaric, galactaric, galacturonic, and salts thereof (e.g.,
sodium, potassium, calcium, magnesium salts or other
physiologically acceptable salts), and combinations thereof.
[0209] Suitable nucleotide additives include, but are not limited
to, inosine monophosphate ("IMP"), guanosine monophosphate ("GMP"),
adenosine monophosphate ("AMP"), cytosine monophosphate (CMP),
uracil monophosphate (UMP), inosine diphosphate, guanosine
diphosphate, adenosine diphosphate, cytosine diphosphate, uracil
diphosphate, inosine triphosphate, guanosine triphosphate,
adenosine triphosphate, cytosine triphosphate, uracil triphosphate,
alkali or alkaline earth metal salts thereof, and combinations
thereof. The nucleotides described herein also may comprise
nucleotide-related additives, such as nucleosides or nucleic acid
bases (e.g., guanine, cytosine, adenine, thymine, uracil).
[0210] The nucleotide is present in the sweetener composition in an
amount effective to provide a concentration from about 5 ppm to
about 1,000 ppm when present in sweetened composition, such as, for
example, a beverage.
[0211] Suitable organic acid additives include any compound which
comprises a --COOH moiety, such as, for example, C2-C30 carboxylic
acids, substituted hydroxyl C2-C30 carboxylic acids, butyric acid
(ethyl esters), substituted butyric acid (ethyl esters), benzoic
acid, substituted benzoic acids (e.g., 2,4-dihydroxybenzoic acid),
substituted cinnamic acids, hydroxyacids, substituted
hydroxybenzoic acids, anisic acid substituted cyclohexyl carboxylic
acids, tannic acid, aconitic acid, lactic acid, tartaric acid,
citric acid, isocitric acid, gluconic acid, glucoheptonic acids,
adipic acid, hydroxycitric acid, malic acid, fruitaric acid (a
blend of malic, fumaric, and tartaric acids), fumaric acid, maleic
acid, succinic acid, chlorogenic acid, salicylic acid, creatine,
caffeic acid, bile acids, acetic acid, ascorbic acid, alginic acid,
erythorbic acid, polyglutamic acid, glucono delta lactone, and
their alkali or alkaline earth metal salt derivatives thereof. In
addition, the organic acid additives also may be in either the D-
or L-configuration.
[0212] Suitable organic acid additive salts include, but are not
limited to, sodium, calcium, potassium, and magnesium salts of all
organic acids, such as salts of citric acid, malic acid, tartaric
acid, fumaric acid, lactic acid (e.g., sodium lactate), alginic
acid (e.g., sodium alginate), ascorbic acid (e.g., sodium
ascorbate), benzoic acid (e.g., sodium benzoate or potassium
benzoate), sorbic acid and adipic acid. The examples of the organic
acid additives described optionally may be substituted with at
least one group chosen from hydrogen, alkyl, alkenyl, alkynyl,
halo, haloalkyl, carboxyl, acyl, acyloxy, amino, amido, carboxyl
derivatives, alkylamino, dialkylamino, arylamino, alkoxy, aryloxy,
nitro, cyano, sulfo, thiol, imine, sulfonyl, sulfenyl, sulfinyl,
sulfamyl, carboxalkoxy, carboxamido, phosphonyl, phosphinyl,
phosphoryl, phosphino, thioester, thioether, anhydride, oximino,
hydrazino, carbamyl, phosphor or phosphonato. In particular
embodiments, the organic acid additive is present in the sweetener
composition in an amount from about 10 ppm to about 5,000 ppm.
[0213] Suitable inorganic acid additives include, but are not
limited to, phosphoric acid, phosphorous acid, polyphosphoric acid,
hydrochloric acid, sulfuric acid, carbonic acid, sodium dihydrogen
phosphate, and alkali or alkaline earth metal salts thereof (e.g.,
inositol hexaphosphate Mg/Ca).
[0214] The inorganic acid additive is present in the sweetener
composition in an amount effective to provide a concentration from
about 25 ppm to about 25,000 ppm when present in a sweetened
composition, such as, for example, a beverage.
[0215] Suitable bitter compound additives include, but are not
limited to, caffeine, quinine, urea, bitter orange oil, naringin,
quassia, and salts thereof.
[0216] The bitter compound is present in the sweetener composition
in an amount effective to provide a concentration from about 25 ppm
to about 25,000 ppm when present in a sweetened composition, such
as, for example, a beverage.
[0217] Suitable flavorant and flavoring ingredient additives for
include, but are not limited to, vanillin, vanilla extract, mango
extract, cinnamon, citrus, coconut, ginger, viridiflorol, almond,
menthol (including menthol without mint), grape skin extract, and
grape seed extract. "Flavorant" and "flavoring ingredient" are
synonymous and can include natural or synthetic substances or
combinations thereof. Flavorants also include any other substance
which imparts flavor and may include natural or non-natural
(synthetic) substances which are safe for human or animals when
used in a generally accepted range. Non-limiting examples of
proprietary flavorants include Dohler.TM. Natural Flavoring
Sweetness Enhancer K14323 (Dohler.TM., Darmstadt, Germany),
Symrise.TM. Natural Flavor Mask for Sweeteners 161453 and 164126
(Symrise.TM., Holzminden, Germany), Natural Advantage.TM.
Bitterness Blockers 1, 2, 9 and 10 (Natural Advantage.TM.,
Freehold, N.J., U.S.A.), and Sucramask.TM. (Creative Research
Management, Stockton, Calif., U.S.A.).
[0218] The flavorant is present in the sweetener composition in an
amount effective to provide a concentration from about 0.1 ppm to
about 3,000 ppm when present in a sweetened composition, such as,
for example, a beverage.
[0219] Suitable polymer additives include, but are not limited to,
chitosan, pectin, pectic, pectinic, polyuronic, polygalacturonic
acid, starch, food hydrocolloid or crude extracts thereof (e.g.,
gum acacia senegal (Fibergum.TM.), gum acacia seyal, carageenan),
poly-L-lysine (e.g., poly-L-.alpha.-lysine or
poly-L-.epsilon.-lysine), poly-L-ornithine (e.g.,
poly-L-.alpha.-ornithine or poly-L-.epsilon.-ornithine),
polypropylene glycol, polyethylene glycol, poly(ethylene glycol
methyl ether), polyarginine, polyaspartic acid, polyglutamic acid,
polyethylene imine, alginic acid, sodium alginate, propylene glycol
alginate, and sodium polyethyleneglycolalginate, sodium
hexametaphosphate and its salts, and other cationic polymers and
anionic polymers.
[0220] The polymer is present in the sweetener composition in an
amount effective to provide a concentration from about 30 ppm to
about 2,000 ppm when present in a sweetened composition, such as,
for example, a beverage.
[0221] Suitable protein or protein hydrolysate additives include,
but are not limited to, bovine serum albumin (BSA), whey protein
(including fractions or concentrates thereof such as 90% instant
whey protein isolate, 34% whey protein, 50% hydrolyzed whey
protein, and 80% whey protein concentrate), soluble rice protein,
soy protein, protein isolates, protein hydrolysates, reaction
products of protein hydrolysates, glycoproteins, and/or
proteoglycans containing amino acids (e.g., glycine, alanine,
serine, threonine, asparagine, glutamine, arginine, valine,
isoleucine, leucine, norvaline, methionine, proline, tyrosine,
hydroxyproline, and the like), collagen (e.g., gelatin), partially
hydrolyzed collagen (e.g., hydrolyzed fish collagen), and collagen
hydrolysates (e.g., porcine collagen hydrolysate).
[0222] The protein hydrosylate is present in the sweetener
composition in an amount effective to provide a concentration from
about 200 ppm to about 50,000 ppm when present in a sweetened
composition, such as, for example, a beverage.
[0223] Suitable surfactant additives include, but are not limited
to, polysorbates (e.g., polyoxyethylene sorbitan monooleate
(polysorbate 80), polysorbate 20, polysorbate 60), sodium
dodecylbenzenesulfonate, dioctyl sulfosuccinate or dioctyl
sulfosuccinate sodium, sodium dodecyl sulfate, cetylpyridinium
chloride (hexadecylpyridinium chloride), hexadecyltrimethylammonium
bromide, sodium cholate, carbamoyl, choline chloride, sodium
glycocholate, sodium taurodeoxycholate, lauric arginate, sodium
stearoyl lactylate, sodium taurocholate, lecithins, sucrose oleate
esters, sucrose stearate esters, sucrose palmitate esters, sucrose
laurate esters, and other emulsifiers, and the like.
[0224] The surfactant additive is present in the sweetener
composition in an amount effective to provide a concentration from
about 30 ppm to about 2,000 ppm when present in a sweetened
composition, such as, for example, a beverage.
[0225] Suitable flavonoid additives are classified as flavonols,
flavones, flavanones, flavan-3-ols, isoflavones, or anthocyanidins.
Non-limiting examples of flavonoid additives include, but are not
limited to, catechins (e.g., green tea extracts such as
Polyphenon.TM. 60, Polyphenon.TM. 30, and Polyphenon.TM. 25 (Mitsui
Norin Co., Ltd., Japan), polyphenols, rutins (e.g., enzyme modified
rutin Sanmelin.TM. AO (San-fi Gen F.F.I., Inc., Osaka, Japan)),
neohesperidin, naringin, neohesperidin dihydrochalcone, and the
like.
[0226] The flavonoid additive is present in the sweetener
composition in an amount effective to provide a concentration from
about 0.1 ppm to about 1,000 ppm when present in sweetened
composition, such as, for example, a beverage.
[0227] Suitable alcohol additives include, but are not limited to,
ethanol. In particular embodiments, the alcohol additive is present
in the sweetener composition in an amount effective to provide a
concentration from about 625 ppm to about 10,000 ppm when present
in a sweetened composition, such as, for example, a beverage.
[0228] Suitable astringent compound additives include, but are not
limited to, tannic acid, europium chloride (EuCl.sub.3), gadolinium
chloride (GdCl.sub.3), terbium chloride (TbCl.sub.3), alum, tannic
acid, and polyphenols (e.g., tea polyphenols). The astringent
additive is present in the sweetener composition in an amount
effective to provide a concentration from about 10 ppm to about
5,000 ppm when present in a sweetened composition, such as, for
example, a beverage.
[0229] In particular embodiments, a sweetener composition comprises
amorphous Rebaudioside X; a polyol selected from erythritol,
maltitol, mannitol, xylitol, sorbitol, and combinations thereof;
and optionally at least one additional sweetener and/or functional
ingredient. In a particular embodiment, the polyol is erythritol.
The amorphous Rebaudioside X can be provided as a pure compound or
as part of a Stevia extract or steviol glycoside mixture, as
described above. Amorphous Rebaudioside X can be present in an
amount from about 5% to about 99% by weight on a dry basis in
either a steviol glycoside mixture or a Stevia extract. In one
embodiment, amorphous Rebaudioside X and the polyol are present in
a sweetener composition in a weight ratio from about 1:1 to about
1:800, such as, for example, from about 1:4 to about 1:800, from
about 1:20 to about 1:600, from about 1:50 to about 1:300 or from
about 1:75 to about 1:150. In another embodiment, amorphous
Rebaudioside X is present in the sweetener composition in an amount
effective to provide a concentration from about 1 ppm to about
10,000 ppm when present in a sweetened composition, such as, for
example, about 500 ppm. The polyol, such as, for example,
erythritol, can be present in the sweetener composition in an
amount effective to provide a concentration from about 100 ppm to
about 250,000 ppm when present in a sweetened composition, such as,
for example, from about 5,000 ppm to about 40,000 ppm, from about
1,000 ppm to about 35,000 ppm.
[0230] In particular embodiments, a sweetener composition comprises
amorphous Rebaudioside X; a carbohydrate sweetener selected from
sucrose, fructose, glucose, maltose and combinations thereof; and
optionally at least one additional sweetener and/or functional
ingredient. The amorphous Rebaudioside X can be provided as a pure
compound or as part of a Stevia extract or steviol glycoside
mixture, as described above. Amorphous Rebaudioside X can be
present in an amount from about 5% to about 99% by weight on a dry
basis in either a steviol glycoside mixture or a Stevia extract. In
one embodiment, amorphous Rebaudioside X and the carbohydrate are
present in a sweetener composition in a weight ratio from about
0.001:14 to about 1:0.01, such as, for example, about 0.06:6. In
one embodiment, amorphous Rebaudioside X is present in the
sweetener composition in an amount effective to provide a
concentration from about 1 ppm to about 10,000 ppm when present in
a sweetened composition, such as, for example, about 500 ppm. The
carbohydrate, such as, for example, sucrose, can be present in the
sweetener composition in an amount effective to provide a
concentration from about 100 ppm to about 140,000 ppm when present
in a sweetened composition, such as, for example, from about 1,000
ppm to about 100,000 ppm, from about 5,000 ppm to about 80,000
ppm.
[0231] In particular embodiments, a sweetener composition comprises
amorphous Rebaudioside X; an amino acid selected from glycine,
alanine, proline and combinations thereof; and optionally at least
one additional sweetener and/or functional ingredient. The
amorphous Rebaudioside X can be provided as a pure compound or as
part of a Stevia extract or steviol glycoside mixture, as described
above. Amorphous Rebaudioside X can be present in an amount from
about 5% to about 99% by weight on a dry basis in either a steviol
glycoside mixture or a Stevia extract. In another embodiment,
amorphous Rebaudioside X is present in the sweetener composition in
an amount effective to provide a concentration from about 1 ppm to
about 10,000 ppm when present in a sweetened composition, such as,
for example, about 500 ppm. The amino acid, such as, for example,
glycine, can be present in the sweetener composition in an amount
effective to provide a concentration from about 10 ppm to about
50,000 ppm when present in a sweetened composition, such as, for
example, from about 1,000 ppm to about 10,000 ppm, from about 2,500
ppm to about 5,000 ppm
[0232] In particular embodiments, a sweetener composition comprises
amorphous Rebaudioside X; a salt selected from sodium chloride,
magnesium chloride, potassium chloride, calcium chloride and
combinations thereof; and optionally at least one additional
sweetener and/or functional ingredient. The amorphous Rebaudioside
X can be provided as a pure compound or as part of a Stevia extract
or steviol glycoside mixture, as described above. Amorphous
Rebaudioside X can be present in an amount from about 5% to about
99% by weight on a dry basis in either a steviol glycoside mixture
or a Stevia extract. In one embodiment, amorphous Rebaudioside X is
present in the sweetener composition in an amount effective to
provide a concentration from about 1 ppm to about 10,000 ppm, such
as, for example, about 100 to about 1,000 ppm. The inorganic salt,
such as, for example, magnesium chloride, is present in the
sweetener composition in an amount effective to provide a
concentration from about 25 ppm to about 25,000 ppm when present in
a sweetened composition, such as, for example, from about 100 ppm
to about 4,000 ppm or from about 100 ppm to about 3,000 ppm.
[0233] Functional Ingredients
[0234] The sweetener composition or sweetened composition can also
contain one or more functional ingredients, which provide a real or
perceived heath benefit to the composition. Functional ingredients
include, but are not limited to, saponins, antioxidants, dietary
fiber sources, fatty acids, vitamins, glucosamine, minerals,
preservatives, hydration agents, probiotics, prebiotics, weight
management agents, osteoporosis management agents, phytoestrogens,
long chain primary aliphatic saturated alcohols, phytosterols and
combinations thereof.
[0235] Saponin
[0236] In certain embodiments, the functional ingredient is at
least one saponin. As used herein, the at least one saponin may
comprise a single saponin or a plurality of saponins as a
functional ingredient for the sweetener composition or sweetened
compositions provided herein. Generally, according to particular
embodiments of this invention, the at least one saponin is present
in the sweetener composition or sweetened composition in an amount
sufficient to promote health and wellness.
[0237] Saponins are glycosidic natural plant products comprising an
aglycone ring structure and one or more sugar moieties. The
combination of the nonpolar aglycone and the water soluble sugar
moiety gives saponins surfactant properties, which allow them to
form a foam when shaken in an aqueous solution.
[0238] The saponins are grouped together based on several common
properties. In particular, saponins are surfactants which display
hemolytic activity and form complexes with cholesterol. Although
saponins share these properties, they are structurally diverse. The
types of aglycone ring structures forming the ring structure in
saponins can vary greatly. Non-limiting examples of the types of
aglycone ring structures in saponin for use in particular
embodiments of the invention include steroids, triterpenoids, and
steroidal alkaloids. Non-limiting examples of specific aglycone
ring structures for use in particular embodiments of the invention
include soyasapogenol A, soyasapogenol B and soyasopogenol E. The
number and type of sugar moieties attached to the aglycone ring
structure can also vary greatly. Non-limiting examples of sugar
moieties for use in particular embodiments of the invention include
glucose, galactose, glucuronic acid, xylose, rhamnose, and
methylpentose moieties. Non-limiting examples of specific saponins
for use in particular embodiments of the invention include group A
acetyl saponin, group B acetyl saponin, and group E acetyl
saponin.
[0239] Saponins can be found in a large variety of plants and plant
products, and are especially prevalent in plant skins and barks
where they form a waxy protective coating. Several common sources
of saponins include soybeans, which have approximately 5% saponin
content by dry weight, soapwort plants (Saponaria), the root of
which was used historically as soap, as well as alfalfa, aloe,
asparagus, grapes, chickpeas, yucca, and various other beans and
weeds. Saponins may be obtained from these sources by using
extraction techniques well known to those of ordinary skill in the
art. A description of conventional extraction techniques can be
found in U.S. Pat. Appl. No. 2005/0123662, the disclosure of which
is expressly incorporated by reference.
[0240] Antioxidant
[0241] In certain embodiments, the functional ingredient is at
least one antioxidant. As used herein, the at least one antioxidant
may comprise a single antioxidant or a plurality of antioxidants as
a functional ingredient for the sweetener composition or sweetened
compositions provided herein. Generally, according to particular
embodiments of this invention, the at least one antioxidant is
present in the sweetener composition or sweetened composition in an
amount sufficient to promote health and wellness.
[0242] As used herein "antioxidant" refers to any substance which
inhibits, suppresses, or reduces oxidative damage to cells and
biomolecules. Without being bound by theory, it is believed that
antioxidants inhibit, suppress, or reduce oxidative damage to cells
or biomolecules by stabilizing free radicals before they can cause
harmful reactions. As such, antioxidants may prevent or postpone
the onset of some degenerative diseases.
[0243] Examples of suitable antioxidants for embodiments of this
invention include, but are not limited to, vitamins, vitamin
cofactors, minerals, hormones, carotenoids, carotenoid terpenoids,
non-carotenoid terpenoids, flavonoids, flavonoid polyphenolics
(e.g., bioflavonoids), flavonols, flavones, phenols, polyphenols,
esters of phenols, esters of polyphenols, nonflavonoid phenolics,
isothiocyanates, and combinations thereof. In some embodiments, the
antioxidant is vitamin A, vitamin C, vitamin E, ubiquinone, mineral
selenium, manganese, melatonin, .alpha.-carotene, .beta.-carotene,
lycopene, lutein, zeanthin, crypoxanthin, reservatol, eugenol,
quercetin, catechin, gossypol, hesperetin, curcumin, ferulic acid,
thymol, hydroxytyrosol, tumeric, thyme, olive oil, lipoic acid,
glutathinone, gutamine, oxalic acid, tocopherol-derived compounds,
butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT),
ethylenediaminetetraacetic acid (EDTA), tert-butylhydroquinone,
acetic acid, pectin, tocotrienol, tocopherol, coenzyme Q10,
zeaxanthin, astaxanthin, canthaxantin, saponins, limonoids,
kaempfedrol, myricetin, isorhamnetin, proanthocyanidins, quercetin,
rutin, luteolin, apigenin, tangeritin, hesperetin, naringenin,
erodictyol, flavan-3-ols (e.g., anthocyanidins), gallocatechins,
epicatechin and its gallate forms, epigallocatechin and its gallate
forms (ECGC) theaflavin and its gallate forms, thearubigins,
isoflavone phytoestrogens, genistein, daidzein, glycitein,
anythocyanins, cyaniding, delphinidin, malvidin, pelargonidin,
peonidin, petunidin, ellagic acid, gallic acid, salicylic acid,
rosmarinic acid, cinnamic acid and its derivatives (e.g., ferulic
acid), chlorogenic acid, chicoric acid, gallotannins,
ellagitannins, anthoxanthins, betacyanins and other plant pigments,
silymarin, citric acid, lignan, antinutrients, bilirubin, uric
acid, R-.alpha.-lipoic acid, N-acetylcysteine, emblicanin, apple
extract, apple skin extract (applephenon), rooibos extract red,
rooibos extract, green, hawthorn berry extract, red raspberry
extract, green coffee antioxidant (GCA), aronia extract 20%, grape
seed extract (VinOseed), cocoa extract, hops extract, mangosteen
extract, mangosteen hull extract, cranberry extract, pomegranate
extract, pomegranate hull extract, pomegranate seed extract,
hawthorn berry extract, pomella pomegranate extract, cinnamon bark
extract, grape skin extract, bilberry extract, pine bark extract,
pycnogenol, elderberry extract, mulberry root extract, wolfberry
(gogi) extract, blackberry extract, blueberry extract, blueberry
leaf extract, raspberry extract, turmeric extract, citrus
bioflavonoids, black currant, ginger, acai powder, green coffee
bean extract, green tea extract, and phytic acid, or combinations
thereof. In alternate embodiments, the antioxidant is a synthetic
antioxidant such as butylated hydroxytolune or butylated
hydroxyanisole, for example. Other sources of suitable antioxidants
for embodiments of this invention include, but are not limited to,
fruits, vegetables, tea, cocoa, chocolate, spices, herbs, rice,
organ meats from livestock, yeast, whole grains, or cereal
grains.
[0244] Particular antioxidants belong to the class of
phytonutrients called polyphenols (also known as "polyphenolics"),
which are a group of chemical substances found in plants,
characterized by the presence of more than one phenol group per
molecule. A variety of health benefits may derived from
polyphenols, including prevention of cancer, heart disease, and
chronic inflammatory disease and improved mental strength and
physical strength, for example. Suitable polyphenols for
embodiments of this invention, include catechins,
proanthocyanidins, procyanidins, anthocyanins, quercerin, rutin,
reservatrol, isoflavones, curcumin, punicalagin, ellagitannin,
hesperidin, naringin, citrus flavonoids, chlorogenic acid, other
similar materials, and combinations thereof.
[0245] In particular embodiments, the antioxidant is a catechin
such as, for example, epigallocatechin gallate (EGCG). Suitable
sources of catechins for embodiments of this invention include, but
are not limited to, green tea, white tea, black tea, oolong tea,
chocolate, cocoa, red wine, grape seed, red grape skin, purple
grape skin, red grape juice, purple grape juice, berries,
pycnogenol, and red apple peel.
[0246] In some embodiments, the antioxidant is chosen from
proanthocyanidins, procyanidins or combinations thereof. Suitable
sources of proanthocyanidins and procyanidins for embodiments of
this invention include, but are not limited to, red grapes, purple
grapes, cocoa, chocolate, grape seeds, red wine, cacao beans,
cranberry, apple peel, plum, blueberry, black currants, choke
berry, green tea, sorghum, cinnamon, barley, red kidney bean, pinto
bean, hops, almonds, hazelnuts, pecans, pistachio, pycnogenol, and
colorful berries.
[0247] In particular embodiments, the antioxidant is a anthocyanin.
Suitable sources of anthocyanins for embodiments of this invention
include, but are not limited to, red berries, blueberries,
bilberry, cranberry, raspberry, cherry, pomegranate, strawberry,
elderberry, choke berry, red grape skin, purple grape skin, grape
seed, red wine, black currant, red currant, cocoa, plum, apple
peel, peach, red pear, red cabbage, red onion, red orange, and
blackberries.
[0248] In some embodiments, the antioxidant is chosen from
quercetin, rutin or combinations thereof. Suitable sources of
quercetin and rutin for embodiments of this invention include, but
are not limited to, red apples, onions, kale, bog whortleberry,
lingonberrys, chokeberry, cranberry, blackberry, blueberry,
strawberry, raspberry, black currant, green tea, black tea, plum,
apricot, parsley, leek, broccoli, chili pepper, berry wine, and
ginkgo.
[0249] In some embodiments, the antioxidant is resveratrol.
Suitable sources of resveratrol for embodiments of this invention
include, but are not limited to, red grapes, peanuts, cranberry,
blueberry, bilberry, mulberry, Japanese Itadori tea, and red
wine.
[0250] In particular embodiments, the antioxidant is an isoflavone.
Suitable sources of isoflavones for embodiments of this invention
include, but are not limited to, soy beans, soy products, legumes,
alfalfa spouts, chickpeas, peanuts, and red clover.
[0251] In some embodiments, the antioxidant is curcumin. Suitable
sources of curcumin for embodiments of this invention include, but
are not limited to, turmeric and mustard.
[0252] In particular embodiments, the antioxidant is chosen from
punicalagin, ellagitannin or combinations thereof. Suitable sources
of punicalagin and ellagitannin for embodiments of this invention
include, but are not limited to, pomegranate, raspberry,
strawberry, walnut, and oak-aged red wine.
[0253] In some embodiments, the antioxidant is a citrus flavonoid,
such as hesperidin or naringin. Suitable sources of citrus
flavonids, such as hesperidin or naringin, for embodiments of this
invention include, but are not limited to, oranges, grapefruits,
and citrus juices.
[0254] In particular embodiments, the antioxidant is chlorogenic
acid. Suitable sources of chlorogenic acid for embodiments of this
invention include, but are not limited to, green coffee, yerba
mate, red wine, grape seed, red grape skin, purple grape skin, red
grape juice, purple grape juice, apple juice, cranberry,
pomegranate, blueberry, strawberry, sunflower, Echinacea,
pycnogenol, and apple peel.
[0255] Dietary Fiber
[0256] In certain embodiments, the functional ingredient is at
least one dietary fiber source. As used herein, the at least one
dietary fiber source may comprise a single dietary fiber source or
a plurality of dietary fiber sources as a functional ingredient for
the sweetener compositions or sweetened compositions provided
herein. Generally, according to particular embodiments of this
invention, the at least one dietary fiber source is present in the
sweetener composition or sweetened composition in an amount
sufficient to promote health and wellness.
[0257] Numerous polymeric carbohydrates having significantly
different structures in both composition and linkages fall within
the definition of dietary fiber. Such compounds are well known to
those skilled in the art, non-limiting examples of which include
non-starch polysaccharides, lignin, cellulose, methylcellulose, the
hemicelluloses, .beta.-glucans, pectins, gums, mucilage, waxes,
inulins, oligosaccharides, fructooligosaccharides, cyclodextrins,
chitins, and combinations thereof.
[0258] Polysaccharides are complex carbohydrates composed of
monosaccharides joined by glycosidic linkages. Non-starch
polysaccharides are bonded with .beta.-linkages, which humans are
unable to digest due to a lack of an enzyme to break the
.beta.-linkages. Conversely, digestable starch polysaccharides
generally comprise .alpha.(1-4) linkages.
[0259] Lignin is a large, highly branched and cross-linked polymer
based on oxygenated phenylpropane units. Cellulose is a linear
polymer of glucose molecules joined by a .beta.(1-4) linkage, which
mammalian amylases are unable to hydrolyze. Methylcellulose is a
methyl esther of cellulose that is often used in foodstuffs as a
thickener, and emulsifier. It is commercially available (e.g.,
Citrucel by GlaxoSmithKline, Celevac by Shire Pharmaceuticals).
Hemicelluloses are highly branched polymers consisting mainly of
glucurono- and 4-O-methylglucuroxylans. .beta.-Glucans are
mixed-linkage (1-3), (1-4) .beta.-D-glucose polymers found
primarily in cereals, such as oats and barley. Pectins, such as
beta pectin, are a group of polysaccharides composed primarily of
D-galacturonic acid, which is methoxylated to variable degrees.
[0260] Gums and mucilages represent a broad array of different
branched structures. Guar gum, derived from the ground endosperm of
the guar seed, is a galactomannan. Guar gum is commercially
available (e.g., Benefiber by Novartis AG). Other gums, such as gum
arabic andpectins, have still different structures. Still other
gums include xanthan gum, gellan gum, tara gum, psylium seed husk
gum, and locust been gum.
[0261] Waxes are esters of ethylene glycol and two fatty acids,
generally occurring as a hydrophobic liquid that is insoluble in
water.
[0262] Inulins comprise naturally occurring oligosaccharides
belonging to a class of carbohydrates known as fructans. They
generally are comprised of fructose units joined by .beta.(2-1)
glycosidic linkages with a terminal glucose unit. Oligosaccharides
are saccharide polymers containing typically three to six component
sugars. They are generally found either O- or N-linked to
compatible amino acid side chains in proteins or to lipid
molecules. Fructooligosaccharides are oligosaccharides consisting
of short chains of fructose molecules.
[0263] Cyclodextrins are a family of cyclic oligosaccharides
composed of .alpha.-D-glucopyranoside units. They can be produced
from starch by means of enzymatic conversion. .alpha.-Cyclodextrin
is a six sugar ring molecule, whereas .beta.- and
.gamma.-cyclodextrins have seven and eight sugar ring molecules,
respectively. Non-cyclic dextrins are known as maltodextrins and
are generally easily digested by humans. Digestion resistant
maltodextrin is commercially available (e.g., Fibersol-2 by
ADM).
[0264] Food sources of dietary fiber include, but are not limited
to, grains, legumes, fruits, and vegetables. Grains providing
dietary fiber include, but are not limited to, oats, rye, barley,
wheat. Legumes providing fiber include, but are not limited to,
peas and beans such as soybeans. Fruits and vegetables providing a
source of fiber include, but are not limited to, apples, oranges,
pears, bananas, berries, tomatoes, green beans, broccoli,
cauliflower, carrots, potatoes, celery. Plant foods such as bran,
nuts, and seeds (such as flax seeds) are also sources of dietary
fiber. Parts of plants providing dietary fiber include, but are not
limited to, the stems, roots, leaves, seeds, pulp, and skin.
[0265] Although dietary fiber generally is derived from plant
sources, indigestible animal products such as chitins are also
classified as dietary fiber. Chitin is a polysaccharide composed of
units of acetylglucosamine joined by .beta.(1-4) linkages, similar
to the linkages of cellulose.
[0266] Sources of dietary fiber often are divided into categories
of soluble and insoluble fiber based on their solubility in water.
Both soluble and insoluble fibers are found in plant foods to
varying degrees depending upon the characteristics of the plant.
Although insoluble in water, insoluble fiber has passive
hydrophilic properties that help increase bulk, soften stools, and
shorten transit time of fecal solids through the intestinal
tract.
[0267] Unlike insoluble fiber, soluble fiber readily dissolves in
water. Soluble fiber undergoes active metabolic processing via
fermentation in the colon, increasing the colonic microflora and
thereby increasing the mass of fecal solids. Fermentation of fibers
by colonic bacteria also yields end-products with significant
health benefits. For example, fermentation of the food masses
produces gases and short-chain fatty acids. Acids produced during
fermentation include butyric, acetic, propionic, and valeric acids
that have various beneficial properties such as stabilizing blood
glucose levels by acting on pancreatic insulin release and
providing liver control by glycogen breakdown. In addition, fiber
fermentation may reduce atherosclerosis by lowering cholesterol
synthesis by the liver and reducing blood levels of LDL and
triglycerides. The acids produced during fermentation lower colonic
pH, thereby protecting the colon lining from cancer polyp
formation. The lower colonic pH also increases mineral absorption,
improves the barrier properties of the colonic mucosal layer, and
inhibits inflammatory and adhesion irritants. Fermentation of
fibers also may benefit the immune system by stimulating production
of T-helper cells, antibodies, leukocytes, splenocytes, cytokinins
and lymphocytes.
[0268] Fatty Acid
[0269] In certain embodiments, the functional ingredient is at
least one fatty acid. As used herein, the at least one fatty acid
may be single fatty acid or a plurality of fatty acids as a
functional ingredient for the sweetener composition or sweetened
compositions provided herein. Generally, according to particular
embodiments of this invention, the at least one fatty acid is
present in the sweetener composition or sweetened composition in an
amount sufficient to promote health and wellness.
[0270] As used herein, "fatty acid" refers to any straight chain
monocarboxylic acid and includes saturated fatty acids, unsaturated
fatty acids, long chain fatty acids, medium chain fatty acids,
short chain fatty acids, fatty acid precursors (including omega-9
fatty acid precursors), and esterified fatty acids. As used herein,
"long chain polyunsaturated fatty acid" refers to any
polyunsaturated carboxylic acid or organic acid with a long
aliphatic tail. As used herein, "omega-3 fatty acid" refers to any
polyunsaturated fatty acid having a first double bond as the third
carbon-carbon bond from the terminal methyl end of its carbon
chain. In particular embodiments, the omega-3 fatty acid may
comprise a long chain omega-3 fatty acid. As used herein, "omega-6
fatty acid" any polyunsaturated fatty acid having a first double
bond as the sixth carbon-carbon bond from the terminal methyl end
of its carbon chain.
[0271] Suitable omega-3 fatty acids for use in embodiments of the
present invention can be derived from algae, fish, animals, plants,
or combinations thereof, for example. Examples of suitable omega-3
fatty acids include, but are not limited to, linolenic acid,
alpha-linolenic acid, eicosapentaenoic acid, docosahexaenoic acid,
stearidonic acid, eicosatetraenoic acid and combinations thereof.
In some embodiments, suitable omega-3 fatty acids can be provided
in fish oils, (e.g., menhaden oil, tuna oil, salmon oil, bonito
oil, and cod oil), microalgae omega-3 oils or combinations thereof.
In particular embodiments, suitable omega-3 fatty acids may be
derived from commercially available omega-3 fatty acid oils such as
Microalgae DHA oil (from Martek, Columbia, Md.), OmegaPure (from
Omega Protein, Houston, Tex.), Marinol C-38 (from Lipid Nutrition,
Channahon, Ill.), Bonito oil and MEG-3 (from Ocean Nutrition,
Dartmouth, NS), Evogel (from Symrise, Holzminden, Germany), Marine
Oil, from tuna or salmon (from Arista Wilton, Conn.), OmegaSource
2000, Marine Oil, from menhaden and Marine Oil, from cod (from
OmegaSource, RTP, NC).
[0272] Suitable omega-6 fatty acids include, but are not limited
to, linoleic acid, gamma-linolenic acid, dihommo-gamma-linolenic
acid, arachidonic acid, eicosadienoic acid, docosadienoic acid,
adrenic acid, docosapentaenoic acid and combinations thereof.
[0273] Suitable esterified fatty acids for embodiments of the
present invention may include, but are not limited to,
monoacylgycerols containing omega-3 and/or omega-6 fatty acids,
diacylgycerols containing omega-3 and/or omega-6 fatty acids, or
triacylgycerols containing omega-3 and/or omega-6 fatty acids and
combinations thereof.
[0274] Vitamin
[0275] In certain embodiments, the functional ingredient is at
least one vitamin. As used herein, the at least one vitamin may be
single vitamin or a plurality of vitamins as a functional
ingredient for the sweetener and sweetened compositions provided
herein. Generally, according to particular embodiments of this
invention, the at least one vitamin is present in the sweetener
composition or sweetened composition in an amount sufficient to
promote health and wellness.
[0276] Vitamins are organic compounds that the human body needs in
small quantities for normal functioning. The body uses vitamins
without breaking them down, unlike other nutrients such as
carbohydrates and proteins. To date, thirteen vitamins have been
recognized, and one or more can be used in the functional sweetener
and sweetened compositions herein. Suitable vitamins include,
vitamin A, vitamin D, vitamin E, vitamin K, vitamin B1, vitamin B2,
vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B9, vitamin
B12, and vitamin C. Many of vitamins also have alternative chemical
names, non-limiting examples of which are provided below.
TABLE-US-00004 Vitamin Alternative names Vitamin A Retinol
Retinaldehyde Retinoic acid Retinoids Retinal Retinoic ester
Vitamin D Calciferol (vitamins D1-D5) Cholecalciferol Lumisterol
Ergocalciferol Dihydrotachysterol 7-dehydrocholesterol Vitamin E
Tocopherol Tocotrienol Vitamin K Phylloquinone Naphthoquinone
Vitamin B1 Thiamin Vitamin B2 Riboflavin Vitamin G Vitamin
Alternative names Vitamin B3 Niacin Nicotinic acid Vitamin PP
Vitamin B5 Pantothenic acid Vitamin B6 Pyridoxine Pyridoxal
Pyridoxamine Vitamin B7 Biotin Vitamin H Vitamin B9 Folic acid
Folate Folacin Vitamin M Pteroyl-L-glutamic acid Vitamin B12
Cobalamin Cyanocobalamin Vitamin C Ascorbic Acid
[0277] Various other compounds have been classified as vitamins by
some authorities. These compounds may be termed pseudo-vitamins and
include, but are not limited to, compounds such as ubiquinone
(coenzyme Q10), pangamic acid, dimethylglycine, taestrile,
amygdaline, flavanoids, para-aminobenzoic acid, adenine, adenylic
acid, and s-methylmethionine. As used herein, the term vitamin
includes pseudo-vitamins.
[0278] In some embodiments, the vitamin is a fat-soluble vitamin
chosen from vitamin A, D, E, K and combinations thereof.
[0279] In other embodiments, the vitamin is a water-soluble vitamin
chosen from vitamin B1, vitamin B2, vitamin B3, vitamin B6, vitamin
B12, folic acid, biotin, pantothenic acid, vitamin C and
combinations thereof.
[0280] Glucosamine
[0281] In certain embodiments, the functional ingredient is
glucosamine. Generally, according to particular embodiments of this
invention, glucosamine is present in the functional sweetener
composition or sweetened composition in an amount sufficient to
promote health and wellness.
[0282] Glucosamine, also called chitosamine, is an amino sugar that
is believed to be an important precurosor in the biochemical
synthesis of glycosylated proteins and lipids. D-glucosamine occurs
naturally in the cartilage in the form of glucosamine-6-phosphate,
which is synthesized from fructose-6-phosphate and glutamine.
However, glucosamine also is available in other forms, non-limiting
examples of which include glucosamine hydrochloride, glucosamine
sulfate, N-acetyl-glucosamine, or any other salt forms or
combinations thereof. Glucosamine may be obtained by acid
hydrolysis of the shells of lobsters, crabs, shrimps, or prawns
using methods well known to those of ordinary skill in the art. In
a particular embodiment, glucosamine may be derived from fungal
biomass containing chitin, as described in U.S. Patent Publication
No. 2006/0172392.
[0283] The sweetener compositions or sweetened composition can
further comprise chondroitin sulfate.
[0284] Mineral
[0285] In certain embodiments, the functional ingredient is at
least one mineral. As used herein, the at least one mineral may be
single mineral or a plurality of minerals as a functional
ingredient for the sweetener compositions or sweetened compositions
provided herein. Generally, according to particular embodiments of
this invention, the at least one mineral is present in the
sweetener composition or sweetened composition in an amount
sufficient to promote health and wellness.
[0286] Minerals, in accordance with the teachings of this
invention, comprise inorganic chemical elements required by living
organisms. Minerals are comprised of a broad range of compositions
(e.g., elements, simple salts, and complex silicates) and also vary
broadly in crystalline structure. They may naturally occur in foods
and beverages, may be added as a supplement, or may be consumed or
administered separately from foods or beverages.
[0287] Minerals may be categorized as either bulk minerals, which
are required in relatively large amounts, or trace minerals, which
are required in relatively small amounts. Bulk minerals generally
are required in amounts greater than or equal to about 100 mg per
day and trace minerals are those that are required in amounts less
than about 100 mg per day.
[0288] In particular embodiments of this invention, the mineral is
chosen from bulk minerals, trace minerals or combinations thereof.
Non-limiting examples of bulk minerals include calcium, chlorine,
magnesium, phosphorous, potassium, sodium, and sulfur. Non-limiting
examples of trace minerals include chromium, cobalt, copper,
fluorine, iron, manganese, molybdenum, selenium, zinc, and iodine.
Although iodine generally is classified as a trace mineral, it is
required in larger quantities than other trace minerals and often
is categorized as a bulk mineral.
[0289] In other particular embodiments of this invention, the
mineral is a trace mineral, believed to be necessary for human
nutrition, non-limiting examples of which include bismuth, boron,
lithium, nickel, rubidium, silicon, strontium, tellurium, tin,
titanium, tungsten, and vanadium.
[0290] The minerals embodied herein may be in any form known to
those of ordinary skill in the art. For example, in a particular
embodiment the minerals may be in their ionic form, having either a
positive or negative charge. In another particular embodiment the
minerals may be in their molecular form. For example, sulfur and
phosphorous often are found naturally as sulfates, sulfides, and
phosphates.
[0291] Preservative
[0292] In certain embodiments, the functional ingredient is at
least one preservative. As used herein, the at least one
preservative may be single preservative or a plurality of
preservatives as a functional ingredient for the sweetener
compositions or sweetened composition provided herein. Generally,
according to particular embodiments of this invention, the at least
one preservative is present in the sweetener composition or
sweetened composition in an amount sufficient to promote health and
wellness.
[0293] In particular embodiments of this invention, the
preservative is chosen from antimicrobials, antioxidants,
antienzymatics or combinations thereof. Non-limiting examples of
antimicrobials include sulfites, propionates, benzoates, sorbates,
nitrates, nitrites, bacteriocins, salts, sugars, acetic acid,
dimethyl dicarbonate (DMDC), ethanol, and ozone.
[0294] According to a particular embodiment, the preservative is a
sulfite. Sulfites include, but are not limited to, sulfur dioxide,
sodium bisulfite, and potassium hydrogen sulfite.
[0295] According to another particular embodiment, the preservative
is a propionate. Propionates include, but are not limited to,
propionic acid, calcium propionate, and sodium propionate.
[0296] According to yet another particular embodiment, the
preservative is a benzoate. Benzoates include, but are not limited
to, sodium benzoate and benzoic acid.
[0297] In another particular embodiment, the preservative is a
sorbate. Sorbates include, but are not limited to, potassium
sorbate, sodium sorbate, calcium sorbate, and sorbic acid.
[0298] In still another particular embodiment, the preservative is
a nitrate and/or a nitrite.
[0299] Nitrates and nitrites include, but are not limited to,
sodium nitrate and sodium nitrite.
[0300] In yet another particular embodiment, the at least one
preservative is a bacteriocin, such as, for example, nisin.
[0301] In another particular embodiment, the preservative is
ethanol.
[0302] In still another particular embodiment, the preservative is
ozone.
[0303] Non-limiting examples of antienzymatics suitable for use as
preservatives in particular embodiments of the invention include
ascorbic acid, citric acid, and metal chelating agents such as
ethylenediaminetetraacetic acid (EDTA).
[0304] Hydration Agent
[0305] In certain embodiments, the functional ingredient is at
least one hydration agent. As used herein, the at least one
hydration agent may be single hydration agent or a plurality of
hydration agents as a functional ingredient for the sweetener
compositions or sweetened composition provided herein. Generally,
according to particular embodiments of this invention, the at least
one hydration agent is present in the sweetener composition or
sweetened composition in an amount sufficient to promote health and
wellness.
[0306] Hydration products help the body to replace fluids that are
lost through excretion. For example, fluid is lost as sweat in
order to regulate body temperature, as urine in order to excrete
waste substances, and as water vapor in order to exchange gases in
the lungs. Fluid loss can also occur due to a wide range of
external causes, non-limiting examples of which include physical
activity, exposure to dry air, diarrhea, vomiting, hyperthermia,
shock, blood loss, and hypotension. Diseases causing fluid loss
include diabetes, cholera, gastroenteritis, shigellosis, and yellow
fever. Forms of malnutrition that cause fluid loss include the
excessive consumption of alcohol, electrolyte imbalance, fasting,
and rapid weight loss.
[0307] In a particular embodiment, the hydration product is a
composition that helps the body replace fluids that are lost during
exercise. Accordingly, in a particular embodiment, the hydration
product is an electrolyte, non-limiting examples of which include
sodium, potassium, calcium, magnesium, chloride, phosphate,
bicarbonate, and combinations thereof. Suitable electrolytes for
use in particular embodiments of this invention are also described
in U.S. Pat. No. 5,681,569, the disclosure of which is expressly
incorporated herein by reference. In particular embodiments, the
electrolytes are obtained from their corresponding water-soluble
salts. Non-limiting examples of salts for use in particular
embodiments include chlorides, carbonates, sulfates, acetates,
bicarbonates, citrates, phosphates, hydrogen phosphates, tartates,
sorbates, citrates, benzoates, or combinations thereof. In other
embodiments, the electrolytes are provided by juice, fruit
extracts, vegetable extracts, tea, or teas extracts.
[0308] In particular embodiments of this invention, the hydration
product is a carbohydrate to supplement energy stores burned by
muscles. Suitable carbohydrates for use in particular embodiments
of this invention are described in U.S. Pat. Nos. 4,312,856,
4,853,237, 5,681,569, and 6,989,171, the disclosures of which are
expressly incorporated herein by reference. Non-limiting examples
of suitable carbohydrates include monosaccharides, disaccharides,
oligosaccharides, complex polysaccharides or combinations thereof.
Non-limiting examples of suitable types of monosaccharides for use
in particular embodiments include trioses, tetroses, pentoses,
hexoses, heptoses, octoses, and nonoses. Non-limiting examples of
specific types of suitable monosaccharides include glyceraldehyde,
dihydroxyacetone, erythrose, threose, erythrulose, arabinose,
lyxose, ribose, xylose, ribulose, xylulose, allose, altrose,
galactose, glucose, gulose, idose, mannose, talose, fructose,
psicose, sorbose, tagatose, mannoheptulose, sedoheltulose,
octolose, and sialose. Non-limiting examples of suitable
disaccharides include sucrose, lactose, and maltose. Non-limiting
examples of suitable oligosaccharides include saccharose,
maltotriose, and maltodextrin. In other particular embodiments, the
carbohydrates are provided by a corn syrup, a beet sugar, a cane
sugar, a juice, or a tea.
[0309] In another particular embodiment, the hydration is a
flavanol that provides cellular rehydration. Flavanols are a class
of natural substances present in plants, and generally comprise a
2-phenylbenzopyrone molecular skeleton attached to one or more
chemical moieties. Non-limiting examples of suitable flavanols for
use in particular embodiments of this invention include catechin,
epicatechin, gallocatechin, epigallocatechin, epicatechin gallate,
epigallocatechin 3-gallate, theaflavin, theaflavin 3-gallate,
theaflavin 3'-gallate, theaflavin 3,3' gallate, thearubigin or
combinations thereof. Several common sources of flavanols include
tea plants, fruits, vegetables, and flowers. In preferred
embodiments, the flavanol is extracted from green tea.
[0310] In a particular embodiment, the hydration product is a
glycerol solution to enhance exercise endurance. The ingestion of a
glycerol containing solution has been shown to provide beneficial
physiological effects, such as expanded blood volume, lower heart
rate, and lower rectal temperature.
[0311] Probiotics/Prebiotics
[0312] In certain embodiments, the functional ingredient is chosen
from at least one probiotic, prebiotic and combination thereof. As
used herein, the at least one probiotic or prebiotic may be single
probiotic or prebiotic or a plurality of probiotics or prebiotics
as a functional ingredient for the sweetener compositions or
sweetened composition provided herein. Generally, according to
particular embodiments of this invention, the at least one
probiotic, prebiotic or combination thereof is present in the
sweetener composition or sweetened composition in an amount
sufficient to promote health and wellness.
[0313] Probiotics, in accordance with the teachings of this
invention, comprise microorganisms that benefit health when
consumed in an effective amount. Desirably, probiotics beneficially
affect the human body's naturally-occurring gastrointestinal
microflora and impart health benefits apart from nutrition.
Probiotics may include, without limitation, bacteria, yeasts, and
fungi.
[0314] According to particular embodiments, the probiotic is a
beneficial microorganisms that beneficially affects the human
body's naturally-occurring gastrointestinal microflora and imparts
health benefits apart from nutrition. Examples of probiotics
include, but are not limited to, bacteria of the genus
Lactobacilli, Bifidobacteria, Streptococci, or combinations
thereof, that confer beneficial effects to humans.
[0315] In particular embodiments of the invention, the at least one
probiotic is chosen from the genus Lactobacilli. Lactobacilli
(i.e., bacteria of the genus Lactobacillus, hereinafter "L.") have
been used for several hundred years as a food preservative and for
promoting human health. Non-limiting examples of species of
Lactobacilli found in the human intestinal tract include L.
acidophilus, L. casei, L. fermentum, L. saliva roes, L. brevis, L.
leichmannii, L. plantarum, L. cellobiosus, L. reuteri, L.
rhamnosus, L. GG, L. bulgaricus, and L. thermophilus.
[0316] According to other particular embodiments of this invention,
the probiotic is chosen from the genus Bifidobacteria.
Bifidobacteria also are known to exert a beneficial influence on
human health by producing short chain fatty acids (e.g., acetic,
propionic, and butyric acids), lactic, and formic acids as a result
of carbohydrate metabolism. Non-limiting species of Bifidobacteria
found in the human gastrointestinal tract include B. angulatum, B.
animalis, B. asteroides, B. bifidum, B. boum, B. breve, B.
catenulatum, B. choerinum, B. coryneforme, B. cuniculi, B. dentium,
B. gallicum, B. gallinarum, B indicum, B. longum, B. magnum, B.
merycicum, B. minimum, B. pseudocatenulatum, B. pseudolongum, B.
psychraerophilum, B. pullorum, B. ruminantium, B. saeculare, B.
scardovii, B. simiae, B. subtile, B. thermacidophilum, B.
thermophilum, B. urinalis, and B. sp.
[0317] According to other particular embodiments of this invention,
the probiotic is chosen from the genus Streptococcus. Streptococcus
thermophilus is a gram-positive facultative anaerobe. It is
classified as a lactic acid bacteria and commonly is found in milk
and milk products, and is used in the production of yogurt. Other
non-limiting probiotic species of this bacteria include
Streptococcus salivarus and Streptococcus cremoris.
[0318] Probiotics that may be used in accordance with this
invention are well-known to those of skill in the art. Non-limiting
examples of foodstuffs comprising probiotics include yogurt,
sauerkraut, kefir, kimchi, fermented vegetables, and other
foodstuffs containing a microbial element that beneficially affects
the host animal by improving the intestinal microbalance.
[0319] Prebiotics, in accordance with the teachings of this
invention, are compositions that promote the growth of beneficial
bacteria in the intestines. Prebiotic substances can be consumed by
a relevant probiotic, or otherwise assist in keeping the relevant
probiotic alive or stimulate its growth. When consumed in an
effective amount, prebiotics also beneficially affect the human
body's naturally-occurring gastrointestinal microflora and thereby
impart health benefits apart from just nutrition. Prebiotic foods
enter the colon and serve as substrate for the endogenous bacteria,
thereby indirectly providing the host with energy, metabolic
substrates, and essential micronutrients. The body's digestion and
absorption of prebiotic foods is dependent upon bacterial metabolic
activity, which salvages energy for the host from nutrients that
escaped digestion and absorption in the small intestine.
[0320] Prebiotics, in accordance with the embodiments of this
invention, include, without limitation, mucopolysaccharides,
oligosaccharides, polysaccharides, amino acids, vitamins, nutrient
precursors, proteins and combinations thereof.
[0321] According to a particular embodiment of this invention, the
prebiotic is chosen from dietary fibers, including, without
limitation, polysaccharides and oligosaccharides. These compounds
have the ability to increase the number of probiotics, which leads
to the benefits conferred by the probiotics. Non-limiting examples
of oligosaccharides that are categorized as prebiotics in
accordance with particular embodiments of this invention include
fructooligosaccharides, inulins, isomalto-oligosaccharides,
lactilol, lactosucrose, lactulose, pyrodextrins, soy
oligosaccharides, transgalacto-oligosaccharides, and
xylo-oligosaccharides.
[0322] According to other particular embodiments of the invention,
the prebiotic is an amino acid. Although a number of known
prebiotics break down to provide carbohydrates for probiotics, some
probiotics also require amino acids for nourishment.
[0323] Prebiotics are found naturally in a variety of foods
including, without limitation, bananas, berries, asparagus, garlic,
wheat, oats, barley (and other whole grains), flaxseed, tomatoes,
Jerusalem artichoke, onions and chicory, greens (e.g., dandelion
greens, spinach, collard greens, chard, kale, mustard greens,
turnip greens), and legumes (e.g., lentils, kidney beans,
chickpeas, navy beans, white beans, black beans).
[0324] Weight Management Agent
[0325] In certain embodiments, the functional ingredient is at
least one weight management agent. As used herein, the at least one
weight management agent may be single weight management agent or a
plurality of weight management agents as a functional ingredient
for the sweetener compositions or sweetened composition provided
herein. Generally, according to particular embodiments of this
invention, the at least one weight management agent is present in
the sweetener composition or sweetened composition in an amount
sufficient to promote health and wellness.
[0326] As used herein, "a weight management agent" includes an
appetite suppressant and/or a thermogenesis agent. As used herein,
the phrases "appetite suppressant", "appetite satiation
compositions", "satiety agents", and "satiety ingredients" are
synonymous. The phrase "appetite suppressant" describes
macronutrients, herbal extracts, exogenous hormones, anorectics,
anorexigenics, pharmaceutical drugs, and combinations thereof, that
when delivered in an effective amount, suppress, inhibit, reduce,
or otherwise curtail a person's appetite. The phrase "thermogenesis
agent" describes macronutrients, herbal extracts, exogenous
hormones, anorectics, anorexigenics, pharmaceutical drugs, and
combinations thereof, that when delivered in an effective amount,
activate or otherwise enhance a person's thermogenesis or
metabolism.
[0327] Suitable weight management agents include macronutrient
selected from the group consisting of proteins, carbohydrates,
dietary fats, and combinations thereof. Consumption of proteins,
carbohydrates, and dietary fats stimulates the release of peptides
with appetite-suppressing effects. For example, consumption of
proteins and dietary fats stimulates the release of the gut hormone
cholecytokinin (CCK), while consumption of carbohydrates and
dietary fats stimulates release of Glucagon-like peptide 1
(GLP-1).
[0328] Suitable macronutrient weight management agents also include
carbohydrates. Carbohydrates generally comprise sugars, starches,
cellulose and gums that the body converts into glucose for energy.
Carbohydrates often are classified into two categories, digestible
carbohydrates (e.g., monosaccharides, disaccharides, and starch)
and non-digestible carbohydrates (e.g., dietary fiber). Studies
have shown that non-digestible carbohydrates and complex polymeric
carbohydrates having reduced absorption and digestibility in the
small intestine stimulate physiologic responses that inhibit food
intake. Accordingly, the carbohydrates embodied herein desirably
comprise non-digestible carbohydrates or carbohydrates with reduced
digestibility. Non-limiting examples of such carbohydrates include
polydextrose; inulin; monosaccharide-derived polyols such as
erythritol, mannitol, xylitol, and sorbitol; disaccharide-derived
alcohols such as isomalt, lactitol, and maltitol; and hydrogenated
starch hydrolysates. Carbohydrates are described in more detail
herein below.
[0329] In another particular embodiment weight management agents is
dietary fat. Dietary fats are lipids comprising combinations of
saturated and unsaturated fatty acids. Polyunsaturated fatty acids
have been shown to have a greater satiating power than
mono-unsaturated fatty acids. Accordingly, the dietary fats
embodied herein desirably comprise poly-unsaturated fatty acids,
non-limiting examples of which include triacylglycerols.
[0330] In a particular embodiment, the weight management agents is
an herbal extract. Extracts from numerous types of plants have been
identified as possessing appetite suppressant properties.
Non-limiting examples of plants whose extracts have appetite
suppressant properties include plants of the genus Hoodia,
Trichocaulon, Caralluma, Stapelia, Orbea, Asclepias, and Camelia.
Other embodiments include extracts derived from Gymnema Sylvestre,
Kola Nut, Citrus Aurantium, Yerba Mate, Griffonia Simplicifolia,
Guarana, myrrh, guggul Lipid, and black current seed oil.
[0331] The herbal extracts may be prepared from any type of plant
material or plant biomass. Non-limiting examples of plant material
and biomass include the stems, roots, leaves, dried powder obtained
from the plant material, and sap or dried sap. The herbal extracts
generally are prepared by extracting sap from the plant and then
spray-drying the sap. Alternatively, solvent extraction procedures
may be employed. Following the initial extraction, it may be
desirable to further fractionate the initial extract (e.g., by
column chromatography) in order to obtain an herbal extract with
enhanced activity. Such techniques are well known to those of
ordinary skill in the art.
[0332] In a particular embodiment, the herbal extract is derived
from a plant of the genus Hoodia, species of which include H.
alstonii, H. currorii, H. dregei, H. flava, H. gordonii, H.
jutatae, H. mossamedensis, H. officinalis, H. parviflorai, H.
pedicellata, H. pilifera, H. ruschii, and H. triebneri. Hoodia
plants are stem succulents native to southern Africa. A sterol
glycoside of Hoodia, known as P57, is believed to be responsible
for the appetite-suppressant effect of the Hoodia species.
[0333] In another particular embodiment, the herbal extract is
derived from a plant of the genus Caralluma, species of which
include C. indica, C. fimbriata, C. attenuate, C. tuberculata, C.
edulis, C. adscendens, C. stalagmifera, C. umbellate, C.
penicillata, C. russeliana, C. retrospicens, C. Arabica, and C.
lasiantha. Carralluma plants belong to the same Subfamily as
Hoodia, Asclepiadaceae. Caralluma are small, erect and fleshy
plants native to India having medicinal properties, such as
appetite suppression, that generally are attributed to glycosides
belonging to the pregnane group of glycosides, non-limiting
examples of which include caratuberside A, caratuberside B,
bouceroside I, bouceroside II, bouceroside III, bouceroside IV,
bouceroside V, bouceroside VI, bouceroside VII, bouceroside VIII,
bouceroside IX, and bouceroside X.
[0334] In another particular embodiment, the at least one herbal
extract is derived from a plant of the genus Trichocaulon.
Trichocaulon plants are succulents that generally are native to
southern Africa, similar to Hoodia, and include the species T.
piliferum and T. officinale.
[0335] In another particular embodiment, the herbal extract is
derived from a plant of the genus Stapelia or Orbea, species of
which include S. gigantean and O. variegate, respectively. Both
Stapelia and Orbea plants belong to the same Subfamily as Hoodia,
Asclepiadaceae. Not wishing to be bound by any theory, it is
believed that they compounds exhibiting appetite suppressant
activity are saponins, such as pregnane glycosides, which include
stavarosides A, B, C, D, E, F, G, H, I, J, and K.
[0336] In another particular embodiment, the herbal extract is
derived from a plant of the genus Asclepias. Asclepias plants also
belong to the Asclepiadaceae family of plants. Non-limiting
examples of Asclepias plants include A. incarnate, A. curassayica,
A. syriaca, and A. tuberose. Not wishing to be bound by any theory,
it is believed that the extracts comprise steroidal compounds, such
as pregnane glycosides and pregnane aglycones, having appetite
suppressant effects.
[0337] In a particular embodiment, the weight management agent is
an exogenous hormone having a weight management effect.
Non-limiting examples of such hormones include CCK, peptide YY,
ghrelin, bombesin and gastrin-releasing peptide (GRP),
enterostatin, apolipoprotein A-IV, GLP-1, amylin, somastatin, and
leptin.
[0338] In another embodiment, the weight management agent is a
pharmaceutical drug. Non-limiting examples include phentenime,
diethylpropion, phendimetrazine, sibutramine, rimonabant,
oxyntomodulin, floxetine hydrochloride, ephedrine, phenethylamine,
or other stimulants.
[0339] The at least one weight management agent may be utilized
individually or in combination as a functional ingredient for the
sweetener compositions provided in this invention.
[0340] Osteoporosis Management Agent
[0341] In certain embodiments, the functional ingredient is at
least one osteoporosis management agent. As used herein, the at
least one osteoporosis management agent may be single osteoporosis
management agent or a plurality of osteoporosis management agent as
a functional ingredient for the sweetener compositions or sweetened
composition provided herein. Generally, according to particular
embodiments of this invention, the at least one osteoporosis
management agent is present in the sweetener composition or
sweetened composition in an amount sufficient to promote health and
wellness.
[0342] Osteoporosis is a skeletal disorder of compromised bone
strength, resulting in an increased risk of bone fracture.
Generally, osteoporosis is characterized by reduction of the bone
mineral density (BMD), disruption of bone micro-architecture, and
changes to the amount and variety of non-collagenous proteins in
the bone.
[0343] In certain embodiments, the osteoporosis management agent is
at least one calcium source. According to a particular embodiment,
the calcium source is any compound containing calcium, including
salt complexes, solubilized species, and other forms of calcium.
Non-limiting examples of calcium sources include amino acid
chelated calcium, calcium carbonate, calcium oxide, calcium
hydroxide, calcium sulfate, calcium chloride, calcium phosphate,
calcium hydrogen phosphate, calcium dihydrogen phosphate, calcium
citrate, calcium malate, calcium citrate malate, calcium gluconate,
calcium tartrate, calcium lactate, solubilized species thereof, and
combinations thereof.
[0344] According to a particular embodiment, the osteoporosis
management agent is a magnesium source. The magnesium source is any
compound containing magnesium, including salt complexes,
solubilized species, and other forms of magnesium. Non-limiting
examples of magnesium sources include magnesium chloride, magnesium
citrate, magnesium gluceptate, magnesium gluconate, magnesium
hydroxide, magnesium picolate, magnesium sulfate, solubilized
species thereof, and mixtures thereof. In another particular
embodiment, the magnesium source comprises an amino acid chelated
or creatine chelated magnesium.
[0345] In other embodiments, the osteoporosis agent is chosen from
vitamins D, C, K, their precursors and/or beta-carotene and
combinations thereof.
[0346] Numerous plants and plant extracts also have been identified
as being effective in the prevention and treatment of osteoporosis.
Not wishing to be bound by any theory, it is believed that the
plants and plant extracts stimulates bone morphogenic proteins
and/or inhibits bone resorption, thereby stimulating bone
regeneration and strength. Non-limiting examples of suitable plants
and plant extracts as osteoporosis management agents include
species of the genus Taraxacum and Amelanchier, as disclosed in
U.S. Patent Publication No. 2005/0106215, and species of the genus
Lindera, Artemisia, Acorus, Carthamus, Carum, Cnidium, Curcuma,
Cyperus, Juniperus, Prunus, Iris, Cichorium, Dodonaea, Epimedium,
Erigonoum, Soya, Mentha, Ocimum, thymus, Tanacetum, Plantago,
Spearmint, Bixa, Vitis, Rosemarinus, Rhus, and Anethum, as
disclosed in U.S. Patent Publication No. 2005/0079232.
[0347] Phytoestrogen
[0348] In certain embodiments, the functional ingredient is at
least one phytoestrogen. As used herein, the at least one
phytoestrogen may be single phytoestrogen or a plurality of
phytoestrogens as a functional ingredient for the sweetener
compositions or sweetened composition provided herein. Generally,
according to particular embodiments of this invention, the at least
one phytoestrogen is present in the sweetener composition or
sweetened composition in an amount sufficient to promote health and
wellness.
[0349] Phytoestrogens are compounds found in plants which can
typically be delivered into human bodies by ingestion of the plants
or the plant parts having the phytoestrogens. As used herein,
"phytoestrogen" refers to any substance which, when introduced into
a body causes an estrogen-like effect of any degree. For example, a
phytoestrogen may bind to estrogen receptors within the body and
have a small estrogen-like effect.
[0350] Examples of suitable phytoestrogens for embodiments of this
invention include, but are not limited to, isoflavones, stilbenes,
lignans, resorcyclic acid lactones, coumestans, coumestrol, equol,
and combinations thereof. Sources of suitable phytoestrogens
include, but are not limited to, whole grains, cereals, fibers,
fruits, vegetables, black cohosh, agave root, black currant, black
haw, chasteberries, cramp bark, dong quai root, devil's club root,
false unicorn root, ginseng root, groundsel herb, licorice,
liferoot herb, motherwort herb, peony root, raspberry leaves, rose
family plants, sage leaves, sarsaparilla root, saw palmetto
berried, wild yam root, yarrow blossoms, legumes, soybeans, soy
products (e.g., miso, soy flour, soymilk, soy nuts, soy protein
isolate, tempen, or tofu) chick peas, nuts, lentils, seeds, clover,
red clover, dandelion leaves, dandelion roots, fenugreek seeds,
green tea, hops, red wine, flaxseed, garlic, onions, linseed,
borage, butterfly weed, caraway, chaste tree, vitex, dates, dill,
fennel seed, gotu kola, milk thistle, pennyroyal, pomegranates,
southemwood, soya flour, tansy, and root of the kudzu vine
(pueraria root) and the like, and combinations thereof.
[0351] Isoflavones belong to the group of phytonutrients called
polyphenols. In general, polyphenols (also known as
"polyphenolics"), are a group of chemical substances found in
plants, characterized by the presence of more than one phenol group
per molecule.
[0352] Suitable phytoestrogcn isoflavones in accordance with
embodiments of this invention include genistein, daidzein,
glycitein, biochanin A, formononetin, their respective naturally
occurring glycosides and glycoside conjugates, matairesinol,
secoisolariciresinol, enterolactone, enterodiol, textured vegetable
protein, and combinations thereof.
[0353] Suitable sources of isoflavones for embodiments of this
invention include, but are not limited to, soy beans, soy products,
legumes, alfalfa spouts, chickpeas, peanuts, and red clover.
[0354] Long-Chain Primary Aliphatic Saturated Alcohol
[0355] In certain embodiments, the functional ingredient is at
least one long chain primary aliphatic saturated alcohol. In one
embodiment, a sweetener composition comprises at least one long
chain primary aliphatic saturated alcohol, Rebaudioside X, and
optionally at least one additive. In another embodiment, a
sweetened composition comprises a sweetenable composition and a
sweetener composition, wherein the sweetener composition comprises
at least one long chain primary aliphatic saturated alcohol,
Rebaudioside X, and optionally at least one additive. As used
herein, the at least one long chain primary aliphatic saturated
alcohol may be single long chain primary aliphatic saturated
alcohol or a plurality of long chain primary aliphatic saturated
alcohols as a functional ingredient for the sweetener compositions
or sweetened composition provided herein. Generally, according to
particular embodiments of this invention, the at least one long
chain primary aliphatic saturated alcohol is present in the
sweetener composition or sweetened composition in an amount
sufficient to promote health and wellness.
[0356] Long-chain primary aliphatic saturated alcohols are a
diverse group of organic compounds. The term alcohol refers to the
fact these compounds feature a hydroxyl group (--OH) bound to a
carbon atom. The term primary refers to the fact that in these
compounds the carbon atom which is bound to the hydroxyl group is
bound to only one other carbon atom. The term saturated refers to
the fact that these compounds feature no carbon to carbon pi bonds.
The term aliphatic refers to the fact that the carbon atoms in
these compounds are joined together in straight or branched chains
rather than in rings. The term long-chain refers to the fact that
the number of carbon atoms in these compounds is at least 8
carbons).
[0357] Non-limiting examples of particular long-chain primary
aliphatic saturated alcohols for use in particular embodiments of
the invention include the 8 carbon atom 1-octanol, the 9 carbon
1-nonanol, the 10 carbon atom 1-decanol, the 12 carbon atom
1-dodecanol, the 14 carbon atom 1-tetradecanol, the 16 carbon atom
1-hexadecanol, the 18 carbon atom 1-octadecanol, the 20 carbon atom
1-eicosanol, the 22 carbon 1-docosanol, the 24 carbon
1-tetracosanol, the 26 carbon 1-hexacosanol, the 27 carbon
1-heptacosanol, the 28 carbon 1-octanosol, the 29 carbon
1-nonacosanol, the 30 carbon 1-triacontanol, the 32 carbon
1-dotriacontanol, and the 34 carbon 1-tetracontanol.
[0358] In a particularly desirable embodiment of the invention, the
long-chain primary aliphatic saturated alcohols is policosanol.
Policosanol is the term for a mixture of long-chain primary
aliphatic saturated alcohols composed primarily of 28 carbon
1-octanosol and 30 carbon 1-triacontanol, as well as other alcohols
in lower concentrations such as 22 carbon 1-docosanol, 24 carbon
1-tetracosanol, 26 carbon 1-hexacosanol, 27 carbon 1-heptacosanol,
29 carbon 1-nonacosanol, 32 carbon 1-dotriacontanol, and 34 carbon
1-tetracontanol.
[0359] Long-chain primary aliphatic saturated alcohols are derived
from natural fats and oils. They may be obtained from these sources
by using extraction techniques well known to those of ordinary
skill in the art. Policosanols can be isolated from a variety of
plants and materials including sugar cane (Saccharum officinarium),
yams (e.g. Dioscorea opposite), bran from rice (e.g. Oryza sativa),
and beeswax. Policosanols may be obtained from these sources by
using extraction techniques well known to those of ordinary skill
in the art. A description of such extraction techniques can be
found in U.S. Pat. Appl. No. 2005/0220868, the disclosure of which
is expressly incorporated by reference.
[0360] Phytosterols
[0361] In certain embodiments, the functional ingredient is at
least one phytosterol, phytostanol or combination thereof.
Generally, according to particular embodiments of this invention,
the at least one phytosterol, phytostanol or combination thereof is
present in the sweetener composition or sweetened composition in an
amount sufficient to promote health and wellness.
[0362] As used herein, the phrases "stanol", "plant stanol" and
"phytostanol" are synonymous.
[0363] Plant sterols and stanols are present naturally in small
quantities in many fruits, vegetables, nuts, seeds, cereals,
legumes, vegetable oils, bark of the trees and other plant sources.
Although people normally consume plant sterols and stanols every
day, the amounts consumed are insufficient to have significant
cholesterol-lowering effects or other health benefits. Accordingly,
it would be desirable to supplement food and beverages with plant
sterols and stanols.
[0364] Sterols are a subgroup of steroids with a hydroxyl group at
C-3. Generally, phytosterols have a double bond within the steroid
nucleus, like cholesterol; however, phytosterols also may comprise
a substituted sidechain (R) at C-24, such as an ethyl or methyl
group, or an additional double bond. The structures of phytosterols
are well known to those of skill in the art.
[0365] At least 44 naturally-occurring phytosterols have been
discovered, and generally are derived from plants, such as corn,
soy, wheat, and wood oils; however, they also may be produced
synthetically to form compositions identical to those in nature or
having properties similar to those of naturally-occurring
phytosterols. According to particular embodiments of this
invention, non-limiting examples of phytosterols well known to
those or ordinary skill in the art include 4-desmethylsterols
(e.g., .beta.-sitosterol, campesterol, stigmasterol,
brassicasterol, 22-dehydrobrassicasterol, and
.DELTA.5-avenasterol), 4-monomethyl sterols, and 4,4-dimethyl
sterols (triterpene alcohols) (e.g., cycloartenol,
24-methylenecycloartanol, and cyclobranol).
[0366] As used herein, the phrases "stanol", "plant stanol" and
"phytostanol" are synonymous. Phytostanols are saturated sterol
alcohols present in only trace amounts in nature and also may be
synthetically produced, such as by hydrogenation of phytosterols.
According to particular embodiments of this invention, non-limiting
examples of phytostanols include .beta.-sitostanol, campestanol,
cycloartanol, and saturated forms of other triterpene alcohols.
[0367] Both phytosterols and phytostanols, as used herein, include
the various isomers such as the .alpha. and .beta. isomers (e.g.,
.alpha.-sitosterol and .beta.-sitostanol, which comprise one of the
most effective phytosterols and phytostanols, respectively, for
lowering serum cholesterol in mammals).
[0368] The phytosterols and phytostanols of the present invention
also may be in their ester form. Suitable methods for deriving the
esters of phytosterols and phytostanols are well known to those of
ordinary skill in the art, and are disclosed in U.S. Pat. Nos.
6,589,588, 6,635,774, 6,800,317, and U.S. Patent Publication Number
2003/0045473, the disclosures of which are incorporated herein by
reference in their entirety. Non-limiting examples of suitable
phytosterol and phytostanol esters include sitosterol acetate,
sitosterol oleate, stigmasterol oleate, and their corresponding
phytostanol esters. The phytosterols and phytostanols of the
present invention also may include their derivatives.
[0369] Tabletop Sweetener Compositions
[0370] Tabletop sweetener compositions comprising Rebaudioside X
are also contemplated herein. The tabletop composition can further
include at least one bulking agent, additive, anti-caking agent,
functional ingredient or combination thereof. In one embodiment,
the Rebaudioside X is amorphous Rebaudioside X. In another
embodiment, a Rebaudioside X complex provides the source of
Rebaudioside X for the tabletop sweetener compositions.
[0371] Suitable "bulking agents" include, but are not limited to,
maltodextrin (10 DE, 18 DE, or 5 DE), corn syrup solids (20 or 36
DE), sucrose, fructose, glucose, invert sugar, sorbitol, xylose,
ribulose, mannose, xylitol, mannitol, galactitol, erythritol,
maltitol, lactitol, isomalt, maltose, tagatose, lactose, inulin,
glycerol, propylene glycol, polyols, polydextrose,
fructooligosaccharides, cellulose and cellulose derivatives, and
the like, and mixtures thereof. Additionally, in accordance with
still other embodiments of the invention, granulated sugar
(sucrose) or other caloric sweeteners such as crystalline fructose,
other carbohydrates, or sugar alcohol can be used as a bulking
agent due to their provision of good content uniformity without the
addition of significant calories.
[0372] As used herein, the phrase "anti-caking agent" and "flow
agent" refer to any composition which assists in content uniformity
and uniform dissolution. In accordance with particular embodiments,
non-limiting examples of anti-caking agents include cream of
tartar, calcium silicate, silicon dioxide, microcrystalline
cellulose (Avicel, FMC BioPolymer, Philadelphia, Pa.), and
tricalcium phosphate. In one embodiment, the anti-caking agents are
present in the tabletop functional sweetener composition in an
amount from about 0.001 to about 3% by weight of the tabletop
functional sweetener composition.
[0373] The tabletop sweetener compositions can be packaged in any
form known in the art. Non-limiting forms include, but are not
limited to, powder form, granular form, packets, tablets, sachets,
pellets, cubes and solids.
[0374] In one embodiment, the tabletop sweetener composition is a
single-serving (portion control) packet comprising a dry-blend.
Dry-blend formulations generally may comprise powder or granules.
Although the tabletop sweetener composition may be in a packet of
any size, an illustrative non-limiting example of conventional
portion control tabletop sweetener packets are approximately 2.5 by
1.5 inches and hold approximately 1 gram of a sweetener composition
having a sweetness equivalent to 2 teaspoons of granulated sugar
(.about.8 g). The amount of Rebaudioside X in a dry-blend tabletop
sweetener formulation can vary. In a particular embodiment, a
dry-blend tabletop sweetener formulation may contain Rebaudioside X
in an amount from about 1% (w/w) to about 10% (w/w) of the tabletop
sweetener composition.
[0375] Solid tabletop sweetener embodiments include cubes and
tablets. A non-limiting example of conventional cubes are
equivalent in size to a standard cube of granulated sugar, which is
approximately 2.2.times.2.2.times.2.2 cm.sup.3 and weigh
approximately 8 g. In one embodiment, a solid tabletop sweetener is
in the form of a tablet or any other form known to those skilled in
the art.
[0376] Generally, the amount of functional ingredient in the
sweetener composition or sweetened composition varies widely
depending on the particular sweetener composition or sweetened
composition and the desired functional ingredient. Those of
ordinary skill in the art will readily ascertain the appropriate
amount of functional ingredient for each sweetener composition or
sweetened composition.
[0377] Sweetened Compositions
[0378] In one embodiment, the Rebaudioside X in sweetened
compositions described herein can be amorphous Rebaudioside X or
sweetener compositions comprising amorphous Rebaudioside X. The
amorphous Rebaudioside X or sweetener composition comprising
Rebaudioside X can be incorporated in any known sweetenable
composition, such as, for example, pharmaceutical compositions,
edible gel mixes and compositions, dental compositions, foodstuffs
(confections, condiments, chewing gum, cereal compositions baked
goods dairy products, and tabletop sweetener compositions)
beverages and beverage products to provide a sweetened
composition.
[0379] In another embodiment, a sweetened composition comprises a
sweetenable composition and amorphous Rebaudioside X. In another
embodiment, the sweetened composition comprises a sweetener
composition comprising amorphous Rebaudioside X. The sweetened
compositions can optionally include additives, sweeteners,
functional ingredients and combinations thereof. Because the
amorphous form of Rebaudioside X does not exist once the material
is dissolved in water/liquid, sweetenable compositions that do not
require dissolution of the amorphous Rebaudioside X include dry
powdered Rebaudioside X. Liquid or semi-liquid sweetened
compositions prepared with amorphous Rebaudioside X will only
contain amorphous Rebaudioside X until dissolution, after which the
Rebaudioside X will be solvated.
[0380] In another embodiment, the Rebaudioside X in the sweetened
compositions described herein can be provided by Rebaudioside X
complexes or sweetener compositions comprising Rebaudioside X
complexes. The Rebaudioside X complex or sweetener composition
comprising Rebaudioside X complex can also be incorporated in any
known sweetenable compositions, such as, for example,
pharmaceutical compositions, edible gel mixes and compositions,
dental compositions, foodstuffs (confections, condiments, chewing
gum, cereal compositions baked goods dairy products, and tabletop
sweetener compositions) beverages and beverage products, to provide
a sweetened composition.
[0381] In a particular embodiment, a sweetened composition
comprises a sweetenable composition and amorphous Rebaudioside X.
In a particular embodiment, the sweetenable composition is a
beverage or beverage product. The beverage or beverage product can
further comprise additional sweeteners, additives and/or functional
ingredients, as detailed herein.
[0382] In another particular embodiment, a sweetened composition
comprises a sweetenable composition and a sweetener composition
comprising amorphous Rebaudioside X. The sweetener composition can
further comprise additional sweeteners, additives and/or functional
ingredients, as detailed herein. In a particular embodiment, the
sweetenable composition is a beverage or beverage product.
[0383] In a particular embodiment, a sweetened composition
comprises a sweetenable composition and a Rebaudioside X complex.
In a particular embodiment, the sweetenable composition is a
beverage or beverage product. The beverage or beverage product can
further comprise additional sweeteners, additives and/or functional
ingredients, as detailed herein.
[0384] In another particular embodiment, a sweetened composition
comprises a sweetenable composition and a sweetener composition
comprising a Rebaudioside X complex. The sweetener composition can
further comprise additional sweeteners, additives and/or functional
ingredients, as detailed herein. In a particular embodiment, the
sweetenable composition is a beverage or beverage product.
[0385] Pharmaceutical Compositions
[0386] In one embodiment, a pharmaceutical composition contains a
pharmaceutically active substance and amorphous Rebaudioside X. In
another embodiment, a pharmaceutical composition contains a
pharmaceutically active substance and a sweetener composition
comprising amorphous Rebaudioside X. The amorphous Rebaudioside X
or sweetener composition comprising Rebaudioside X can be present
as an excipient material in the pharmaceutical composition, which
can mask a bitter or otherwise undesirable taste of a
pharmaceutically active substance or another excipient
material.
[0387] In another embodiment, a pharmaceutical composition contains
a pharmaceutically active substance and a Rebaudioside X complex.
In another embodiment, a pharmaceutical composition contains a
pharmaceutically active substance and a sweetener composition
comprising a Rebaudioside X complex. The Rebaudioside X complex or
sweetener composition comprising a Rebaudioside X complex can be
present as an excipient material in the pharmaceutical composition,
which can mask a bitter or otherwise undesirable taste of a
pharmaceutically active substance or another excipient
material.
[0388] The pharmaceutical composition may be in the form of a
tablet, a capsule, an aerosol, a powder, an effervescent tablet or
powder, a syrup, an emulsion, a suspension, a solution, or any
other form for providing the pharmaceutical composition to a
patient. In particular embodiments, the pharmaceutical composition
may be in a form for oral administration, buccal administration,
sublingual administration, or any other route of administration as
known in the art.
[0389] As referred to herein, "pharmaceutically active substance"
means any drug, drug formulation, medication, prophylactic agent,
therapeutic agent, or other substance having biological activity.
As referred to herein, "excipient material" refers to any inactive
substance used as a vehicle for an active ingredient, such as any
material to facilitate handling, stability, dispersibility,
wettability, and/or release kinetics of a pharmaceutically active
substance.
[0390] Suitable pharmaceutically active substances include, but are
not limited to, medications for the gastrointestinal tract or
digestive system, for the cardiovascular system, for the central
nervous system, for pain or consciousness, for musculo-skeletal
disorders, for the eye, for the ear, nose and oropharynx, for the
respiratory system, for endocrine problems, for the reproductive
system or urinary system, for contraception, for obstetrics and
gynecology, for the skin, for infections and infestations, for
immunology, for allergic disorders, for nutrition, for neoplastic
disorders, for diagnostics, for euthanasia, or other biological
functions or disorders. Examples of suitable pharmaceutically
active substances for embodiments of the present invention include,
but are not limited to, antacids, reflux suppressants,
antiflatulents, antidopaminergics, proton pump inhibitors,
cytoprotectants, prostaglandin analogues, laxatives,
antispasmodics, antidiarrhoeals, bile acid sequestrants, opioids,
beta-receptor blockers, calcium channel blockers, diuretics,
cardiac glycosides, antiarrhythmics, nitrates, antianginals,
vasoconstrictors, vasodilators, peripheral activators, ACE
inhibitors, angiotensin receptor blockers, alpha blockers,
anticoagulants, heparin, antiplatelet drugs, fibrinolytics,
anti-hemophilic factors, haemostatic drugs, hypolipidaemic agents,
statins, hynoptics, anaesthetics, antipsychotics, antidepressants,
anti-emetics, anticonvulsants, antiepileptics, anxiolytics,
barbiturates, movement disorder drugs, stimulants, benzodiazepines,
cyclopyrrolones, dopamine antagonists, antihistamines,
cholinergics, anticholinergics, emetics, cannabinoids, analgesics,
muscle relaxants, antibiotics, aminoglycosides, anti-virals,
anti-fungals, anti-inflammatories, anti-gluacoma drugs,
sympathomimetics, steroids, ceruminolytics, bronchodilators,
NSAIDS, antitussive, mucolytics, decongestants, corticosteroids,
androgens, antiandrogens, gonadotropins, growth hormones, insulin,
antidiabetics, thyroid hormones, calcitonin, diphosphonates,
vasopressin analogues, alkalizing agents, quinolones,
anticholinesterase, sildenafil, oral contraceptives, Hormone
Replacement Therapies, bone regulators, follicle stimulating
hormones, luteinizings hormones, gamolenic acid, progestogen,
dopamine agonist, oestrogen, prostaglandin, gonadorelin,
clomiphene, tamoxifen, diethylstilbestrol, antileprotics,
antituberculous drugs, antimalarials, anthelmintics, antiprotozoal,
antiserums, vaccines, interferons, tonics, vitamins, cytotoxic
drugs, sex hormones, aromatase inhibitors, somatostatin inhibitors,
or similar type substances, or combinations thereof. Such
components generally are recognized as safe (GRAS) and/or are U.S.
Food and Drug Administration (FDA)-approved.
[0391] The pharmaceutically active substance is present in the
pharmaceutical composition in widely ranging amounts depending on
the particular pharmaceutically active agent being used and its
intended applications. An effective dose of any of the herein
described pharmaceutically active substances can be readily
determined by the use of conventional techniques and by observing
results obtained under analogous circumstances. In determining the
effective dose, a number of factors are considered including, but
not limited to: the species of the patient; its size, age, and
general health; the specific disease involved; the degree of
involvement or the severity of the disease; the response of the
individual patient; the particular pharmaceutically active agent
administered; the mode of administration; the bioavailability
characteristic of the preparation administered; the dose regimen
selected; and the use of concomitant medication. The
pharmaceutically active substance is included in the
pharmaceutically acceptable carrier, diluent, or excipient in an
amount sufficient to deliver to a patient a therapeutic amount of
the pharmaceutically active substance in vivo in the absence of
serious toxic effects when used in generally acceptable amounts.
Thus, suitable amounts can be readily discerned by those skilled in
the art.
[0392] According to particular embodiments of the present
invention, the concentration of pharmaceutically active substance
in the pharmaceutical composition will depend on absorption,
inactivation, and excretion rates of the drug as well as other
factors known to those of skill in the art. It is to be noted that
dosage values will also vary with the severity of the condition to
be alleviated. It is to be further understood that for any
particular subject, specific dosage regimes should be adjusted over
time according to the individual need and the professional judgment
of the person administering or supervising the administration of
the pharmaceutical compositions, and that the dosage ranges set
forth herein are exemplary only and are not intended to limit the
scope or practice of the claimed composition. The pharmaceutically
active substance may be administered at once, or may be divided
into a number of smaller doses to be administered at varying
intervals of time.
[0393] The pharmaceutical composition also may comprise other
pharmaceutically acceptable excipient materials. Examples of
suitable excipient materials for embodiments of this invention
include, but are not limited to, antiadherents, binders (e.g.,
microcrystalline cellulose, gum tragacanth, or gelatin), coatings,
disintegrants, fillers, diluents, softeners, emulsifiers, flavoring
agents, coloring agents, adjuvants, lubricants, functional agents
(e.g., nutrients), viscosity modifiers, bulking agents, glidiants
(e.g., colloidal silicon dioxide) surface active agents, osmotic
agents, diluents, or any other non-active ingredient, or
combinations thereof. For example, the pharmaceutical compositions
of the present invention may include excipient materials selected
from the group consisting of calcium carbonate, coloring agents,
whiteners, preservatives, and flavors, triacetin, magnesium
stearate, sterotes, natural or artificial flavors, essential oils,
plant extracts, fruit essences, gelatins, or combinations
thereof.
[0394] The excipient material of the pharmaceutical composition may
optionally include other artificial or natural sweeteners, bulk
sweeteners, or combinations thereof. Bulk sweeteners include both
caloric and non-caloric compounds. In a particular embodiment, the
additive functions as the bulk sweetener. Non-limiting examples of
bulk sweeteners include sucrose, dextrose, maltose, dextrin, dried
invert sugar, fructose, high fructose corn syrup, levulose,
galactose, corn syrup solids, tagatose, polyols (e.g., sorbitol,
mannitol, xylitol, lactitol, erythritol, and maltitol),
hydrogenated starch hydrolysates, isomalt, trehalose, and mixtures
thereof. In particular embodiments, the bulk sweetener is present
in the pharmaceutical composition in widely ranging amounts
depending on the degree of sweetness desired. Suitable amounts of
both sweeteners would be readily discernable to those skilled in
the art.
[0395] Edible Gel Mixes and Edible Gel Compositions
[0396] In one embodiment, an edible gel or edible gel mix comprises
amorphous Rebaudioside X. In another embodiment, an edible gel or
edible gel mix comprises a sweetener composition comprising
amorphous Rebaudioside X. The edible gel or edible gel mixes can
optionally include additives, functional ingredients or
combinations thereof.
[0397] In another embodiment, an edible gel or edible gel mix
comprises a Rebaudioside X complex. In another embodiment, an
edible gel or edible gel mix comprises a sweetener composition
comprising a Rebaudioside X complex. The edible gel or edible gel
mixes can optionally include additives, functional ingredients or
combinations thereof.
[0398] Edible gels are gels that can be eaten. A gel is a colloidal
system in which a network of particles spans the volume of a liquid
medium. Although gels mainly are composed of liquids, and thus
exhibit densities similar to liquids, gels have the structural
coherence of solids due to the network of particles that spans the
liquid medium. For this reason, gels generally appear to be solid,
jelly-like materials. Gels can be used in a number of applications.
For example, gels can be used in foods, paints, and adhesives.
[0399] Non-limiting examples of edible gel compositions for use in
particular embodiments include gel desserts, puddings, jellies,
pastes, trifles, aspics, marshmallows, gummy candies, or the like.
Edible gel mixes generally are powdered or granular solids to which
a fluid may be added to form an edible gel composition.
Non-limiting examples of fluids for use in particular embodiments
include water, dairy fluids, dairy analogue fluids, juices,
alcohol, alcoholic beverages, and combinations thereof.
Non-limiting examples of dairy fluids which may be used in
particular embodiments include milk, cultured milk, cream, fluid
whey, and mixtures thereof. Non-limiting examples of dairy analogue
fluids which may be used in particular embodiments include, for
example, soy milk and non-dairy coffee whitener. Because edible gel
products found in the marketplace typically are sweetened with
sucrose, it is desirable to sweeten edible gels with an alternative
sweetener in order provide a low-calorie or non-calorie
alternative.
[0400] As used herein, the term "gelling ingredient" denotes any
material that can form a colloidal system within a liquid medium.
Non-limiting examples of gelling ingredients for use in particular
embodiments include gelatin, alginate, carageenan, gum, pectin,
konjac, agar, food acid, rennet, starch, starch derivatives, and
combinations thereof. It is well known to those having ordinary
skill in the art that the amount of gelling ingredient used in an
edible gel mix or an edible gel composition varies considerably
depending on a number of factors, such as the particular gelling
ingredient used, the particular fluid base used, and the desired
properties of the gel.
[0401] It is well known to those having ordinary skill in the art
that the edible gel mixes and edible gels may be prepared using
other ingredients in addition to Rebaudioside X and the gelling
agent. Non-limiting examples of other ingredients for use in
particular embodiments include a food acid, a salt of a food acid,
a buffering system, a bulking agent, a sequestrant, a cross-linking
agent, one or more flavors, one or more colors, and combinations
thereof. Non-limiting examples of food acids for use in particular
embodiments include citric acid, adipic acid, fumaric acid, lactic
acid, malic acid, and combinations thereof. Non-limiting examples
of salts of food acids for use in particular embodiments include
sodium salts of food acids, potassium salts of food acids, and
combinations thereof. Non-limiting examples of bulking agents for
use in particular embodiments include raftilose, isomalt, sorbitol,
polydextrose, maltodextrin, and combinations thereof. Non-limiting
examples of sequestrants for use in particular embodiments include
calcium disodium ethylene tetra-acetate, glucono delta-lactone,
sodium gluconate, potassium gluconate, ethylenediaminetetraacetic
acid (EDTA), and combinations thereof. Non-limiting examples of
cross-linking agents for use in particular embodiments include
calcium ions, magnesium ions, sodium ions, and combinations
thereof.
[0402] Dental Compositions
[0403] In one embodiment, a dental composition comprises amorphous
Rebaudioside X. In another embodiment, a dental composition
comprises a sweetener composition comprising amorphous Rebaudioside
X. Dental compositions generally comprise an active dental
substance and a base material. Amorphous Rebaudioside X, or a
sweetener composition comprising amorphous Rebaudioside X, can be
used as the base material to sweeten the dental composition.
[0404] In one embodiment, a dental composition comprises a
Rebaudioside X complex. In another embodiment, a dental composition
comprises a sweetener composition comprising a Rebaudioside X
complex. Dental compositions generally comprise an active dental
substance and a base material. Rebaudioside X complexes, or a
sweetener composition comprising Rebaudioside X complexes, can be
used as the base material to sweeten the dental composition.
[0405] The dental composition may be in the form of any oral
composition used in the oral cavity such as mouth freshening
agents, gargling agents, mouth rinsing agents, toothpaste, tooth
polish, dentifrices, mouth sprays, teeth-whitening agent, dental
floss, and the like, for example.
[0406] As referred to herein, "active dental substance" means any
composition which can be used to improve the aesthetic appearance
and/or health of teeth or gums or prevent dental caries. As
referred to herein, "base material" refers to any inactive
substance used as a vehicle for an active dental substance, such as
any material to facilitate handling, stability, dispersibility,
wettability, foaming, and/or release kinetics of an active dental
substance.
[0407] Suitable active dental substances for embodiments of this
invention include, but are not limited to, substances which remove
dental plaque, remove food from teeth, aid in the elimination
and/or masking of halitosis, prevent tooth decay, and prevent gum
disease (i.e., Gingiva). Examples of suitable active dental
substances for embodiments of the present invention include, but
are not limited to, anticaries drugs, fluoride, sodium fluoride,
sodium monofluorophosphate, stannos fluoride, hydrogen peroxide,
carbamide peroxide (i.e., urea peroxide), antibacterial agents,
plaque removing agents, stain removers, anticalculus agents,
abrasives, baking soda, percarbonates, perborates of alkali and
alkaline earth metals, or similar type substances, or combinations
thereof. Such components generally are recognized as safe (GRAS)
and/or are U.S. Food and Drug Administration (FDA)-approved.
[0408] According to particular embodiments of the invention, the
active dental substance is present in the dental composition in an
amount ranging from about 50 ppm to about 3000 ppm of the dental
composition. Generally, the active dental substance is present in
the dental composition in an amount effective to at least improve
the aesthetic appearance and/or health of teeth or gums marginally
or prevent dental caries. For example, a dental composition
comprising a toothpaste may include an active dental substance
comprising fluoride in an amount of about 850 to 1,150 ppm.
[0409] The dental composition also may comprise other base
materials in addition to Rebaudioside X. Examples of suitable base
materials for embodiments of this invention include, but are not
limited to, water, sodium lauryl sulfate or other sulfates,
humectants, enzymes, vitamins, herbs, calcium, flavorings (e.g.,
mint, bubblegum, cinnamon, lemon, or orange), surface-active
agents, binders, preservatives, gelling agents, pH modifiers,
peroxide activators, stabilizers, coloring agents, or similar type
materials, and combinations thereof.
[0410] The base material of the dental composition may optionally
include other artificial or natural sweeteners, bulk sweeteners, or
combinations thereof. Bulk sweeteners include both caloric and
non-caloric compounds. Non-limiting examples of bulk sweeteners
include sucrose, dextrose, maltose, dextrin, dried invert sugar,
fructose, high fructose corn syrup, levulose, galactose, corn syrup
solids, tagatose, polyols (e.g., sorbitol, mannitol, xylitol,
lactitol, erythritol, and maltitol), hydrogenated starch
hydrolysates, isomalt, trehalose, and mixtures thereof.
[0411] Generally, the amount of bulk sweetener present in the
dental composition ranges widely depending on the particular
embodiment of the dental composition and the desired degree of
sweeteness. Those of ordinary skill in the art will readily
ascertain the appropriate amount of bulk sweetener. In particular
embodiments, the bulk sweetener is present in the dental
composition in an amount in the range of about 0.1 to about 5
weight percent of the dental composition.
[0412] According to particular embodiments of the invention, the
base material is present in the dental composition in an amount
ranging from about 20 to about 99 percent by weight of the dental
composition. Generally, the base material is present in an amount
effective to provide a vehicle for an active dental substance.
[0413] Generally, the amount of the sweetener varies widely
depending on the nature of the particular dental composition and
the desired degree of sweetness. Those skilled in the art will be
able to discern a suitable amount of sweetener for such dental
composition. In a particular embodiment, amorphous Rebaudioside X
is present in the dental composition in an amount in the range of
about 1 to about 5,000 ppm of the dental composition and the at
least one additive is present in the dental composition in an
amount in the range of about 0.1 to about 100,000 ppm of the dental
composition.
[0414] Foodstuffs include, but are not limited to, confections,
condiments, chewing gum, cereal, baked goods, and dairy
products.
[0415] Confections
[0416] In one embodiment, a confection comprises amorphous
Rebaudioside X. In another embodiment, a confection comprises a
sweetener composition comprising amorphous Rebaudioside X.
[0417] In one embodiment, a confection comprises a Rebaudioside X
complex. In another embodiment, a confection comprises a sweetener
composition comprising a Rebaudioside X complex.
[0418] As referred to herein, "confection" can mean a sweet, a
lollie, a confectionery, or similar term. The confection generally
contains a base composition component and a sweetener component.
The confection may be in the form of any food that is typically
perceived to be rich in sugar or is typically sweet. According to
particular embodiments of the present invention, the confections
may be bakery products such as pastries; desserts such as yogurt,
jellies, drinkable jellies, puddings, Bavarian cream, blancmange,
cakes, brownies, mousse and the like, sweetened food products eaten
at tea time or following meals; frozen foods; cold confections,
e.g. types of ice cream such as ice cream, ice milk, lacto-ice and
the like (food products in which sweeteners and various other types
of raw materials are added to milk products, and the resulting
mixture is agitated and frozen), and ice confections such as
sherbets, dessert ices and the like (food products in which various
other types of raw materials are added to a sugary liquid, and the
resulting mixture is agitated and frozen); general confections,
e.g., baked confections or steamed confections such as crackers,
biscuits, buns with bean-jam filling, halvah, alfajor, and the
like; rice cakes and snacks; table top products; general sugar
confections such as chewing gum (e.g. including compositions which
comprise a substantially water-insoluble, chewable gum base, such
as chicle or substitutes thereof, including jetulong, guttakay
rubber or certain comestible natural synthetic resins or waxes),
hard candy, soft candy, mints, nougat candy, jelly beans, fudge,
toffee, taffy, Swiss milk tablet, licorice candy, chocolates,
gelatin candies, marshmallow, marzipan, divinity, cotton candy, and
the like; sauces including fruit flavored sauces, chocolate sauces
and the like; edible gels; cremes including butter cremes, flour
pastes, whipped cream and the like; jams including strawberry jam,
marmalade and the like; and breads including sweet breads and the
like or other starch products, and combinations thereof.
[0419] As referred to herein, "base composition" means any
composition which can be a food item and provides a matrix for
carrying the sweetener component.
[0420] Suitable base compositions for embodiments of this invention
may include flour, yeast, water, salt, butter, eggs, milk, milk
powder, liquor, gelatin, nuts, chocolate, citric acid, tartaric
acid, fumaric acid, natural flavors, artificial flavors, colorings,
polyols, sorbitol, isomalt, maltitol, lactitol, malic acid,
magnesium stearate, lecithin, hydrogenated glucose syrup,
glycerine, natural or synthetic gum, starch, and the like, and
combinations thereof. Such components generally are recognized as
safe (GRAS) and/or are U.S. Food and Drug Administration
(FDA)-approved. According to particular embodiments of the
invention, the base composition is present in the confection in an
amount ranging from about 0.1 to about 99 weight percent of the
confection.
[0421] The base composition of the confection may optionally
include other artificial or natural sweeteners, bulk sweeteners, or
combinations thereof. Bulk sweeteners include both caloric and
non-caloric compounds. Non-limiting examples of bulk sweeteners
include sucrose, dextrose, maltose, dextrin, dried invert sugar,
fructose, high fructose corn syrup, levulose, galactose, corn syrup
solids, tagatose, polyols (e.g., sorbitol, mannitol, xylitol,
lactitol, erythritol, and maltitol), hydrogenated starch
hydrolysates, isomalt, trehalose, and mixtures thereof. Generally,
the amount of bulk sweetener present in the confection ranges
widely depending on the particular embodiment of the confection and
the desired degree of sweeteness. Those of ordinary skill in the
art will readily ascertain the appropriate amount of bulk
sweetener.
[0422] In a particular embodiment, a confection comprises
Rebaudioside X and a base composition. Generally, the amount of
Rebaudioside X in the confection ranges widely depending on the
particular embodiment of the confection and the desired degree of
sweetness. Those of ordinary skill in the art will readily
ascertain the appropriate amount of sweetener. In a particular
embodiment, Rebaudioside X is present in the confection in an
amount in the range of about 30 ppm to about 6000 ppm of the
confection. In another embodiment, Rebaudioside X is present in the
confection in an amount in the range of about 1 ppm to about 10,000
ppm of the confection. In embodiments where the confection
comprises hard candy, Rebaudioside X is present in an amount in the
range of about 150 ppm to about 2250 ppm of the hard candy.
[0423] Condiment Compositions
[0424] In one embodiment, a condiment comprises amorphous
Rebaudioside X. In another embodiment a condiment comprises a
sweetener composition comprising amorphous Rebaudioside X.
[0425] In another embodiment, a condiment comprises a Rebaudioside
X complex. In another embodiment a condiment comprises a sweetener
composition comprising a Rebaudioside X complex.
[0426] Condiments, as used herein, are compositions used to enhance
or improve the flavor of a food or beverage. Non-limiting examples
of condiments include ketchup (catsup); mustard; barbecue sauce;
butter; chili sauce; chutney; cocktail sauce; curry; dips; fish
sauce; horseradish; hot sauce; jellies, jams, marmalades, or
preserves; mayonnaise; peanut butter; relish; remoulade; salad
dressings (e.g., oil and vinegar, Caesar, French, ranch, bleu
cheese, Russian, Thousand Island, Italian, and balsamic
vinaigrette), salsa; sauerkraut; soy sauce; steak sauce; syrups;
tartar sauce; and Worcestershire sauce.
[0427] Condiment bases generally comprise a mixture of different
ingredients, non-limiting examples of which include vehicles (e.g.,
water and vinegar); spices or seasonings (e.g., salt, pepper,
garlic, mustard seed, onion, paprika, turmeric, and combinations
thereof); fruits, vegetables, or their products (e.g., tomatoes or
tomato-based products (paste, puree), fruit juices, fruit juice
peels, and combinations thereof); oils or oil emulsions,
particularly vegetable oils; thickeners (e.g., xanthan gum, food
starch, other hydrocolloids, and combinations thereof); and
emulsifying agents (e.g., egg yolk solids, protein, gum arabic,
carob bean gum, guar gum, gum karaya, gum tragacanth, carageenan,
pectin, propylene glycol esters of alginic acid, sodium
carboxymethyl-cellulose, polysorbates, and combinations thereof).
Recipes for condiment bases and methods of making condiment bases
are well known to those of ordinary skill in the art.
[0428] Generally, condiments also comprise caloric sweeteners, such
as sucrose, high fructose corn syrup, molasses, honey, or brown
sugar. In exemplary embodiments of the condiments provided herein,
Rebaudioside X or sweetener compositions comprising Rebaudioside X
are used instead of traditional caloric sweeteners. Accordingly, a
condiment composition desirably comprises Rebaudioside X or a
sweetener composition comprising Rebaudioside X and a condiment
base.
[0429] The condiment composition optionally may include other
natural and/or synthetic high-potency sweeteners, bulk sweeteners,
pH modifying agents (e.g., lactic acid, citric acid, phosphoric
acid, hydrochloric acid, acetic acid, and combinations thereof),
fillers, functional agents (e.g., pharmaceutical agents, nutrients,
or components of a food or plant), flavorings, colorings, or
combinations thereof.
[0430] Chewing Gum Compositions
[0431] In one embodiment, a chewing gum composition comprises
amorphous Rebaudioside X. In another embodiment, a chewing gum
composition comprises a sweetener composition comprising amorphous
Rebaudioside X.
[0432] In another embodiment, a chewing gum composition comprises a
Rebaudioside X complex. In another embodiment, a chewing gum
composition comprises a sweetener composition comprising a
Rebaudioside X complex.
[0433] Chewing gum compositions generally comprise a water-soluble
portion and a water-insoluble chewable gum base portion. The water
soluble portion, which typically includes the sweetener or
sweetener composition, dissipates with a portion of the flavoring
agent over a period of time during chewing while the insoluble gum
base portion is retained in the mouth. The insoluble gum base
generally determines whether a gum is considered chewing gum,
bubble gum, or a functional gum.
[0434] The insoluble gum base, which is generally present in the
chewing gum composition in an amount in the range of about 15 to
about 35 weight percent of the chewing gum composition, generally
comprises combinations of elastomers, softeners (plasticizers),
emulsifiers, resins, and fillers. Such components generally are
considered food grade, recognized as safe (GRA), and/or are U.S.
Food and Drug Administration (FDA)-approved.
[0435] Elastomers, the primary component of the gum base, provide
the rubbery, cohesive nature to gums and can include one or more
natural rubbers (e.g., smoked latex, liquid latex, or guayule);
natural gums (e.g., jelutong, perillo, sorva, massaranduba balata,
massaranduba chocolate, nispero, rosindinha, chicle, and gutta hang
kang); or synthetic elastomers (e.g., butadiene-styrene copolymers,
isobutylene-isoprene copolymers, polybutadiene, polyisobutylene,
and vinyl polymeric elastomers). In a particular embodiment, the
elastomer is present in the gum base in an amount in the range of
about 3 to about 50 weight percent of the gum base.
[0436] Resins are used to vary the firmness of the gum base and aid
in softening the elastomer component of the gum base. Non-limiting
examples of suitable resins include a rosin ester, a terpene resin
(e.g., a terpene resin from .alpha.-pinene, .beta.-pinene and/or
d-limonene), polyvinyl acetate, polyvinyl alcohol, ethylene vinyl
acetate, and vinyl acetate-vinyl laurate copolymers. Non-limiting
examples of rosin esters include a glycerol ester of a partially
hydrogenated rosin, a glycerol ester of a polymerized rosin, a
glycerol ester of a partially dimerized rosin, a glycerol ester of
rosin, a pentaerythritol ester of a partially hydrogenated rosin, a
methyl ester of rosin, or a methyl ester of a partially
hydrogenated rosin. In a particular embodiment, the resin is
present in the gum base in an amount in the range of about 5 to
about 75 weight percent of the gum base.
[0437] Softeners, which also are known as plasticizers, are used to
modify the ease of chewing and/or mouthfeel of the chewing gum
composition. Generally, softeners comprise oils, fats, waxes, and
emulsifiers. Non-limiting examples of oils and fats include tallow,
hydrogenated tallow, large, hydrogenated or partially hydrogenated
vegetable oils (e.g., soybean, canola, cottonseed, sunflower, palm,
coconut, corn, safflower, or palm kernel oils), cocoa butter,
glycerol monostearate, glycerol triacetate, glycerol abietate,
leithin, monoglycerides, diglycerides, triglycerides acetylated
monoglycerides, and free fatty acids. Non-limiting examples of
waxes include polypropylene/polyethylene/Fisher-Tropsch waxes,
paraffin, and microcrystalline and natural waxes (e.g., candelilla,
beeswas and carnauba). Microcrystalline waxes, especially those
with a high degree of crystallinity and a high melting point, also
may be considered as bodying agents or textural modifiers. In a
particular embodiment, the softeners are present in the gum base in
an amount in the range of about 0.5 to about 25 weight percent of
the gum base.
[0438] Emulsifiers are used to form a uniform dispersion of the
insoluble and soluble phases of the chewing gum composition and
also have plasticizing properties. Suitable emulsifiers include
glycerol monostearate (GMS), lecithin (Phosphatidyl choline),
polyglycerol polyricinoleic acid (PPGR), mono and diglycerides of
fatty acids, glycerol distearate, tracetin, acetylated
monoglyceride, glycerol triactetate, and magnesium stearate. In a
particular embodiment, the emulsifiers are present in the gum base
in an amount in the range of about 2 to about 30 weight percent of
the gum base.
[0439] The chewing gum composition also may comprise adjuvants or
fillers in either the gum base and/or the soluble portion of the
chewing gum composition. Suitable adjuvants and fillers include
lecithin, inulin, polydextrin, calcium carbonate, magnesium
carbonate, magnesium silicate, ground limestome, aluminum
hydroxide, aluminum silicate, talc, clay, alumina, titanium
dioxide, and calcium phosphate. In particular embodiments, lecithin
can be used as an inert filler to decrease the stickiness of the
chewing gum composition. In other particular embodiments, lactic
acid copolymers, proteins (e.g., gluten and/or zein) and/or guar
can be used to create a gum that is more readily biodegradable. The
adjuvants or fillers are generally present in the gum base in an
amount up to about 20 weight percent of the gum base. Other
optional ingredients include coloring agents, whiteners,
preservatives, and flavors.
[0440] In particular embodiments of the chewing gum composition,
the gum base comprises about 5 to about 95 weight percent of the
chewing gum composition, more desirably about 15 to about 50 weight
percent of the chewing gum composition, and even more desirably
from about 20 to about 30 weight percent of the chewing gum
composition.
[0441] The soluble portion of the chewing gum composition may
optionally include other artificial or natural sweeteners, bulk
sweeteners, softeners, emulsifiers, flavoring agents, coloring
agents, adjuvants, fillers, functional agents (e.g., pharmaceutical
agents or nutrients), or combinations thereof. Suitable examples of
softeners and emulsifiers are described above.
[0442] Bulk sweeteners include both caloric and non-caloric
compounds. Non-limiting examples of bulk sweeteners include
sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose,
high fructose corn syrup, levulose, galactose, corn syrup solids,
tagatose, polyols (e.g., sorbitol, mannitol, xylitol, lactitol,
erythritol, and maltitol), hydrogenated starch hydrolysates,
isomalt, trehalose, and mixtures thereof. In particular
embodiments, the bulk sweetener is present in the chewing gum
composition in an amount in the range of about 1 to about 75 weight
percent of the chewing gum composition.
[0443] Flavoring agents may be used in either the insoluble gum
base or soluble portion of the chewing gum composition. Such
flavoring agents may be natural or artificial flavors. In a
particular embodiment, the flavoring agent comprises an essential
oil, such as an oil derived from a plant or a fruit, peppermint
oil, spearmint oil, other mint oils, clove oil, cinnamon oil, oil
of wintergreen, bay, thyme, cedar leaf, nutmeg, allspice, sage,
mace, and almonds. In another particular embodiment, the flavoring
agent comprises a plant extract or a fruit essence such as apple,
banana, watermelon, pear, peach, grape, strawberry, raspberry,
cherry, plum, pineapple, apricot, and mixtures thereof. In still
another particular embodiment, the flavoring agent comprises a
citrus flavor, such as an extract, essence, or oil of lemon, lime,
orange, tangerine, grapefruit, citron, or kumquat.
[0444] In a particular embodiment, a chewing gum composition
comprises Rebaudioside X or a sweetener composition comprising
Rebaudioside X and a gum base. In a particular embodiment,
Rebaudioside X is present in the chewing gum composition in an
amount in the range of about 1 ppm to about 10,000 ppm of the
chewing gum composition.
[0445] Cereal Compositions
[0446] In one embodiment, a cereal composition comprises amorphous
Rebaudioside X. In another embodiment, a cereal composition
comprises a sweetener composition comprising amorphous Rebaudioside
X.
[0447] In one embodiment, a cereal composition comprises a
Rebaudioside X complex. In another embodiment, a cereal composition
comprises a sweetener composition comprising a Rebaudioside X
complex.
[0448] Cereal compositions typically are eaten either as staple
foods or as snacks. Non-limiting examples of cereal compositions
for use in particular embodiments include ready-to-eat cereals as
well as hot cereals. Ready-to-eat cereals are cereals which may be
eaten without further processing (i.e. cooking) by the consumer.
Examples of ready-to-eat cereals include breakfast cereals and
snack bars. Breakfast cereals typically are processed to produce a
shredded, flaky, puffy, or extruded form. Breakfast cereals
generally are eaten cold and are often mixed with milk and/or
fruit. Snack bars include, for example, energy bars, rice cakes,
granola bars, and nutritional bars. Hot cereals generally are
cooked, usually in either milk or water, before being eaten.
Non-limiting examples of hot cereals include grits, porridge,
polenta, rice, and rolled oats.
[0449] Cereal compositions generally comprise at least one cereal
ingredient. As used herein, the term "cereal ingredient" denotes
materials such as whole or part grains, whole or part seeds, and
whole or part grass. Non-limiting examples of cereal ingredients
for use in particular embodiments include maize, wheat, rice,
barley, bran, bran endosperm, bulgur, soghums, millets, oats, rye,
triticale, buchwheat, fonio, quinoa, bean, soybean, amaranth, teff,
spelt, and kaniwa.
[0450] In a particular embodiment, the cereal composition comprises
Rebaudioside X or a sweetener composition comprising Rebaudioside X
and at least one cereal ingredient. Rebaudioside X or the sweetener
composition comprising Rebaudioside X may be added to the cereal
composition in a variety of ways, such as, for example, as a
coating, as a frosting, as a glaze, or as a matrix blend (i.e.
added as an ingredient to the cereal formulation prior to the
preparation of the final cereal product).
[0451] Accordingly, in a particular embodiment, Rebaudioside X or a
sweetener composition comprising Rebaudioside X is added to the
cereal composition as a matrix blend. In one embodiment,
Rebaudioside X or a sweetener composition comprising Rebaudioside X
is blended with a hot cereal prior to cooking to provide a
sweetened hot cereal product. In another embodiment, Rebaudioside X
or a sweetener comprising Rebaudioside X is blended with the cereal
matrix before the cereal is extruded.
[0452] In another particular embodiment, Rebaudioside X or a
sweetener composition comprising Rebaudioside X is added to the
cereal composition as a coating, such as, for example, by combining
Rebaudioside X or a sweetener comprising Rebaudioside X with a food
grade oil and applying the mixture onto the cereal. In a different
embodiment, Rebaudioside X or a sweetener composition comprising
Rebaudioside X and the food grade oil may be applied to the cereal
separately, by applying either the oil or the sweetener first.
Non-limiting examples of food grade oils for use in particular
embodiments include vegetable oils such as corn oil, soybean oil,
cottonseed oil, peanut oil, coconut oil, canola oil, olive oil,
sesame seed oil, palm oil, palm kernel oil, and mixtures thereof.
In yet another embodiment, food grade fats may be used in place of
the oils, provided that the fat is melted prior to applying the fat
onto the cereal.
[0453] In another embodiment, the Rebaudioside X or a sweetener
composition comprising Rebaudioside X is added to the cereal
composition as a glaze. Non-limiting examples of glazing agents for
use in particular embodiments include corn syrup, honey syrups and
honey syrup solids, maple syrups and maple syrup solids, sucrose,
isomalt, polydextrose, polyols, hydrogenated starch hydrosylate,
aqueous solutions thereof, and mixtures thereof. In another such
embodiment, Rebaudioside X or a sweetener composition comprising
Rebaudioside X is added as a glaze by combining with a glazing
agent and a food grade oil or fat and applying the mixture to the
cereal. In yet another embodiment, a gum system, such as, for
example, gum acacia, carboxymethyl cellulose, or algin, may be
added to the glaze to provide structural support. In addition, the
glaze also may include a coloring agent, and also may include a
flavor.
[0454] In another embodiment, Rebaudioside X or a sweetener
composition comprising Rebaudioside X is added to the cereal
composition as a frosting. In one such embodiment, Rebaudioside X
or a sweetener composition comprising Rebaudioside X is combined
with water and a frosting agent and then applied to the cereal.
Non-limiting examples of frosting agents for use in particular
embodiments include maltodextrin, sucrose, starch, polyols, and
mixtures thereof. The frosting also may include a food grade oil, a
food grade fat, a coloring agent, and/or a flavor.
[0455] Generally, the amount of Rebaudioside X in a cereal
composition varies widely depending on the particular type of
cereal composition and its desired sweetness. Those of ordinary
skill in the art can readily discern the appropriate amount of
sweetener to put in the cereal composition. In a particular
embodiment, Rebaudioside X is present in the cereal composition in
an amount in the range of about 0.02 to about 1.5 weight percent of
the cereal composition and the at least one additive is present in
the cereal composition in an amount in the range of about 1 to
about 5 weight percent of the cereal composition.
[0456] Baked Goods
[0457] In one embodiment, a baked good comprises amorphous
Rebaudioside X. In another embodiment, a baked good comprises a
sweetener composition comprising amorphous Rebaudioside X.
[0458] In another embodiment, a baked good comprises a Rebaudioside
X complex. In another embodiment, a baked good comprises a
sweetener composition comprising a Rebaudioside X complex.
[0459] Baked goods, as used herein, include ready to eat and all
ready to bake products, flours, and mixes requiring preparation
before serving. Non-limiting examples of baked goods include cakes,
crackers, cookies, brownies, muffins, rolls, bagels, donuts,
strudels, pastries, croissants, biscuits, bread, bread products,
and buns.
[0460] Preferred baked goods in accordance with embodiments of this
invention can be classified into three groups: bread-type doughs
(e.g., white breads, variety breads, soft buns, hard rolls, bagels,
pizza dough, and flour tortillas), sweet doughs (e.g., danishes,
croissants, crackers, puff pastry, pie crust, biscuits, and
cookies), and batters (e.g., cakes such as sponge, pound, devil's
food, cheesecake, and layer cake, donuts or other yeast raised
cakes, brownies, and muffins). Doughs generally are characterized
as being flour-based, whereas batters are more water-based.
[0461] Baked goods in accordance with particular embodiments of
this invention generally comprise a combination of sweetener,
water, and fat. Baked goods made in accordance with many
embodiments of this invention also contain flour in order to make a
dough or a batter. The term "dough" as used herein is a mixture of
flour and other ingredients stiff enough to knead or roll. The term
"batter" as used herein consists of flour, liquids such as milk or
water, and other ingredients, and is thin enough to pour or drop
from a spoon. Desirably, in accordance with particular embodiments
of the invention, the flour is present in the baked goods in an
amount in the range of about 15 to about 60% on a dry weight basis,
more desirably from about 23 to about 48% on a dry weight
basis.
[0462] The type of flour may be selected based on the desired
product. Generally, the flour comprises an edible non-toxic flour
that is conventionally utilized in baked goods. According to
particular embodiments, the flour may be a bleached bake flour,
general purpose flour, or unbleached flour. In other particular
embodiments, flours also may be used that have been treated in
other manners. For example, in particular embodiments flour may be
enriched with additional vitamins, minerals, or proteins.
Non-limiting examples of flours suitable for use in particular
embodiments of the invention include wheat, corn meal, whole grain,
fractions of whole grains (wheat, bran, and oatmeal), and
combinations thereof. Starches or farinaceous material also may be
used as the flour in particular embodiments. Common food starches
generally are derived from potato, corn, wheat, barley, oat,
tapioca, arrow root, and sago. Modified starches and pregelatinized
starches also may be used in particular embodiments of the
invention.
[0463] The type of fat or oil used in particular embodiments of the
invention may comprise any edible fat, oil, or combination thereof
that is suitable for baking. Non-limiting examples of fats suitable
for use in particular embodiments of the invention include
vegetable oils, tallow, lard, marine oils, and combinations
thereof. According to particular embodiments, the fats may be
fractionated, partially hydrogenated, and/or interesterified. In
another particular embodiment, the fat desirably comprises reduced,
low calorie, or non-digestible fats, fat substitutes, or synthetic
fats. In yet another particular embodiment, shortenings, fats, or
mixtures of hard and soft fats also may be used. In particular
embodiments, shortenings may be derived principally from
triglycerides derived from vegetable sources (e.g., cotton seed
oil, soybean oil, peanut oil, linseed oil, sesame oil, palm oil,
palm kernel oil, rapeseed oil, safflower oil, coconut oil, corn
oil, sunflower seed oil, and mixtures thereof). Synthetic or
natural triglycerides of fatty acids having chain lengths from 8 to
24 carbon atoms also may be used in particular embodiments.
Desirably, in accordance with particular embodiments of this
invention, the fat is present in the baked good in an amount in the
range of about 2 to about 35% by weight on a dry basis, more
desirably from about 3 to about 29% by weight on a dry basis.
[0464] Baked goods in accordance with particular embodiments of
this invention also comprise water in amounts sufficient to provide
the desired consistency, enabling proper forming, machining and
cutting of the baked good prior or subsequent to cooking. The total
moisture content of the baked good includes any water added
directly to the baked good as well as water present in separately
added ingredients (e.g., flour, which generally includes about 12
to about 14% by weight moisture). Desirably, in accordance with
particular embodiments of this invention, the water is present in
the baked good in an amount up to about 25% by weight of the baked
good.
[0465] Baked goods in accordance with particular embodiments of
this invention also may comprise a number of additional
conventional ingredients such as leavening agents, flavors, colors,
milk, milk by-products, egg, egg by-products, cocoa, vanilla or
other flavoring, as well as inclusions such as nuts, raisins,
cherries, apples, apricots, peaches, other fruits, citrus peel,
preservative, coconuts, flavored chips such a chocolate chips,
butterscotch chips, and caramel chips, and combinations thereof. In
particular embodiments, the baked goods may also comprise
emulsifiers, such as lecithin and monoglycerides.
[0466] According to particular embodiments of this invention,
leavening agents may comprise chemical leavening agents or yeast
leavening agents. Non-limiting examples of chemical leavening
agents suitable for use in particular embodiments of this invention
include baking soda (e.g., sodium, potassium, or aluminum
bicarbonate), baking acid (e.g., sodium aluminum phosphate,
monocalcium phosphate, or dicalcium phosphate), and combinations
thereof.
[0467] In accordance with another particular embodiment of this
invention, cocoa may comprise natural or "Dutched" chocolate from
which a substantial portion of the fat or cocoa butter has been
expressed or removed by solvent extraction, pressing, or other
means. In a particular embodiment, it may be necessary to reduce
the amount of fat in a baked good comprising chocolate because of
the additional fat present in cocoa butter. In particular
embodiments, it may be necessary to add larger amounts of chocolate
as compared to cocoa in order to provide an equivalent amount of
flavoring and coloring.
[0468] Baked goods generally also comprise caloric sweeteners, such
as sucrose, high fructose corn syrup, erythritol, molasses, honey,
or brown sugar. In exemplary embodiments of the baked goods
provided herein, the caloric sweetener is replaced partially or
totally with Rebaudioside X or a sweetener composition comprising
Rebaudioside X. Accordingly, in one embodiment a baked good
comprises Rebaudioside X or a sweetener composition comprising
Rebaudioside X in combination with a fat, water, and optionally
flour. In a particular embodiment, the baked good optionally may
include other natural and/or synthetic high-potency sweeteners
and/or bulk sweeteners.
[0469] Dairy Products
[0470] In one embodiment, a dairy product comprises amorphous
Rebaudioside X. In another embodiment, a dairy product comprises a
sweetener composition comprising amorphous Rebaudioside X.
[0471] In another embodiment, a dairy product comprises a
Rebaudioside X complex. In another embodiment, a dairy product
comprises a sweetener composition comprising a Rebaudioside X
complex.
[0472] Dairy products and processes for making dairy products
suitable for use in this invention are well known to those of
ordinary skill in the art. Dairy products, as used herein, comprise
milk or foodstuffs produced from milk. Non-limiting examples of
dairy products suitable for use in embodiments of this invention
include milk, milk cream, sour cream, creme fraiche, buttermilk,
cultured buttermilk, milk powder, condensed milk, evaporated milk,
butter, cheese, cottage cheese, cream cheese, yogurt, ice cream,
frozen custard, frozen yogurt, gelato, vla, piima, filmjolk,
kajmak, kephir, viili, kumiss, airag, ice milk, casein, ayran,
lassi, khoa, or combinations thereof.
[0473] Milk is a fluid secreted by the mammary glands of female
mammals for the nourishment of their young. The female ability to
produce milk is one of the defining characteristics of mammals and
provides the primary source of nutrition for newborns before they
are able to digest more diverse foods. In particular embodiments of
this invention, the dairy products are derived from the raw milk of
cows, goats, sheep, horses, donkeys, camels, water buffalo, yaks,
reindeer, moose, or humans.
[0474] In particular embodiments of this invention, the processing
of the dairy product from raw milk generally comprises the steps of
pasteurizing, creaming, and homogenizing. Although raw milk may be
consumed without pasteurization, it usually is pasteurized to
destroy harmful microorganisms such as bacteria, viruses, protozoa,
molds, and yeasts. Pasteurizing generally comprises heating the
milk to a high temperature for a short period of time to
substantially reduce the number of microorganisms, thereby reducing
the risk of disease.
[0475] Creaming traditionally follows pasteurization step, and
involves the separation of milk into a higher-fat cream layer and a
lower-fat milk layer. Milk will separate into milk and cream layers
upon standing for twelve to twenty-four hours. The cream rises to
the top of the milk layer and may be skimmed and used as a separate
dairy product. Alternatively, centrifuges may be used to separate
the cream from the milk. The remaining milk is classified according
to the fat content of the milk, non-limiting examples of which
include whole, 2%, 1%, and skim milk.
[0476] After removing the desired amount of fat from the milk by
creaming, milk is often homogenized. Homogenization prevents cream
from separating from the milk and generally involves pumping the
milk at high pressures through narrow tubes in order to break up
fat globules in the milk. Pasteurization, creaming, and
homogenization of milk are common but are not required to produce
consumable dairy products. Accordingly, suitable dairy products for
use in embodiments of this invention may undergo no processing
steps, a single processing step, or combinations of the processing
steps described herein. Suitable dairy products for use in
embodiments of this invention may also undergo processing steps in
addition to or apart from the processing steps described
herein.
[0477] Particular embodiments of this invention comprise dairy
products produced from milk by additional processing steps. As
described above, cream may be skimmed from the top of milk or
separated from the milk using machine-centrifuges. In a particular
embodiment, the dairy product comprises sour cream, a dairy product
rich in fats that is obtained by fermenting cream using a bacterial
culture. The bacteria produce lactic acid during fermentation,
which sours and thickens the cream. In another particular
embodiment, the dairy product comprises creme fraiche, a heavy
cream slightly soured with bacterial culture in a similar manner to
sour cream. Creme fraiche ordinarily is not as thick or as sour as
sour cream. In yet another particular embodiment, the dairy product
comprises cultured buttermilk. Cultured buttermilk is obtained by
adding bacteria to milk. The resulting fermentation, in which the
bacterial culture turns lactose into lactic acid, gives cultured
buttermilk a sour taste. Although it is produced in a different
manner, cultured buttermilk generally is similar to traditional
buttermilk, which is a by-product of butter manufacture.
[0478] According to other particular embodiments of this invention,
the dairy products comprise milk powder, condensed milk, evaporated
milk, or combinations thereof. Milk powder, condensed milk, and
evaporated milk generally are produced by removing water from milk.
In a particular embodiment, the dairy product comprises a milk
powder comprising dried milk solids with a low moisture content. In
another particular embodiment, the dairy product comprises
condensed milk. Condensed milk generally comprises milk with a
reduced water content and added sweetener, yielding a thick, sweet
product with a long shelf-life. In yet another particular
embodiment, the dairy product comprises evaporated milk. Evaporated
milk generally comprises fresh, homogenized milk from which about
60% of the water has been removed, that has been chilled, fortified
with additives such as vitamins and stabilizers, packaged, and
finally sterilized. According to another particular embodiment of
this invention, the dairy product comprises a dry creamer and
Rebaudioside X or a Rebaudioside X sweetener composition.
[0479] In another particular embodiment, the dairy product provided
herein comprises butter. Butter generally is made by churning fresh
or fermented cream or milk. Butter generally comprises butterfat
surrounding small droplets comprising mostly water and milk
proteins. The churning process damages the membranes surrounding
the microscopic globules of butterfat, allowing the milk fats to
conjoin and to separate from the other parts of the cream. In yet
another particular embodiment, the dairy product comprises
buttermilk, which is the sour-tasting liquid remaining after
producing butter from full-cream milk by the churning process.
[0480] In still another particular embodiment, the dairy product
comprises cheese, a solid foodstuff produced by curdling milk using
a combination of rennet or rennet substitutes and acidification.
Rennet, a natural complex of enzymes produced in mammalian stomachs
to digest milk, is used in cheese-making to curdle the milk,
causing it to separate into solids known as curds and liquids known
as whey. Generally, rennet is obtained from the stomachs of young
ruminants, such as calves; however, alternative sources of rennet
include some plants, microbial organisms, and genetically modified
bacteria, fungus, or yeast. In addition, milk may be coagulated by
adding acid, such as citric acid. Generally, a combination of
rennet and/or acidification is used to curdle the milk. After
separating the milk into curds and whey, some cheeses are made by
simply draining, salting, and packaging the curds. For most
cheeses, however, more processing is needed. Many different methods
may be used to produce the hundreds of available varieties of
cheese. Processing methods include heating the cheese, cutting it
into small cubes to drain, salting, stretching, cheddaring,
washing, molding, aging, and ripening. Some cheeses, such as the
blue cheeses, have additional bacteria or molds introduced to them
before or during aging, imparting flavor and aroma to the finished
product. Cottage cheese is a cheese curd product with a mild flavor
that is drained but not pressed so that some whey remains. The curd
is usually washed to remove acidity. Cream cheese is a soft,
mild-tasting, white cheese with a high fat content that is produced
by adding cream to milk and then curdling to form a rich curd.
Alternatively, cream cheese can be made from skim milk with cream
added to the curd. It should be understood that cheese, as used
herein, comprises all solid foodstuff produced by the curdling
milk.
[0481] In another particular embodiment of this invention, the
dairy product comprises yogurt. Yogurt generally is produced by the
bacterial fermentation of milk. The fermentation of lactose
produces lactic acid, which acts on proteins in milk to give the
yogurt a gel-like texture and tartness. In particularly desirable
embodiments, the yogurt may be sweetened with a sweetener and/or
flavored. Non-limiting examples of flavorings include, but are not
limited to, fruits (e.g., peach, strawberry, banana), vanilla, and
chocolate. Yogurt, as used herein, also includes yogurt varieties
with different consistencies and viscosities, such as dahi, dadih
or dadiah, labneh or labaneh, bulgarian, kefir, and matsoni. In
another particular embodiment, the dairy product comprises a
yogurt-based beverage, also known as drinkable yogurt or a yogurt
smoothie. In particularly desirable embodiments, the yogurt-based
beverage may comprise sweeteners, flavorings, other ingredients, or
combinations thereof.
[0482] Other dairy products beyond those described herein may be
used in particular embodiments of this invention. Such dairy
products are well known to those of ordinary skill in the art,
non-limiting examples of which include milk, milk and juice,
coffee, tea, vla, piima, filmjolk, kajmak, kephir, viili, kumiss,
airag, ice milk, casein, ayran, lassi, and khoa.
[0483] According to particular embodiments of this invention, the
dairy compositions also may comprise other additives. Non-limiting
examples of suitable additives include sweeteners and flavorants
such as chocolate, strawberry, and banana. Particular embodiments
of the dairy compositions provided herein also may comprise
additional nutritional supplements such as vitamins (e.g., vitamin
D) and minerals (e.g., calcium) to improve the nutritional
composition of the milk.
[0484] In a particularly desirable embodiment, the dairy
composition comprises Rebaudioside X or a sweetener composition
comprising Rebaudioside X in combination with a dairy product. In a
particular embodiment, Rebaudioside X is present in the dairy
composition in an amount in the range of about 200 to about 20,000
weight percent of the dairy composition.
[0485] Rebaudioside X or sweetener compositions comprising
Rebaudioside X are also suitable for use in processed agricultural
products, livestock products or seafood; processed meat products
such as sausage and the like; retort food products, pickles,
preserves boiled in soy sauce, delicacies, side dishes; soups;
snacks such as potato chips, cookies, or the like; as shredded
filler, leaf, stem, stalk, homogenized leaf cured and animal
feed.
Methods for Preparing Sweetener Compositions and Sweetened
Compositions
[0486] Sweetener Compositions
[0487] In one embodiment, a method for preparing a sweetener
composition comprises combining Rebaudioside X with one or more
additional sweetener, additive, functional ingredients or
combinations thereof.
[0488] In a particular embodiment, a method for preparing a
sweetener composition comprises combining amorphous Rebaudioside X
with one or more additional sweetener, additive, functional
ingredient or combination thereof.
[0489] In another embodiment, a method for preparing a sweetener
composition comprises combining a Rebaudioside X complex with one
or more additional sweetener, additive, functional ingredient or
combination thereof.
[0490] Any of the sweeteners, additives and functional ingredients
described herein can be used in the sweetener compositions of the
present invention.
[0491] Sweetened Compositions
[0492] In one embodiment, the invention provides a method for
preparing a sweetened composition comprising combining a
sweetenable composition with amorphous Rebaudioside X or a
sweetener composition comprising amorphous Rebaudioside X
[0493] In another embodiment, the invention provides a method for
preparing a sweetened composition comprising combining a
sweetenable composition with a Rebaudioside X complex or a
sweetener compositing comprising a Rebaudioside X complex.
[0494] The sweetenable composition can be any sweetenable
composition described herein, including, for example,
pharmaceutical compositions, edible gel mixes and compositions,
dental compositions, foodstuffs (confections, condiments, chewing
gum, cereal compositions, baked goods, dairy products, beverages
and beverage products. In a particular embodiment, the sweetenable
composition is an unsweetened beverage. In another particular
embodiment, the sweetenable composition is a sweetened
beverage.
[0495] Beverage and Beverage Products
[0496] In one embodiment, the invention provides a method for
preparing a beverage or beverage product comprising combining a
unsweetened beverage with amorphous Rebaudioside X or a sweetener
composition comprising amorphous Rebaudioside X.
[0497] In another embodiment, the invention provides a method for
preparing a beverage or beverage product comprising combining a
unsweetened beverage with a Rebaudioside X complex or a sweetener
composition comprising a Rebaudioside complex. As used herein, the
term "unsweetened beverage" refers to a beverage that does not
contain a sweetener component.
[0498] In one embodiment, the invention provides a method for
preparing a beverage or beverage product comprising combining a
sweetened beverage with amorphous Rebaudioside X or a sweetener
compositions comprising amorphous Rebaudioside X.
[0499] In another embodiment, the invention provides a method for
preparing a beverage or beverage product comprising combining a
sweetened beverage with a Rebaudioside X complex or a sweetener
composition comprising a Rebaudioside X complex.
[0500] As used herein, the term "sweetened beverage" refers to a
beverage that contains one or more non-Rebaudioside X sweeteners,
including natural or synthetic sweeteners.
[0501] As used herein, a "beverage or beverage product" is a
ready-to-drink beverage, a beverage concentrate, a beverage syrup,
or a powdered beverage. Suitable ready-to-drink beverages include
carbonated and non-carbonated beverages. Carbonated beverages
include, but are not limited to, cola, lemon-lime flavored
sparkling beverage, orange flavored sparkling beverage, grape
flavored sparkling beverage, strawberry flavored sparkling
beverage, pineapple flavored sparkling beverage, ginger-ale, soft
drinks and root beer. Non-carbonated beverages include, but are not
limited to fruit juice, fruit-flavored juice, juice drinks,
nectars, vegetable juice, vegetable-flavored juice, sports drinks,
energy drinks, enhanced water with vitamins, near water drinks
(e.g., water with natural or synthetic flavorants), coconut water,
tea type (e.g. black tea, green tea, red tea, oolong tea), coffee,
cocoa drink, beverage containing milk components (e.g. milk
beverages, coffee containing milk components, cafe au lait, milk
tea, fruit milk beverages), beverages containing cereal extracts,
smoothies and combinations thereof.
[0502] Beverage concentrates and beverage syrups are prepared with
an initial volume of liquid matrix (e.g. water) and the desired
beverage ingredients. Full strength beverages are then prepared by
adding further volumes of water. Powdered beverages are prepared by
dry-mixing all of the beverage ingredients in the absence of a
liquid matrix. Full strength beverages are then prepared by adding
the full volume of water.
[0503] Beverages contain a liquid matrix, i.e. the basic ingredient
in which the ingredients--including the sweetener or sweetener
compositions--are dissolved. In one embodiment, the liquid matrix
is water of beverage quality, such as, for example deionized water,
distilled water, reverse osmosis water, carbon-treated water,
purified water, demineralized water and combinations thereof, can
be used. Additional suitable liquid matrices include, but are not
limited to phosphoric acid, phosphate buffer, citric acid, citrate
buffer and carbon-treated water.
[0504] In one embodiment, amorphous Rebaudioside X is provided as
the sole sweetener in the beverage.
[0505] In another embodiment, a beverage comprises a sweetener
composition comprising amorphous Rebaudioside X.
[0506] In still another embodiment, a beverage comprises a
Rebaudioside X complex. In yet another embodiment, a beverage
comprises a sweetener composition comprising a Rebaudioside X
complex. The Rebaudioside X complex may comprise Rebaudioside X and
at least one polyol, for example erythritol. In another embodiment,
the Rebaudioside X complex comprises Rebaudioside X and
maltodextrin. In still another embodiment, the Rebaudioside X
complex comprises Rebaudioside X and at least one cyclodextrin.
[0507] Any sweetener composition comprising Rebaudioside X detailed
herein can be used to prepare the beverages. The sweetener
composition can further include at least one additional sweetener.
Any of the sweeteners detailed herein can be used, including
natural, non-natural, or synthetic sweeteners.
[0508] Carbohydrate sweeteners can be present in the beverage in a
concentration from about 100 ppm to about 140,000 ppm. Synthetic
sweeteners may be present in the beverage in a concentration from
about 0.3 ppm to about 3,500 ppm. Natural high potency sweeteners
may be preset in the beverage in a concentration from about 0.1 ppm
to about 3,000 ppm.
[0509] The sweetener composition can further include additives
including, but are not limited to, carbohydrates, polyols, amino
acids and their corresponding salts, poly-amino acids and their
corresponding salts, sugar acids and their corresponding salts,
nucleotides, organic acids, inorganic acids, organic salts
including organic acid salts and organic base salts, inorganic
salts, bitter compounds, caffeine, flavorants and flavoring
ingredients, astringent compounds, proteins or protein
hydrolysates, surfactants, emulsifiers, weighing agents, juice,
dairy, cereal and other plant extracts, flavonoids, alcohols,
polymers and combinations thereof. Any suitable additive described
herein can be used.
[0510] In one embodiment, the polyol can be present in the beverage
in a concentration from about 100 ppm to about 250,000 ppm, such
as, for example, from about 5,000 ppm to about 40,000 ppm.
[0511] In another embodiment, the amino acid can be present in the
beverage in a concentration from about 10 ppm to about 50,000 ppm,
such as, for example, from about 1,000 ppm to about 10,000 ppm,
from about 2,500 ppm to about 5,000 ppm or from about 250 ppm to
about 7,500 ppm.
[0512] In still another embodiment, the nucleotide can be present
in the beverage in a concentration from about 5 ppm to about 1,000
ppm.
[0513] In yet another embodiment, the organic acid additive can be
present in the beverage in a concentration from about 10 ppm to
about 5,000 ppm.
[0514] In yet another embodiment, the inorganic acid additive can
be present in the beverage in a concentration from about 25 ppm to
about 25,000 ppm.
[0515] In still another embodiment, the bitter compound can be
present in the beverage in a concentration from about 25 ppm to
about 25,000 ppm.
[0516] In yet another embodiment, the flavorant can be present in
the beverage a concentration from about 0.1 ppm to about 3,000
ppm.
[0517] In a still further embodiment, the polymer can be present in
the beverage in a concentration from about 30 ppm to about 2,000
ppm.
[0518] In another embodiment, the protein hydrosylate can be
present in the beverage in a concentration from about 200 ppm to
about 50,000.
[0519] In yet another embodiment, the surfactant additive can be
present in the beverage in a concentration from about 30 ppm to
about 2,000 ppm.
[0520] In still another embodiment, the flavonoid additive can be
present in the beverage a concentration from about 0.1 ppm to about
1,000 ppm.
[0521] In yet another embodiment, the alcohol additive can be
present in the beverage in a concentration from about 625 ppm to
about 10,000 ppm.
[0522] In a still further embodiment, the astringent additive can
be present in the beverage in a concentration from about 10 ppm to
about 5,000 ppm.
[0523] The sweetener composition can further contain one or more
functional ingredients, detailed above. Functional ingredients
include, but are not limited to, vitamins, minerals, antioxidants,
preservatives, glucosamine, polyphenols and combinations thereof.
Any suitable functional ingredient described herein can be
used.
[0524] In one embodiment, a beverage comprises Rebaudioside X in an
amount ranging from about 1 ppm to about 10,000 ppm, such as, for
example, from about 25 ppm to about 800 ppm. In another embodiment,
Rebaudioside X is present in a beverage in an amount ranging from
about 100 ppm to about 600 ppm. In yet other embodiments,
Rebaudioside X is present in a beverage in an amount ranging from
about 100 to about 200 ppm, from about 100 ppm to about 300 ppm,
from about 100 ppm to about 400 ppm, or from about 100 ppm to about
500 ppm. In still another embodiment, Rebaudioside X is present in
a beverage in an amount ranging from about 300 to about 700 ppm,
such as, for example, from about 400 ppm to about 600 ppm. In a
particular embodiment, Rebaudioside X is present in an amount of
about 500 ppm.
[0525] In another embodiment, a beverage comprises a sweetener
composition containing Rebaudioside X, wherein Rebaudioside X is
present in the beverage in an amount ranging from about 1 ppm to
about 10,000 ppm, such as, for example, from about 25 ppm to about
800 ppm. In another embodiment, Rebaudioside X is present in the
beverage in an amount ranging from about 100 ppm to about 600 ppm.
In yet other embodiments, Rebaudioside X is present in the beverage
in an amount ranging from about 100 to about 200 ppm, from about
100 ppm to about 300 ppm, from about 100 ppm to about 400 ppm, or
from about 100 ppm to about 500 ppm. In still another embodiment,
Rebaudioside X is present in the beverage in an amount ranging from
about 300 to about 700 ppm, such as, for example, from about 400
ppm to about 600 ppm. In a particular embodiment, Rebaudioside X is
present in the beverage in an amount of about 500 ppm.
[0526] It is contemplated that the pH of the sweetened composition,
such as, for example, a beverage, does not materially or adversely
affect the taste of the sweetener. A non-limiting example of the pH
range of the sweetenable composition may be from about 1.8 to about
10. A further example includes a pH range from about 2 to about 5.
In a particular embodiment, the pH of beverage can be from about
2.5 to about 4.2. On of skill in the art will understand that the
pH of the beverage can vary based on the type of beverage. Dairy
beverages, for example, can have pHs greater than 4.2.
[0527] The titratable acidity of a beverage comprising Rebaudioside
X may, for example, range from about 0.01 to about 1.0% by weight
of beverage.
[0528] In one embodiment, the sparkling beverage product has an
acidity from about 0.01 to about 1.0% by weight of the beverage,
such as, for example, from about 0.05% to about 0.25% by weight of
beverage.
[0529] The carbonation of a sparkling beverage product has 0 to
about 2% (w/w) of carbon dioxide or its equivalent, for example,
from about 0.1 to about 1.0% (w/w).
[0530] The temperature of a beverage comprising Rebaudioside X may,
for example, range from about 4.degree. C. to about 100.degree. C.,
such as, for example, from about 4.degree. C. to about 25.degree.
C.
[0531] The beverage can be a full-calorie beverage that has up to
about 120 calories per 8 oz serving.
[0532] The beverage can be a mid-calorie beverage that has up to
about 60 calories per 8 oz serving.
[0533] The beverage can be a low-calorie beverage that has up to
about 40 calories per 8 oz serving.
[0534] The beverage can be a zero-calorie that has less than about
5 calories per 8 oz. serving.
[0535] In one embodiment, a beverage comprises between about 200
ppm and about 500 ppm Rebaudioside X, wherein the liquid matrix of
the beverage is selected from the group consisting of water,
phosphoric acid, phosphate buffer, citric acid, citrate buffer,
carbon-treated water and combinations thereof. The pH of the
beverage can be from about 2.5 to about 4.2. The beverage can
further include additives, such as, for example, erythritol. The
beverage can further include functional ingredients, such as
vitamins.
[0536] In particular embodiments, a method for preparing a beverage
comprises combining an unsweetened or sweetened beverage with
amorphous Rebaudioside X; a polyol selected from erythritol,
maltitol, mannitol, xylitol, glycerol, sorbitol, and combinations
thereof; and optionally at least one additional sweetener and/or
functional ingredient. In a particular embodiment, the polyol is
erythritol. In one embodiment, amorphous Rebaudioside X and the
polyol are present in the beverage in a weight ratio from about 1:1
to about 1:800, such as, for example, from about 1:4 to about
1:800, from about 1:20 to about 1:600, from about 1:50 to about
1:300 or from about 1:75 to about 1:150. In another embodiment,
Rebaudioside X is present in the beverage in a concentration from
about 1 ppm to about 10,000 ppm, such as, for example, about 500
ppm. The polyol, such as, for example, erythritol, is present in
the beverage in a concentration from about 100 ppm to about 250,000
ppm, such as, for example, from about 5,000 ppm to about 40,000
ppm, from about 1,000 ppm to about 35,000 ppm.
[0537] In particular embodiments, a method for preparing a beverage
comprises combining an unsweetened or sweetened beverage with
amorphous Rebaudioside X; a carbohydrate sweetener selected from
sucrose, fructose, glucose, maltose and combinations thereof; and
optionally at least one additional sweetener and/or functional
ingredient. In one embodiment, amorphous Rebaudioside X and the
carbohydrate are present in a sweetener composition in a weight
ratio from about 0.001:14 to about 1:0.01, such as, for example,
about 0.06:6. In one embodiment, Rebaudioside X is present in the
beverage in a concentration from about 1 ppm to about 10,000 ppm,
such as, for example, about 500 ppm. The carbohydrate, such as, for
example, sucrose, is present in the beverage a concentration from
about 100 ppm to about 140,000 ppm, such as, for example, from
about 1,000 ppm to about 100,000 ppm, from about 5,000 ppm to about
80,000 ppm.
[0538] In particular embodiments, a method for preparing a beverage
comprises combining an unsweetened or sweetened beverage with
amorphous Rebaudioside X; an amino acid selected from glycine,
alanine, proline, taurine and combinations thereof; and optionally
at least one additional sweetener and/or functional ingredient. In
one embodiment, Rebaudioside X is present in the beverage in a
concentration from about 1 ppm to about 10,000 ppm, such as, for
example, about 500 ppm. The amino acid, such as, for example,
glycine, can be present in the beverage in a concentration from
about 10 ppm to about 50,000 ppm when present in a sweetened
composition, such as, for example, from about 1,000 ppm to about
10,000 ppm, from about 2,500 ppm to about 5,000 ppm
[0539] In particular embodiments, a method for preparing a beverage
comprises combining an unsweetened or sweetened beverage with
amorphous Rebaudioside X; a salt selected from sodium chloride,
magnesium chloride, potassium chloride, calcium chloride, phosphate
salts and combinations thereof; and optionally at least one
additional sweetener and/or functional ingredient. In one
embodiment, Rebaudioside X is present in the beverage in a
concentration from about 1 ppm to about 10,000 ppm, such as, for
example, about 500 ppm. The inorganic salt, such as, for example,
magnesium chloride, is present in the beverage in a concentration
from about 25 ppm to about 25,000 ppm, such as, for example, from
about 100 ppm to about 4,000 ppm or from about 100 ppm to about
3,000 ppm.
[0540] In another embodiment, a method for preparing a beverage
comprises combining an unsweetened or sweetened beverage with a
Rebaudioside X complex. In one embodiment, the Rebaudioside X
complex comprises Rebaudioside X and at least one polyol, for
example erythritol. In another embodiment, the Rebaudioside X
complex comprises Rebaudioside X and maltodextrin. In still another
embodiment, the Rebaudioside X complex comprises Rebaudioside X and
at least one cyclodextrin. The beverage can optionally contain
other sweeteners, additives and/or functional ingredients. In one
embodiment, a Rebaudioside X complex is present in a beverage in a
concentration from about 1 ppm to about 10,000 pp.
[0541] Improving Temporal and/or Flavor Profile
[0542] A method for imparting a more sugar-like temporal profile,
flavor profile, or both to a sweetenable composition comprises
combining a sweetenable composition with amorphous Rebaudioside X
or the sweetener compositions of the present invention, i.e.,
sweetener compositions containing amorphous Rebaudioside X. The
Rebaudioside X is in dry powdered form. In a particular embodiment,
the sweetenable composition is an unsweetened beverage.
[0543] The sweetener compositions include the addition of other
sweeteners, additives, functional ingredients and combinations
thereof. Any sweetener, additive or functional ingredient detailed
herein can be used.
[0544] As used herein, the "sugar-like" characteristics include any
characteristic similar to that of sucrose and include, but are not
limited to, maximal response, flavor profile, temporal profile,
adaptation behavior, mouthfeel, concentration/response function,
tastant/and flavor/sweet taste interactions, spatial pattern
selectivity, and temperature effects.
[0545] The flavor profile of a sweetener is a quantitative profile
of the relative intensities of all of the taste attributes
exhibited. Such profiles often are plotted as histograms or radar
plots.
[0546] These characteristics are dimensions in which the taste of
sucrose is different from the tastes of Rebaudioside X. Of these,
however, the flavor profile and temporal profile are particularly
important. In a single tasting of a sweet food or beverage,
differences (1) in the attributes that constitute a sweetener's
flavor profile and (2) in the rates of sweetness onset and
dissipation, which constitute a sweetener's temporal profile,
between those observed for sucrose and for Rebaudioside X can be
noted.
[0547] Whether or not a characteristic is more sugar-like is
determined by an expert sensory panel who taste compositions
comprising sugar and compositions comprising Rebaudioside X, both
with and without additives, and provide their impression as to the
similarities of the characteristics of the sweetener compositions,
both with and without additives, with those comprising sugar. A
suitable procedure for determining whether a composition has a more
sugar-like taste is described in embodiments described herein
below.
[0548] In a particular embodiment, a panel of assessors is used to
measure the reduction of sweetness linger. Briefly described, a
panel of assessors (generally 8 to 12 individuals) is trained to
evaluate sweetness perception and measure sweetness at several time
points from when the sample is initially taken into the mouth until
3 minutes after it has been expectorated. Using statistical
analysis, the results are compared between samples containing
additives and samples that do not contain additives. A decrease in
score for a time point measured after the sample has cleared the
mouth indicates there has been a reduction in sweetness
perception.
[0549] The panel of assessors may be trained using procedures well
known to those of ordinary skill in the art. In a particular
embodiment, the panel of assessors may be trained using the
Spectrum.TM. Descriptive Analysis Method (Meilgaard et al, Sensory
Evaluation Techniques, 3.sup.rd edition, Chapter 11). Desirably,
the focus of training should be the recognition of and the measure
of the basic tastes; specifically, sweet. In order to ensure
accuracy and reproducibility of results, each assessor should
repeat the measure of the reduction of sweetness linger about three
to about five times per sample, taking at least a five minute break
between each repetition and/or sample and rinsing well with water
to clear the mouth.
[0550] Generally, the method of measuring sweetness comprises
taking a 10 mL sample into the mouth, holding the sample in the
mouth for 5 seconds and gently swirling the sample in the mouth,
rating the sweetness intensity perceived at 5 seconds,
expectorating the sample (without swallowing following
expectorating the sample), rinsing with one mouthful of water
(e.g., vigorously moving water in mouth as if with mouth wash) and
expectorating the rinse water, rating the sweetness intensity
perceived immediately upon expectorating the rinse water, waiting
45 seconds and, while waiting those 45 seconds, identifying the
time of maximum perceived sweetness intensity and rating the
sweetness intensity at that time (moving the mouth normally and
swallowing as needed), rating the sweetness intensity after another
10 seconds, rating the sweetness intensity after another 60 seconds
(cumulative 120 seconds after rinse), and rating the sweetness
intensity after still another 60 seconds (cumulative 180 seconds
after rinse). Between samples take a 5 minute break, rinsing well
with water to clear the mouth.
EXAMPLES
Instrumentation
Inel XRG-3000 Diffractometer
[0551] XRPD patterns were collected with an Inel XRG-3000
diffractometer. An incident beam of Cu-K.alpha. radiation was
produced using a fine-focus tube and a parabolically graded
multilayer mirror. Prior to the analysis, a silicon specimen (NIST
SRM 640d) was analyzed to verify the observed position of the Si
111 peak is consistent with the NIST-certified position. A specimen
of the sample was packed into a thin-walled glass capillary and a
beam-stop was used to minimize the background from air. Diffraction
patterns were collected in transmission geometry using Windif v.
6.6 software and a curved position-sensitive Equinox detector with
a 2.theta. range of 120.degree.. The data acquisition parameters
for each pattern are displayed 2.5-40.degree. 20.
PANalytical X'Pert PRO Diffractometer
[0552] High resolution XRPD patterns were collected with a
PANalytical X'Pert PRO MPD diffractometer using an incident beam of
Cu radiation produced using an Optix long, fine-focus source. An
elliptically graded multilayer mirror was used to focus Cu K.alpha.
X-rays through the specimen and onto the detector. Prior to the
analysis, a silicon specimen (NIST SRM 640d) was analyzed to verify
the observed position of the Si 111 peak is consistent with the
NIST-certified position. A specimen of the sample was sandwiched
between 3-.mu.m-thick films and analyzed in transmission geometry.
A beam-stop, short antiscatter extension and antiscatter knife edge
were used to minimize the background generated by air. Soller slits
for the incident and diffracted beams were used to minimize
broadening from axial divergence. Diffraction patterns were
collected using a scanning position-sensitive detector
(X'Celerator) located 240 mm from the specimen and Data Collector
software v. 2.2b.
Example 1
Purification of Reb X from Stevia rebaudiana Bertoni Plant
Leaves
[0553] Two kg of Stevia rebaudiana Bertoni plant leaves were dried
at 45.degree. C. to an 8.0% moisture content and ground to 10-20 mm
particles. The content of different glycosides in the leaves was as
follows: Stevioside--2.55%, Reb A--7.78%, Reb B--0.01%, Reb
C--1.04%, Reb D--0.21%, Reb F--0.14%, Reb X--0.10% Dulcoside
A--0.05%, and Steviolbioside--0.05%. The dried material was loaded
into a continuous extractor and the extraction was carried out with
40.0 L of water at a pH of 6.5 at 40.degree. C. for 160 min. The
filtrate was collected and subjected to chemical treatment. Calcium
oxide in the amount of 400 g was added to the filtrate to adjust
the pH within the range of 8.5-9.0, and the mixture was maintained
for 15 min with slow agitation. Then, the pH was adjusted to around
3.0 by adding 600 g of FeCl.sub.3 and the mixture was maintained
for 15 min with slow agitation. A small amount of calcium oxide was
further added to adjust the pH to 8.5-9.0 and the mixture was
maintained for 30 min with slow agitation. The precipitate was
removed by filtration on a plate-and-frame filter press using
cotton cloth as the filtration material. The slightly yellow
filtrate was passed through the column, packed with cation-exchange
resin Amberlite FCP22 (H.sup.+) and then, through the column with
anion-exchange resin Amberlite FPA53 (OH.sup.-). The flow rate in
both columns was maintained at SV=0.8 hour.sup.-1. After completion
both columns were washed with RO water to recover the steviol
glycosides left in the columns and the filtrates were combined. The
portion of combined solution containing 120 g total steviol
glycosides was passed through seven columns, wherein each column
was packed with specific macroporous polymeric adsorbent YWD-03
(Cangzhou Yuanwei, China). The first column with the size of 1/3 of
the others acted as a "catcher column". The SV was around 1.0
hour.sup.-1. After all extract was passed through the columns, the
resin sequentially was washed with 1 volume of water, 2 volumes of
0.5% NaOH, 1 volume of water, 2 volumes of 0.5% HCl, and finally
with water until the pH was 7.0. The "catcher column" was washed
separately.
[0554] Desorption of the adsorbed steviol glycosides was carried
out with 52% ethanol at SV=1.0 hour.sup.-1. Desorption of the first
"catcher column" was carried out separately and the filtrate was
not mixed with the main solution obtained from other columns.
Desorption of the last column also was carried out separately. The
quality of extract from different columns with specific macroporous
adsorbent is shown in Table 3.
TABLE-US-00005 TABLE 3 Steviol Glycoside Content Column Total
steviol glycosides, % 1 (catcher) 55.3 2 92.7 3 94.3 4 96.1 5 96.3
6 95.8 7 80.2
[0555] The total steviol glycoside content can be determined
experimentally by HPLC or HPLC/MS. For example, chromatographic
analysis can be performed on a HPLC/MS system comprising an Agilent
1200 series (USA) liquid chromatograph equipped with binary pump,
autosampler, thermostatted column compartment, UV detector (210
nm), and Agilent 6110 quadrupole MS detector interfaced with
Chemstation data acquisition software. The column can be a
"Phenomenex Prodigy 5u ODS3 250.times.4.6 mm; 5 m (P/No.
00G-4097-E0)" column maintained at 40.degree. C. The mobile phase
can be 30:70 (vol/vol.) acetonitrile and water (containing 0.1%
formic acid) and the flow rate through the column can be 0.5
mL/min. The steviol glycosides can be identified by their retention
times in such a method, which are generally around 2.5 minutes for
Reb D, around 2.9 minutes for Reb X, 5.5 minutes for Reb A, 5.8
minutes for Stevioside, 7.1 minutes for Reb F, 7.8 minutes for Reb
C, 8.5 minutes for Dulcoside A, 11.0 minutes for Rubusoside, 15.4
minutes for Reb B and 16.4 minutes for Steviolbioside. One of skill
in the art will appreciate that the retention times for the various
steviol glycosides given above can vary with changes in solvent
and/or equipment.
[0556] Eluates from second to sixth columns were combined and
treated separately. The combined solution of steviol glycosides was
mixed with 0.3% of activated carbon from the total volume of
solution. The suspension was maintained at 25.degree. C. for 30 min
with continuous agitation. Separation of carbon was carried out on
a press-filtration system. For additional decolorization the
filtrate was passed through the columns packed with cation-exchange
resin Amberlite FCP22 (H.sup.+) followed with anion-exchange resin
Amberlite FPA53 A30B (OH.sup.-). The flow rate in both columns was
around SV=0.5 hour.sup.-1. The ethanol was distilled using a vacuum
evaporator. The solids content in the final solution was around
15%. The concentrate was passed through the columns packed with
cation-exchange resin Amberlite FCP22 (H.sup.+) and anion-exchange
resin Amberlite FPA53 (OH.sup.-) with SV=0.5 hour.sup.-1. After all
the solution was passed through the columns, both resins were
washed with RO water to recover the steviol glycosides left in the
columns. The resulting refined extract was transferred to the
nano-filtration device, concentrated to around 52% of solids
content and spray dried to provide a highly purified mixture of
steviol glycosides. The yield was 99.7 g. The mixture contained
Stevioside--20.5%, Reb A--65.6%, Reb B--0.1%, Reb C--8.4%, Reb
D--0.5%, Reb F--1.1%, Reb X--0.1%, Dulcoside A--0.4%, and
Steviolbioside--0.4%.
[0557] The combined eluate from the last column, contained about
5.3 g of total steviol glycosides including 2.3 g Reb D and around
1.9 g Reb X (35.8% Reb X/TSG ratio). It was deionized and
decolorized as discussed above and then concentrated to a 33.5%
content of total solids.
[0558] The concentrate was mixed with two volumes of anhydrous
methanol and maintained at 20-22.degree. C. for 24 hours with
intensive agitation.
[0559] The resulting precipitate was separated by filtration and
washed with about two volumes of absolute methanol. The yield of
Rebaudioside X was 1.5 g with around 80% purity.
[0560] For the further purification the precipitate was suspended
in three volumes of 60% methanol and treated at 55.degree. C. for
30 min, then cooled down to 20-22.degree. C. and agitated for
another 2 hours.
[0561] The resulting precipitate was separated by filtration and
washed with about two volumes of absolute methanol and subjected to
similar treatment with a mixture of methanol and water.
[0562] The yield of Rebaudioside X was 1.2 g with 97.3% purity.
Example 2
Structural Elucidation of Rebaudioside X
[0563] HRMS: HRMS (High Resolution Mass Spectrum) data was
generated with a Waters Premier Quadrupole Time-of-Flight (Q-TOF)
mass spectrometer equipped with an electrospray ionization source
operated in the positive-ion mode. Samples were diluted and eluted
with a gradient of 2:2:1 methanol:acetonitrile:water and introduced
50 .mu.L via infusion using the onboard syringe pump
[0564] NMR: The sample was dissolved in deuterated pyridine
(C.sub.5D.sub.5N) and NMR spectra were acquired on Varian Unity
Plus 600 MHz instruments using standard pulse sequences. The
chemical shifts are given in .delta. (ppm), and coupling constants
are reported in Hz.
[0565] The complete .sup.1H and .sup.13C NMR spectral assignments
for the diterpene glycoside rebaudioside X determined on the basis
of 1D (.sup.1H and .sup.13C) and 2D (COSY, HMQC and HMBC) NMR as
well as high resolution mass spectroscopic data:
##STR00002##
[0566] Discussion
[0567] The molecular formula was deduced as
C.sub.56H.sub.90O.sub.33 on the basis of its positive high
resolution (HR) mass spectrum which showed an [M+NH.sub.4.sup.+]
ion at mlz 1308.5703 together with an [M+Na+] adduct at mlz
1313.5274. This composition was supported by .sup.13C NMR spectral
data (FIGS. 11A and 11B). The .sup.1H NMR spectrum (FIGS. 12A and
12B) showed the presence of two methyl singlets at .delta. 1.32 and
1.38, two olefinic protons as singlets at .delta. 4.90 and 5.69 of
an exocyclic double bond, nine methylene and two methine protons
between .delta. 0.75-2.74 characteristic for the ent-kaurane
diterpenoids isolated earlier from the genus Stevia.
[0568] The basic skeleton of ent-kaurane diterpenoids was supported
by COSY (FIG. 13): H-1/H-2; H-2/H-3; H-5/H-6; H-6/H-7; H-9/H-11;
H-11/H-12 correlations.
[0569] The basic skeleton of ent-kaurane diterpenoids was also
supported by HMBC (FIG. 14): H-1/C-2, C-1O; H-3/C-1, C-2, C-4, C-5,
C-18, C-19; H-5/C-4, C-6, C-7, C-9, C-10, C-18, C-19, C-20;
H-9/C-8, C-10, C-11, C-12, C-14, C-15; H-14/C-8, C-9, C-13, C-15,
C-16 and H-17/C-13, C-15, C-16 correlations.
[0570] The .sup.1H NMR spectrum also showed the presence of
anomeric protons resonating at .delta. 5.31, 5.45, 5.46, 5.48,
5.81, and 6.39; suggesting six sugar units in its structure.
Enzymatic hydrolysis furnished an aglycone which was identified as
steviol by comparison of co-TLC with standard compound. Acid
hydrolysis with 5% H.sub.2SO.sub.4 afforded glucose which was
identified by direct comparison with authentic samples by TLC. The
.sup.1H and .sup.13C NMR values for all protons and carbons were
assigned on the basis of COSY, HMQC and HMBC correlations (Table
3).
TABLE-US-00006 TABLE 3 .sup.1H and .sup.13C NMR spectral data for
Rebaudioside X in C.sub.5D.sub.5N .sup.a-c. Position .sup.13C NMR
.sup.1H NMR 1 40.3 0.75 t (13.2) 1.76 m 2 19.6 1.35 m 2.24 m 3 38.4
1.01 m 2.30 d (13.3) 4 44.3 -- 5 57.4 1.06 d (12.8) 6 23.5 2.23 m
2.41 q (13.2) 7 42.6 1.41 m 1.80 m 8 41.2 -- 9 54.3 0.91 d (7.7) 10
39.7 -- 11 20.2 1.65 m 1.75 m 12 38.5 1.86 m 2.73 m 13 87.6 -- 14
43.3 2.02 m 2.74 m 15 46.5 1.88 d (16.4) 2.03 m 16 153.3 -- 17
104.9 4.90 s 5.69 s 18 28.2 1.32 s 19 176.9 -- 20 16.8 1.38 s 1'
94.9 6.39 d (8.2) 2' 76.9 4.51 t (8.5) 3' 88.6 5.09 t (8.5) 4' 70.1
4.18 m 5' 78.4 4.13 m 6' 61.8 4.20 m 4.31 m 1'' 96.2 5.46 d (7.1)
2'' 81.4 4.13 m 3'' 87.9 4.98 t (8.5) 4'' 70.4 4.07 t (9.6) 5''
77.7 3.94 m 6'' 62.6 4.19 m 4.32 m 1''' 104.8 5.48 d (7.7) 2'''
75.8 4.15 m 3''' 78.6 4.13 m 4''' 73.2 3.98 m 5''' 77.6 3.74 ddd
(2.8, 6.4, 9.9) 6''' 64.0 4.27 m 4.51 m 1'''' 103.9 5.45 d (7.5)
2'''' 75.6 3.98 m 3'''' 77.8 4.50 t (7.8) 4'''' 71.3 4.14 m 5''''
78.0 3.99 m 6'''' 62.1 4.20 m 4.32 m 1''''' 104.2 5.81 d (7.2)
2''''' 75.5 4.20 m 3''''' 78.4 4.20 m 4''''' 73.6 4.10 m 5'''''
77.8 3.90 ddd (2.8, 6.4, 9.9) 6''''' 64.0 4.32 m 4.64 d (10.3)
1'''''' 104.1 5.31 d (8.0) 2'''''' 75.5 3.95 m 3'''''' 78.0 4.37 t
(9.1) 4'''''' 71.1 4.10 m 5'''''' 78.1 3.85 ddd (1.7, 6.1,9.9)
6'''''' 62.1 4.10 m 4.32 m .sup.a assignments made on the basis of
COSY, HMQC and HMBC correlations; .sup.b Chemical shift values are
in .delta. (ppm); .sup.c Coupling constants are in Hz.
[0571] Based on the results from NMR spectral data, it was
concluded that there are six glucosyl units. A close comparison of
the .sup.1H and .sup.13C NMR spectrum of Reb X with rebaudioside D
suggested that Reb X was also a steviol glycoside which had three
glucose residues that attached at the C-13 hydroxyl as a
2,3-branched glucotriosyl substituent and another 2,3-branched
glucotriosyl moiety in the form of an ester at C-19.
[0572] The key COSY and HMBC correlations suggested the placement
of the sixth glucosyl moiety at the C-3 position of Sugar I. The
large coupling constants observed for the six anomeric protons of
the glucose moieties at .delta. 5.31 (d, J=8.0 Hz), 5.45 (d, J=7.5
Hz), 5.46 (d, J=7.1 Hz), 5.48 (d, J=7.7 Hz), 5.81 (d, J=7.2 Hz),
and 6.39 (d, J=8.2 Hz), suggested their .beta.-orientation as
reported for steviol glycosides. Based on the results of NMR and
mass spectral studies and in comparison with the spectral values of
rebaudioside A and rebaudioside D, Reb X was assigned as
13-[(2-O-.beta.-D-glucopyranosyl-3-O-.beta.-D-glucopyranosyl-.beta.-D--
glucopyranosyl)oxy]ent kaur-16-en-19-oic
acid-[(2-O-.beta.-D-glucopyranosyl-3-O-.beta.-D-glucopyranosyl-.beta.-D-g-
lucopyranosyl)ester].
Example 3
Preparation and Characterization of Form A Rebaudioside X
[0573] X-ray amorphous Rebaudioside X was added to a 1:1 mixture of
methanol and water to provide a slurry. The slurry was stirred at
room temperature overnight. The X-ray diffraction pattern of the
Rebaudioside X obtained is shown in FIG. 1. Form A was successfully
indexed, indicating that the sample is composed primarily of a
single crystalline phase. Prominent peaks are provided below:
TABLE-US-00007 TABLE 1 Form A Rebaudioside X Prominent XPRD
.degree.2.THETA. d space (.ANG.) Intensity (%) 3.76 .+-. 0.20
23.489 .+-. 1.319 67 6.50 .+-. 0.20 13.594 .+-. 0.431 58 6.62 .+-.
0.20 13.354 .+-. 0.416 89 6.79 .+-. 0.20 13.025 .+-. 0.395 100 9.93
.+-. 0.20 8.909 .+-. 0.183 36 12.33 .+-. 0.20 7.176 .+-. 0.118 40
12.45 .+-. 0.20 7.109 .+-. 0.116 49 13.69 .+-. 0.20 6.469 .+-.
0.095 44 14.06 .+-. 0.20 6.301 .+-. 0.090 50 15.44 .+-. 0.20 5.738
.+-. 0.075 37 16.25 .+-. 0.20 5.456 .+-. 0.068 46 16.80 .+-. 0.20
5.278 .+-. 0.063 66 20.44 .+-. 0.20 4.345 .+-. 0.042 48
[0574] Non-systematic peak shifts between the X-ray diffraction
patterns of Form A are observed (FIG. 2) and are likely due to unit
cell volume differences and indicate Form A is a variable
hydrate/solvate. The unit cell volume may change to accommodate
varying X-ray diffraction pattern peak positions are a direct
result of the unit cell parameters.
[0575] Approximate methanol content was estimated using proton NMR
spectroscopy. A NMR spectrum was collected on freshly prepared wet
solids isolated by centrifugation. No further drying was applied to
the sample analyzed. The spectrum indicates the presence of
approximately 16 moles of methanol per one mole of Rebaudioside X
(.about.28% of the solvent).
[0576] Approximate water content was estimated by exposing Form A
to ambient relative humidity and measurement by coulometric Karl
Fischer analysis using a Mettler Toledo DL239 Karl Fischer titrator
with a Stromboli oven attachment. Briefly, two replicates of the
sample were placed into the drying oven set at a temperature of
approximately 170.degree. C. The drying oven was purged into the
titrator vessel with dry nitrogen. The samples were then titrated
by means of a generator electrode, which produces iodine by
electrochemical oxidation (2I.sup.-.fwdarw.I.sub.2+2e.sup.-). A
NIST-traceable water standard (Hydranal Water Standard 10.0) was
analyzed to check the operation of the coulometer.
[0577] A water content of .about.11.4% was determined (average of
two experiments) for Form A exposed to relative humidity
(.about.23% RH) for three days, with is consistent with
approximately 9 moles of water.
[0578] Hot stage microscopy (HSM) was performed using a Linkam hot
stage (FTIR 600) mounted on a Leica DM LP microscope equipped with
a SPOT Insight.TM. color digital camera. Temperature calibrations
were performed using USP melting point standards. Samples were
placed on a cover glass, and a second cover glass was placed on top
of the sample. As the stage was heated, each sample was visually
observed using a 20.times. objective with crossed polarizers and a
first order red compensator. Images were captured using SPOT
software (v. 4.5.9). Analysis was conducted under mineral oil and
volatilization (as determined by evolution of gas) was observed at
109.4.degree. C., which supports the observation of desolvation
endotherm from DSC. Recrystallization was not observed upon cooling
to ambient temperature and re-heating to over 200.degree. C.
[0579] The Dynamic Vapor Sorption (DVS) DVS data were collected on
a VTI SGA-100 Vapor Sorption Analyzer. NaCl and PVP were used as
calibration standards. The sample was not dried prior to analysis.
Sorption and desorption data were collected over a range from 5 to
95% RH at 10% RH increments under a nitrogen purge. The equilibrium
criterion used for analysis was less than 0.0100% weight change in
5 minutes with a maximum equilibration time of 3 hours. Data were
not corrected for the initial moisture content of the samples. The
isotherm of the material is shown in FIG. 3.
Example 4
Preparation of Amorphous Rebaudioside X Via Water Process
[0580] A 100 g sample containing Rebaudioside D (1.18%), Form A
Rebaudioside X (97.4%), Rebaudioside A (0.04%)--all percentages
being on a percent dry weight basis--and having water solubility of
0.05%, was mixed with 300 g of water and incubated in thermostatted
oil bath. The temperature was increased at 1.degree. C. per minute
to 121.degree. C. The mixture was maintained at 121.degree. C. for
1 hour and then the temperature was decreased to room temperature
(25.degree. C.) at 1.degree. C. per minute to give a concentrated
solution of Rebaudioside X.
[0581] 100 g of the concentrated solution was dried using YC-015
laboratory spray drier (Shanghai Pilotech Instrument &
Equipment Co. Ltd., China) operating at 175.degree. C. inlet and
100.degree. C. outlet temperature. 20 g of amorphous Rebaudioside X
powder was obtained that had a water solubility greater than 1%.
The X-ray diffraction pattern of the material is shown in FIG.
4.
Example 5
Preparation of Amorphous Rebaudioside X Via Ethanol Process
[0582] 2.5 g Form A Rebaudioside X (97.4% purity, obtained from
Pure Circle) in anhydrous absolute ethanol (500 mL) was refluxed
for 2 hours under a nitrogen atmosphere then cooled to room
temperature. The solvent was then evaporated and dried under vacuum
at 40 C for 2.5 days to provide 2.35 g of a white solid. The X-ray
diffraction pattern of the resulting amorphous Rebaudioside X is
shown in FIG. 4.
Example 6
Characterization of Amorphous Rebaudioside X
[0583] Modulated DSC analysis performed in an attempt to determine
the T.sub.g of the amorphous Rebaudioside X was inconclusive; i.e.
no clear glass transition event was observed under instrumental
parameters examined. A broad endotherm was observed at
approximately 71.degree. C. (peak) from heat flow signal due to the
loss of volatiles (FIG. 5) Dark brown material was noticed at the
end of the test, suggesting degradation.
[0584] Differential Scanning Calorimetry (DSC) was conducted on a
TA Instruments 2920 differential scanning calorimeter. Temperature
calibration was performed using NIST-traceable indium metal. The
sample was placed into an aluminum DSC pan, covered with a lid
(T0CMP--Tzero crimped pan, manual pinhole), and the weight was
accurately recorded. A weighed aluminum pan configured as the
sample pan was placed on the reference side of the cell. The method
was run starting from -30.degree. C. to 250.degree. C., at
10.degree. C./min.
[0585] The DVS isotherm of amorphous Rebaudioside X is shown in
FIG. 6. The material exhibited a 3.1 wt % loss upon equilibration
at 5% RH and gained 26.3 wt % with increasing the relative humidity
from 5% to 95% RH. The material exhibited evidence of hysteresis
with a 26.0 wt % loss upon desorption from 95% to 5% RH. The large
weight change suggests that the material is hygroscopic. The solids
recovered after DVS is x-ray amorphous, suggesting that
crystallization had not occurred during the DVS analysis.
Example 7
Crystallinity of Form A and Amorphous Rebaudioside X
[0586] Polarized Light Microscopy (PLM) was performed using a Leica
MZ12.5 stereomicroscope. Samples were viewed in situ or on a glass
slide (generally covered in mineral oil) with crossed polarizers
and a first order red compensator using various objectives ranging
from 0.8-10.times.. Crystallinity is indicated by the observance of
birefringence and extinction. The results are shown in Table 5.
Polarized Light Microscopy experiments on Form A Rebaudioside X
indicate the material is crystalline. Polarized Light Microscopy
experiments on amorphous Rebaudioside X indicate the material is
non-crystalline.
TABLE-US-00008 TABLE 5 Polarized Light Microscopy Material Result
Form A birefringence and extinction Amorphous (water process)
glass, no birefringence Amorphous (ethanol process) glass, no
birefringence
Example 8
Approximate Water Solubility of Form A and Amorphous Rebaudioside
X
[0587] The approximate water solubility of Form A and amorphous
Rebaudioside X were determined by a solvent addition method in
which a weighed sample was treated with aliquots of water. The
mixture was generally vortexed and/or sonicated between additions
to facilitate dissolution. Complete dissolution of the test
material was determined by visual inspection. Solubility was
estimated based on the total solvent used to provide complete
dissolution. The actual solubility may be greater than the value
calculated because of the use of solvent aliquots that were too
large or due to a slow rate of dissolution.
TABLE-US-00009 TABLE 6 Approximate Water Solubility of Rebaudioside
X Forms Approximate Water Rebaudioside X Form Solubility (mg/mL)
Form A 1.4 Amorphous (water process) >10 Amorphous (ethanol
process) >10
[0588] As shown in Table 6, the approximate water solubility for
amorphous Rebaudioside X--prepared by using either water or ethanol
as the solvent--is substantially increased compared to the
approximate water solubility of Form A Rebaudioside X.
Example 9
Water Solubility of Amorphous Rebaudioside X
[0589] The water solubility of amorphous Rebaudioside X prepared
according to Example 4 was compared in various test material/water
ratios with or without filtration prior to solubility
determination. The results are shown in Table 7. Generally,
filtration performed after dissolution of sample assist the
duration of clarity of the sample (or delays the
precipitation/recrystallization of sample). Based on the benefit of
the filtration process, amorphous Reabudioside X can be sieved to
less than 200 nm of particle size to improve its solubility profile
in aqueous solution.
TABLE-US-00010 TABLE 7 Duration of Rebaudioside X Clarity of Sample
mg/mL water Filtered.dagger. Sample 1 250/500 No >60 days .sup.a
2 500/500 No >60 days .sup.a 3 750/500 No >3 h 4 1000/500 No
--.sup.b 5 625/250 Yes >1 day 6 1750/500 No ~3 h 7 1750/500 Yes
>1 day 8 1000/100 Yes ~2 h .dagger.0.22 .mu.m membrane filter
used using vacuum filtration apparatus. Only ~10 mg of Rebaudioside
X from 1 g of Rebaudioside X remained on the filter. .sup.a The
solution is still clear and the observation is stopped. .sup.bMost
Rebaudioside X dissolved quickly. However, a small amount of
floating particles remained.
Example 10
Determination of Equilibrium Solubility of Rebaudioside X
[0590] Samples were analyzed with a Cary 50 UV-Vis dual beam
spectrophotometer. The detector was zeroed with a cuvette filled
with water prior to sample analysis. Samples were analyzed at room
temperature in 1.0 cm quartz cuvette using a scan rate of 600
nm/min in a range of 200-400 nm.
[0591] 25.8 mg of amorphous Rebaudioside X was added to a 10-mL
volumetric flask and dissolved 10 mL with water. This stock
solution was diluted to five concentration levels for UV
measurement. The UV spectrum of Rebaudioside X was determined at
five concentration levels as listed in Table 8:
TABLE-US-00011 TABLE 8 Stock Solution Final Concentration
Absorbance Sample Volume (mL) Volume (mL) (mg/mL) (205 nm) 1 1.0
500.0 0.00479 0.01981 2 1.0 100.0 0.02394 0.11903 3 1.0 50.0
0.04787 0.24857 4 1.0 10.0 0.23937 1.22797 5 1.0 5.0 0.48784
2.41871
[0592] A calibration curve at 205 nm was established (Abs at 205 nm
vs. concentration) to provide the equation y=5.0625x+0.0022.
R.sup.2 was 0.9999. This equation was used for the subsequent
determination of Rebaudioside X concentrations.
[0593] 250 mg of amorphous Rebaudioside X was added to an amber
vial and 10 mL of water was added. The mixture was stirred at room
temperature about 10 minutes to yield a transparent solution with
only small amount of solid remaining. The mixture became opaque
rapidly. The mixture was placed on a mechanical oscillator set at a
speed of 250 and 25.degree. C. At the sampling time point of 1, 16,
24, 48, 72, 96, and 192 hours, an aliquot of the slurry was
transferred to a centrifuge tube and separated at a speed of 16K
rcf for 15 minutes. 200 .mu.L of the clear supernatant was
transferred to a 50-mL volumetric flask, 10 mL of water was added
and mixed well before UV analysis. The results are summarized in
Table 9.
TABLE-US-00012 TABLE 9 Original Test Test Original Sampling Sample
Sample Sample Test Sample Sample Time Volume Volume Abs
Concentration Concentration Sample (hrs) (mL) (mL) (205 nm) (mg/mL)
(mg/mL) 1 1 0.2 50.0 0.11961 0.02319 5.8 2 16 0.2 10.2 0.26601
0.05211 2.7 3 24 0.2 10.2 0.25924 0.05077 2.6 4 48 0.2 10.2 0.24951
0.04885 2.5 5 72 0.2 10.2 0.27681 0.05424 2.8 6 96 0.2 10.2 0.27687
0.05426 2.8 7 192 0.2 10.2 0.25929 0.05078 2.6 Average Sample
Concentration = 2.6
[0594] Equilibrium was established within 16 hours and equilibrium
solubility was determined to be 2.6 mg/mL. XRPD pattern of the
solids recovered after 8 days solubility testing was consistent
with Form A, indicating conversion.
Example 11
Preparation and Characterization of Form B Rebaudioside X
[0595] Amorphous Rebaudioside X (151.1 mg) was combined with
ethanol (3 mL) to give a slurry. The slurry was stirred at
approximately 40.degree. C. for 5 days, resulting in a white
suspension. The solid was isolated by centrifugation using a
centrifuge tube equipped with a filter. White damp solids were air
dried for approximately 2 hours to provide Form B Rebaudioside X.
The X-ray diffraction pattern is shown in FIGS. 7A and 7B. Form B
was successfully indexed, indicating that the sample is composed
primarily of a single crystalline phase. Non-systematic peak shifts
between the X-ray diffraction patterns of Form B are observed and
are likely due to unit cell volume differences and indicate Form B
is a variable hydrate/solvate. The unit cell volume may change to
accommodate varying X-ray diffraction pattern peak positions are a
direct result of the unit cell parameters. The angular positions
(two theta) of the prominent X-ray diffraction peaks are as
follows:
TABLE-US-00013 TABLE 2 Form B Rebaudioside X Prominent XPRD
.degree.2.THETA. d space (.ANG.) Intensity (%) 4.20 .+-. 0.20
21.058 .+-. 1.053 100 5.17 .+-. 0.20 17.108 .+-. 0.689 41 6.47 .+-.
0.20 13.664 .+-. 0.435 78 7.40 .+-. 0.20 11.939 .+-. 0.331 54 7.92
.+-. 0.20 11.159 .+-. 0.289 99 13.40 .+-. 0.20 6.606 .+-. 0.100 70
14.46 .+-. 0.20 6.127 .+-. 0.085 57 16.08 .+-. 0.20 5.513 .+-.
0.069 65 17.48 .+-. 0.20 5.073 .+-. 0.058 91 18.15 .+-. 0.20 4.888
.+-. 0.054 71
Example 10
Conversion of Material E Rebaudioside X to Form A Rebaudioside
X
[0596] Material E Rebaudioside X was combined with water (6 mL) to
give a slurry. The slurry was agitated on a shaker block at
approximately 60.degree. C. for 6 days. The resulting solids were
isolated by centrifugation for 5 min using a centrifuge tube
equipped with a PVDF membrane filter to provide Form A Rebaudioside
X.
[0597] Material E Rebaudioside X (58.5 mg) was combined with water
(5 mL). The mixture was then stirred at 87.degree. C. to obtain a
clear solution. The solution was cool slowly to ambient temperature
by switching the heat off and left overnight. The resulting solids
were isolated by centrifugation utilizing centrifuge tube equipped
with a PVDF membrane filter to provide Form A Rebaudioside X.
[0598] The DSC of Material E displays a broad endotherm at
approximately 81.degree. C. (peak), likely due to the loss of
volatiles (FIG. 8). An endotherm was observed at -219.degree. C.
(onset), attributable to melting, based on Hot-Stage Microscopy
(HSM) observations.
Example 13
Rebaudioside X Complexes
[0599] 1:4 Mixture of Rebaudioside X and .gamma.-Cyclodextrin
[0600] Rebaudioside X (1.0 g) and .gamma.-cyclodextrin (4.0 g) were
added to water (100 mL) and heated between 100.degree. C. and
120.degree. C. until all materials were dissolved and the mixture
was clear by visual inspection. The mixture was cooled to room
temperature and freeze-dried for two days to provide a white solid
(4.28 g, 86% yield).
[0601] 1:2 Mixture of Rebaudioside X and .gamma.-Cyclodextrin
[0602] Rebaudioside X (2.0 g) and .gamma.-cyclodextrin (4.0 g) were
added to water (100 mL) and heated between 100.degree. C. and
120.degree. C. until all materials were dissolved and the mixture
was clear by visual inspection. The mixture was cooled to room
temperature and freeze-dried for two days to provide a white solid
(5.27 g, 88% yield).
[0603] 1:1 Mixture of Rebaudioside X and .gamma.-Cyclodextrin
[0604] Rebaudioside X (2.0 g) and .gamma.-cyclodextrin (2.0 g) were
added to water (100 mL) and heated between 100.degree. C. and
120.degree. C. until all materials were dissolved and the mixture
was clear by visual inspection. The mixture was cooled to room
temperature and freeze-dried for two days to provide a white solid
(3.37 g, 84%).
1:1 Mixture of Rebaudioside X and Maltodextrin
[0605] Rebaudioside X (1.0 g) and maltodextrin (1.0 g) were added
to water (100 mL) and heated between 100.degree. C. and 120.degree.
C. until all materials were dissolved and the mixture was clear by
visual inspection. The mixture was cooled to room temperature and
freeze-dried for two days to provide a white solid.
[0606] 1:1 Mixture of Rebaudioside X and Erythritol
[0607] Rebaudioside X (1.0 g) and erythritol (1.0 g) were added to
water (100 mL) and heated between 100.degree. C. and 120.degree. C.
until all materials were dissolved and the mixture was clear by
visual inspection. The mixture was cooled to room temperature and
freeze-dried for two days to provide a white solid (1.87 g,
93%).
[0608] The approximate solubility of the complexes was measured by
a solvent addition method in which a weighed sample was treated
with aliquots of water. The mixture was generally vortexed and/or
sonicated between additions to facilitate dissolution. Complete
dissolution of the test material was determined by visual
inspection. Solubility was estimated based on the total solvent
used to provide complete dissolution. The actual solubility may be
greater than the value calculated because of the use of solvent
aliquots that were too large or due to a slow rate of dissolution.
The results are provided in Table 10.
TABLE-US-00014 TABLE 10 Approximate Water Rebaudioside X Complex
Solubility (mg/mL) Rebaudioside X:.gamma.-cyclodextrin (1:4)
>250 Rebaudioside X:.gamma.-cyclodextrin (1:2) >150
Rebaudioside X:.gamma.-cyclodextrin (1:1) >75 Rebaudioside
X:maltodextrin (1:1) >100 Rebaudioside X:erythritol (1:1)
>100
DISCUSSION
[0609] The approximate water solubility of all of the Rebaudioside
X complexes was greater than the approximate solubility of Form A
Rebaudioside X alone (14 mg/mL). Within the complexes, the 1:2 and
1:4 complexes of Rebaudioside X and .gamma.-cyclodextrin provided
the greatest water solubility. The 1:1 complex of Rebaudioside X
and maltodextrin and the 1:1 complex of Rebaudioside X and
erythritol both had water solubilities >100 mg/mL. The 1:1
Rebaudioside X and cyclodextrin complex had a water solubility of
>75 mg/mL.
* * * * *