U.S. patent application number 13/980760 was filed with the patent office on 2013-12-05 for flavour composition comprising menthol and menthane carboxamides.
This patent application is currently assigned to GIVAUDAN S.A.. The applicant listed for this patent is Tracy Bartholomew, Paul Alexander Talsma. Invention is credited to Tracy Bartholomew, Paul Alexander Talsma.
Application Number | 20130323388 13/980760 |
Document ID | / |
Family ID | 43881537 |
Filed Date | 2013-12-05 |
United States Patent
Application |
20130323388 |
Kind Code |
A1 |
Talsma; Paul Alexander ; et
al. |
December 5, 2013 |
FLAVOUR COMPOSITION COMPRISING MENTHOL AND MENTHANE
CARBOXAMIDES
Abstract
The invention relates to flavour compositions comprising a
mixture of coolant compounds comprising menthol and a menthane
carboxamide selected from N-(4-cyanomethylphenyl)
p-menthanecarboxamide,
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide,
or a mixture of N-(4-cyanomethylphenyl) p-menthanecarboxamide and
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide,
wherein the total amount of menthane carboxamide is about 0.1 to
10%.
Inventors: |
Talsma; Paul Alexander;
(Ashford Kent, GB) ; Bartholomew; Tracy; (Ashford
Kent, GB) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Talsma; Paul Alexander
Bartholomew; Tracy |
Ashford Kent
Ashford Kent |
|
GB
GB |
|
|
Assignee: |
GIVAUDAN S.A.
Vernier
CH
|
Family ID: |
43881537 |
Appl. No.: |
13/980760 |
Filed: |
February 23, 2012 |
PCT Filed: |
February 23, 2012 |
PCT NO: |
PCT/EP12/53082 |
371 Date: |
August 15, 2013 |
Current U.S.
Class: |
426/533 |
Current CPC
Class: |
A61K 8/42 20130101; A23L
27/203 20160801; A61K 8/4926 20130101; A23V 2002/00 20130101; A61K
2800/805 20130101; A61Q 11/00 20130101; A61K 8/34 20130101; A61K
2800/92 20130101; A23L 27/205 20160801; A61K 2800/244 20130101;
A23L 27/2054 20160801 |
Class at
Publication: |
426/533 |
International
Class: |
A61Q 11/00 20060101
A61Q011/00; A23L 1/226 20060101 A23L001/226 |
Foreign Application Data
Date |
Code |
Application Number |
Feb 23, 2011 |
GB |
1103103.6 |
Claims
1. A flavour composition comprising a mixture of coolant compounds
comprising menthol and a menthane carboxamide selected from
N-(4-cyanomethyl phenyl) p-menthanecarboxamide,
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide,
or a mixture of N-(4-cyanomethylphenyl) p-menthane carboxamide and
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexane
carboxamide, wherein the amount of menthol represents less than 50%
by weight of the total flavour composition and the total amount of
menthane carboxamide is about 0.1 to 10%.
2. The flavour composition according to claim 1 wherein the amount
of menthol in the flavour composition is about 1% to 50% by
weight.
3. The flavour composition according to claim 1 wherein the total
amount of menthane carboxamide in the flavour composition is about
0.1 to 10% by weight.
4. The flavour composition according to claim 1 wherein the
menthane carboxamide consists of N-(4-cyanomethylphenyl)
p-menthanecarboxamide in an amount of 0.1 to 3% by weight of the
flavour composition.
5. The flavour composition according to claim 1 wherein the
menthane carboxamide consists of
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide
in an amount of 0.1 to 10% by weight of the flavour
composition.
6. The flavour composition according to claim 1 wherein the
menthane carboxamide consists of a mixture of
N-(4-cyanomethylphenyl) p-menthanecarboxamide and
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexane
carboxamide, said mixture being provided in an amount of 0.1 to 13%
by weight. of the flavour composition.
7. The flavour composition according to claim 1 wherein the mixture
of N-(4-cyanomethylphenyl) p-menthanecarboxamide and
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide
is provided in a ratio of 1:100 to 30:1.
8. A consumer product composition comprising a flavour composition
as defined in claim 1.
9. The consumer product composition according to claim 8 that is an
oral care product.
10. A method of compacting the amount of menthol employed in a
flavour composition, comprising the step of adding to said flavour
composition a mixture of menthol and menthane carboxamide as
defined in claim 1.
11. A method of compacting the amount of coolant employed in a
flavour composition, comprising the step of adding to said flavour
composition a mixture of menthol and menthane carboxamide as
defined in claim 1.
12. A method of compacting the amount of coolant in a composition
comprising the steps of: I) screening the composition comprising
menthol against a panel of consumers to determine a first
preference score for said composition; II) removing an amount of
menthol from said composition and adding an amount of
N-(4-cyanomethylphenyl) p-menthanecarboxamide,
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide,
or a mixture of N-(4-cyanomethylphenyl) p-menthane carboxamide and
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexane
carboxamide, which amount carboxamide added is lower than the
amount of menthol removed on a weight basis, and subjecting it to a
screening against a panel of consumers to obtain a second
preference score that is higher than said first preference
score.
13. The flavour composition according to claim 1 wherein the amount
of menthol in the flavour composition is 5 to 30% by weight.
14. The flavour composition according to claim 1 wherein the total
amount of menthane carboxamide in the flavour composition is 0.5 to
8% by weight.
15. The flavour composition according to claim 1 wherein the
menthane carboxamide consists of N-(4-cyanomethylphenyl)
p-menthanecarboxamide in an amount of 0.5 to 2% by weight of the
flavour composition.
16. The flavour composition according to claim 1 wherein the
menthane carboxamide consists of
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexane
carboxamide in an amount of 0.5 to 7% by weight of the flavour
composition.
17. The flavour composition according to claim 1 wherein the
menthane carboxamide consists of a mixture of
N-(4-cyanomethylphenyl) p-menthanearboxamide and
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide,
said mixture being provided in an amount of 1 to 9% by weight of
the flavour composition.
18. The flavour composition according to claim 1 wherein the
mixture of N-(4-cyanomethylphenyl) p-menthanecarboxamide and
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide
is provided in a ratio of 1:15 to 4:1.
Description
[0001] The present invention is concerned with flavour compositions
comprising menthol and menthane carboxamides, and in particular,
with such compositions containing low levels of menthol. The
invention is also concerned with consumable products, in particular
oral care products, containing said flavour compositions.
[0002] A large number of coolant compounds of natural or synthetic
origin have been described in the art. However, the most well-known
compound is menthol, particularly I-menthol, which is found
naturally in peppermint oil, notably of Mentha arvensis L and
Mentha viridis L. Of the isomers of menthol, the I-isomer occurs
most widely in nature and is typically what is referred by the name
menthol having coolant properties. L-menthol has the characteristic
peppermint odor, has a clean fresh taste and exerts a cooling
sensation when applied to the skin and mucosal surfaces.
[0003] In order to deliver a strong consumer perception of
freshness and cooling, flavours, in particular peppermint flavours,
can exceed 50% by weight of menthol and it is not uncommon to find
60% or more.
[0004] However, despite it having gained very wide acceptance and
use, menthol, when used alone, has an initial high flavour impact,
but the flavour impact drops sharply within a few minutes after use
and it tends to distort flavour notes and render the products
containing it bitter. Furthermore, as well as bitterness problems,
very high levels of menthol can restrict flavour creation and cause
additional processing constraints.
[0005] In order to address some of the drawbacks of menthol use, it
has become increasingly common to use it in admixture with other
coolant compounds, most notably the N-substituted-p-menthane
carboxamides. For example, GB233873 discloses such mixtures in
order to provide different cooling profiles and even longer lasting
coolant effects. Menthol-only formulations are compared with
mixtures in which the amounts of menthol are reduced and replaced
with like amounts of a menthane carboxamide coolant.
[0006] A challenge faced by the flavours industry today, is the
drive from the consumer products companies to reduce the levels of
non-active materials contained in their compositions. This is
related, obviously to cost, but also to the need for
sustainability, and the need to deliver greener products to the
marketplace.
[0007] Accordingly, it is desirable to reduce the level of menthol
without the loss of sensorial attributes and consumer liking
attendant with its use. If one can reduce or compact the amount of
a major component used in a flavour composition, one can, in turn,
compact the amount of flavour composition used in consumer
products, or alternatively one can exploit the use of lower levels
of menthol to permit the use of more flavour ingredients thereby
increasing a flavourist's latitude to create new and interesting
flavour profiles and drive consumer preference. None of this would
be possible, of course, if by reducing menthol one simply replaces
it with other coolant materials in like amounts.
[0008] The applicant has now found that by employing certain
menthane carboxamides in a flavour composition, it is possible to
significantly reduced the amount of menthol conventionally employed
in such compositions, whilst at the same time providing
compositions having acceptable coolant and freshness effects, and
which are favourably received by consumers in preference tests.
[0009] The invention provides in a first aspect a flavour
composition comprising a mixture of coolant compounds consisting of
menthol and a menthane carboxamide selected from
N-(4-cyanomethylphenyl) p-menthanecarboxamide,
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide,
or a mixture of N-(4-cyanomethylphenyl) p-menthanecarboxamide and
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide,
wherein the total amount of menthane carboxamide is about 0.1 to
10%.
[0010] In a particular embodiment of the invention there is
provided a flavour composition comprising a mixture of coolant
compounds consisting of menthol and a menthane carboxamide selected
from N-(4-cyanomethylphenyl) p-menthanecarboxamide,
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide,
or a mixture of N-(4-cyanomethylphenyl) p-menthanecarboxamide and
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide,
wherein the amount of menthol represents less than 70%, more
particularly less than 50% by weight of the total flavour
compositions and the total amount of menthane carboxamide is about
0.1 to 10%.
[0011] In a preferred embodiment of the invention, menthol is used
in admixture with
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide
alone or in combination with N-(4-cyanomethylphenyl)
p-menthanecarboxamide.
[0012] The total amount of menthol used in the flavour compositions
of the present invention is an effective amount, when taken in
conjunction with the menthane carboxamides, to provide a good
cooling and breath freshening perception without bitterness. The
exact amount of the menthol employed in the cooling compositions is
a matter of preference subject to such factors as the degree of
vapour action desired. Thus, the amount of menthol may be varied
within the limits stated herein in order to obtain the result
desired in the final product and such variations are within the
capabilities of those skilled in the art without the need for undue
experimentation.
[0013] In a particular embodiment of the invention the amount of
menthol in the total flavour is about 1% to 50% by weight, still
more particularly 5 to 30% by weight.
[0014] In a particular embodiment of the invention the total amount
of menthane carboxamide in the total flavour is about 0.1 to 10% by
weight, still more particularly 0.5 to 8% by weight.
[0015] In a particular embodiment the menthane carboxamide consists
of N-(4-cyanomethylphenyl) p-menthanecarboxamide in an amount of
0.1 to 3% by weight in the total flavour, more particularly 0.5 to
2% by weight.
[0016] In yet another particular embodiment the menthane
carboxamide consists of
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide
in an amount of 0.1 to 10% by weight, more particularly 0.5 to 7%
by weight.
[0017] In yet another particular embodiment the menthane
carboxamide consists of a mixture of N-(4-cyanomethylphenyl)
p-menthanecarboxamide and
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide,
said mixture being provided in an amount of 0.1 to 13% by weight,
more particularly 1 to 9% by weight of the total flavour
composition.
[0018] In yet another particular aspect of the invention the
mixture of N-(4-cyanomethylphenyl) p-menthanecarboxamide and
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide
is provided in a ratio of 1:100 to 30:1, more particularly 1:15 to
4:1.
[0019] The flavour compositions of the present invention
surprisingly provided cooling and freshening effects that meet with
high ratings in consumer preference testing despite reducing or
compacting the amount of menthol and not replacing it with a
similar amount of the menthane carboxamides. In other words, both
menthol and the total coolant compounds are compacted. This result
is indeed surprising as one cannot simply rationalise the finding
on the basis that the menthane carboxamides are simply exerting a
far greater cooling effect than menthol. The consumer preference
tests do not merely reflect the intensity of cooling, indeed, if a
coolant composition is too intense it can be offensive and
unpleasant and rate poorly in consumer preference tests. Rather,
the tests reflect an overall impression of liking and
pleasantness.
[0020] Furthermore, particularly in consumer product compositions
that are functional, such as oral care compositions, the coolant
properties of a composition can act as a sensorial cue, informing
the user of the compositions efficacy, and this can drive
preference or liking for these types of products also. Both of the
menthane carboxamides employed in the present invention exhibit a
rather pronounced tingling sensation when applied to mucosal
surfaces, particular the oral mucosa, which is particularly of
interest in imparting this sensorial cue.
[0021] The invention provides in another of its aspects a method of
compacting the amount of menthol employed in a flavour composition,
comprising the step of adding to said flavour composition a mixture
of menthol and menthane carboxamides as hereinabove defined.
[0022] The invention provides in yet another of its aspects a
method of compacting the amount of coolant compounds employed in a
flavour composition, comprising the step adding to said flavour
composition a mixture of menthol and menthane carboxamides as
hereinabove defined.
[0023] In a particular embodiment of the present invention there is
provided a method of compacting the amount of menthol contained in
a composition comprising the steps of:
[0024] I) screening the composition comprising menthol against a
panel of consumers to determine a first preference score for said
composition;
[0025] II) removing an amount of menthol from said composition and
adding an amount of N-(4-cyanomethylphenyl) p-menthanecarboxamide,
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide,
or a mixture of N-(4-cyanomethylphenyl) p-menthanecarboxamide and
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide,
which amount added is lower than the amount of menthol removed on a
weight basis, and subjecting it to a screening against a panel of
consumers to obtain a second preference score that is higher than
said first preference score.
[0026] The consumer test employed may be any of those test designs
known and used by market researchers for determining preference or
liking for taste of consumer products. For example, the test may be
a Sequential Monadic evaluation of a pre-defined balanced Latin
Square design wherein all products are tested by respondents.
Further particulars of a suitable test are provided in the
examples, below.
[0027] The menthane carboxamides as referred to above are described
in International Publications WO 2005/049553 and WO
2007/019719.
[0028] The menthane carboxamides employed in the present invention
contain asymmetric carbon atoms. Such diasteromeric mixtures can be
separated into their individual diastereomers on the basis of their
physical chemical differences by methods known per se, for example,
by chromatography and/or fractional crystallization. Enantiomers
can be separated by converting the enantiomeric mixtures into a
diastereomric mixture by reaction with an appropriate optically
active compound separating the diastereomers and converting the
individual diastereomers to the corresponding pure enantiomers. All
such isomers, including diastereomers mixtures and pure enantiomers
are considered as part of the invention.
[0029] Particular examples of menthane carboxamides are the optical
isomers shown below:
##STR00001##
[0030] The flavour compositions according to the invention may
additionally comprise flavouring agents, sweetening agents and
other auxiliaries commonly used in the formulation of such
compositions.
[0031] Flavouring agents include but are not limited to:
[0032] natural flavors, artificial flavors, spices, seasonings, and
the like. Exemplary flavoring agents include synthetic flavor oils
and flavoring aromatics and/or oils, oleoresins, essences,
distillates, and extracts derived from plants, leaves, flowers,
fruits, and so forth, and a combination comprising at least one of
the foregoing.
[0033] Exemplary flavor oils include spearmint oil, cinnamon oil,
oil of wintergreen (methyl salicylate), peppermint oil, Japanese
mint oil, clove oil, bay oil, anise oil, eucalyptus oil, thyme oil,
cedar leaf oil, oil of nutmeg, allspice, oil of sage, mace, oil of
bitter almonds, and cassia oil; useful flavoring agents include
artificial, natural and synthetic fruit flavors such as vanilla,
and citrus oils including lemon, orange, lime, grapefruit, yazu,
sudachi, and fruit essences including apple, pear, peach, grape,
blueberry, strawberry, raspberry, cherry, plum, prune, raisin,
cola, guarana, neroli, pineapple, apricot, banana, melon, apricot,
ume, cherry, raspberry, blackberry, tropical fruit, mango,
mangosteen, pomegranate, papaya and so forth. Additional exemplary
flavors imparted by a flavoring agent include a milk flavor, a
butter flavor, a cheese flavor, a cream flavor, and a yogurt
flavor; a vanilla flavor; tea or coffee flavors, such as a green
tea flavor, an oolong tea flavor, a tea flavor, a cocoa flavor, a
chocolate flavor, and a coffee flavor; mint flavors, such as a
peppermint flavor, a spearmint flavor, and a Japanese mint flavor;
spicy flavors, such as an asafetida flavor, an ajowan flavor, an
anise flavor, an angelica flavor, a fennel flavor, an allspice
flavor, a cinnamon flavor, a chamomile flavor, a mustard flavor, a
cardamom flavor, a caraway flavor, a cumin flavor, a clove flavor,
a pepper flavor, a coriander flavor, a sassafras flavor, a savory
flavor, a Zanthoxyli Fructus flavor, a perilla flavor, a juniper
berry flavor, a ginger flavor, a star anise flavor, a horseradish
flavor, a thyme flavor, a tarragon flavor, a dill flavor, a
capsicum flavor, a nutmeg flavor, a basil flavor, a marjoram
flavor, a rosemary flavor, a bayleaf flavor, and a wasabi (Japanese
horseradish) flavor; a nut flavor such as an almond flavor, a
hazelnut flavor, a macadamia nut flavor, a peanut flavor, a pecan
flavor, a pistachio flavor, and a walnut flavor; alcoholic flavors,
such as a wine flavor, a whisky flavor, a brandy flavor, a rum
flavor, a gin flavor, and a liqueur flavor; floral flavors; and
vegetable flavors, such as an onion flavor, a garlic flavor, a
cabbage flavor, a carrot flavor, a celery flavor, mushroom flavor,
and a tomato flavor.
[0034] In some embodiments, other flavoring agents include
aldehydes and esters such as cinnamyl acetate, cinnamaldehyde,
citral diethylacetal, dihydrocarvyl acetate, eugenyl 49 formate,
p-methylamisol, and so forth can be used. Further examples of
aldehyde flavorings include acetaldehyde (apple), benzaldehyde
(cherry, almond), anisic aldehyde (licorice, anise), cinnamic
aldehyde (cinnamon), citral, i.e., alpha-citral (lemon, lime),
neral, i.e., beta-citral (lemon, lime), decanal (orange, lemon),
ethyl vanillin (vanilla, cream), heliotrope, i.e., piperonal
(vanilla, cream), vanillin (vanilla, cream), alpha-amyl
cinnamaldehyde (spicy fruity flavors), butyraldehyde (butter,
cheese), valeraldehyde (butter, cheese), citronellal (modifies,
many types), decanal (citrus fruits), aldehyde C-8 (citrus fruits),
aldehyde C-9 (citrus fruits), aldehyde C-12 (citrus fruits),
2-ethyl butyraldehyde (berry fruits), hexenal, i.e., trans-2 (berry
fruits), tolyl aldehyde (cherry, almond), veratraldehyde (vanilla),
2,6-dimethyl-5-heptenal, i.e., melonal (melon), 2,6-dimethyloctanal
(green fruit), and 2-dodecenal (citrus, mandarin), and the like.
Generally any flavoring or food additive such as those described in
Chemicals Used in Food Processing, publication 1274, pages 63-258,
by the National Academy of Sciences, can be used. This publication
is incorporated herein by reference.
[0035] Some of the flavour ingredients useful in the present
invention may contain menthol, for example peppermint oil. For the
purpose of the present invention, the amounts of menthol referred
to herein relate to the amounts of free menthol added to the
flavour composition and it does not relate to any menthol that
might be contained in a flavour ingredient, such as a flavour
oil.
[0036] The amount of flavouring agents employed in the flavour
formulation may typically be from about 1% to about 99%, and the
particular amounts may vary depending on the nature of the flavour
formulation created.
[0037] Sweetening agents include but are not limited:
[0038] high intensity sweetening agents. High intensity sweetening
agents have a sweetness intensity substantially greater than that
of sucrose. Suitable high intensity sweetening agents include
water-soluble natural sweetening agents such as dihydrochalcones,
monellin, Stevia Rebaudiana (steviosides), glycyrrhizin, and
mixtures thereof. Suitable water-soluble artificial sweetening
agents include saccharin and its soluble salts, i.e., sodium and
calcium saccharin salts, cyclamate and its salts,
3,4-dihydro-6-methyl 1.2,3-oxathiazine4-one-2.2-dioxide
(Acesulfame) and the sodium ammonium, and calcium salts thereof,
and especially the potassium salt of
3,4-dihydro-6-methyl-1,2,3-oxathiazine4-one-2.2-dioxide
(Acesulfame-K).
[0039] Suitable dipeptide based sweetening agents include
L-aspartic acid derived sweetening agents such as
L-aspartyl-L-phenvlalanine methyl ester (Aspartame), compounds
described in U.S. Pat. No. 3,492,131, L-alpha
aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide hydrate
(Alitame), methyl esters of L-aspartvl-L-phenylglycerine and
L-aspartyl-L-2,5-dihvdrophenylglycine,
Laspartyl-2.5-dihydro-L-phenyl-alanine, and
L-aspartyl-L-(I-cyclohexen)alanine.
[0040] Other suitable water-soluble sweetening agents include those
derived from naturally occurring water-soluble sweetening agents
such as chlorinated derivatives of sucrose, e.g., chlorodeoxysugar
derivatives such as derivatives of chlorodeoxysucrose and
chlorodeoxy-galactosucrose. Examples of chlorodeoxysucrose and
chlorodeoxygalactosucrose derivatives include but are not limited
to I-chloro-I'-deoxysucrose;
4-chloro-4-deoxy-alpha-D-galacto-pyranosyl-alpha-D-fructofuranoside,
or 4-chloro-4-deoxygalactosucrose;
4-chloro-4-deoxy-alpha-D-galacto-pyranosyl-1-chloro-I
deoxy-beta-D-fructo-ftrranoside, or
4,1'-dichloro-4,1'dideoxygalactosucrose;
1',6'-dichloro-I',6'-dideoxysucrose;
4-chloro-4-deoxy-alpha-D-galacto-pyranosyl-1,6-dichloro-I,6-dideoxy-beta--
D-fructo-furanoside, or
4,1',6'-trichloro-4,1',6'-trideoxygalacto-sucrose;
4,6dichloro-4,6-dideoxy-alpha-D-galacto-pvranosvl-6-chloro-6-deoxy-beta-D-
-fructo-furanoside, or
4,6,6'-trichloro-4,6,6'-trideoxygalacto-sucrose,
6,1',6'-trichloro-6,1',6'-trideoxysucrose;
4,6-dichloro4,6-dideoxy-alpha-D-galacto-pvranosyl-I.6-dichloro-I,6-di-deo-
xy-beta-D-fructofuranoside, or
4,6,1',6'-tetrachloro-4,6,1',6'-tetradeoxygalacto-sucrose; and
4,6,1',6'-tetrachloro4,6,1',6'-tetradeoxy-sucrose. In a preferred
embodiment, the chlorodeoxysugar derivative is 4,1',6'
trichloro-4,1',6'-trideoxygalacto-sucrose, or 4-chloro
4-deoxy-alpha-D-galactopyranosyl-1,6dichloro
1,6dideoxy-beta-D-fructofuranoside, which is commercially available
under the tradename Sucralose from McNeil Specialty Products
Company, Skillman, N.J.
[0041] Other suitable high intensity sweetening agents include
protein based sweetening agents such as talin (thaumaoccous
danielli, Thaumatin I and II).
[0042] The amount of sweetening agent employed in the flavour
formulation may typically be from about 0.001% to about 1%, but
greater or lesser amounts may be employed depending on the nature
of the flavour formulation created.
[0043] Auxilliaries are materials used in flavour formulations for
their attributes and properties other than their ability to impart
flavour or sweetening effects. Auxilliaries include additives,
surfactants, emulsifiers, superfatting agents, bodying agents,
thickeners, polymers, silicone compounds, fats, waxes, stabilizers,
preservatives, antioxidants, dyes, antimicrobial agents, solvents
and co-solvents; viscosity and rheology modifiers; gelling agents;
preservative materials such as fungicides and bactericides;
pigments, dyestuffs and colouring matters; extenders, fillers and
reinforcing agents; stabilisers against the detrimental effects of
heat and light; bulking agents, which may include mineral
adjuvants, which may serve as fillers and textural agents. Suitable
mineral adjuvants include calcium carbonate, magnesium carbonate,
alumina, aluminum hydroxide, aluminum silicate, talc, tricalcium
phosphate, tricalcium phosphate and the like, which can serve as
fillers and textural agents.
[0044] Additional bulking agents (carriers, extenders) suitable for
use include sweetening agents such as monosaccharides,
disaccharides, polysaccharides, sugar alcohols, polydextrose, and
maltodextrins; minerals, such as calcium carbonate, talc, titanium
dioxide, dicalcium phosphate; and combinations thereof.
[0045] Fillers modify the texture and aid processing. Examples of
such fillers include magnesium and aluminum silicates, clay,
alumina, talc, titanium oxide, cellulose polymers, and the
like.
[0046] Other suitable and desirable additives are described in
standard texts, such as "Handbook of Industrial Chemical
Additives", ed. M. and I. Ash, 2.sup.nd Ed., (Synapse 2000).
[0047] The flavour compositions, or particular ingredients thereof
may be provided in many distinct physical forms, for example solid,
liquid or encapsulated forms. Selection of the particular form may
be selected by reason of ease of handling or storage, or in order
to achieve a particular effect such as sustained or controlled
release. By "encapsulated form" is meant that a material or
ingredient is contained within an encapsulating material, which
protects and/or retains it and permits its release either gradually
or completely. All known methods of encapsulation, may be used, for
example, coacervation, spray drying, absorption into a porous
substrate and the like. All possible encapsulation materials may
also be used, for example, natural fibres, minerals of large
surface area and polymeric materials.
[0048] The amount of flavour composition employed in a consumer
product may vary according to the particular effect that is
desired. Typically, however, the flavour composition may be used in
an amount of about 0.01 to 2% by weight based on the weight of the
consumer product, more particularly 0.1 to 1.5% by weight.
[0049] The flavour compositions according to the invention may be
used in any manner of consumable products. By "consumable products"
is meant any product intended to be applied to the body, or placed
in the mouth before discarding (e.g. by rinsing) or ingesting, for
the purpose of therapy, treatment, nourishment or enjoyment.
Consumable products may be in any physical form such as creams,
gels, lotions, alcoholic and aqueous/alcoholic solutions,
emulsions, dispersions, stick preparations or the like.
[0050] Flavour compositions may be employed in consumable products
for use in oral care.
[0051] In relation to consumable products, "oral care" relates to
any product applied to the oral cavity for the purposes of
cleaning, freshening, healing, deodorising the cavity or any part
thereof. Such compositions include, but are not limited to,
toothpastes, toothgels, tooth powders, tooth whitening products,
mouthwashes, lozenges, dental floss, tooth picks, anti-plaque and
anti-gingivitis compositions, throat lozenges, throat drops,
inflammatory compositions, compositions for treatment of nasal
symptoms, cold symptoms and upper gastrointestinal tract distress,
compositions for cold relief, for alleviating discomfort of hot
flash, gargle compositions.
[0052] Oral care products utilising these compounds may be prepared
by blending a flavour composition with one or more of the
conventional ingredients normally associated with such products, in
standard quantities. Examples of such standard ingredients include,
but are not limited to, Mentha Arvensis, Mentha Piperita, Mentha
Spicata, Mentha Cardiaca, Synthetic Mints, Anethole, Methyl
Salicylate, Eucalyptol, Cinnamic Aldehyde, Eugenol, Calcium
Carbonate, Silica (Precipitates & Xerogels), Dicalcium
Phosphate, Alumina, Sodium Lauryl Sulphate, Betaine, Glycerine,
Sorbitol, Water, Saccharin, Sodium Cyclamate, Aspartame, Xylitol,
Sodium Carboymethyl Cellulose, Methyl Cellulose, Sodium
Carageenate, Xanthan Gum, Polyvinyl Pyrrolidone, Sodium
Tripolyphosphate, Ethyl Alcohol, Sodium Fluoride, Sodium
Monofluorophosphate, Stannous Fluoride, Potassium Citrate,
Potassium Chloride, Potassium Nitrate, Strontium Acetate, Strontium
Chloride, Sodium Tripolyphosphate, Cetyl Pyridinium Chloride,
Hexetidine, Sanguinarine, Triclosan, Chlorhexidine, Zinc Citrate,
Zinc Sulphate, Zinc Chloride, Calcium Glycerophosphate, Sodium
Bicarbonate, Tetra Sodium Pyrophosphate, Tetra Potassium
Pyrophosphate.
[0053] Some of these materials may be present in encapsulated form,
as this term is described above.
[0054] The flavour compositions according to the invention may be
used in personal care products such as pharmaceuticals, cosmetics
and toiletries.
[0055] When used within cosmetics and toiletries, the formulations
can be used in any of the "Reported Product Categories" listed by
the Cosmetic, Toiletries and Fragrance Association's `International
Cosmetic Ingredient Dictionary and Handbook`, and with any one or
more of the ingredients cited as being used for the reported
product categories.
[0056] The Reported Product Categories are: Aftershave lotions,
Baby lotions, oils, powders and creams, Baby products
miscellaneous, Baby shampoos, Basecoats and undercoats, Bath
capsules, Bath oils, tablets and salts, Bath preparations
miscellaneous, Bath soaps and detergents, Beard softeners,
Blushers, Body and hand preparations, Bubble baths, Cleaning
products, Colognes and toilet waters, Cuticle softeners,
Dentifrices, Deodorants, Depilatories, Douches, Eye lotions, Eye
makeup preparations miscellaneous, Eye makeup removers, Eye
shadows, Eyebrow pencils, Eyeliners, Face and neck preparations,
Face powders, Feminine hygiene deodorants, Foot powders and sprays,
foundations, Fragrance preparations miscellaneous, Hair bleaches,
Hair colour sprays, Hair colouring preparations miscellaneous, Hair
conditioners, Hair dyes and colours, Hair lighteners with colour,
Hair preparations, Hair rinses, Hair shampoos, Hair sprays, Hair
straighteners, Hair tints, Hair wave sets, Indoor tanning
preparations, Leg and body paints, Lipsticks, Makeup bases, Makeup
fixatives, Makeup preparations, Manicuring preparations
miscellaneous, Mascara, Men's talcum, Moisturising preparations,
Mouthwashes and breath fresheners, Nail creams and lotions, Nail
extenders, Nail polish and enamel removers, Nail polish and
enamels, Night skin care preparations, Oral hygiene products
miscellaneous, Paste masks, Perfumes, Permanent waves, Personal
cleanliness products miscellaneous, Powders, Preshave lotions,
Rouges, Sachets, Shampoos, Shaving cream, Shaving preparations
miscellaneous, Shaving soap, Skin care preparations miscellaneous,
Skin fresheners, Suntan gels, creams and liquids, Suntan
preparations miscellaneous, Tonics, dressings and other hair
grooming aids.
[0057] In the preparation of the abovementioned products, there may
be used all or any of the standard Auxilliaries found in such
products and desribed above, used in art-recognised quantities.
[0058] Other suitable and desirable additives or auxilliaries are
described in standard texts, such as "Handbook of Industrial
Chemical Additives", ed. M. and I. Ash, 2.sup.nd Ed., (Synapse
2000).
[0059] Further formulation details useful in association with these
compounds may be found in standard texts, for example, "Handbook of
Cosmetic Science and Technology", ed. Pays, Barel & Maibach,
2.sup.nd Ed. (Dekker, 2005).
[0060] Flavour compositions according to the invention may be used
in foodstuffs of all kinds, confectionery, baked goods, sweet
goods, dairy products and beverages.
[0061] The term "confectionery" includes, but is not limited
to:
[0062] chewing gum (which includes sugarized gum, sugar-free gum,
functional gum and bubble gum), center-fill confections, chocolate
and other chocolate confectionery, medicated confectionery,
lozenges, tablets, pastilles, mints, standard mints, power mints,
chewy candies, hard candies, boiled candies, breath and other oral
care films or strips, candy canes, lollipops, gummies, jellies,
fudge, caramel, hard and soft panned goods, toffee, taffy,
liquorice, gelatin candies, gum drops, jelly beans, nougats,
fondants, or combinations of one or more of these, or edible
compositions incorporating one or more of these.
[0063] The confectionery compositions can be incorporated into an
otherwise conventional hard or soft confectionery format using
standard techniques and equipment known to those of ordinary skill
in the art. The confectionery compositions can also be center
filled and/or coated with hard, soft, or particulate coatings.
[0064] The term "baked goods" includes, but is not limited to:
[0065] alfajores, bread, packaged/industrial bread,
unpackaged/artisanal bread, pastries, cakes, packaged/industrial
cakes, unpackaged/artisanal cakes, cookies, chocolate coated
biscuits, sandwich biscuits, filled biscuits, savory biscuits and
crackers, bread substitutes,
[0066] The term "sweet goods" includes, but is not limited to:
[0067] breakfast cereals, ready-to-eat ("rte") cereals, family
breakfast cereals, flakes, muesli, other rte cereals, children's
breakfast cereals and hot cereals.
[0068] The term "dairy products" includes, but is not limited
to:
[0069] ice cream, impulse ice cream, single portion dairy ice
cream, single portion water ice cream, multi-pack dairy ice cream,
multi-pack water ice cream, take-home ice cream, take-home dairy
ice cream, ice cream desserts, bulk ice cream, take-home water ice
cream, frozen yoghurt, artisanal ice cream, dairy products, milk,
fresh/pasteurized milk, full fat fresh/pasteurized milk, semi
skimmed fresh/pasteurized milk, long-life/uht milk, full fat long
life/uht milk, semi skimmed long life/uht milk, fat-free long
life/uht milk, goat milk, condensed/evaporated milk, plain
condensed/evaporated milk, flavored, functional and other condensed
milk, flavored milk drinks, dairy only flavored milk drinks,
flavored milk drinks with fruit juice, soy milk, sour milk drinks,
fermented dairy drinks, coffee whiteners, powder milk, flavored
powder milk drinks, cream, yoghurt, plain/natural yoghurt, flavored
yoghurt, fruited yoghurt, probiotic yoghurt, drinking yoghurt,
regular drinking yoghurt, probiotic drinking yoghurt, chilled and
shelf-stable desserts, dairy-based desserts and soy-based
desserts.
[0070] Other foodstuff includes, but is not limited to:
[0071] chilled snacks, sweet and savory snacks, fruit snacks,
chips/crisps, extruded snacks, tortilla/corn chips, popcorn,
pretzels, nuts, other sweet and savory snacks, snack bars, granola
bars, breakfast bars, energy bars, fruit bars, other snack bars,
meal replacement products, slimming products, convalescence drinks,
ready meals, canned ready meals, frozen ready meals, dried ready
meals, chilled ready meals, dinner mixes, frozen pizza, chilled
pizza, soup, canned soup, dehydrated soup, instant soup, chilled
soup, uht soup, frozen soup, pasta, canned pasta, dried pasta,
chilled/fresh pasta, noodles, plain noodles, instant noodles,
cups/bowl instant noodles, pouch instant noodles, chilled noodles,
snack noodles, dried food, dessert mixes, sauces, dressings and
condiments, herbs and spices, spreads, jams and preserves, honey,
chocolate spreads, nut-based spreads, and yeast-based spreads.
[0072] The term "beverage" as used herein means any drinkable
liquid or semi-liquid, including for example:
[0073] flavored water, soft drinks, fruit drinks, coffee-based
drinks, tea-based drinks, juice-based drinks (includes fruit and
vegetable), milk-based drinks, gel drinks, carbonated or
non-carbonated drinks, powdered drinks, alcoholic or non-alcoholic
drinks.
[0074] In the preparation of the abovementioned products, there may
be used all or any of the standard ingredients found in such
products, used in art-recognised quantities. Examples of such
ingredients include (but are by no means limited to) solvents and
co-solvents; surfactants and emulsifiers; viscosity and rheology
modifiers; thickening and gelling agents; preservative materials;
pigments, dyestuffs and colouring matters; extenders, fillers and
reinforcing agents; stabilisers against the detrimental effects of
heat and light, bulking agents, flavoring and flavor-enhancing
agents, warming agents, breath fresheners, mouth moisteners,
coloring agents, acidulants, buffering agents and antioxidants.
[0075] With respect to chewing gum compositions in particular,
suitable components include in addition to a water-insoluble gum
base portion, a water soluble bulk portion and various additives.
The water soluble portion may include sweetening agents, bulking
agents, softening agents and/or plasticizers, waxes, emulsifiers,
thickening agents, flavor enhancing agents, warming agents, breath
fresheners, mouth moisteners, acidulants, coloring agents,
buffering agents, antioxidants, nutraceuticals, medicaments and
other conventional chewing gum additives that provide desired
attributes. Other conventional chewing gum additives known to one
having ordinary skill in the art may also be used in the water
soluble bulk portion.
[0076] Softeners and plasticizers may be used to provide a variety
of desirable textures and consistency properties. Suitable
plasticizers and softeners may include lanolin, palmitic acid,
oleic acid, stearic acid, sodium stearate, potassium stearate,
glyceryl triacetate, glyceryl lecithin, glyceryl monostearate,
propylene glycol monostearate, acetylated monoglyceride, glycerine,
and a combination comprising at least one of the foregoing. Because
of the low molecular weights of these softeners and plasticizers,
they are able to penetrate the fundamental structure of the gum
base, making it plastic and less viscous.
[0077] Waxes may be used in the gum base to soften the elastomer,
improve the elasticity of the gum base, and obtain a variety of
desirable textures and consistency properties. Suitable waxes may
include natural and synthetic waxes, hydrogenated vegetable oils,
petroleum waxes such as polyurethane waxes, polyethylene waxes,
paraffin waxes, microcrystalline waxes, fatty waxes, sorbitan
monostearate, tallow, and propylene glycol. Low melting waxes may
be used in the gum compositions. These waxes typically have a
melting point below about 60.degree. C., and specifically about 45
to about 55.degree. C. High melting waxes may also be used in the
gum base. Such high melting waxes include beeswax, vegetable wax,
candelilla wax, camauba wax, most petroleum waxes, and the like,
and combinations thereof.
[0078] Suitable emulsifiers include distilled monoglycerides,
acetic acid esters of mono and diglycerides, citric acid esters of
mono and diglycerides, lactic acid esters of mono and diglycerides,
mono and diglycerides, polyglycerol esters of fatty acids,
ceteareth-20, polyglycerol polyricinoleate, propylene glycol esters
of fatty acids, polyglyceryl laurate, glyceryl cocoate, gum arabic,
acacia gum, sorbitan monostearates, sorbitan tristearates, sorbitan
monolaurate, sorbitan monooleate, sodium stearoyl lactylates,
calcium stearoyl lactylates, diacetyl tartaric acid esters of mono-
and diglycerides, glyceryl tricaprylate-caprate/medium chain
triglycerides, glyceryl dioleate, glyceryl oleate, glyceryl lacto
esters of fatty acids, glyceryl lacto palmitate, glyceryl stearate,
glyceryl laurate, glycerlyl di laurate, glyceryl monoricinoleate,
triglyceryl monostearate, hexaglyceryl distearate, decaglyceryl
monostearate, decaglyceryl dipalmitate, decaglyceryl monooleate,
polyglyceryl 10 hexaoleate, medium chain triglycerides,
caprylic/capric triglyceride, propylene glycol monostearate,
polysorbate 20, polysorbate 40, polysorbate 60, polysorbate 80,
polysorbate 65, hexylglyceryl distearate, triglyceryl monostearate,
tweens, spans, stearoyl lactylates, calcium stearoyl-2-lactylate,
sodium stearoyl-2-lactylate lecithin, ammonium phosphatide, sucrose
esters of fatty acids, sucroglycerides, propane-1,2-diol esters of
fatty acids, and combinations comprising at least one of the
foregoing.
[0079] Suitable thickening agents include cellulose ethers (e.g.,
hydroxyethyl cellulose, hydroxypropylmethyl cellulose, or
hydroxypropyl cellulose), methylcellulose, carboxymethylcellulose,
and combinations thereof. Additional polymers useful as thickeners
include carbomer, polyvinyl pyrrolidone, polyvinyl alcohol, sodium
alginate, polyethylene glycol, natural gums like xanthan gum,
tragacantha, guar gum, acacia gum, arabic gum, water-dispersible
polyacrylates like polyacrylic acid, methyl methacrylate copolymer,
and carboxyvinyl copolymers.
[0080] A chewing gum composition may additionally contain bulking
agents and fillers, nutraceuticals, medicaments and flavoring
agents, as hereinabove described.
[0081] The chewing gum composition may be coated or compressed, and
be in the form of slabs, sticks, pellets, cubes, trapezoids,
rectangles, or balls. The compositions of the different forms of
the gum compositions will be similar but may vary with regard to
the ratios of the ingredients. Center-filled gum is another common
gum form, the center-fill is typically an aqueous liquid or gel,
which is injected into the center of the gum during processing. The
center-filled gum may also be optionally coated and may be prepared
in various forms, such as in the form of a lollipop.
[0082] There now follows a series of examples that serve to
illustrate the invention.
EXAMPLE 1
[0083] The following three flavours were prepared with propylene
glycol as a diluent to make the flavours up to 100%:
TABLE-US-00001 (A) (B) (C) % w/w % w/w % w/w Peppermint Heart 43.00
43.00 43.00 Menthol 50.00 10.00 10.00 Propylene Glycol 7.00 42.00
45.00 Evercool 190 -- 5.00 -- Evercool 180 -- -- 2.00
[0084] The Flavours were each incorporated into a standard silica
toothpaste base at 1%:
TABLE-US-00002 (1) % (2) % (3) % Silica toothpaste base 99.00 99.00
99.00 Flavour A 1.00 -- -- Flavour B -- 1.00 -- Flavour C -- --
1.00 Evercool 190 =
2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide
Evercool 180 = N-(4-cyanomethylphenyl) p-menthanecarboxamide
[0085] All three toothpastes were coded and given to 37 naive
volunteers. The volunteers were asked to brush the teeth for 30
seconds and score each toothpaste (0-10 scale) for cooling,
tingling and freshness at each of six time points: 0 minutes, 5
minutes, 10 minutes, 20 minutes, 30 minutes and 60 minutes. At the
end of the 60 minutes, they were also asked for their overall
preference scores (0-10 scale). The results are shown in FIGS. 1
through 4.
[0086] Flavour B, containing 10% added menthol and 5% Evercool 190,
performed the best for cooling, tingling and freshness and was most
preferred.
[0087] Flavour C, containing 10% added menthol and 2% Evercool 180,
performed better than flavour A after 10 minutes and was the
strongest performing at 60 minutes. This had similar overall
preference to that of flavour A.
[0088] Low levels of Evercool 190 or Evercool 180 can replace high
levels of menthol in a toothpaste flavour and still provide
superior sensorial benefits and be preferred to the flavour with
the high levels of menthol.
EXAMPLE 2
[0089] Two consumer acceptable flavours containing 74% and 63%
added menthol respectively, had the added menthol removed and
substituted with either Evercool 190 or Evercool 190 and Evercool
180.
TABLE-US-00003 Flavour 1 Flavour 2 Flavour 1 Mod Flavour 2 Mod
Peppermint 26% 26% Heart (Flavour 1) Peppermint 37% 37% Heart
(Flavour 2) Menthol 74% 63% Evercool 190 4% 4% Evercool 180
1.2%
[0090] The flavours were dosed into typical silica toothpaste
according to the following, such that the modified flavours were
dosed at a lower, compacted level:
TABLE-US-00004 Flavour 1 1.20% Flavour 2 1.00% Flavour 1 mod 0.37%
Flavour 2 mod 0.42%
[0091] The two sets of samples were coded and given to 16 naive
volunteers who were asked to brush their teeth for 30 seconds and
score (0-10 scale) for cooling, freshness and tingling at 0
minutes, 5 minutes, 10 minutes, 20 minutes, 30 minutes and 60
minutes. Overall preference was also scored for each flavour (0-10
scale). The results are shown in FIGS. 5 through 8.
[0092] From this study we can conclude that Flavour 2 mod with the
Evercool 190/180 combination was the preferred flavour overall and
gave the best cooling after 5 minutes and the best long lasting
freshness and tingling.
* * * * *