U.S. patent application number 11/732942 was filed with the patent office on 2007-09-27 for cooling compositions including menthyl esters.
This patent application is currently assigned to Cadbury Adams USA LLC.. Invention is credited to Joan E. Harvey, Jesse Kiefer.
Application Number | 20070221236 11/732942 |
Document ID | / |
Family ID | 39831755 |
Filed Date | 2007-09-27 |
United States Patent
Application |
20070221236 |
Kind Code |
A1 |
Kiefer; Jesse ; et
al. |
September 27, 2007 |
Cooling compositions including menthyl esters
Abstract
This description provides cooling compositions that deliver a
prolonged physiological cooling sensation to the skin or a mucous
membrane. The cooling compositions may be present alone or in
product such as a chewing gum or a confection. In some embodiments,
the cooling compositions include menthyl glutarate and at least one
additional cooling agent, which may be WS-3 or WS-23, and
optionally menthol. The cooling compositions may be in a liquid
form at room temperature.
Inventors: |
Kiefer; Jesse; (Oxford,
NJ) ; Harvey; Joan E.; (Morgantown, PA) |
Correspondence
Address: |
HOFFMANN & BARON, LLP
6900 JERICHO TURNPIKE
SYOSSET
NY
11791
US
|
Assignee: |
Cadbury Adams USA LLC.
|
Family ID: |
39831755 |
Appl. No.: |
11/732942 |
Filed: |
April 5, 2007 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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11543473 |
Oct 5, 2006 |
|
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11732942 |
Apr 5, 2007 |
|
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60723698 |
Oct 5, 2005 |
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Current U.S.
Class: |
131/352 |
Current CPC
Class: |
A61K 8/345 20130101;
A23G 4/06 20130101; A61K 2800/244 20130101; A61K 8/34 20130101;
A61K 8/42 20130101; A23G 3/36 20130101; A61K 8/37 20130101; A61Q
11/00 20130101; A23L 27/204 20160801 |
Class at
Publication: |
131/352 |
International
Class: |
A24B 15/00 20060101
A24B015/00 |
Claims
1. A cooling composition consisting essentially of: about 5% to
about 60% by weight menthyl glutarate; about 5% to about 50% by
weight of at least one cooling agent selected from the group
consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl
butanamide and combinations thereof; and about 15% to about 85% by
weight menthol.
2. The cooling composition of claim 1, wherein said menthyl
glutarate is selected from the group consisting of monomenthyl
monomenthyl 2-methylmaleatementhyl glutarate (FEMA 4006),
monomenthyl glutarate ester, dimenthyl glutarate ester, and a
menthyl half acid ester derivative.
3. A chewing gum composition comprising the cooling composition of
claim 1.
4. A confectionery composition comprising the cooling composition
of claim 1.
5. A cooling composition consisting essentially of: about 5% to
about 60% by weight of at least two menthyl esters; about 5% to
about 50% by weight of at least one cooling agent selected from the
group consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl
isopropyl butanamide and combinations thereof; and about 15% to
about 85% by weight menthol.
6. The cooling composition of claim 5, wherein said at least two
menthyl esters are selected from the group consisting of
monomenthyl monomenthyl 2-methylmaleatementhyl glutarate (FEMA
4006), monomenthyl glutarate ester, dimenthyl glutarate ester, a
menthyl half acid ester derivative, menthyl acetate, 1-menthyl
acetate, d,1-menthyl acetate, homomenthyl acetate, menthyl lactate,
1-menthyl lactate, menthyl succinate, monomenthyl succinate, and
combinations thereof.
7. A chewing gum composition comprising the cooling composition of
claim 5.
8. A confectionery composition comprising the cooling composition
of claim 5.
9. A cooling composition comprising: about 5% to about 60% by
weight menthyl glutarate; about 5% to about 50% by weight of at
least one cooling agent selected from the group consisting of
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof; and at least about 75% by weight of the
menthyl glutarate and the at least one cooling agent, wherein said
composition is liquid at 25.degree. C.
10. The cooling composition of claim 9, further comprising menthol
in amounts of about 15% to about 85% by weight of the
composition.
11. The cooling composition of claim 9, wherein said menthyl
glutarate is selected from the group consisting monomenthyl
2-methylmaleatementhyl glutarate (FEMA 4006), monomenthyl glutarate
ester, dimenthyl glutarate ester, and a menthyl half acid ester
derivative.
12. A chewing gum composition comprising the cooling composition of
claim 9.
13. A confectionery composition comprising the cooling composition
of claim 9.
14. A cooling composition comprising: about 5% to about 60% by
weight of at least two menthyl esters; about 5% to about 50% by
weight of at least one cooling agent selected from the group
consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl
butanamide and combinations thereof; and at least about 75% by
weight of the at least two menthyl esters and the at least one
cooling agent, wherein said composition is liquid at 25.degree.
C.
15. The cooling composition of claim 14, further comprising menthol
in amounts of about 15% to about 85% by weight of the
composition.
16. The cooling composition of claim 14, wherein said at least two
menthyl esters are selected from the group consisting of
monomenthyl monomenthyl 2-methylmaleatementhyl glutarate (FEMA
4006), monomenthyl glutarate ester, dimenthyl glutarate ester, a
menthyl half acid ester derivative, menthyl acetate, 1-menthyl
acetate, d,1-menthyl acetate, homomenthyl acetate, menthyl lactate,
1-menthyl lactate, menthyl succinate, monomenthyl succinate, and
combinations thereof.
17. A chewing gum composition comprising the cooling composition of
claim 14.
18. A confectionery composition comprising the cooling composition
of claim 14.
19. A cooling composition consisting essentially of: about 5% to
about 60% by weight menthyl glutarate; about 5% to about 50% by
weight of at least one cooling agent selected from the group
consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl
butanamide and combinations thereof; and about 15% to about 85% by
weight menthol, wherein said composition is liquid at 25.degree.
C.
20. The cooling composition of claim 19, wherein said menthyl
glutarate is selected from the group consisting of monomenthyl
monomenthyl 2-methylmaleatementhyl glutarate (FEMA 4006),
monomenthyl glutarate ester, dimenthyl glutarate ester, and a
menthyl half acid ester derivative.
21. A chewing gum composition comprising the cooling composition of
claim 19.
22. A confectionery composition comprising the cooling composition
of claim 19.
23. A cooling composition consisting essentially of: about 5% to
about 60% by weight of at least two menthyl esters; about 5% to
about 50% by weight of at least one cooling agent selected from the
group consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl
isopropyl butanamide and combinations thereof; and about 15% to
about 85% by weight menthol, wherein said composition is liquid at
25.degree. C.
24. The cooling composition of claim 23, wherein said at least two
menthyl esters are selected from the group consisting of
monomenthyl monomenthyl 2-methylmaleatementhyl glutarate (FEMA
4006), monomenthyl glutarate ester, dimenthyl glutarate ester, a
menthyl half acid ester derivative, menthyl acetate, 1-menthyl
acetate, d,1-menthyl acetate, homomenthyl acetate, menthyl lactate,
1-menthyl lactate, menthyl succinate, monomenthyl succinate, and
combinations thereof.
25. A chewing gum composition comprising the cooling composition of
claim 23.
26. A confectionery composition comprising the cooling composition
of claim 23.
27. A cooling composition comprising: menthyl succinate; a second
cooling agent selected from the group consisting of
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof; and a third cooling agent selected from
the group consisting of 1-isopulegol, p-menthane-3,8-diol and
combinations thereof.
28. The cooling composition of claim 27, wherein said menthyl
succinate is selected from the group consisting of monomenthyl
succinate, dimenthyl succinate and monomenthyl
.alpha.,.alpha.-dimethyl succinate.
29. A chewing gum composition comprising the cooling composition of
claim 27.
30. A confectionery composition comprising the cooling composition
of claim 27.
31. A method of preparing a cooling composition which is liquid at
25.degree. C., comprising the steps of: (a) providing menthyl
glutarate in a liquid form; and (b) adding at least one cooling
agent selected from the group consisting of
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof to the menthyl glutarate and dissolving or
suspending the at least one cooling agent therein to form the
liquid cooling composition, wherein the menthyl glutarate is
present in amounts of about 5% to about 60% by weight of the
composition and the at least one cooling agent selected from the
group consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl
isopropyl butanamide and combinations thereof is present in amounts
of about 5% to about 50% by weight of the composition.
32. The method of claim 31, further comprising the step of adding
menthol in amounts of about 15% to about 85% by weight of the
cooling composition.
33. A method of preparing a cooling composition which is liquid at
25.degree. C., comprising the steps of: (a) combining menthyl
glutarate and at least one cooling agent selected from the group
consisting of N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl
butanamide and combinations thereof; (b) heating the menthyl
glutarate and the at least one cooling agent to form a liquid
composition; and (c) cooling the composition of the menthyl
glutarate and the at least one cooling agent to less than
30.degree. C. while maintaining the composition in a liquid state
to form the liquid cooling composition.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application is a continuation-in-part of U.S.
application Ser. No. 11/543,473, filed Oct. 5, 2006, which claims
the benefit of U.S. Provisional Application No. 60/723,698, filed
Oct. 5, 2005, the contents of which are incorporated herein by
reference.
FIELD
[0002] This description relates to cooling compositions that may be
delivered orally or to the skin or mucous membranes. The
compositions contain one or more cooling agents in combination with
a menthyl ester. The cooling agent(s) and menthyl ester may be
provided in one composition or they may be provided separately in
distinct formulations separated over time or geographically.
BACKGROUND
[0003] Many substances are known to provide a sensation of cooling
on application and are called "cooling agents." Exemplary cooling
agents include menthol, isopulegol, 3-(1-menthoxy)propane-1,2-diol,
3-(1-menthoxy)-2-methylpropane-1,2-diol, p-menthane-2,3-diol,
p-menthane-3,8-diol,
6-isopropyl-9-methyl-1,4-dioxaspiro[4,5]decane-2-methanol, menthyl
succinate and its alkaline earth metal salts,
trimethylcyclohexanol,
N-ethyl-2-isopropyl-5-methylcyclohexanecarboxamide, Japanese mint
oil, peppermint oil, menthone, menthone glycerol ketal, menthyl
lactate, 3-(1-menthoxy)ethan-1-ol, 3-(1-menthoxy)propan-1-ol,
3-(1-menthoxy)butan-1-ol, 1-menthylacetic acid N-ethylamide,
1-menthyl-4-hydroxypentanoate, 1-menthyl-3-hydroxybutyrate,
N,2,3-trimethyl-2-(1-methylethyl)-butanamide, n-ethyl-t-2-c-6
nonadienamide, N,N-dimethyl menthyl succinamide, and menthyl
pyrrolidone carboxylate.
[0004] Despite the existence in the prior art and in commerce of
such a vast number and variety of cooling agents, a need exists for
a cooling composition that will contribute a long-lasting cooling
sensation to products in which it is found without unwanted
harshness or flavor characteristics. It would also be desirable to
provide a clean, high-quality flavor chewing gum with a good
cooling effect without leaving a significant aftertaste. Including
mono menthyl ester-based compounds in food, cosmetic and fragrance
applications may supply a need for cooler compounds which provide
strong and substantive refreshing and cooling attributes in the
absence of negative taste, negative aroma and negative cooling
attributes. There remains a need to provide cooling compositions
which provide good onset of effect and prolonged cooling.
SUMMARY
[0005] The compounds and compositions described herein provide
cooling compositions that deliver a prolonged physiological cooling
sensation to the skin or a mucous membrane. The cooling
compositions may be present alone or in product such as a chewing
gum or a confection.
[0006] In some instances, the cooling compositions may provide for
delivering a sensation substantially similar to that delivered by
WS-3 or WS-23 alone by administering a composition containing a
menthyl ester but where the amount of WS-3 or WS-23 present in the
composition can be reduced relative to the amount of WS-3 or WS-23
alone required to provide a substantially similar sensation.
[0007] In a first embodiment, there is provided a cooling
composition consisting essentially of: about 5% to about 60% by
weight menthyl glutarate; about 5% to about 50% by weight of at
least one cooling agent selected from
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof; and about 15% to about 85% by weight
menthol.
[0008] In some embodiments, there is provided a cooling composition
consisting essentially of: about 5% to about 60% by weight of at
least two menthyl esters; about 5% to about 50% by weight of at
least one cooling agent selected from
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof; and about 15% to about 85% by weight
menthol.
[0009] Some embodiments provide a cooling composition including:
about 5% to about 60% by weight menthyl glutarate; about 5% to
about 50% by weight of at least one cooling agent selected from
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof; and at least about 75% by weight of the
menthyl glutarate and the at least one cooling agent, wherein the
composition is liquid at 25.degree. C.
[0010] Some other embodiments provide a cooling composition
including: about 5% to about 60% by weight of at least two menthyl
esters; about 5% to about 50% by weight of at least one cooling
agent selected from N-ethyl-p-menthane-3-carboxamide, trimethyl
isopropyl butanamide and combinations thereof, and at least about
75% by weight of the at least two menthyl esters and the at least
one cooling agent, wherein the composition is liquid at 25.degree.
C.
[0011] In some embodiments, there is a cooling composition
consisting essentially of: about 5% to about 60% by weight menthyl
glutarate; about 5% to about 50% by weight of at least one cooling
agent selected from N-ethyl-p-menthane-3-carboxamide, trimethyl
isopropyl butanamide and combinations thereof; and about 15% to
about 85% by weight menthol, wherein the composition is liquid at
25.degree. C.
[0012] Some embodiments provide a cooling composition consisting
essentially of: about 5% to about 60% by weight of at least two
menthyl esters; about 5% to about 50% by weight of at least one
cooling agent selected from N-ethyl-p-menthane-3-carboxamide,
trimethyl isopropyl butanamide and combinations thereof; and about
15% to about 85% by weight menthol, wherein the composition is
liquid at 25.degree. C.
[0013] Some other embodiments provide a cooling composition
including: menthyl succinate; a second cooling agent selected from
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof; and a third cooling agent selected from
1-isopulegol, p-menthane-3,8-diol and combinations thereof.
[0014] In some embodiments, there is provided a method of preparing
a cooling composition which is liquid at 25.degree. C., including
the steps of: [0015] (a) providing menthyl glutarate in a liquid
form; and [0016] (b) adding at least one cooling agent selected
from N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl
butanamide and combinations thereof to the menthyl glutarate and
dissolving or suspending the at least one cooling agent therein to
form the liquid cooling composition, [0017] wherein the menthyl
glutarate is present in amounts of about 5% to about 60% by weight
of the composition and the at least one cooling agent selected from
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof is present in amounts of about 5% to about
50% by weight of the composition.
[0018] Some other embodiments provide a method of preparing a
cooling composition which is liquid at 25.degree. C., including the
steps of: [0019] (a) combining menthyl glutarate and at least one
cooling agent selected from N-ethyl-p-menthane-3-carboxamide,
trimethyl isopropyl butanamide and combinations thereof; [0020] (b)
heating the menthyl glutarate and the at least one cooling agent to
form a liquid composition; and [0021] (c) cooling the composition
of the menthyl glutarate and the at least one cooling agent to less
than 30.degree. C. while maintaining the composition in a liquid
state to form the liquid cooling composition.
DETAILED DESCRIPTION
[0022] The description extends to products that otherwise may
contain cooling compositions such as preferably flavoring agents,
foodstuffs, confections, beverages, gums, dentifrices, mouthwashes,
toiletries, liniments lotions for topical application and
cigarettes, such products comprising a composition that provides a
physiological sensation substantially the same as that provided by
menthol. The cooling compositions provide a substantially cooling
physiological sensation.
[0023] Menthol is known for its physiological cooling effect on the
skin and mucous membranes of the mouth and has been extensively
used as a flavouring agent, being a major constituent of oil of
peppermint in foodstuffs, beverages, dentifrices, mouthwashes, etc.
and as a component in a wide range of toiletries, liniments and
lotions for topical application. Menthol is also a well known
tobacco additive for producing a "cool" sensation in the mouth when
smoking. Carvomenthol has also been reported as having a
physiological cooling effect as have N,N-dimethyl-2-ethyl
butanamide and N,N-diethyl-2-ethyl butanamide as described in, for
instance, French Patent No. 1,572,332.
[0024] It is well established that the "cooling" effect of menthol
is a physiological effect due to the direct action of menthol on
the nerve endings of the human body responsible for the detection
of hot and cold. Menthol directly stimulates cold receptors. Some
non-menthol compounds providing a physiological effect similar to
menthol are described in U.S. Pat. No. 4,296,255, herein
incorporated by reference.
[0025] Peppermint oil may be used to create a "cooling" in oral
products such as toothpaste, mouthwash, chewing gum, candy and
other food products. Peppermint oil generally comprises about
45-55% menthol, about 20-25% menthone, about 5% menthyl acetate,
about 5% eucalyptol and many other constituents. Peppermint oil is
even used in non-peppermint products, such as spearmint or
wintergreen flavored products, in order to create this desired
cooling effect. However, peppermint notes are then found in the
resulting non-peppermint flavored products.
[0026] Menthol is also known for its physiological cooling effect
on the skin and mucous membranes of the mouth. Being a major
constituent of peppermint oil, menthol has been used extensively in
foods, beverages, dentifrices, mouthwashes, toiletries, lotions and
the like. The disadvantages of using menthol, however, are its
strong minty odor and the harsh notes it imparts to compositions in
which it is found. Menthol has been used in conjunction with other
cooling agents because, among other things, it acts to prepare
taste buds to receive non-menthol cooling agents. Menthol provides
a light, fresh, minty sensation and in some regards prepares taste
buds to receive a cooling sensation. It has been reported that some
cooling agents, e.g. WS-3 and WS-23, may in fact deliver an initial
warming sensation if supplied without menthol.
[0027] Most confectionery products which are promoted for breath
freshening are mint flavored products which contain moderate to
high levels of menthol. The disadvantages of using menthol,
however, are its strong minty odor and the harsh notes it imparts
to compositions in which it is found. A need, therefore, exists for
a cooling composition that will contribute a long-lasting cooling
sensation to products in which it is found without the unwanted
harshness or flavor characteristics that come from adding
menthol.
[0028] In some consumer products, especially chewing gums, it is
desirable to provide a burst of intense flavor over a slow, gentle
flavor release. In order to provide a favorable flavor impact, some
chewing gum manufacturers have added flavors to the coating of a
coated chewing gum. These flavors include spearmint flavor,
peppermint flavor, wintergreen flavor and fruit flavors. In
addition, very strong flavors such as menthol have often been used
to provide a burst of flavor. However, at concentrations effective
to provide a burst of flavor, menthol or mint flavors also manifest
a bitter, harsh, burning taste sometimes described as a "harsh
note".
[0029] Efforts have been directed at perfecting the use of
physiological cooling agents within chewing gum formulations to
enhance flavor composition and control their release to enhance the
flavor of chewing gum. U.S. Pat. No. 5,326,574 discloses a process
for codrying the physiological cooling agent
3-1-menthoxypropane-1,2-diol with a food acceptable, water-soluble
carrier and mixing the resulting product into chewing gum.
[0030] L-Monomenthyl glutarate has the chemical name
(L)-Monomenthane-3-yl glutarate, is sometimes known as Pentadienoic
acid, mono[5 methyl-2-1(1-methylethyl)cyclohexyl]ester, [1L];
[1R(-)] monomenthyl glutarate, and has the chemical formula
C.sub.15H.sub.26O.sub.4. It may be located by JECFA Number 1414,
FEMA number 4006 and CAS number 220621-22-7. It is present as a
clear viscous fluid having a minty, menthol-like aroma.
Cooling Agents
[0031] The term "physiological cooling agent" encompasses any
number of physiological cooling agents. However, in the context of
this description, the term "physiological cooling agent" does not
include traditional flavor-derivatives such as menthol or menthone.
Preferred physiological cooling agents do not have a perceptible
flavor of their own, but simply provide a cooling effect.
[0032] An optional additional component of the cooling compositions
is a physiological cooling agent. Suitable levels of the cooling
agent are from about 0.001 to about 85%, preferably from about 0.01
to about 50%, more preferably from about 0.05 to about 15% by
weight of the cooling composition, and still more preferably from
about 0.10 to about 5% by weight of the composition.
[0033] Generally, the compositions will contain an amount of the
active cooling compounds sufficient to stimulate the cold receptors
in the areas of the skin or mucous membrane with which the
compositions come into contact and thereby promote the desired cold
sensation. As the degree and longevity of cooling sensation varies
from compound to compound the quantity of stimulant used in each
composition will vary widely. As a guide, it may be said that, with
the more active compounds, a significant cooling sensation, which,
in some cases, may persist for several hours, can be achieved upon
application to the mucosa or skin of as little as 0.05 ml. of a
1.0% weight percent solution of the active ingredient in ethanol.
For the less active compounds a significant cooling effect can be
achieved only with more concentrated solutions, e.g. 5.0% by weight
or more of the active ingredient. It must also be admitted that
such skin tests are somewhat subjective, some individuals
experiencing a greater or lesser cooling sensation than others when
subjected to the same test.
[0034] Cooling agents are well known in the art and are described
in, for instance, U.S. Pat. Nos. 4,032,661, 4,070,449, 4,033,994,
4,296,093, 4,296,255, 4,230,688, 4,034,109, 4,020,153, 4,136,163,
5,266,592, U.S. Publication Nos. 2004/0067970 and 2005/0019455, and
by Leffingwell et al., "Cool without Menthol & Cooler than
Menthol and Cooling Compounds as Insect Repellents," the
disclosures of which are herein incorporated by reference. A test
for physiological cooling agents is described in GB-A-1,452,291,
published Oct. 13, 1976, reproduced in part herein below for
convenience. Cooling agents are well known in the art. Preferred
physiological cooling agents do not have a perceptible flavor of
their own, but simply provide a cooling effect. Since the
physiological cooling agents do not have their own perceptible
flavor, they can be used with other types of flavors to offer new
and unique advantages, such as breath freshening. Several U.S. and
foreign references disclose specific compounds and classes of
compounds that are physiological cooling agents that may be used in
the present compositions. Some of these disclose the use of
physiological cooling agents in chewing gum. These include, for
instance, U.S. Pat. No. 5,451,404 (a ketal combined with another
coolant (menthol or carboxamides)); U.S. Pat. No. 5,372,824
(physiological cooling agents and reduced menthol); U.S. Pat. No
5,348,750 (menthone ketals); U.S. Pat. No. 5,326,574 (a spray dried
3-1-menthoxypropane-1,2-diol-); U.S. Pat. No. 5,266,592 (menthone
glycerol ketals); U.S. Pat. No. 5,165,943 (a cyclodextrin complex
with physiological cooling agents); U.S. Pat. No. 5,009,893
(p-menthane carboxamide physiological cooling agent with menthol
for reduced bitterness); U.S. Pat. No. 4,459,425
(3-1-menthoxypropane-1,2-diol); U.S. Pat. No. 4,296,093
(substituted cyclohexanamides); U.S. Pat. Nos. 4,248,859 and
4,318,900 (alkyl substituted alicyclic carboxylic acids, esters or
amides); U.S. Pat. Nos. 4,157,384 and 4,029,759 (various
3-substituted p-menthanes); U.S. Pat. No. 4,081,480
(alpha-oxy(oxo)mercaptan alkanes); U.S. Pat. No. 4,070,449
(sulphoxides and sulphones); U.S. Pat. Nos. 4,060,091; 4,190,643
and 4,136,163 (substituted p-menthane-3-carboxamides); U.S. Pat.
Nos. 4,153,679; 4,296,255 and 4,230,688 (acyclic carboxamides);
U.S. Pat. No. 4,034,109 (acyclic sulphonamides and sulphinamides);
U.S. Pat. No. 4,033,994 (p-menthane-3-carboxylates); U.S. Pat. Nos.
3,793,446 and 3,644,613 (ketoesters of menthol); U.S. Pat. No.
3,720,762 (spilanthol with menthol or peppermint oil); Canadian
Patent No. 2,101,790 (carbonic acids having free polar groups);
German Patent No. 2,608,226 (menthyl lactate); German Patent No.
2,433,165 (N-acetylglycine menthyl ester); French Patent No.
2,577,922 (L-menthyl-3-hydroxybutyrate); Japanese Patent No.
94/065023 (2-isopropenyl-5-methylcyclohexanol); Great Britain
Patent No. 1,502,680 (bicyclic acids, esters, amides and
substituted menthanols); Great Britain Patent No. 1,476,351 (cyclic
and acyclic amides, ureas and sulphonarnides); Great Britain Patent
No. 1,442,998 (trialkyl-substituted cyclohexane carboxamides);
Great Britain Patents Nos. 1,421,744 and 1,421,743 (novel amides);
Great Britain Patent No. 1,411,786 (cyclohexanamides); Great
Britain Patent No. 1,404,596 (acyclic secondary and tertiary
alkanols); PCT Publication No. WO 97/07771 (menthyl succinate and
carboxamides); PCT Publication No. WO 96/28133 (coolant composition
for comestibles); PCT Publication No. WO 96/17524 (a cooling
composition comprising N-substituted p-menthane carboxamides and
menthol); PCT Publication No. WO 94/010117 (cyclohexanol
derivatives); and U.S. S. Pat. No. 3,639,569 (physiological cooling
agents). U.S. Pat. Nos. 4,032,661, 4,070,449, 4,033,994, 4,296,093,
4,296,093, 4,296,255, 4,230,688, 4,034,109, 4,020,153, 5,009,893,
5,698,181, 5,266,592, U.S. Publication Nos. 2004/0067970 and
2005/0019455, and Leffingwell et al., "Cool without Menthol &
Cooler than Menthol and Cooling Compounds as Insect Repellents,"
the disclosures of which are also herein incorporated by reference
provide yet further examples. A test for physiological cooling
agents is described in GB-A-1,452,291, published Oct. 13, 1976,
reproduced in part herein below for convenience.
[0035] Among the useful cooling agents are included xylitol,
erythritol, dextrose, sorbitol, menthane, menthone, ketals,
menthone ketals, menthone glycerol ketals, substituted p-menthanes,
acyclic carboxamides, mono menthyl glutarate, substituted
cyclohexanamides, substituted cyclohexane carboxamides, substituted
ureas and sulfonamides, substituted menthanols, hydroxymethyl and
hydroxymethyl derivatives of p-menthane, 2-mercapto-cyclo-decanone,
hydroxycarboxylic acids with 2-6 carbon atoms, cyclohexanamides,
menthyl acetate, menthyl salicylate, N,2,3-trimethyl-2-isopropyl
butanamide (WS-23), N-ethyl-p-menthane-3-carboxamide (WS-3), ethyl
ester of N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine
(WS5), as well as the substantially pure ethyl ester of
N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine as
disclosed in U.S. Pat. No. 7,189760 to Erman, et al which is
incorporated in its entirety herein by reference, isopulegol,
menthyloxy propane diol, 3-(1-menthoxy)propane-1,2-diol,
3-(1-menthoxy)-2-methylpropane-1,2-diol, p-menthane-2,3-diol,
p-menthane-3,8-diol,
6-isopropyl-9-methyl-1,4-dioxaspiro[4,5]decane-2-methanol, menthyl
succinate and its alkaline earth metal salts,
trimethylcyclohexanol,
N-ethyl-2-isopropyl-5-methylcyclohexanecarboxamide, Japanese mint
oil, peppermint oil, 3-(1-menthoxy)ethan-1-ol,
3-(1-menthoxy)propan-1-ol, 3-(1-menthoxy)butan -1-ol,
1-menthylacetic acid N-ethylamide, 1-menthyl-4-hydroxypentanoate,
1-menthyl-3-hydroxybutyrate,
N,2,3-trimethyl-2-(1-methylethyl)-butanamide, n-ethyl-t-2-c-6
nonadienamide, N,N-dimethyl menthyl succinamide, substituted
p-menthanes, substituted p-menthane-carboxamides,
2-isopropanyl-5-methylcyclohexanol (from Hisamitsu Pharmaceuticals,
hereinafter "isopregol"); menthone glycerol ketals (FEMA 3807,
tradename FRESCOLAT.RTM. type MGA); 3-1-menthoxypropane-1,2-diol
(from Takasago, FEMA 3784); and menthyl lactate; (from Haarman
& Reimer, FEMA 3748, tradename FRESCOLAT.RTM. type ML), WS-30,
WS-14, Eucalyptus extract (p-Mehtha-3,8-Diol), Menthol (its natural
or synthetic derivatives), Menthol PG carbonate, Menthol EG
carbonate, Menthol glyceryl ether,
N-tertbutyl-p-menthane-3-carboxamide, P-menthane-3-carboxylic acid
glycerol ester, Methyl-2-isopryl-bicyclo (2.2.1),
Heptane-2-carboxamide; Menthol methyl ether, menthyl pyrrolidone
carboxylate, cyclic .alpha.-keto enamines, cyclotene derivatives
such as cyclopentenes including
3-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one and
5-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one, compounds of the
formula: ##STR1## wherein B is selected from H, CH3, C2H5, OCH3,
0C2H5; and OH; and wherein A is a moiety of the formula-CO-D,
wherein D is selected from the following moieties: (i)-NR1R2,
wherein R' and R2 are independently selected from H and C 1-C8
straight or branched-chain aliphatic, alkoxyalkyl, hydroxyalkyl,
araliphatic and cycloalkyl groups, or R1 and R2 together with the
nitrogen atom to which they are attached form part of an
optionally-substituted, five-or six-membered heterocyclic ring;
(ii)-NIICH2COOCH2CH3, --NHCH2CONH2, --NHCH2CH2OCH3, --NHCH2CH2OH,
--NHCH2CH(OH)CH2OH and (iii) a moiety selected from the group
consisting of: ##STR2## as disclosed in PCT Patent Application
WO2006/125334 to Bell et al which is incorporated in its entirety
herein by reference, among others. These and other suitable cooling
agents are further described in the following U.S. patents, all of
which are incorporated in their entirety by reference hereto: U.S.
Pat. No. 4,230,688; 4,032,661; 4,459,425; 4,178,459; 4,296,255;
4,136,163; 5,009,893; 5,266,592; 5,698,181; 6,277,385; 6,627,233;
7,030,273. Still other suitable cooling agents are further
described in the following U.S. Patent Applications, all of which
are incorporated in their entirety by reference hereto: U.S.
2005/0222256; 2005/0265930.
[0036] Particular examples of physiological cooling agents include,
for instance, substituted p-menthanes, substituted
p-menthane-carboxamides (e.g., N-ethyl-p-menthane-3-carboxamide
(FEMA 3455)), acyclic carboxamides, substituted cyclohexanamides,
substituted cyclohexane carboxamides, substituted ureas and
sulphonamides, and substituted menthanols (all from Wilkinson
Sword); hydroxymethyl and hydroxyethyl derivatives of p-menthane
(from Lever Bros.); menthyl succinate; 2-mercapto-cyclo-decanone
(from International Flavors and Fragrances);
2-isopropanyl-5-methylcyclohexanol (from Hisamitsu Pharmaceuticals,
hereinafter "isopregol"); hydroxycarboxylic acids with 2-6 carbon
atoms; menthone glycerol ketals (FEMA 3807, trade name
FRESCOLAT.RTM. type MGA); 3-1-menthoxypropane-1,2-diol (from
Takasago, FEMA 3784, (hereinafter "TCA")); and menthyl lactate;
(from Haarman & Reimer, FEMA 3748, trade name FRESCOLAT.RTM.
type ML).
[0037] While any of the above-disclosed physiological cooling
agents may be used in chewing gum and confectioneries, some
preferred physiological cooling agents are substituted p-menthane
carboxamides (PMC), such as those disclosed in U.S. Pat. Nos.
4,060,091; 4,190,643 and 4,136,163, all assigned to Wilkinson
Sword, especially N-ethyl-p-menthane-3-carboxamide (called WS-3);
acyclic carboxamides (AC), such as those disclosed in U.S. Pat.
Nos. 4,296,255; 4,230,688; and 4,153,679; all assigned to Wilkinson
Sword, especially N-2,3-trimethyl-2-isopropyl butanamide (called
WS-23); menthone glycerol ketal (MGK); menthyl lactate (ML);
menthyl succinate (MS); and 3-1-menthoxypropane-1,2-diol (TCA).
[0038] Other preferred physiological cooling agents are described
in W097/06695. Some include menthol, peppermint oil,
N-substituted-p-menthane-3-carboxamides, acyclic tertiary and
secondary carboxamides, 3-1-menthoxy propan-1,2-diol and mixtures
thereof. Some carboxamides found most useful are those described in
U.S. Pat. No. 4,136,163, Jan. 23, 1979 to Watson et al., and U.S.
Pat. No. 4,230,688, Oct. 28, 1980 to Rowsell et al. The
carboxamides in U.S. Pat. No. 4,136,163 are
N-substituted-p-menthane-3-carboxamides.
N-ethyl-p-menthane-3-carboxamide, commercially available as WS-3
from Wilkinson Sword, is preferred herein. The carboxamides of U.S.
Pat. No. 4,230,688 are certain acyclic tertiary and secondary
carboxamides, of which trimethyl isopropyl butanamide, commercially
available as WS-23 from Wilkinson Sword is one preferred cooling
agent for use herein. Other preferred acyclic carboxamides include
acyclic tertiary and secondary carboxamides including the compounds
commercially known as Ice 6000, 10000, and 11000. Other cooling
compounds include WS-3, WS-14, WS-23, WS-5 and the like.
[0039] The following test procedure can be used as a means to
identify compounds having a physiological cooling activity. This
test is intended purely as a means for identifying compounds having
a physiological cooling agent activity and useful in the present
compositions and for giving an indication of the different relative
activities of the compounds, as between themselves and as compared
with menthol, when applied in particular manner to a particular
part of the body. The results are not necessarily indicative of the
activity of these compounds in other formulations and other parts
of the body where other factors come into play. For example, a
controlling factor in the onset of cooling effect, its intensity
and longevity will be the rate of penetration of the compounds
through the epidermis or mucous membrane and this will vary in
different locations on the human body. The formulation of actual
products will therefore be done largely on an empirical basis
although the test results and other figures given herein will be
useful as a guide, particularly in the formulation of products for
oral administration, since the test procedure to be described
involves oral application of the compound. A similar test may, of
course, be devised for the purposes of measuring the relative
activities of the compounds of another area of the body, for
example, the face or forearm, and this will be a useful guide in
the choice of compounds to be used in preparations for external
topical usage. It will also be noted that the described test
procedure can be done on a statistical basis. This is necessary
since sensitivity to these compounds will vary not only from
compound to compound and from one part of the body to another, but
also from one individual to another. Tests of this nature are
commonly used in the testing of the organoleptic properties e.g.
taste and smell of organic and inorganic compounds, see
Kirk-Othmer: Encyclopedia of Chemical Technology, 2nd Ed. (1967)
Vol. 14, pages 336-344.
[0040] The following test procedure is aimed at determining the
minimum quantity of the test compound required to produce a
noticeable cooling effect in a person of average sensitivity, this
minimum quantity being termed the threshold for that particular
compound. The tests are carried out on a selected panel of 6 people
of median sensitivity to 1-menthol.
[0041] In some embodiments, the following procedure may be used to
select a panel. Known quantities of 1-menthol in solution in
petroleum ether (bp. 40-60.degree. C.) are placed on 5 mm squares
of filter paper, after which the solvent can be allowed to
evaporate. A panel of observers can be enrolled and asked to place
one impregnated square at a time on the tongue and to report on the
presence or absence of a cooling effect. The quantity of 1-menthol
on each impregnated square is gradually reduced from a value
substantially above 0.25 micrograms per square to substantially
below 0.25 micrograms, the precise range being immaterial.
Conveniently, one starts with squares containing 2.0 micrograms
being half that of the preceding square, i.e. the second test
square will contain 1.0 microgram, the third 0.5 microgram, and so
on. Each quantity can be tested on the tongue at least ten times.
In this way, the thresholds to cold receptor stimulus by 1-menthol
are determined for each individual of the panel, the threshold for
each individual being that amount of 1-menthol for which, in a
series of not less than ten test applications, a cooling effect is
reported 50% of the time. Six panel members can be selected whose
threshold to 1-menthol is in the range 0.1 micrograms to 10
micrograms and whose average threshold is approximately 0.25
micrograms, this select panel being regarded as the test panel of
average sensitivity.
[0042] To test the activity of cooling agents, the above procedure
can be repeated using only the six selected panel members of
average sensitivity to 1-menthol. The individual thresholds for
each test compound on each of the six selected panel members are
determined and averaged. Those compounds whose average threshold on
the select test panel is 100 micrograms or less, preferably 50
micrograms or less are regarded as having cooling activity.
[0043] The balance of the cooling composition can be made up of a
suitable appropriate carrier, such as water or a bulk sweetener,
described in more detail below.
Menthyl Esters
[0044] U.S. Pat. No. 3,111,127 incorporated herein by reference
discloses such monomenthyl esters as monomenthyl succinate,
monomenthyl .alpha..alpha.-dimethyl succinate and monomenthyl
2-methylmaleate. U.S. Pat. No. 4,150,052 incorporated herein by
reference discloses the use of N-ethyl p-menthane-3-carboxamide for
its physiological cooling action on the skin, and discloses its use
in, for example, chewing gum. U.S. Pat. Nos. 5,725,865 and
5,843,466 incorporated herein by reference disclose the use of mono
menthyl succinate for its physiological cooling action and disclose
its use in, for example, carbonated beverages, alcoholic beverages
and chewing gum. U.S. Pat. No. 6,365,215 incorporated herein by
reference discloses the use of mono menthyl glutarate in oral
sensory perception-affecting compositions for use with such
consumable materials as chewing gums. U.S. Pat. No. 6,451,844
incorporated herein by reference discloses the use of menthyl
2-pyrrolidone-5-carboxylate (QUESTICE L, Quest International, B.V.
of Naarden, Netherlands) in skin care and hair care compositions
for their insect repellency properties.
[0045] Furthermore, L-mono menthyl glutarate has been registered as
a GRAS flavoring substance, FEMA No. 4006 and, in Smith et al.,
"GRAS Flavoring Substances 20", Food Technology, Vol. 55, No. 12,
December 2001 at page 53 is indicated to have uses in nonalcoholic
beverages, alcoholic beverages, chewing gum, confectionery
frosting, hard candy, soft candy and snack foods.
[0046] A number of the mono menthyl half acid ester derivatives are
found to be useful such as (i) L-menthyl hydrogen adipate (n=3);
(ii) L-menthyl hydrogen pimelate (n=4); and (iii) L-menthyl
hydrogen suberate (n=5) as disclosed by Rule et al., "Optical
Activity and the Polarity of Substituent Groups Part VIII.
Growing-chain Effects and the ortho-Effect in Benzoic Esters", J.
Chem. Soc. 1928 (Part 1), pp. 1347-1361.
[0047] In addition, a lower adjacent methylene homologue of the
genus of novel compounds is disclosed in "SciFinder" (Nov. 20,
2002; Trademark of Chemical Abstracts Services), to with: malonamic
acid, p-menth-3-yl ester, (.+-.)-(8CI) having CAS Registry Number
6129-88-0.
Definitions
[0048] By "cooling agent" is meant any agent whether described
herein, known in the art as producing, or otherwise capable of
producing a sensation described as cooling by those experiencing it
on the skin, oral cavity or mucous membranes.
[0049] By "aroma" is meant a minty or freshening physiological
sensation perceived as a sense of smell.
[0050] By "cooling effect" is meant a sensation described as
cooling by those experiencing it on the skin, oral cavity or mucous
membranes.
[0051] By phrases such as "the amount of WS-23 present in the
composition, chewing gum or confection is reduced relative to the
amount of WS-23 alone required to provide the substantially similar
sensation" or "the amount of WS-3 present in the composition,
chewing gum or confection is reduced relative to the amount of WS-3
alone required to provide the substantially similar sensation" is
meant that on average, respondents evaluating the "cooling"
sensation provided by the cooling composition quantify the
"cooling" sensation as substantially equivalent to that provided by
WS-23 or WS-3 alone even though WS-23 or WS-3 are present in
amounts that are at least 5%, at least 10%, at least 20%, at least
30% or at least 40% or even 50% less by mass.
[0052] By "Menthyl ester" is meant a class of compounds such as
those described in, for instance, U.S. Pat. No. 3,111,127, U.S.
Pat. No. 6,365,215 and U.S. Pat. No. 6,884,906 the disclosures of
which are herein incorporated by reference, including monomenthyl
succinate, dimenthyl succinate, monomenthyl
.alpha.,.alpha.-dimethyl succinate and monomenthyl
2-methylmaleatementhyl glutarate, FEMA 4006, as described, supra.
Also, are intended derivatives thereof, such as for example, the
menthyl half acid ester derivatives set forth in U.S. Pat. No.
6,884,906. The term is also intended to embrace the alkali metal
salts and alkaline earth metal salts of the menthyl compounds such
as monomenthyl succinate and monomenthyl glutarate. Menthyl esters
also include menthyl acetate, 1-menthyl acetate, d,1-menthyl
acetate, homomenthyl acetate, menthyl lactate, and 1-menthyl
lactate.
Cooling Compositions
[0053] Some embodiments provide cooling compositions including
about 5% to about 60% by weight menthyl glutarate, about 5% to
about 50% by weight of at least one cooling agent selected from
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof, and about 15% to about 85% by weight
menthol. The cooling composition may consist essentially of these
components in some embodiments.
[0054] In some embodiments, the cooling compositions include about
5% to about 60% by weight of at least two menthyl esters, about 5%
to about 50% by weight of at least one cooling agent selected from
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof, and about 15% to about 85% by weight
menthol. The cooling composition may consist essentially of these
components in some embodiments.
[0055] Some other embodiments provide cooling compositions
including menthyl succinate, a second cooling agent selected from
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof, and a third cooling agent selected from
1-isopulegol, p-menthane-3,8-diol and combinations thereof. The
cooling composition may consist essentially of these components in
some embodiments. The menthyl succinate may be present in amounts
of about 5% to about 60% by weight of the composition. The second
cooling agent may be present in amounts of about 5% to about 50% by
weight of the composition. The third cooling agent may be present
in amounts of about 2% to about 50% by weight of the
composition.
[0056] In some embodiments, the cooling composition may be a liquid
at room temperature (about 25.degree. C.). For instance, a cooling
composition, which is liquid at 25.degree. C., may include about 5%
to about 60% by weight menthyl glutarate and about 5% to about 50%
by weight of at least one cooling agent selected from
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof. The combination of the menthyl glutarate
and the at least one cooling agent may be present in amounts of at
least about 75% by weight of the cooling composition. Menthol also
may be included in some embodiments, for instance, about 15% to
about 85% by weight.
[0057] In some embodiments, cooling compositions that are liquid at
25.degree. C. may include about 5% to about 60% by weight of at
least two menthyl esters and about 5% to about 50% by weight of at
least one cooling agent selected from
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof. The combination of the at least two
menthyl esters and the at least one cooling agent may be present in
amounts of at least about 75% by weight of the cooling composition,
Menthol also may be included in some embodiments, for instance,
about 15% to about 85% by weight.
[0058] In some embodiments, the cooling composition, which is
liquid at 25.degree. C., may consist essentially of about 5% to
about 60% by weight menthyl glutarate, about 5% to about 50% by
weight of at least one cooling agent selected from
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof, and about 15% to about 85% by weight
menthol.
[0059] In some other embodiments, the cooling composition, which is
liquid at 25.degree. C., may consist essentially of about 5% to
about 60% by weight of at least two menthyl esters, about 5% to
about 50% by weight of at least one cooling agent selected from
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof, and about 15% to about 85% by weight
menthol.
[0060] The liquid cooling compositions may be prepared by first
providing menthyl glutarate, or at least two menthyl esters in some
embodiments, in liquid form. Because menthyl glutarate has a low
melting point, it is a liquid at room temperature (about 25.degree.
C.). At least one cooling agent selected from
N-ethyl-p-menthane-3-carboxamide, trimethyl isopropyl butanamide
and combinations thereof may be added to the liquid menthyl
glutarate. N-ethyl-p-menthane-3-carboxamide and trimethyl isopropyl
butanamide are both solids at room temperature. Solid cooling
agents are typically dissolved in a solvent prior to incorporation
into chewing gums and confectioneries to improve the ability to mix
them into such products. Because menthyl glutarate is a liquid, the
solid cooling agents may be dissolved or suspended directly in the
liquid menthyl glutarate to form the liquid cooling composition.
This may be done at room temperature in the absence of added heat.
This composition can be formed as a premix at room temperature.
Accordingly, an additional solvent is not needed to dissolve the
solid cooling agents.
[0061] In some embodiments, it may be desirable to heat the
combination of cooling agents to melt the cooling agents that are
solids at room temperature. In particular, although menthyl
glutarate is a liquid, many cooling agents are solids at room
temperature. After being melted, such cooling agents will solidify
and recrystallize upon cooling. Such recrystallization can make it
difficult to add these cooling agents into chewing gums and
confectioneries. For instance, the following cooling agents have
melting points near or above room temperature: menthol (43.degree.
C.); WS-3 (88.degree. C.); WS-23 (62-64.degree. C.); menthyl
lactate (40-42.degree. C.); menthyl succinate (59-61.degree. C.);
and menthyl acetate ester (23-24.degree. C.). Once such additional
cooling agents are added to the menthyl glutarate, or at least two
menthyl esters, therefore, it may be desirable to heat the
composition to melt the cooling agents that are solids. For
instance, in some embodiments, the composition may be heated to
melt WS-3, WS-23 and/or menthol. The composition may be heated to a
temperature of at least about 65.degree. C. The liquid composition
then may be cooled to less than about 30.degree. C., more
specifically about 25.degree. C., while maintaining the composition
in a liquid state. This provides a liquid cooling composition that
is stable for a period of time at room temperature without
recrystallization of the cooling agents that are typically solids
at room temperature. For instance, the liquid cooling composition
desirably is stable at room temperature for a period of at least
about one hour.
[0062] The cooling compositions can be used in any products
intended for oral, skin or mucosal delivery as a component for
providing sensation of cooling and for providing a physiological
effect that is substantially cooling. The products for which the
compositions are useful include, but are not limited to, food and
drink, such as candies, drops, chewing gums, tablets, chocolates,
cakes, cookies, snack food, bread, tea, coffee, juice, fruit
drinks, fruit wine, dairy drinks, carbonated beverages, alcoholic
beverages and seasonings; and oral care preparations, such as
mouthwash, toothpaste, nebulizers, drinks, medicinal drops,
gargles, and chewables.
[0063] The following illustrate a more comprehensive range of
products into which the active cooling composition can be
incorporated. These include, for instance, edible or potable
compositions including alcoholic and non-alcoholic beverages,
confectionery, chewing gum; cachous; ice cream; jellies. These
further include toiletries including after shave lotions, shaving
soaps, creams and foams, toilet water, deodorants and
antiperspirants, "solid colognes," toilet soaps, bath oils and
salts, shampoos, hair oils, talcum powders, face creams, hand
creams, sunburn lotions, cleansing tissues, dentifrices,
toothpicks, mouthwashes, hair tonics, eye drops. Additionally, the
range extends to medicaments including antiseptic ointments, pile
ointments, liniments, lotions, decongestants, counter-irritants,
cough mixtures, throat lozenges, antacid and indigestion
preparations, oral analgesics. Also contemplated are tobacco
preparations including cigars, cigarettes, pipe tobacco, chewing
tobacco and snuff; tobacco filters, especially filter tips for
cigarettes. Even further are contemplated miscellaneous
compositions such as water soluble adhesive compositions for
envelopes, postage stamps, adhesive labels etc.
[0064] The edible and potable compositions will contain the active
cooling composition in combination with an edible carrier and
usually a flavoring or coloring agent. In general, the cooling
composition may be present in amounts in the range 0.0005 to 5% by
weight based on the total composition. Similar considerations apply
to the formulation of beverages. In general, the amount of the
cooling composition used will generally be in the range 0.0005 to
2.5% by weight based on the total composition. Because of the
cooling sensation imparted to the skin, the amount of the cooling
composition added to toiletries will usually be in the range 0.1 to
10% by weight based on the total composition. Medicaments will
normally feature an amount of the cooling composition of from 0.01
to 2.0% by weight. Tobacco preparations may contain as little as
0.1 mg. of the composition.
[0065] In addition to the cooling composition described herein,
these products can contain other additives according to use. For
example, additives permitted by Food Sanitation Law can be added to
food and drink according to necessity. Useful additives include
saccharides, sweeteners, inorganic salts, emulsifiers, acidifiers,
flavorings, colors, antioxidants, raising agents, thickeners,
vegetable oils, milk, and other dairy products. In some detail,
bakery products can comprise wheat flour (base), butter, a raising
agent, e.g., baking powder, an emulsifier, e.g., a sucrose fatty
acid ester, saccharides, e.g., sugar, inorganic salts, and
flavorings. Chocolate can comprise cacao mass (base) cacao butter,
saccharides, e.g., sugar, milk, and an emulsifier. Emulsified
dressings can comprise salad oil, water, vinegar, sugar, thickening
polysaccharides, and sweeteners. Chewing gum can comprise a gum
base, saccharides, such as sugar, glucose and starch syrup, and
flavors. Candy can comprise saccharides, acidifiers, e.g., citric
acid, sweeteners, flavorings, and colors. Orange fruit drinks can
comprise orange juice, sweeteners, e.g., isomerized sugars,
acidifiers, e.g., citric acid, and antioxidants, e.g., vitamin C.
Fruit milk drinks can comprise fruit juice, dairy products such as
milk and powdered skim milk, saccharides, e.g., sugar, stabilizers,
e.g., carboxymethyl cellulose, acidifiers, e.g., citric acid, and
flavorings, e.g., a pineapple flavor.
[0066] In particular embodiments, the cooling compositions are used
in chewing gums. Some chewing gum formulations are described in,
for instance, U.S. Pat. No. 6,627,233, 6,685,916 and 6,696,044,
herein incorporated by reference. Additives which can be used in
the preparations include inorganic salts, inorganic oxides, organic
salts, thickeners, wetting agents, emulsifiers, surface active
agents, humectants, alcohols, color additives, flavorings, and, if
desired, medical ingredients such as crude drugs, hemostatics,
circulation stimulants, anti-inflammatory agents, astringents,
antibacterial and/or antifungal agents, and bactericides. In
particular embodiments, toothpaste can comprise abrasives, such
calcium phosphate, as calcium carbonate, aluminum hydroxide,
silica, and calcium pyrophosphate; wetting agents, such as
glycerin, sorbitol, and propylene glycol; tackifiers, such as
carboxymethyl cellulose, carrageenan, and hydroxyethyl cellulose;
surface active agents, such as sodium laurylsulfate,
N-acylglutaminates, and sucrose fatty acid esters; sweeteners, such
as saccharin sodium, stevioside, and xylitol; and medicinal
components, such as vitamin E, azulene, aluminum chlorohydroxy
allanthoinate, dextranase, hinokitiol, lysozyme chloride, and
chlorhexidine.
Chewing Gum Compositions
[0067] In particular embodiments, the cooling compositions are used
in chewing gums and confectioneries. Compositions of chewing gum
and confectionaries are well known in the art and described in
depth in, for instance, U.S. Pat. Nos. 6,685,916, 6,627,233,
6,685,916 and 6,696,044, the disclosures of which are incorporated
by reference and some of which is summarized herein.
[0068] Chewing gum compositions typically include one or more of
gum bases, flavoring agent and bulk sweeteners. The term
"confectioneries" as used herein includes, but is not limited to:
nougats, candies, panning goods, gel confections, fondants,
lozenges, hard boiled candies, mints, troches, pastilles,
microcapsules, and fast-dissolving solid forms including freeze
dried forms (cakes, wafers, thin films, and tablets) and fast
dissolving solid forms including compressed tablets. The term "fast
dissolving solid form" as used herein means that the solid dosage
form dissolves in less than about 60 seconds, preferably less than
about 15 seconds, more preferably less than about 5 seconds, in the
oral cavity. Lozenges include discoid shaped solids comprising a
therapeutic agent in a flavored base. The base may be a hard sugar
candy, glycerinated gelatin, or a combination of sugar with
sufficient mucilage to give it form. Lozenge compositions
(compressed tablet type) typically include one or more fillers
(compressible sugar), flavoring agents and lubricants.
[0069] The chewing gum compositions may be coated or uncoated and
be in the form of slabs, sticks, pellets, balls, compressed
tablets, and the like. The composition of the different forms of
the chewing gum compositions will be similar but may vary with
regard to the ratio of the ingredients. For example, coated gum
compositions may contain a lower percentage of softeners. Pellets
and balls have a small chewing gum core, which can then be coated
with either a sugar solution or a sugarless solution to create a
hard shell. Slabs and sticks are usually formulated to be softer in
texture than the chewing gum core. In order to overcome any
detrimental softening effect the surfactant active may have on the
gum base, it is preferred to formulate a slab or stick gum having a
firmer texture (i.e. with less softener than is typically
employed). Compressed tablets are formed from compressible
mixtures.
[0070] The cooling compositions may be used in either regular
chewing gum, pressed gum or bubble gum, a subset of "chewing gums."
Center filled gum is another common chewing gum form. The gum
portion has a similar composition and mode of manufacture to that
described above. However, the center fill is typically an aqueous
solution or gel, which can be injected into the center of the gum
during processing. The cooling agents and compositions could
optionally be incorporated together or singly into the center fill
during manufacture of the fill or into the chewing gum. The center
fill gum may also be optionally coated and may be prepared in
various forms such as in the form of a lollipop.
[0071] It is preferred to use a coated gum wherein the cooling
compositions described herein are in at least one of the core and
the coating.
[0072] The chewing gum composition includes gum base and most of
the other typical chewing gum composition components such as
sweeteners, softeners, flavoring agents and the like. The chewing
gum composition may contain a reduced amount of softening agents
such as lecithin or glycerin or may eliminate softeners. In
addition, the chewing gum composition may contain a larger or
smaller amount of sugar alcohols than conventional chewing gum
compositions to facilitate delivery.
[0073] In accordance with one aspect of the chewing gum
composition, the cooling compositions are added during the
manufacture of the chewing gum composition, that is, with the
sweeteners, flavoring agents and the like.
[0074] In a further aspect, the gum base generally comprises
elastomers, elastomer plasticizers, waxes, fats, oils, emulsifiers,
fillers, texturizers and may include a desirable combination of the
heating and cooling agents or warming composition. Elastomers
constitute from about 5% to 95% by weight of the base, preferably
10% to 70% by weight and most preferably 15% to 45% by weight.
Examples of elastomers include synthetic elastomers such as
polyisobutylene, polybutylene, isobutylene-isoprene co-polymers,
styrene-butadiene co-polymers, polyvinylacetate and the like.
Elastomers may also include natural elastomers such as natural
rubber as well as natural gums such as jelutong, lechi caspi,
perillo, massaranduba balata, chicle, gutta hang kang or mixtures
thereof. Other elastomers are known to those of ordinary skill in
the art.
[0075] Elastomer plasticizers modify the firmness of the finished
gum when used in the gum base. Elastomer plasticizers are typically
present in an amount of up to about 75% by weight of the gum base,
preferably from about 5% to 45% by weight and more preferably from
about 10% to 30% by weight. Examples of elastomer plasticizers
include natural rosin esters such as glycerol ester of partially
hydrogenated rosin, glycerol ester of tall oil rosin,
pentaerythritol esters of partially hydrogenated rosin, methyl and
partially hydrogenated methyl esters of rosin, and the like.
Synthetic elastomer plasticizers such as terpene resins may also be
employed in gum base composition.
[0076] Waxes include synthetic and naturally occurring waxes such
as polyethylene, bees wax, carnauba and the like. Petroleum waxes
such paraffin may also be used. The waxes may be present in the
amount of up to about 30% by weight of the gum base. Waxes aid in
the curing of the finished gum and help improve the release of
flavor and may extend the shelf life of the product.
[0077] Fillers modify the texture of the gum base and aid
processing. Examples of such fillers include magnesium and aluminum
silicates, clay, alumina, talc, titanium oxide, cellulose polymers,
and the like. Fillers are typically present in an amount of from 1%
to 60% by weight.
[0078] Examples of softeners used in the gum base include
hydrogenated and partially hydrogenated vegetable oils, cocoa
butter, glycerol monostearate, glycerol triacetate, di- and
triglycerides, fatty acids such as stearic acid, palmitic acid,
oleic acid, linoleic acid, linolenic acid and the like.
[0079] The gum base constitutes between 5% and 95% by weight of the
chewing gum composition, more typically 10% to 50% by weight, and
most typically from about 25% to 35% by weight of the chewing gum.
A higher amount of gum base is preferred.
[0080] Other ingredients used in chewing gum compositions include
sweeteners, both natural and artificial and both sugar and
sugarless. Sweeteners are typically present in the chewing gum
compositions in amounts of from about 20% to 80% by weight,
preferably from about 30% to 60% by weight. Sugarless sweeteners
include, but are not limited sugar alcohols such as sorbitol,
mannitol, xylitol, hydrogenated starch hydrolysates, maltitol and
the like may also be present. High intensity sweeteners such as
sucralose, aspartame, neotame, salts of acesulfame, and the like
are typically present up to about 1.0% by weight.
[0081] Flavoring agents, which can vary over a wide range, may be
selected in amounts from about 0. 1% to 10.0% by weight, preferably
from about 0.5% to 5.0% by weight. Flavoring agents for use in
chewing gum compositions are well known and include citrus oils,
peppermint oil, spearmint oil, oil of wintergreen, menthol,
cinnamon, ginger and the like.
[0082] Softeners may be present to modify the texture of the
chewing gum composition. As in typical gum compositions, softeners
in the compositions are typically present in amounts of from about
0.5% to 10% by weight based on the total weight of the chewing gum
composition.
[0083] Other materials, which may be present in the gum composition
include antioxidants (e.g. butylated hydroxyanisole, butylated
hydroxytoluene, beta-carotenes, tocopherols), colorants, flavoring
agents and the like.
[0084] Coating techniques for applying a coating for a chewing gum
composition such as pan and spray coating are well known. Preferred
is coating with solutions adapted to build a hard candy layer. Both
sugar and sugar alcohols may be used for this purpose together with
high intensity sweeteners, colorants, flavoring agents, binders and
other conventional additives. When the combination of stain
removing agents is provided in the coating of a chewing gum
composition, a solution of the stain removing agents is preferably,
alternately applied with the flavoring agent.
[0085] The sweetener may be present in an amount of from about 30%
to 80% by weight of the coating syrup. A binder such as magnesium
stearate may be added to the coating syrup in an amount of from
about 1% to 15% by weight of the coating syrup to enhance or
promote adhesion. Optionally, minor amounts of conventional
additives may also be present. The sweeteners suitable for use in
the coating syrup comprise sugarless sweeteners such as the
polyhydric alcohols, e.g., xylitol, sorbitol, mannitol, and
mixtures, thereof; as well as maltitol, isomaltitol, hydrogenated
starch hydrolysates, and hydrogenated glucose syrups. Mono, di- and
polysaccharide may also be included. For example, sugars such as
sucrose, fructose, glucose, galactose and maltose may also be
employed as a sweetener. Other sweeteners suitable for use in the
coating syrup include, but are not limited to free saccharin acid,
water soluble salts of saccharin, cyclamate salts, palatinit
dihydrochalcones, glycyrrhizin, L-aspartyl-L-phenylalanine methyl
ester, amino acid based sweeteners, talin, steviosides,
dihydrochalcone compounds, acesulfame salts and mixtures
thereof.
[0086] Other ingredients may be added in minor amounts to the
coating syrup and include moisture absorbing compounds,
anti-adherent compounds, dispersing agents and film forming agents.
The moisture absorbing compounds suitable for use in the coating
syrups include mannitol or dicalcium phosphate. Examples of useful
anti-adherent compounds, which may also function as filler, include
talc, magnesium trisilicate and calcium carbonate. These
ingredients may be employed in amounts of about 0.5% to 5% by
weight of the syrup. Examples of dispersing agents, which may be
employed in the coating syrup, include titanium dioxide, talc or
other anti-adherent compounds as set forth above.
[0087] The coating syrup can be heated and a portion thereof
deposited on the cores. Usually a single deposition of the coating
syrup is not sufficient to provide the desired amount or thickness
of coating and it usually will be necessary to apply second, third
or more coats of the coating syrup in order to build up the weight
and thickness of the coating to desired levels with layers allowed
to dry in-between coats.
[0088] In some embodiments of the chewing gum composition, the
cooling compositions can be added to the coating. They are
preferably applied subsequent to the syrup coating. Further details
regarding the preparation of chewing gum compositions can be found
in Skuse's Complete Confectioner (13th Edition) (1957) including
pp. 41-71, 133-144, and 255-262; and Sugar Confectionery
Manufacture (2nd Edition) (1995), E. B. Jackson, Editor, pp.
258-286, the content of which is incorporated herein by
reference.
Confectionary Compositions
[0089] The present description also encompasses confectionery
products containing a composition of individual agents that in
total impart a physiological effect that can be substantially
cooling. Confectionery compositions include compressed tablets such
as mints, hard boiled candies, nougats, gels, center fill
confections, fondants, panning goods and other compositions falling
within the generally accepted definition of confectionery
compositions.
[0090] Confectionery compositions in the form of pressed tablets
such as mints may generally be made by combining finely sifted
sugar or sugar substitute, flavoring agent (e.g. peppermint
flavor), bulking agent such as gum arabic, and an optional coloring
agent. The flavoring agent and the bulking agent are combined and
then gradually the sugar or sugar substitute are added along with a
coloring agent, if needed.
[0091] The product then can be granulated by passing through a
sieve of desired mesh size (e.g. 12 mesh) and then dried at
typically 55.degree. C. to 60.degree. C. The resulting powder can
be fed into a tableting machine fitted with a large size punch and
the resulting pellets are broken into granules and then
pressed.
[0092] High boiled candies typically contain sugar or sugar
substitute, glucose, water, flavoring agent and optional coloring
agent. The sugar can be dissolved in the water and glucose can be
then added. The mixture can be brought to a boil. The resulting
liquid to which may previously have been added a coloring agent can
be poured onto an oiled slab and cooled. The flavoring agent then
can be added and kneaded into the cooled mass. The resulting
mixture then can be fed to a drop roller assembly known in the art
to form the final hard candy shape.
[0093] A nougat composition typically includes two principal
ingredients, a high boiled candy and a frappe. By way of example,
egg albumen or substitute thereof can be combined with water and
whisked to form a light foam. Sugar and glucose are added to water
and boiled typically at about 130.degree. C. to 140.degree. C. and
the resulting boiled product can be poured into a mixing machine
and beat until creamy. The beaten albumen and flavoring agent are
combined with the creamy product and the combination can be
thereafter thoroughly mixed.
[0094] Further details regarding the preparation of confectionery
compositions can be found in Skuse's Complete Confectioner (13th
Edition) (1957) including pp. 41-71, 133-144, and 255-262; and
Sugar Confectionery Manufacture (2nd Edition) (1995), E. B.
Jackson, Editor, pp. 129-168, 169-188, 189-216, 218-234, and
236-258, the content of which is incorporated herein by
reference.
Additional Components
[0095] In addition to the cooling compositions described herein,
the chewing gum and confectionery compositions may include a
variety of optional additives, such as, but not limited to,
sensates, mouth moistening agents, potentiators, sweeteners,
effervescent agents, acids and flavors.
Flavorants
[0096] In some embodiments, flavorants may include those flavors
known to the skilled artisan, such as natural and artificial
flavors. These flavorings may be chosen from synthetic flavor oils
and flavoring aromatics and/or oils, oleoresins and extracts
derived from plants, leaves, flowers, fruits, and so forth, and
combinations thereof. Nonlimiting representative 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. Also useful flavorings are 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, pineapple, apricot, banana, melon,
apricot, ume, cherry, raspberry, blackberry, tropical fruit, mango,
mangosteen, pomegranate, papaya and so forth. Other potential
flavors whose release profiles can be managed 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, a 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 camomile 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; 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. These flavoring agents may be used in liquid or
solid form and may be used individually or in admixture. Commonly
used flavors include mints such as peppermint, menthol, spearmint,
artificial vanilla, cinnamon derivatives, and various fruit
flavors, whether employed individually or in admixture. Flavors may
also provide breath freshening properties, particularly the mint
flavors when used in combination with the cooling agents, described
herein below.
[0097] In some embodiments, other flavorings include aldehydes and
esters such as cinnamyl acetate, cinnamaldehyde, citral
diethylacetal, dihydrocarvyl acetate, eugenyl formate,
p-methylamisol, and so forth may be used. 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, may be used. This publication is incorporated herein
by reference. These may include natural as well as synthetic
flavors.
[0098] Further examples of aldehyde flavorings include but are not
limited to 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, .e., melonal (melon), 2,6-dimethyloctanal
(green fruit), and 2-dodecenal (citrus, mandarin), cherry, grape,
blueberry, blackberry, strawberry shortcake, and mixtures
thereof.
[0099] In some embodiments, flavoring agents are used at levels
that provide a perceptible sensory experience i.e. at or above
their threshold levels. In other embodiments, flavoring agents are
used at levels below their threshold levels such that they do not
provide an independent perceptible sensory experience. At
sub-threshold levels, the flavoring agents may provide an ancillary
benefit such as flavor enhancement or potentiation.
[0100] In some embodiments, a flavoring agent may be employed in
either liquid form and/or dried form. When employed in the latter
form, suitable drying means such as spray drying the liquid may be
used. Alternatively, the flavoring agent may be absorbed onto water
soluble materials, such as cellulose, starch, sugar, maltodextrin,
gum arabic and so forth or may be encapsulated. In still other
embodiments, the flavoring agent may be adsorbed onto silicas,
zeolites, and the like.
[0101] In some embodiments, the flavoring agents may be used in
many distinct physical forms. Without being limited thereto, such
physical forms include free forms, such as spray dried, powdered,
beaded forms, encapsulated forms, and mixtures thereof.
[0102] Illustrations of the encapsulation of flavors as well as
other additional components can be found in the examples provided
herein. Typically, encapsulation of a component will result in a
delay in the release of the predominant amount of the component
during consumption of a confectionery composition that includes the
encapsulated component (e.g., as part of a delivery system added as
an ingredient to the chewing confectionery composition). In some
embodiments, the release profile of the ingredient (e.g., the
flavor, sweetener, etc.) can be managed by managing various
characteristics of the ingredient, delivery system containing the
ingredient, and/or the confectionery composition containing the
delivery system and/or how the delivery system is made. For
example, characteristics might include one or more of the
following: tensile strength of the delivery system, water
solubility of the ingredient, water solubility of the encapsulating
material, water solubility of the delivery system, ratio of
ingredient to encapsulating material in the delivery system,
average or maximum particle size of ingredient, average or maximum
particle size of ground delivery system, the amount of the
ingredient or the delivery system in the confectionery composition,
ratio of different polymers used to encapsulate one or more
ingredients, hydrophobicity of one or more polymers used to
encapsulate one or more ingredients, hydrophobicity of the delivery
system, the type or amount of coating on the delivery system, the
type or amount of coating on an ingredient prior to the ingredient
being encapsulated, etc.
Sweetening Ingredients
[0103] The sweeteners involved may be selected from a wide range of
materials including water-soluble sweeteners, water-soluble
artificial sweeteners, water-soluble sweeteners derived from
naturally occurring water-soluble sweeteners, dipeptide based
sweeteners, and protein based sweeteners, including mixtures
thereof. Without being limited to particular sweeteners,
representative categories and examples include:
[0104] (a) water-soluble sweetening agents such as
dihydrochalcones, monellin, steviosides, lo han quo, glycyrrhizin,
dihydroflavenol, and sugar alcohols such as sorbitol, mannitol,
maltitol, xylitol, erythritol, and L-aminodicarboxylic acid
aminoalkenoic acid ester amides, such as those disclosed in U.S.
Pat. No. 4,619,834, which disclosure is incorporated herein by
reference, and mixtures thereof;
[0105] (b) water-soluble artificial sweeteners such as soluble
saccharin salts, i.e., sodium or calcium saccharin salts, cyclamate
salts, the sodium, ammonium or calcium salt of
3,4-dihydro-6-methyl-1,2,3-oxathiazine-4-one-2,2-dioxide, the
potassium salt of
3,4-dihydro-6-methyl-1,2,3-oxathiazine-4-one-2,2-dioxide
(Acesulfame-K), the free acid form of saccharin, and mixtures
thereof;
[0106] (c) dipeptide based sweeteners, such as L-aspartic acid
derived sweeteners, such as L-aspartyl-L-phenylalanine methyl ester
(Aspartame),
N-[N-(3,3-dimethylbutyl)-L-.alpha.-aspartyl]-L-phenylalanine
1-methyl ester (Neotame), and materials described in U.S. Pat. No.
3,492,131,
L-alphaaspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide
hydrate (Alitame), methyl esters of L-aspartyl-L-phenylglycerine
and L-aspartyl-L-2,5-dihydrophenylglycine,
L-aspartyl-2,5-dihydro-L-phenylalanine;
L-aspartyl-L-(1-cyclohexen)-alanine, and mixtures thereof;
[0107] (d) water-soluble sweeteners derived from naturally
occurring water-soluble sweeteners, such as chlorinated derivatives
of ordinary sugar (sucrose), e.g., chlorodeoxysugar derivatives
such as derivatives of chlorodeoxysucrose or
chlorodeoxygalactosucrose, known, for example, under the product
designation of Sucralose or Splenda.TM.; examples of
chlorodeoxysucrose and chlorodeoxygalactosucrose derivatives
include but are not limited to: 1-chloro-1'-deoxysucrose;
4-chloro-4-deoxy-alpha-D-galactopyranosyl-alpha-D-fructofuranoside,
or 4-chloro-4-deoxygalactosucrose;
4-chloro-4-deoxy-alpha-D-galactopyranosyl-1-chloro-1-deoxy-beta-D-fructof-
uranoside, or 4,1'-dichloro-4,1'-dideoxygalactosucrose;
1',6'-dichloro 1',6'-dideoxysucrose;
4-chloro-4-deoxy-alpha-D-galactopyranosyl-1,6-dichloro-1,6-dideoxy-beta-D-
-fructofuranoside, or
4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose;
4,6-dichloro-4,6-dideoxy-alpha-D-galactopyranosyl-6-chloro-6-deoxy-beta-D-
-fructofuranoside, or
4,6,6'-trichloro-4,6,6'-trideoxygalactosucrose;
6,1',6'-trichloro-6,1',6'-trideoxysucrose;
4,6-dichloro-4,6-dideoxy-alpha-D-galacto-pyranosyl-1,6-dichloro-1,6-dideo-
xy-beta-D-fructo-furanoside, or 4,6,1',6'-tetrachloro
4,6,1',6'-tetradeoxygalacto-sucrose; and
4,6,1',6'-tetradeoxy-sucrose, and mixtures thereof;
[0108] (e) protein based sweeteners such as thaumaoccous danielli
(Thaumatin I and II) and talin; and [0109] the sweetener monatin
(2-hydroxy-2-(indol-3-ylmethyl)-4-aminoglutaric acid) and its
derivatives.
[0110] The intense sweetening agents may be used in many distinct
physical forms well-known in the art to provide an initial burst of
sweetness and/or a prolonged sensation of sweetness. Without being
limited thereto, such physical forms include free forms, spray
dried forms, powdered forms, beaded forms, encapsulated forms, and
mixtures thereof. In one embodiment, the sweetener is a high
intensity sweetener such as aspartame, sucralose, and acesulfame
potassium (e.g., Ace-K or acesulfame-K).
[0111] In some embodiments, the sweetener may be a polyol. Polyols
can include, but are not limited to glycerol, sorbitol, maltitol,
maltitol syrup, mannitol, isomalt, erythritol, xylitol,
hydrogenated starch hydrolysates, polyglycitol syrups, polyglycitol
powders, lactitol, and combinations thereof.
[0112] The active component (e.g., sweetener), which is part of the
delivery system, may be used in amounts necessary to impart the
desired effect associated with use of the active component (e.g.,
sweetness). In general, an effective amount of intense sweetener
may be utilized to provide the level of sweetness desired, and this
amount may vary with the sweetener selected. The intense sweetener
may be present in amounts from about 0.001% to about 3%, by weight
of the composition, depending upon the sweetener or combination of
sweeteners used. The exact range of amounts for each type of
sweetener may be selected by those skilled in the art.
Sensate Ingredients
[0113] In addition to cooling agents, as described above, sensate
compounds can include warming agents, tingling agents, effervescent
agents, and combinations thereof.
[0114] In some embodiments, warming components may be selected from
a wide variety of compounds known to provide the sensory signal of
warming to the user. These compounds offer the perceived sensation
of warmth, particularly in the oral cavity, and often enhance the
perception of flavors, sweeteners and other organoleptic
components. In some embodiments, useful warming compounds can
include vanillyl alcohol n-butylether (TK-1000) supplied by
Takasago Perfumary Company Limited, Tokyo, Japan, vanillyl alcohol
n-propylether, vanillyl alcohol isopropylether, vanillyl alcohol
isobutylether, vanillyl alcohol n-aminoether, vanillyl alcohol
isoamyleather, vanillyl alcohol n-hexyleather, vanillyl alcohol
methylether, vanillyl alcohol ethylether, gingerol, shogaol,
paradol, zingerone, capsaicin, dihydrocapsaicin,
nordihydrocapsaicin, homocapsaicin, homodihydrocapsaicin, ethanol,
isopropyl alcohol, iso-amylalcohol, benzyl alcohol, glycerine, and
combinations thereof.
[0115] In some embodiments, a tingling sensation can be provided.
One such tingling sensation is provided by adding jambu, oleoresin,
or spilanthol to some examples. In some embodiments, alkylamides
extracted from materials such as jambu or sanshool can be included.
Additionally, in some embodiments, a sensation is created due to
effervescence. Such effervescence is created by combining an
alkaline material with an acidic material. In some embodiments, an
alkaline material can include alkali metal carbonates, alkali metal
bicarbonates, alkaline earth metal carbonates, alkaline earth metal
bicarbonates and mixtures thereof. In some embodiments, an acidic
material can include acetic acid, adipic acid, ascorbic acid,
butyric acid, citric acid, formic acid, fumaric acid, glyconic
acid, lactic acid, phosphoric acid, malic acid, oxalic acid,
succinic acid, tartaric acid, aspartic acid, benzoic acid,
caffeotannic acid, iso-citric acid, citramalic acid, galacturonic
acid, glucuronic acid, glyceric acid, glycolic acid, ketoglutaric
acid, a-ketoglutaric acid, lactoisocitric acid, oxalacetic acid,
pyruvic acid, quinic acid, shikimic acid, succinic acid, tannic
acid, hydroxyacetic acid, suberic acid, sebacic acid, azelaic acid,
pimelic acid, capric cid, and combinations thereof. Examples of
"tingling" type sensates can be found in U.S. Pat. No. 6,780,443,
the entire contents of which are incorporated herein by reference
for all purposes.
[0116] Sensate components may also be referred to as "trigeminal
stimulants" such as those disclosed in U.S. Patent Application No.
2005/0202118, which is incorporated herein by reference. Trigeminal
stimulants are defined as an orally consumed product or agent that
stimulates the trigeminal nerve. Examples of cooling agents which
are trigeminal stimulants include menthol, WS-3, N-substituted
p-menthane carboxamide, acyclic carboxamides including WS-23, WS-5,
WS-14, methyl succinate, and menthone glycerol ketals. Trigeminal
stimulants can also include flavors, tingling agents, Jambu
extract, vanillyl alkyl ethers, such as vanillyl n-butyl ether,
spilanthol, Echinacea extract, Northern Prickly Ash extract,
capsaicin, capsicum oleoresin, red pepper oleoresin, black pepper
oleoresin, piperine, ginger oleoresin, gingerol, shoagol, cinnamon
oleoresin, cassia oleoresin, cinnamic aldehyde, eugenol, cyclic
acetal of vanillin and menthol glycerin ether, unsaturated amides,
and combinations thereof. Other cooling compounds can include
derivatives of 2,3-dimethyl-2-isopropylbutyric acid such as those
disclosed in U.S. Pat. No. 7,030,273, which is incorporated herein
by reference.
[0117] In addition to trigeminal nerve stimulants and cooling
compounds, a cooling sensation can be provided by materials
exhibiting a negative heat of solution including, but not limited
to, polyols such as xylitol, erythritol, dextrose, and sorbitol,
and combinations thereof.
[0118] In some embodiments, sensate components are used at levels
that provide a perceptible sensory experience i.e. at or above
their threshold levels. In other embodiments, sensate components
are used at levels below their threshold levels such that they do
not provide an independent perceptible sensory experience. At
subthreshold levels, the sensates may provide an ancillary benefit
such as flavor or sweetness enhancement or potentiation.
Effervescing System Ingredients
[0119] An effervescent system may include one or more edible acids
and one or more edible alkaline materials. The edible acid(s) and
the edible alkaline material(s) may react together to generate
effervescence.
[0120] In some embodiments, the alkaline material(s) may be
selected from, but is not limited to, alkali metal carbonates,
alkali metal bicarbonates, alkaline earth metal carbonates,
alkaline earth metal bicarbonates, and combinations thereof. The
edible acid(s) may be selected from, but is not limited to, citric
acid, phosphoric acid, tartaric acid, malic acid, ascorbic acid,
and combinations thereof. In some embodiments, an effervescing
system may include one or more other ingredients such as, for
example, carbon dioxide, oral care ingredients, flavorants,
etc.
[0121] For examples of use of an effervescing system in a chewing
confectionery, refer to U.S. Provisional Patent No. 60/618,222
filed Oct. 13, 2004, and entitled "Effervescent Pressed
Confectionery Tablet Compositions," the contents of which are
incorporated herein by reference for all purposes. Other examples
can be found in U.S. Pat. No. 6,235,318, the contents of which are
incorporated herein by reference for all purposes.
Potentiator Ingredients
[0122] Potentiators can consist of materials that may intensify,
supplement, modify or enhance the taste and/or aroma perception of
an original material without introducing a characteristic taste
and/or aroma perception of their own. In some embodiments,
potentiators designed to intensify, supplement, modify, or enhance
the perception of flavor, sweetness, tartness, umami, kokumi,
saltiness and combinations thereof can be included.
[0123] In some embodiments, examples of suitable potentiators, also
known as taste potentiators include, but are not limited to,
neohesperidin dihydrochalcone, optically active S-alkyl 2-methyl
butane thioate compounds such as those disclosed in PCT Application
Number WO 2007/032262 to Ogura et al, which is incorporated in its
entirety herein by reference, chlorogenic acid, alapyridaine,
cynarin, miraculin, glupyridaine, pyridinium-betain compounds,
glutamates, such as monosodium glutamate and monopotassium
glutamate, neotame, thaumatin, tagatose, trehalose, salts, such as
sodium chloride, monoammonium glycyrrhizinate, vanilla extract (in
ethyl alcohol), sugar acids, potassium chloride, sodium acid
sulfate, hydrolyzed vegetable proteins, hydrolyzed animal proteins,
yeast extracts, adenosine monophosphate (AMP), glutathione,
nucleotides, such as inosine monophosphate, disodium inosinate,
xanthosine monophosphate, guanylate monophosphate, alapyridaine
(N-(1-carboxyethyl)-6-(hydroxymethyl)pyridinium-3-ol inner salt,
compositions comprising 5'-nucleotides such as those disclosed in
US 2006/0078972 to Noordam et al, which is incorporated in its
entirety herein by reference, sugar beet extract (alcoholic
extract), sugarcane leaf essence (alcoholic extract), curculin,
strogin, mabinlin, gymnemic acid, hydroxybenzoic acids,
3-hydrobenzoic acid, 2,4-dihydrobenzoic acid, citrus aurantium,
vanilla oleoresin, sugarcane leaf essence, maltol, ethyl maltol,
vanillin, licorice glycyrrhizinates, compounds that respond to the
TRPM5 ion channel that mediates taste receptors for sweet, bitter,
and savory tastes as disclosed in U.S. Patent Application Number
2005/0019830 to Penner et al, which is incorporated in its entirety
herein by reference, pyridinium betain compounds as disclosed in
U.S. Pat. No. 7,175,872 to Hofmann et al, which is incorporated in
its entirety herein by reference, compounds that respond to
G-protein coupled receptors (T2Rs and T1Rs) and taste potentiator
compositions that impart kokumi, as disclosed in U.S. Pat. No.
5,679,397 to Kuroda et al., which is incorporated in its entirety
herein by reference. "Kokumi" refers to materials that impart
"mouthfulness" and "good body".
[0124] Sweetener potentiators, which are a type of taste
potentiator, enhance the taste of sweetness. In some embodiments,
exemplary sweetener potentiators include, but are not limited to,
monoammonium glycyrrhizinate, licorice glycyrrhizinates, citrus
aurantium, alapyridaine, alapyridaine
(N-(1-carboxyethyl)-6-(hydroxymethyl)pyridinium-3-ol) inner salt,
miraculin, curculin, strogin, mabinlin, gymnemic acid, cynarin,
glupyridaine, pyridinium-betain compounds, sugar beet extract,
neotame, thaumatin, neohesperidin dihydrochalcone, hydroxybenzoic
acids, tagatose, trehalose, maltol, ethyl maltol, vanilla extract,
vanilla oleoresin, vanillin, sugar beet extract (alcoholic
extract), sugarcane leaf essence (alcoholic extract), compounds
that respond to G-protein coupled receptors (T2Rs and T1Rs) and
combinations thereof.
[0125] Additional examples of potentiators for the enhancement of
salt taste include acidic peptides, such as those disclosed in U.S.
Pat. No. 6,974,597, herein incorporated by reference. Acidic
peptides include peptides having a larger number of acidic amino
acids, such as aspartic acid and glutamic acid, than basic amino
acids, such as lysine, arginine and histidine. The acidic peptides
are obtained by peptide synthesis or by subjecting proteins to
hydrolysis using endopeptidase, and if necessary, to deamidation.
Suitable proteins for use in the production of the acidic peptides
or the peptides obtained by subjecting a protein to hydrolysis and
deamidation include plant proteins, (e.g. wheat gluten, corn
protein (e.g., zein and gluten meal), soybean protein isolate),
animal proteins (e.g., milk proteins such as milk casein and milk
whey protein, muscle proteins such as meat protein and fish meat
protein, egg white protein and collagen), and microbial proteins
(e.g., microbial cell protein and polypeptides produced by
microorganisms).
[0126] The sensation of warming or cooling effects may also be
prolonged with the use of a hydrophobic sweetener as described in
U.S. Patent Application Publication 2003/0072842 A1 which is
incorporated in its entirety herein by reference. For example, such
hydrophobic sweeteners include those of the formulae I-XI as set
forth below: ##STR3## wherein X, Y and Z are selected from the
group consisting of CH.sub.2, O and S; ##STR4## wherein X and Y are
selected from the group consisting of S and O; ##STR5## wherein X
is S or O; Y is O or CH.sub.2; Z is CH.sub.2, SO.sub.2 or S; R is
OCH.sub.3, OH or H; R.sup.1 is SH or OH and R.sup.2 is H or OH;
##STR6## wherein X is C or S; R is OH or H and R.sup.1 is OCH.sub.3
or OH; ##STR7## wherein R, R.sup.2 and R.sup.3 are OH or H and
R.sup.1 is H or COOH; ##STR8## wherein X is O or CH.sub.2 and R is
COOH or H; ##STR9## wherein R is CH.sub.3CH.sub.2, OH, N
(CH3).sub.2 or Cl; ##STR10##
[0127] Perillartine may also be added as described in U.S. Pat. No.
6,159,509 also
[0128] incorporated in its entirety herein by reference.
Food Acid Ingredients
[0129] Acids can include, but are not limited to acetic acid,
adipic acid, ascorbic acid, butyric acid, citric acid, formic acid,
fumaric acid, glyconic acid, lactic acid, phosphoric acid, malic
acid, oxalic acid, succinic acid, tartaric acid, aspartic acid,
benzoic acid, caffeotannic acid, iso-citric acid, citramalic acid,
galacturonic acid, glucuronic acid, glyceric acid, glycolic acid,
ketoglutaric acid, a-ketoglutaric acid, lactoisocitric acid,
oxalacetic acid, pyruvic acid, quinic acid, shikimic acid, succinic
acid, tannic acid, hydroxyacetic acid, suberic acid, sebacic acid,
azelaic acid, pimelic acid, capric cid, and combinations
thereof.
Mouth Moistening Ingredients
[0130] Mouth moisteners can include, but are not limited to, saliva
stimulators such as acids and salts and combinations thereof. In
some embodiments, acids can include acetic acid, adipic acid,
ascorbic acid, butyric acid, citric acid, formic acid, fumaric
acid, glyconic acid, lactic acid, phosphoric acid, malic acid,
oxalic acid, succinic acid, tartaric acid and combinations
thereof.
[0131] Mouth moisteners can also include hydrocolloid materials
that hydrate and may adhere to oral surface to provide a sensation
of mouth moistening. Hydrocolloid materials can include naturally
occurring materials such as plant exudates, seed gums, and seaweed
extracts or they can be chemically modified materials such as
cellulose, starch, or natural gum derivatives. In some embodiments,
hydrocolloid materials can include pectin, gum arabic, acacia gum,
alginates, agar, carageenans, guar gum, xanthan gum, locust bean
gum, gelatin, gellan gum, cassia gum, galactomannans, tragacanth
gum, karaya gum, curdlan, konjac, chitosan, xyloglucan, beta
glucan, furcellaran, gum ghatti, tamarin, bacterial gums, and
combinations thereof. Additionally, in some embodiments, modified
natural gums such as propylene glycol alginate, carboxymethyl
locust bean gum, low methoxyl pectin, and their combinations can be
included. In some embodiments, modified celluloses can be included
such as microcrystalline cellulose, carboxymethlcellulose (CMC),
methylcellulose (MC), hydroxypropylmethylcellulose (HPCM), and
hydroxypropylcellulose (MPC), and combinations thereof.
[0132] Similarly, humectants which can provide a perception of
mouth hydration can be included. Such humectants can include, but
are not limited to glycerol, sorbitol, polyethylene glycol,
erythritol, and xylitol. Additionally, in some embodiments, fats
can provide a perception of mouth moistening. Such fats can include
medium chain triglycerides, vegetable oils, fish oils, mineral
oils, and combinations thereof.
[0133] Mouth moisteners can also include pellitorine extracts,
extracts of Anacyclus pyrethrum, trans-pellitorin,
N-isobutyl-trans-2-trans-4-decadienamide, alkadienamides including
N-isobutyl-E2, E4-decadienamide; N-isobutyl-E2, E4-undecadienamide;
N-pyrollidyl-E2, E4-decadienamide; N-piperidl-E2, E4-decadienamdie,
or combinations thereof as disclosed in U.S. Patent Application No.
2007/0075368 which is incorporated in its entirety herein by
reference; blends of n-isobutyldeca-trans-2-trans-4-dienamide with
food acids as disclosed in U.S. Patent Application No. 2006/0204551
which is incorporated in its entirety herein by reference; blends
of compounds according to formula (I): wherein R.sub.1 represents
C1-C2 n-alkyl; R.sub.2 is 2-methyl-1-propyl and R.sub.3 is
hydrogen, or R.sub.2 and R.sub.3 taken together is a moiety having
the formula --(CH.sub.2).sub.n-- wherein n is 4 or 5, or mixtures
thereof with cooling compounds as disclosed in U.S. Patent
Application No. 2007/0036838 to Keenan et al, which is incorporated
in its entirety herein by reference. ##STR11## Quantitative
Descriptive Analysis
[0134] Many sensory test methods such as descriptive analysis
depend upon the judgments of panelists about the perceived strength
of individual sensory characteristics in a product. These perceived
intensity estimates are often given as scale numbers or choices on
a rating scale. Judgments are often made relative to some frame of
reference, which is sometimes explicit in the training of the
panel. However, human judgments tend to shift as a function of the
immediate context, and the set of products evaluated within a
sensory test session can skew the ratings of an individual judge.
There can be a stabilizing effect of training and reference
standards in reducing such context effects and the resistance of
different scaling methods to contextual shifting.
[0135] One text covering all the basic techniques of sensory
testing is Sensory Evaluation of Food: Principles & Practices,
by Harry T. Lawless and Hildegarde Heymann, the disclosure of which
is herein incorporated by reference. Statistics used in sensory
evaluation are demonstrated as integrated applications in the
context of appropriate sensory methods and are also presented as
stand-alone material in appendices. Statistical applications are
tailored to common analyses encountered to sensory work, together
with instructions on how tests should be conducted. One exemplary
application of the principles of quantitative descriptive analysis
with respect to milk products is provided by Chapman et al., J.
Dairy Science 84:12-20 (2001).
[0136] A panel of respondents may be assembled for sensory
evaluation. Attribute terms for evaluation of samples are selected.
Normally, ballot development and respondent training is carried out
initially. Descriptive terms are developed for major sensory
attribute categories. Exemplary attribute qualities include aroma,
flavor, texture, aftertaste, sweetness, etc. Attributes are
quantified with an intensity scale of from, e.g. 0 to 10; where 0
indicates that the attribute is not detected and 10 indicates the
attribute is extremely strong. Overall quality rating may be
measured with a scale of from, e.g. 1 to 10 where less than 6 is
considered "poor," 6 to 7 is "fair," and 8 to 10 is "good."
[0137] Physical reference standards are determined by a panel
consensus so that proper descriptive language may be developed.
Panelists may be trained in evaluating certain samples until a
consensus is attained.
[0138] Overall quality ratings and quantified intensity ratings may
be analyzed with such programs as Minitab ver. 12 or SAS ver. 6.11.
Descriptive statistical measures may be calculated for all
attributes. Analysis of variance may be performed on each attribute
using a randomized block design for balanced data with panelists as
repeated measures as described by Ott, "Analysis of variance for
some standard experimental designs," pp. 844-856 in An Introduction
to Statistical Methods and Data Analysis. Wadsworth Publishing.
Belmont, Calif. Where F-test indicates a significant difference
between treatment means, Tukey paired comparisons and orthogonal
comparisons may be used to determine where the means are different.
Significance of differences may be defined as P less than 0.05.
Principal components analysis (PCA) may be applied with the factor
analysis described by Lawless and Heymann, 1998, pp. 606-608 in
Sensory Evaluation of Food: Principles and Practices. Chapman &
Hall, New York, 1998. PCA may be applied to the attributes.
Attributes may be omitted if the values are consistently low
indicating that the attribute is not often present, if the
attribute has a high standard deviation or if the attribute is
highly correlated to another attribute. Kaiser's criterion may be
applied (eigen value greater than 1) to determine the number of
final factors from the initial ones as described by Massart et al.,
"Principal components and factor analysis," pp. 339-369 in
Chemometrics: A Textbook. Elsevier, Amsterdam, 1988. To facilitate
the interpretation of results, the factors may be orthogonally
rotated leading to uncorrelated factors following the Varimax
method described by Massart et al., supra.
[0139] The overall quality ratings (dependent variables) may be
modeled as a function of the Varimax rotated PC scores for the
products (independent variables). Models may be constructed using
ordinary least squares (OLS), principal components regression
(PCR), and partial least squares regression (PLS) routines in SCAN
for Windows Release 1.1. PCR and PLS models may be calculated with,
for instance, one to four components. In each case, the best fit
equations (those with the highest R.sup.2) and those with the best
predictive ability (lowest residual predictive sum of squares, or
residual PRESS) are obtained.
[0140] Further, respondents can score each product at three time
points; one minute, fifteen minutes, and thirty minutes for overall
liking and intensity of four attributes: flavor, sweetness,
cooling/warming and texture. A fifteen minute rest period can be
provided between each product allowing for palate cleansing. The
tests can be performed generally according to the criterion set
forth above. Such statistical processes as set forth above may be
used to analyze the data collected.
[0141] The present cooling compositions and methods will now be
illustrated in greater detail with reference to Examples in view of
Comparative Examples, but it should be understood that the methods
and compositions are not limited thereto. Unless otherwise noted,
all the percents are by weight.
[0142] In some embodiments, cooling compositions can be formulated
to contain a menthyl glutarate ester in the following amounts
expressed as weight percent. Additionally, the cooling compositions
can be coupled with a flavor composition as indicated. WS-3 and
WS-23 are shown together to indicate that they can be used
interchangeably. TABLE-US-00001 TABLE 1 Example Number % w/w
Component 1 2 3 4 5 6 7 8 9 Menthyl 5-60 5-60 5-60 5-60 glutarate
Menthyl 5-60 5-60 5-60 5-60 lactate Menthyl 5-60 5-60 5-60 5-60
succinate Menthyl 5-60 5-60 5-60 acetate WS3 or 5-50 5-50 5-50 5-50
WS23 WS5 5-50 Ice 6000 5-50 Ice 10000 5-50 Ice 11000 5-50 Menthol
15-85 15-85 15-85 15-85 15-85 Isopulegol 2-50 p-menthane 2-50 3,8
diol
[0143] TABLE-US-00002 TABLE 2 Chewing Gum Compositions 1. Gum Base
20-50% Sugar 35-80% Glucose Syrup 8-25% Sweetener 0.01-1.5%
Lecithin 0.2-1.2% Glycerin 1-8% Color 0.01-0.05% Peppermint Flavor
1.2-2.5% Cooling Composition 0.2-1.2% 2. Gum Base 20-50% Sugar
35-80% Glucose Syrup 8-25% Sweetener 0.01-1.5% Lecithin 0.2-1.2%
Glycerin 1-8% Color 0.01-0.05% Wintergreen Flavor 0.9-2.3%
Peppermint Flavor 0.5-1.5% Cooling Composition 0.2-1.2% 3. Gum Base
20-50% Sugar 35-80% Glucose Syrup 8-25% Sweetener 0.01-1.5%
Lecithin 0.2-1.2% Glycerin 1-8% Color 0.01-0.05% Spearmint Flavor
1.2-2.5% Cooling Composition 0.2-1.2% 4. Gum Base 20-50% Sugar
35-80% Glucose Syrup 8-25% Sweetener 0.01-1.5% Lecithin 0.2-1.2%
Glycerin 1-8% Color 0.01-0.05% Cinnamon Flavor 1.5-2.5% Cooling
Composition 0.2-1.2% 5. Gum Base 20-50% Sugar 35-80% Glucose Syrup
8-25% Sweetener 0.01-1.5% Lecithin 0.2-1.2% Glycerin 1-8% Color
0.01-0.05% Fruit Flavor 1.2-2.5% Cooling Composition 0.2-1.2% 6.
Gum Base 20-50% Sorbitol Powder 35-80% Sweetener 0.01-1.5% Lecithin
0.2-1.2% Glycerin 3-15% Color 0.01-0.05% Peppermint Flavor 1.2-2.5%
Cooling Composition 0.2-1.2% 7. Gum Base 20-50% Mannitol Powder
35-80% Sweetener 0.01-1.5% Lecithin 0.2-1.2% Glycerin 3-15% Color
0.01-0.05% Peppermint Flavor 1.2-2.5% Cooling Composition 0.2-1.2%
8. Gum Base 20-50% Xylitol Powder 35-80% Sweetener 0.01-1.5%
Lecithin 0.2-1.2% Glycerin 3-15% Color 0.01-0.05% Peppermint Flavor
1.2-2.5% Cooling Composition 0.2-1.2% 9. Gum Base 20-50% Xylitol
Powder 35-80% Erythritol Powder 35-80% Sweetener 0.01-1.5% Lecithin
0.2-1.2% Glycerin 3-15% Color 0.01-0.05% Peppermint Flavor 1.2-2.5%
Cooling Composition 0.2-1.2%
[0144] TABLE-US-00003 TABLE 3 Confectionery Compositions % w/w
Ingredient 10 11 12 13 14 Sucrose 10%-35% 10%-30% 30%-60% Corn
Syrup 2%-18% 10%-30% 60%-30% Water 3%-12% 3%-18% 3%-15% 10-30%
10%-20% Fat 0%-5% 0%-5% 0%-5% Hydrocolloids 0%-5% 0%-5% Lecithin
0%-0.5% 0%-0.6% 0%-0.6% 0%-0.6% GMS 0%-0.5% 0%-0.6% 0%-0.6% 0%-0.6%
Hydrogenated 0%-6% Starch Hydrolysates Sorbitol 0%-35% Erythritol
0%-9% 0%-25% Xylitol 0%-60% Maltitol 0-60% Isomalt 0%-50% 0%-18%
Mannitol 0-15% Flavor 0.15%-3.0% 0.1%-1.5% 0.1%-1.5% 0.1%-1.5%
0.3%-3.0% Acid(s) 0.1%-1.5% 0.1%-1.5% 0.1%-1.5% Color(s) 0%-0.15%
0%-0.12% 0%-0.12% 0%-0.12% 0%-0.12% Free Sweetener 0.1%-0.5%
0.01-0.2% 0.01-0.2% Encapsulated 0.5%-7% 0.1%-2% 0.1%-2% 0.1%-2%
Sweetener Cooling 0.01-0.25% 0.01-0.25% 0.01-0.25% Composition
Totals: 100 100 100 100 100
[0145] To prepare the confectionery products, portions of the
sugar, corn syrup, sorbitol, xylitol, erythritol, maltitol,
mannitol, isomalt and water are weighed, as indicated in Table 3
above, and combined. The mixture is heated to start boiling. While
boiling the fat, lecithin, and GMS are added and mixed. The mixture
is boiled to cook temperature. The hydrocolloid is added in a
pre-dissolved slurry format. The flavors, acids and colors are
added. The mixture is mixed thoroughly and shaped into the desired
format.
Chewing Gum and Confectionary Compositions Providing a
Physiological Cooling Sensation
[0146] In some embodiments, chewing gum and confectionaries will be
prepared having some of the components provided below in amounts
within those amounts recommended by the United Sattes government as
not exceeding the amounts set forth below. The chewing gums and
confectionary compositions will demonstrate an ability to impart a
physiological cooling sensation. TABLE-US-00004 TABLE 4 FEMA FEMA
FEMA recomm. recomm. recomm. levels in levels in GRAS levels in
HARD SOFT # Compound names GUM CANDY CANDY 2665 Menthol 1,100 400
400 2667 Menthone 8.7 71 71 2668 Menthyl acetate 5.2 26 26 2962
Isopulegol NA 23 23 3455 WS-3 1,200 10 10 3460 Isomenthone 600 60
60 3748 Menthyl Lactate 800 NA NA 3784 3-1-menthoxy- 4,000 500 500
propane- 1,2-diol 3804 WS-23 3,000 50 NA 3805 1-menthol 20,000
2,000 NA ethylene glycol carbonate 3806 1-menthol-1and2- 10,000
3,000 NA propylene glycol carbonate 3807 1-menthone 1,2 800 NA 80
glycerol ketal 3808 d,1-menthone 1,2 800 NA 80 glycerol ketal 3810
Mono-menthyl 3,750 600 600 succinate (physcool) 3992 d,1 menthol
20,000 2,000 2,000 propyleneglycol carbonate 4006 L-monomenthyl
4,000 700 600 glutarate
[0147] From the foregoing description, various modifications and
changes in the compositions and methods will occur to those skilled
in the art. All such modifications coming within the scope of the
appended claims are intended to be included therein.
[0148] All publications, including but not limited to patents and
patent applications, cited in this specification are herein
incorporated by reference as if each individual publication were
specifically and individually fully set forth.
* * * * *