US20070221236A1 - Cooling compositions including menthyl esters - Google Patents

Cooling compositions including menthyl esters Download PDF

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US20070221236A1
US20070221236A1 US11732942 US73294207A US2007221236A1 US 20070221236 A1 US20070221236 A1 US 20070221236A1 US 11732942 US11732942 US 11732942 US 73294207 A US73294207 A US 73294207A US 2007221236 A1 US2007221236 A1 US 2007221236A1
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composition
cooling
menthyl
weight
glutarate
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US11732942
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Jesse Kiefer
Joan Harvey
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Intercontinental Great Brands LLC
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Cadbury Adams USA LLC
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00Chewing gum
    • A23G4/06Chewing gum characterised by the composition containing organic or inorganic compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20Synthetic spices, flavouring agents or condiments
    • A23L27/204Aromatic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/345Alcohols containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42Amides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24Thermal properties
    • A61K2800/244Endothermic; Cooling; Cooling sensation

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.

Description

    CROSS-REFERENCE TO RELATED APPLICATIONS
  • 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
  • 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
  • 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.
  • 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
  • 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.
  • 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.
  • 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.
  • 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.
  • 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° C.
  • 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° C.
  • 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° C.
  • 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° C.
  • 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.
  • In some embodiments, there is provided a method of preparing a cooling composition which is liquid at 25° C., including the steps of:
    • (a) providing menthyl glutarate in a liquid form; and
    • (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,
    • 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.
  • Some other embodiments provide a method of preparing a cooling composition which is liquid at 25° C., including the steps of:
    • (a) combining menthyl glutarate and at least one cooling agent selected from 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° C. while maintaining the composition in a liquid state to form the liquid cooling composition.
    DETAILED DESCRIPTION
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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”.
  • 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.
  • 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 C15H26O4. 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
  • 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.
  • 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.
  • 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.
  • 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.
  • 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® type MGA); 3-1-menthoxypropane-1,2-diol (from Takasago, FEMA 3784); and menthyl lactate; (from Haarman & Reimer, FEMA 3748, tradename FRESCOLAT® 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 α-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:
    Figure US20070221236A1-20070927-C00001

    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:
    Figure US20070221236A1-20070927-C00002

    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.
  • 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® 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® type ML).
  • 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).
  • 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.
  • 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.
  • 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.
  • 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° 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.
  • 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.
  • 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
  • U.S. Pat. No. 3,111,127 incorporated herein by reference discloses such monomenthyl esters as monomenthyl succinate, monomenthyl αα-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.
  • 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.
  • 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.
  • 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
  • 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.
  • By “aroma” is meant a minty or freshening physiological sensation perceived as a sense of smell.
  • By “cooling effect” is meant a sensation described as cooling by those experiencing it on the skin, oral cavity or mucous membranes.
  • 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.
  • 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 α,α-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
  • 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.
  • 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.
  • 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.
  • In some embodiments, the cooling composition may be a liquid at room temperature (about 25° C.). For instance, a cooling composition, which is liquid at 25° 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.
  • In some embodiments, cooling compositions that are liquid at 25° 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.
  • In some embodiments, the cooling composition, which is liquid at 25° 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.
  • In some other embodiments, the cooling composition, which is liquid at 25° 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.
  • 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° 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.
  • 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° C.); WS-3 (88° C.); WS-23 (62-64° C.); menthyl lactate (40-42° C.); menthyl succinate (59-61° C.); and menthyl acetate ester (23-24° 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° C. The liquid composition then may be cooled to less than about 30° C., more specifically about 25° 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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
  • 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.
  • 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.
  • 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° C. to 60° 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.
  • 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.
  • 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° C. to 140° 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.
  • 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
  • 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
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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
  • 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:
  • (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;
  • (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;
  • (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-α-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;
  • (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™; 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-fructofuranoside, 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-dideoxy-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;
  • (e) protein based sweeteners such as thaumaoccous danielli (Thaumatin I and II) and talin; and
    • the sweetener monatin (2-hydroxy-2-(indol-3-ylmethyl)-4-aminoglutaric acid) and its derivatives.
  • 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).
  • 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.
  • 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
  • In addition to cooling agents, as described above, sensate compounds can include warming agents, tingling agents, effervescent agents, and combinations thereof.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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
  • 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.
  • 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.
  • 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
  • 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.
  • 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”.
  • 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.
  • 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).
  • 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:
    Figure US20070221236A1-20070927-C00003

    wherein X, Y and Z are selected from the group consisting of CH2, O and S;
    Figure US20070221236A1-20070927-C00004

    wherein X and Y are selected from the group consisting of S and O;
    Figure US20070221236A1-20070927-C00005

    wherein X is S or O; Y is O or CH2; Z is CH2, SO2 or S; R is OCH3, OH or H; R1 is SH or OH and R2 is H or OH;
    Figure US20070221236A1-20070927-C00006

    wherein X is C or S; R is OH or H and R1 is OCH3 or OH;
    Figure US20070221236A1-20070927-C00007

    wherein R, R2 and R3 are OH or H and R1 is H or COOH;
    Figure US20070221236A1-20070927-C00008

    wherein X is O or CH2 and R is COOH or H;
    Figure US20070221236A1-20070927-C00009

    wherein R is CH3CH2, OH, N (CH3)2 or Cl;
    Figure US20070221236A1-20070927-C00010
  • Perillartine may also be added as described in U.S. Pat. No. 6,159,509 also
  • incorporated in its entirety herein by reference.
  • Food Acid Ingredients
  • 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
  • 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.
  • 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.
  • 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.
  • 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 R1 represents C1-C2 n-alkyl; R2 is 2-methyl-1-propyl and R3 is hydrogen, or R2 and R3 taken together is a moiety having the formula —(CH2)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.
    Figure US20070221236A1-20070927-C00011

    Quantitative Descriptive Analysis
  • 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.
  • 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).
  • 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.”
  • 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.
  • 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.
  • 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 R2) and those with the best predictive ability (lowest residual predictive sum of squares, or residual PRESS) are obtained.
  • 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.
  • 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.
  • 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 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
  • 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%
  • 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
  • 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
  • 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 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
  • 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.
  • 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.

Claims (33)

  1. 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. 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. 3. A chewing gum composition comprising the cooling composition of claim 1.
  4. 4. A confectionery composition comprising the cooling composition of claim 1.
  5. 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. 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. 7. A chewing gum composition comprising the cooling composition of claim 5.
  8. 8. A confectionery composition comprising the cooling composition of claim 5.
  9. 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° C.
  10. 10. The cooling composition of claim 9, further comprising menthol in amounts of about 15% to about 85% by weight of the composition.
  11. 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. 12. A chewing gum composition comprising the cooling composition of claim 9.
  13. 13. A confectionery composition comprising the cooling composition of claim 9.
  14. 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° C.
  15. 15. The cooling composition of claim 14, further comprising menthol in amounts of about 15% to about 85% by weight of the composition.
  16. 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. 17. A chewing gum composition comprising the cooling composition of claim 14.
  18. 18. A confectionery composition comprising the cooling composition of claim 14.
  19. 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° C.
  20. 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. 21. A chewing gum composition comprising the cooling composition of claim 19.
  22. 22. A confectionery composition comprising the cooling composition of claim 19.
  23. 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° C.
  24. 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. 25. A chewing gum composition comprising the cooling composition of claim 23.
  26. 26. A confectionery composition comprising the cooling composition of claim 23.
  27. 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. 28. The cooling composition of claim 27, wherein said menthyl succinate is selected from the group consisting of monomenthyl succinate, dimenthyl succinate and monomenthyl α,α-dimethyl succinate.
  29. 29. A chewing gum composition comprising the cooling composition of claim 27.
  30. 30. A confectionery composition comprising the cooling composition of claim 27.
  31. 31. A method of preparing a cooling composition which is liquid at 25° 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. 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. 33. A method of preparing a cooling composition which is liquid at 25° 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° C. while maintaining the composition in a liquid state to form the liquid cooling composition.
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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070077331A1 (en) * 2005-10-05 2007-04-05 Cadbury Adams Usa Llc. Cooling compositions
US20080089850A1 (en) * 2006-10-11 2008-04-17 Ariel Haskel Compositions Comprising Combinations of Sensates
WO2009140783A1 (en) * 2008-05-22 2009-11-26 Givaudan Sa Cooling composition
US20100018540A1 (en) * 2008-07-28 2010-01-28 David James Doolittle Smokeless tobacco products and processes
US20100273887A1 (en) * 2007-08-16 2010-10-28 Symrise Gmbh & Co. Kg Mixtures comprising pellitorin and uses thereof
US20100278991A1 (en) * 2009-04-29 2010-11-04 John Christian Haught Methods for Improving Taste and Oral Care Compositions With Improved Taste
US20110237674A1 (en) * 2008-10-16 2011-09-29 Novartis Ag Topical nsaid compositions having sensate component
WO2011159927A1 (en) 2010-06-18 2011-12-22 Wm. Wrigley Jr. Company Chewing gum products containing ethyl ester of n-[[5-methyl-2-(1-methylethyl)-cyclohexyl] carbonyl] glycine
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US20140113971A1 (en) * 2008-10-16 2014-04-24 Joanna Zhang Topical NSAID Compositions Having Sensate Component
WO2014173922A1 (en) 2013-04-24 2014-10-30 Perfetti Van Melle S.P.A. Chewing gum with long-lasting freshness and its manufacturing process
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WO2017079506A1 (en) * 2015-11-05 2017-05-11 Wm. Wrigley Jr. Company Natural cooling formulations

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* Cited by examiner, † Cited by third party
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ES2626230T3 (en) 2008-11-20 2017-07-24 The Procter & Gamble Company Personal care compositions that provide enhanced cooling sensation
CN102355825A (en) * 2009-01-15 2012-02-15 卡夫食品环球品牌有限责任公司 Compositions and methods for treatment of throat discomfort
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US9675699B2 (en) 2011-12-22 2017-06-13 International Flavors & Fragrances Inc. Cooling enhancing compositions

Citations (73)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3857964A (en) * 1973-02-09 1974-12-31 Brook D Controlled release flavor compositions
US3897566A (en) * 1973-12-06 1975-07-29 Gen Foods Corp Chewing gums having longer lasting sweetness and flavor
US3930026A (en) * 1974-08-28 1975-12-30 Squibb & Sons Inc Chewing gum having enhanced flavor
US4032661A (en) * 1972-07-20 1977-06-28 Wilkinson Sword Limited Cyclic sulphoxides and sulphones having a physiological cooling action on the human body
US4033994A (en) * 1972-01-28 1977-07-05 Wilkinson Sword Limited Substituted p-menthanes
US4059118A (en) * 1972-01-28 1977-11-22 Wilkinson Sword Limited Tobacco and tobacco-containing manufactures containing an ingredient having physiological cooling activity
US4060091A (en) * 1972-01-28 1977-11-29 Wilkinson Sword Limited Tobacco and tobacco-containing manufactures containing an ingredient having physiological cooling activity
US4070449A (en) * 1972-10-24 1978-01-24 Wilkinson Sword Limited Compounds having a physiological cooling effect and compositions containing them
US4136163A (en) * 1971-02-04 1979-01-23 Wilkinson Sword Limited P-menthane carboxamides having a physiological cooling effect
US4193936A (en) * 1971-02-04 1980-03-18 Wilkinson Sword Limited N-substituted paramenthane carboxamides
US4230688A (en) * 1972-04-18 1980-10-28 Wilkinson Sword Limited Acyclic carboxamides having a physiological cooling effect
US4271197A (en) * 1979-06-21 1981-06-02 Walter Hopkins Chewing gum containing sugar substitute
US4352822A (en) * 1980-12-15 1982-10-05 Nabisco Brands Inc. Gum base, chewing gum containing same and method
US4388328A (en) * 1981-10-15 1983-06-14 Warner-Lambert Company Sorbitol containing mixture encapsulated flavor
US4459425A (en) * 1981-11-20 1984-07-10 Takasago Perfumery Co., Ltd. 3-Levo-Menthoxypropane-1,2-diol
US4485118A (en) * 1983-04-21 1984-11-27 Warner-Lambert Company Gum composition with plural time releasing flavors and method of preparation
US4497832A (en) * 1983-04-18 1985-02-05 Warner-Lambert Company Chewing gum composition having enhanced flavor-sweetness
US4568560A (en) * 1984-03-16 1986-02-04 Warner-Lambert Company Encapsulated fragrances and flavors and process therefor
US4590075A (en) * 1984-08-27 1986-05-20 Warner-Lambert Company Elastomer encapsulation of flavors and sweeteners, long lasting flavored chewing gum compositions based thereon and process of preparation
US4722845A (en) * 1986-12-23 1988-02-02 Warner-Lambert Company Stable cinnamon-flavored chewing gum composition
US4751095A (en) * 1983-07-28 1988-06-14 Karl Curtis L Aspartame stabilization with cyclodextrin
US4752481A (en) * 1986-06-19 1988-06-21 Warner-Lambert Company Flavor emulsions and chewing gum compositions containing the same
US4803082A (en) * 1987-10-28 1989-02-07 Warner-Lambert Company Flavor and sweetness enhancement delivery systems and method of preparation
US4918182A (en) * 1986-07-15 1990-04-17 Tate & Lyle Public Limited Company Sweetener
US4927646A (en) * 1986-11-13 1990-05-22 Tate & Lyle Plc Sucralose sweetening composition
US4929447A (en) * 1986-01-07 1990-05-29 Warner-Lambert Company Encapsulation composition for use with chewing gum and edible products
US4933190A (en) * 1986-12-23 1990-06-12 Warner-Lambert Co. Multiple encapsulated sweetener delivery system
US4971797A (en) * 1988-12-22 1990-11-20 Warner-Lambert Company Stabilized sucralose complex
US4981698A (en) * 1986-12-23 1991-01-01 Warner-Lambert Co. Multiple encapsulated sweetener delivery system and method of preparation
US5004595A (en) * 1986-12-23 1991-04-02 Warner-Lambert Company Multiple encapsulated flavor delivery system and method of preparation
US5009900A (en) * 1989-10-02 1991-04-23 Nabisco Brands, Inc. Glassy matrices containing volatile and/or labile components, and processes for preparation and use thereof
US5009893A (en) * 1989-07-17 1991-04-23 Warner-Lambert Company Breath-freshening edible compositions of methol and a carboxamide
US5041294A (en) * 1990-04-24 1991-08-20 Wm. Wrigley Jr. Company Sorbitol-modified flavor
US5158790A (en) * 1991-09-17 1992-10-27 Wm. Wrigley, Jr. Company L-carvone enhanced fruit flavored chewing gum
US5244670A (en) * 1991-04-04 1993-09-14 The Procter & Gamble Company Ingestible pharmaceutical compositions for treating upper gastrointestinal tract distress
US5266335A (en) * 1990-05-04 1993-11-30 Warner-Lambert Company Microencapsulated flavoring agents and methods for preparing same
US5266592A (en) * 1991-04-05 1993-11-30 Haarmann & Reimer Gmbh Compositions which have a physiological cooling effect, and active compounds suitable for these compositions
US5284659A (en) * 1990-03-30 1994-02-08 Cherukuri Subraman R Encapsulated flavor with bioadhesive character in pressed mints and confections
US5372824A (en) * 1993-03-25 1994-12-13 The Wm. Wrigley Jr. Company Mint flavored chewing gum having reduced bitterness and methods for making same
US5405604A (en) * 1992-10-16 1995-04-11 The Procter & Gamble Company Concentrated mouthrinse for efficient delivery of antimicrobials
US5407665A (en) * 1993-12-22 1995-04-18 The Procter & Gamble Company Ethanol substitutes
US5415880A (en) * 1994-04-12 1995-05-16 Wm. Wrigley Jr. Company Fruit flavored chewing gum with prolonged flavor intensity
US5429827A (en) * 1994-04-12 1995-07-04 Wm. Wrigley Jr. Company Method of making improved gum base for fruit-flavored chewing gum
US5458879A (en) * 1994-03-03 1995-10-17 The Procter & Gamble Company Oral vehicle compositions
US5545424A (en) * 1994-10-12 1996-08-13 Takasago International Corporation 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or its derivatives and flavor composition containing the same
US5603971A (en) * 1993-04-16 1997-02-18 Mccormick & Company, Inc. Encapsulation compositions
US5633027A (en) * 1994-08-05 1997-05-27 Fuisz Technologies Ltd. Confectioneries containing stabilized highly odorous flavor component delivery systems
US5725865A (en) * 1995-08-29 1998-03-10 V. Mane Fils S.A. Coolant compositions
US5783725A (en) * 1996-02-27 1998-07-21 Haarmann & Reimer Gmbh Stabilized lactic acid menthyl ester
US5800848A (en) * 1995-06-20 1998-09-01 The Wm. Wrigley Jr. Company Chewing gum containing sucrose polyesters
US6159509A (en) * 1996-10-28 2000-12-12 Wm. Wrigley Jr. Company Method of making chewing gum products containing perillartine
US6306429B1 (en) * 1997-04-21 2001-10-23 The Procter & Gamble Company Confectionery compositions
US6365215B1 (en) * 2000-11-09 2002-04-02 International Flavors & Fragrances Inc. Oral sensory perception-affecting compositions containing dimethyl sulfoxide, complexes thereof and salts thereof
US20020044968A1 (en) * 1996-10-28 2002-04-18 General Mills, Inc. Embedding and encapsulation of sensitive components into a matrix to obtain discrete controlled release particles
US6379652B1 (en) * 2000-10-16 2002-04-30 Colgate Palmolive Company Oral compositions for reducing mouth odors
US20020119231A1 (en) * 2000-12-12 2002-08-29 Takasago International Corporation Warming composition for food and drink or for oral care preparation
US20020150616A1 (en) * 1997-06-05 2002-10-17 Roger Petrus Gerebern Vandecruys Pharmaceutical compositions comprising cyclodextrins
US6623266B2 (en) * 2001-01-19 2003-09-23 Cadbury Adams Usa Llc Apparatus for making a center-filled gum lollipop with hard candy shell
US6627233B1 (en) * 1997-09-18 2003-09-30 Wm. Wrigley Jr. Company Chewing gum containing physiological cooling agents
US20030215532A1 (en) * 2000-02-04 2003-11-20 Takasago International Corporation New sensate composition imparting initial sensation upon contact
US6673844B2 (en) * 2000-12-12 2004-01-06 Takasago International Corporation Warming composition
US20040086546A1 (en) * 2002-06-25 2004-05-06 Maxwell James Roy Breath freshening and oral cleansing product with cinnamaldehyde
US20040141927A1 (en) * 2002-11-14 2004-07-22 Johnson Sonya S. Oral products containing novel flavor composition
US20040238993A1 (en) * 2002-01-10 2004-12-02 Daniel Benczedi Process for the preparation of extruded delivery systems
US6884906B2 (en) * 2003-07-01 2005-04-26 International Flavors & Fragrances Inc. Menthyl half acid ester derivatives, processes for preparing same, and uses thereof for their cooling/refreshing effect in consumable materials
US20050196517A1 (en) * 2005-02-14 2005-09-08 Mars, Incorporated Edible product having discrete regions with different heats of solution
US20060159819A1 (en) * 2004-12-29 2006-07-20 Witkewitz David L Combinations of cooling agents for use in confections
US7087255B2 (en) * 2000-12-27 2006-08-08 Wm. Wrigley Jr. Company Chewing gums that provide breath freshening characteristics
US20070036733A1 (en) * 2005-08-12 2007-02-15 Takasago International Corp. (Usa) Sensation masking composition
US20070048424A1 (en) * 2005-09-01 2007-03-01 Moza Ashok K Liquid composition of 2-Isopropyl-N,2,3-trimethylbutyramide and N-Ethyl-p-menthane-3-carboxamide, its preparation method and its applications as a cooling agent and flavor enhancer
US7189760B2 (en) * 2004-04-02 2007-03-13 Millennium Specialty Chemicals Physiological cooling compositions containing highly purified ethyl ester of N-[[5-methyl-2-(1-methylethyl) cyclohexyl] carbonyl]glycine
US20070077331A1 (en) * 2005-10-05 2007-04-05 Cadbury Adams Usa Llc. Cooling compositions
US7482378B2 (en) * 2004-05-28 2009-01-27 Millenium Specialty Chemicals, Inc. Physiological cooling compositions

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4018032B2 (en) * 2003-06-17 2007-12-05 高砂香料工業株式会社 Hair and body cleansing composition
ES2488634T3 (en) * 2005-12-23 2014-08-28 Intercontinental Great Brands Llc Composition providing a refreshing feeling significantly similar to that provided by menthol
US20080063748A1 (en) * 2006-09-08 2008-03-13 Cadbury Adams Usa Llc. Center-fill confectionery and chewing gum compositions containing suspended saccharide particles

Patent Citations (78)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4136163A (en) * 1971-02-04 1979-01-23 Wilkinson Sword Limited P-menthane carboxamides having a physiological cooling effect
US4193936A (en) * 1971-02-04 1980-03-18 Wilkinson Sword Limited N-substituted paramenthane carboxamides
US4033994A (en) * 1972-01-28 1977-07-05 Wilkinson Sword Limited Substituted p-menthanes
US4059118A (en) * 1972-01-28 1977-11-22 Wilkinson Sword Limited Tobacco and tobacco-containing manufactures containing an ingredient having physiological cooling activity
US4060091A (en) * 1972-01-28 1977-11-29 Wilkinson Sword Limited Tobacco and tobacco-containing manufactures containing an ingredient having physiological cooling activity
US4230688A (en) * 1972-04-18 1980-10-28 Wilkinson Sword Limited Acyclic carboxamides having a physiological cooling effect
US4032661A (en) * 1972-07-20 1977-06-28 Wilkinson Sword Limited Cyclic sulphoxides and sulphones having a physiological cooling action on the human body
US4070449A (en) * 1972-10-24 1978-01-24 Wilkinson Sword Limited Compounds having a physiological cooling effect and compositions containing them
US3857964A (en) * 1973-02-09 1974-12-31 Brook D Controlled release flavor compositions
US3897566A (en) * 1973-12-06 1975-07-29 Gen Foods Corp Chewing gums having longer lasting sweetness and flavor
US3930026A (en) * 1974-08-28 1975-12-30 Squibb & Sons Inc Chewing gum having enhanced flavor
US4271197A (en) * 1979-06-21 1981-06-02 Walter Hopkins Chewing gum containing sugar substitute
US4352822A (en) * 1980-12-15 1982-10-05 Nabisco Brands Inc. Gum base, chewing gum containing same and method
US4352822B1 (en) * 1980-12-15 1985-09-03
US4388328A (en) * 1981-10-15 1983-06-14 Warner-Lambert Company Sorbitol containing mixture encapsulated flavor
US4459425A (en) * 1981-11-20 1984-07-10 Takasago Perfumery Co., Ltd. 3-Levo-Menthoxypropane-1,2-diol
US4497832A (en) * 1983-04-18 1985-02-05 Warner-Lambert Company Chewing gum composition having enhanced flavor-sweetness
US4485118A (en) * 1983-04-21 1984-11-27 Warner-Lambert Company Gum composition with plural time releasing flavors and method of preparation
US4751095A (en) * 1983-07-28 1988-06-14 Karl Curtis L Aspartame stabilization with cyclodextrin
US4568560A (en) * 1984-03-16 1986-02-04 Warner-Lambert Company Encapsulated fragrances and flavors and process therefor
US4590075A (en) * 1984-08-27 1986-05-20 Warner-Lambert Company Elastomer encapsulation of flavors and sweeteners, long lasting flavored chewing gum compositions based thereon and process of preparation
US4929447A (en) * 1986-01-07 1990-05-29 Warner-Lambert Company Encapsulation composition for use with chewing gum and edible products
US4752481A (en) * 1986-06-19 1988-06-21 Warner-Lambert Company Flavor emulsions and chewing gum compositions containing the same
US4918182A (en) * 1986-07-15 1990-04-17 Tate & Lyle Public Limited Company Sweetener
US4927646A (en) * 1986-11-13 1990-05-22 Tate & Lyle Plc Sucralose sweetening composition
US4981698A (en) * 1986-12-23 1991-01-01 Warner-Lambert Co. Multiple encapsulated sweetener delivery system and method of preparation
US5004595A (en) * 1986-12-23 1991-04-02 Warner-Lambert Company Multiple encapsulated flavor delivery system and method of preparation
US4933190A (en) * 1986-12-23 1990-06-12 Warner-Lambert Co. Multiple encapsulated sweetener delivery system
US4722845A (en) * 1986-12-23 1988-02-02 Warner-Lambert Company Stable cinnamon-flavored chewing gum composition
US4803082A (en) * 1987-10-28 1989-02-07 Warner-Lambert Company Flavor and sweetness enhancement delivery systems and method of preparation
US4971797A (en) * 1988-12-22 1990-11-20 Warner-Lambert Company Stabilized sucralose complex
US5009893A (en) * 1989-07-17 1991-04-23 Warner-Lambert Company Breath-freshening edible compositions of methol and a carboxamide
US5009900A (en) * 1989-10-02 1991-04-23 Nabisco Brands, Inc. Glassy matrices containing volatile and/or labile components, and processes for preparation and use thereof
US5284659A (en) * 1990-03-30 1994-02-08 Cherukuri Subraman R Encapsulated flavor with bioadhesive character in pressed mints and confections
US5041294A (en) * 1990-04-24 1991-08-20 Wm. Wrigley Jr. Company Sorbitol-modified flavor
US5266335A (en) * 1990-05-04 1993-11-30 Warner-Lambert Company Microencapsulated flavoring agents and methods for preparing same
US5244670A (en) * 1991-04-04 1993-09-14 The Procter & Gamble Company Ingestible pharmaceutical compositions for treating upper gastrointestinal tract distress
US5266592A (en) * 1991-04-05 1993-11-30 Haarmann & Reimer Gmbh Compositions which have a physiological cooling effect, and active compounds suitable for these compositions
US5158790A (en) * 1991-09-17 1992-10-27 Wm. Wrigley, Jr. Company L-carvone enhanced fruit flavored chewing gum
US5405604A (en) * 1992-10-16 1995-04-11 The Procter & Gamble Company Concentrated mouthrinse for efficient delivery of antimicrobials
US5372824A (en) * 1993-03-25 1994-12-13 The Wm. Wrigley Jr. Company Mint flavored chewing gum having reduced bitterness and methods for making same
US5603971A (en) * 1993-04-16 1997-02-18 Mccormick & Company, Inc. Encapsulation compositions
US5407665A (en) * 1993-12-22 1995-04-18 The Procter & Gamble Company Ethanol substitutes
US5458879A (en) * 1994-03-03 1995-10-17 The Procter & Gamble Company Oral vehicle compositions
US5415880A (en) * 1994-04-12 1995-05-16 Wm. Wrigley Jr. Company Fruit flavored chewing gum with prolonged flavor intensity
US5429827A (en) * 1994-04-12 1995-07-04 Wm. Wrigley Jr. Company Method of making improved gum base for fruit-flavored chewing gum
US5633027A (en) * 1994-08-05 1997-05-27 Fuisz Technologies Ltd. Confectioneries containing stabilized highly odorous flavor component delivery systems
US5744180A (en) * 1994-08-05 1998-04-28 Fuisz Technologies Ltd. Comestibles containing stabilized highly odorous flavor component delivery systems
US5545424A (en) * 1994-10-12 1996-08-13 Takasago International Corporation 4-(1-menthoxymethyl)-2-phenyl-1,3-dioxolane or its derivatives and flavor composition containing the same
US5800848A (en) * 1995-06-20 1998-09-01 The Wm. Wrigley Jr. Company Chewing gum containing sucrose polyesters
US5725865A (en) * 1995-08-29 1998-03-10 V. Mane Fils S.A. Coolant compositions
US5783725A (en) * 1996-02-27 1998-07-21 Haarmann & Reimer Gmbh Stabilized lactic acid menthyl ester
US6159509A (en) * 1996-10-28 2000-12-12 Wm. Wrigley Jr. Company Method of making chewing gum products containing perillartine
US20020044968A1 (en) * 1996-10-28 2002-04-18 General Mills, Inc. Embedding and encapsulation of sensitive components into a matrix to obtain discrete controlled release particles
US6306429B1 (en) * 1997-04-21 2001-10-23 The Procter & Gamble Company Confectionery compositions
US20020150616A1 (en) * 1997-06-05 2002-10-17 Roger Petrus Gerebern Vandecruys Pharmaceutical compositions comprising cyclodextrins
US6627233B1 (en) * 1997-09-18 2003-09-30 Wm. Wrigley Jr. Company Chewing gum containing physiological cooling agents
US20050019445A1 (en) * 1997-09-18 2005-01-27 Wm. Wrigley Jr. Company Chewing gum containing physiological cooling agents
US20030215532A1 (en) * 2000-02-04 2003-11-20 Takasago International Corporation New sensate composition imparting initial sensation upon contact
US6780443B1 (en) * 2000-02-04 2004-08-24 Takasago International Corporation Sensate composition imparting initial sensation upon contact
US6379652B1 (en) * 2000-10-16 2002-04-30 Colgate Palmolive Company Oral compositions for reducing mouth odors
US6365215B1 (en) * 2000-11-09 2002-04-02 International Flavors & Fragrances Inc. Oral sensory perception-affecting compositions containing dimethyl sulfoxide, complexes thereof and salts thereof
US20020119231A1 (en) * 2000-12-12 2002-08-29 Takasago International Corporation Warming composition for food and drink or for oral care preparation
US6673844B2 (en) * 2000-12-12 2004-01-06 Takasago International Corporation Warming composition
US7087255B2 (en) * 2000-12-27 2006-08-08 Wm. Wrigley Jr. Company Chewing gums that provide breath freshening characteristics
US6623266B2 (en) * 2001-01-19 2003-09-23 Cadbury Adams Usa Llc Apparatus for making a center-filled gum lollipop with hard candy shell
US20040238993A1 (en) * 2002-01-10 2004-12-02 Daniel Benczedi Process for the preparation of extruded delivery systems
US20040086546A1 (en) * 2002-06-25 2004-05-06 Maxwell James Roy Breath freshening and oral cleansing product with cinnamaldehyde
US20040141927A1 (en) * 2002-11-14 2004-07-22 Johnson Sonya S. Oral products containing novel flavor composition
US6884906B2 (en) * 2003-07-01 2005-04-26 International Flavors & Fragrances Inc. Menthyl half acid ester derivatives, processes for preparing same, and uses thereof for their cooling/refreshing effect in consumable materials
US7189760B2 (en) * 2004-04-02 2007-03-13 Millennium Specialty Chemicals Physiological cooling compositions containing highly purified ethyl ester of N-[[5-methyl-2-(1-methylethyl) cyclohexyl] carbonyl]glycine
US7482378B2 (en) * 2004-05-28 2009-01-27 Millenium Specialty Chemicals, Inc. Physiological cooling compositions
US7767243B2 (en) * 2004-12-29 2010-08-03 WH. Wrigley Jr. Company Combinations of cooling agents for use in confections
US20060159819A1 (en) * 2004-12-29 2006-07-20 Witkewitz David L Combinations of cooling agents for use in confections
US20050196517A1 (en) * 2005-02-14 2005-09-08 Mars, Incorporated Edible product having discrete regions with different heats of solution
US20070036733A1 (en) * 2005-08-12 2007-02-15 Takasago International Corp. (Usa) Sensation masking composition
US20070048424A1 (en) * 2005-09-01 2007-03-01 Moza Ashok K Liquid composition of 2-Isopropyl-N,2,3-trimethylbutyramide and N-Ethyl-p-menthane-3-carboxamide, its preparation method and its applications as a cooling agent and flavor enhancer
US20070077331A1 (en) * 2005-10-05 2007-04-05 Cadbury Adams Usa Llc. Cooling compositions

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070077331A1 (en) * 2005-10-05 2007-04-05 Cadbury Adams Usa Llc. Cooling compositions
US20080089850A1 (en) * 2006-10-11 2008-04-17 Ariel Haskel Compositions Comprising Combinations of Sensates
US8084050B2 (en) 2006-10-11 2011-12-27 Colgate-Palmolive Company Compositions comprising combinations of sensates
US20100273887A1 (en) * 2007-08-16 2010-10-28 Symrise Gmbh & Co. Kg Mixtures comprising pellitorin and uses thereof
WO2009140783A1 (en) * 2008-05-22 2009-11-26 Givaudan Sa Cooling composition
US20110091531A1 (en) * 2008-05-22 2011-04-21 Giv Audan Sa Cooling Composition
US20100018540A1 (en) * 2008-07-28 2010-01-28 David James Doolittle Smokeless tobacco products and processes
US20110237674A1 (en) * 2008-10-16 2011-09-29 Novartis Ag Topical nsaid compositions having sensate component
US20140113971A1 (en) * 2008-10-16 2014-04-24 Joanna Zhang Topical NSAID Compositions Having Sensate Component
EP2398337A4 (en) * 2009-02-18 2014-10-08 Intercontinental Great Brands Llc Confectioneries providing mouth-moistening refreshment
EP2398337A2 (en) * 2009-02-18 2011-12-28 Kraft Foods Global Brands LLC Confectioneries providing mouth-moistening refreshment
US8962057B2 (en) 2009-04-29 2015-02-24 The Procter & Gamble Company Methods for improving taste and oral care compositions with improved taste
US20100278991A1 (en) * 2009-04-29 2010-11-04 John Christian Haught Methods for Improving Taste and Oral Care Compositions With Improved Taste
US20130177669A1 (en) * 2010-06-18 2013-07-11 Wm. Wrigley Jr. Company Chewing gum products containing ethyl ester of n-[[5-methyl-2-(1-methylethyl)-cyclohexyl] carbonyl] glycine
WO2011159927A1 (en) 2010-06-18 2011-12-22 Wm. Wrigley Jr. Company Chewing gum products containing ethyl ester of n-[[5-methyl-2-(1-methylethyl)-cyclohexyl] carbonyl] glycine
US20130095159A1 (en) * 2010-06-30 2013-04-18 Colgate-Palmolive Company Flavor release from multilayer film during brushing
EP2793877A4 (en) * 2011-12-21 2015-10-28 Wrigley W M Jun Co Chewing gum products containing [(2-isopropyl-5-methyl-cyclohexanecarbonyl)-amino]-acetic acid isopropyl ester
CN104394718A (en) * 2012-07-02 2015-03-04 西姆莱斯股份公司 A method of flavouring a smoking product
WO2014005614A1 (en) * 2012-07-02 2014-01-09 Symrise Ag A method of flavouring a smoking product
WO2014173922A1 (en) 2013-04-24 2014-10-30 Perfetti Van Melle S.P.A. Chewing gum with long-lasting freshness and its manufacturing process
WO2017079506A1 (en) * 2015-11-05 2017-05-11 Wm. Wrigley Jr. Company Natural cooling formulations

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