EP2129234A1 - Compositions rafraichissantes contenant des esters de menthyle - Google Patents

Compositions rafraichissantes contenant des esters de menthyle

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Publication number
EP2129234A1
EP2129234A1 EP08745205A EP08745205A EP2129234A1 EP 2129234 A1 EP2129234 A1 EP 2129234A1 EP 08745205 A EP08745205 A EP 08745205A EP 08745205 A EP08745205 A EP 08745205A EP 2129234 A1 EP2129234 A1 EP 2129234A1
Authority
EP
European Patent Office
Prior art keywords
composition
cooling
menthyl
weight
glutarate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP08745205A
Other languages
German (de)
English (en)
Other versions
EP2129234A4 (fr
Inventor
Jesse Kiefer
Joan E. Harvey
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Intercontinental Great Brands LLC
Original Assignee
Cadbury Adams USA LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cadbury Adams USA LLC filed Critical Cadbury Adams USA LLC
Publication of EP2129234A1 publication Critical patent/EP2129234A1/fr
Publication of EP2129234A4 publication Critical patent/EP2129234A4/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/204—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • A61K2800/244—Endothermic; Cooling; Cooling sensation

Definitions

  • 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.
  • cooling agents include menthol, isopulegol, 3-(l- menthoxy)propane-l ,2-diol, 3-(l-menthoxy)-2-methylpropane-l ,2-diol, p-menthane-2,3-diol, p-menthane-3,8-diol, 6-isopropyl-9-methyl-l ,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-(l-menthoxy)ethan-l-ol, 3-(l-menthoxy)prop
  • 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,
  • 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.
  • 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.
  • 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 bulanamide 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.
  • cooling composition consisting essentially of: about 5% to about 60% by weight menthyl glutarate; about 5% to about 50% by weight of at ieast 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.
  • a method of preparing a cooling composition which is liquid at 25°C including the steps of:
  • Some other embodiments provide a method of preparing a cooling composition which is liquid at 25 0 C, including the steps of;
  • 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 pros ⁇ des 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.
  • 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% menthonc, 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.
  • some cooling agents e.g. WS-3 and WS-23
  • U.S. Pat. No. 5,326,574 discloses a process for codrying the physiological cooling agent 3-l-menthoxypropane-l ,2-diol with a food acceptable, water- soluble carrier and mixing the resulting product into chewing gum.
  • L-Monomenthyl giutarate has the chemical name (L)-Monomenthane-3-yI glutarate, is sometimes known as Pentadienoic acid, mono[5 methyl-2-l ( l -methylethyl ' ) eyclohexyljester, [ I L]; [ 1R(-)] monomenthyl glutarate, and has the chemical formula Ci 5 H 26 O 4. It may be located by JECFA Number 1414, FEMA number 4006 and CAS number 220621-22-7. It is present as a clear viscous fluid having a minty, menthol-like aroma.
  • 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 35% by weight of the cooling composition, and still more preferably from about 0. i 0 to about 5% by weight of the composition,
  • 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.
  • the degree and longevity of cooling sensation varies from compound to compound the quantity of stimulant used in each composition will vary widely.
  • a significant cooling sensation which, in some cases, may persist for several hours, can be achieved upon application to the mucosa or skirt of as little as 0.05 ml. of a 1.0% weight percent solution of the active ingredient in ethanol.
  • 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. Patents 4,032,663 , 4,070,449, 4,033,994, 4,296,093, 4,296,255, 4,230,688, 4,034,109, 4,020,153, 4,136, 363, 5,266,592, U.S. Publication Nos. 2004/0067970 and 2005/0019455, and by Leffingwell et ai, "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-] ,452,291 , published Oct.
  • 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.
  • Pat. No. 3,720,762 (sp ⁇ lanthol with menthol or peppermint oil); Canadian Patent No. 2,101 ,790 (carbonic acids having free poiar 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.
  • WO 96/28133 coolant composition for comestibles
  • PCT Publication No. WO 96/17524 a cooling composition comprising N-substituted p-nienthane carboxamides and menthol
  • PCT Publication No. WO 94/0101 17 cyclohexanol derivatives
  • U.S. S. Pat. No. 3,639,569 physiological cooling agents.
  • xylitol erythritol, dextrose, sorbitol, menthane, menthone, ketals, menthone ketals, menthone glycerol ketals, substituted p-menthan ⁇ s, 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),
  • Patent No, 7,189760 to Erman, et al which is incorporated in its entirety herein by reference, isopulegol, menthyloxy propane diol, 3-(l-menthoxy)propane- l ,2-diol, 3-(l- menthoxy)-2-methylpropane-l ,2-diol, p-menthane-2,3-diol, p-menthane-3,8-diol, 6- isopropyl-9-methyl- l,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-(l-menthoxy)ethan-l- ol, 3-(l-menthoxy)propan-l-ol, 3-(I-menthoxy
  • Eucalyptus extract (p- Mehtha-3,8-DioJ), 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 ⁇ -keto enamines, cyclotene derivatives such as cyclopentenes including 3-methyl-2-( l-pyrrolidinyl)-
  • 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: (0-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 Rl 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)-NHCH2COOCH2CH3,- NHCH2CONH2,-NHCH2CH2OCH3,-NHCH2CH2OH,-NHCH2CH(OH)CH2OH and ( ⁇ i) a moiety selected from the group consisting 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,
  • 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.
  • PMC p-menthane carboxamides
  • AC acyclic 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 1 1000.
  • Other cooling compounds include WS-3, WS-14, WS-23, WS-5 and the like.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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 te ⁇ ned the threshold for that particular compound.
  • the tests are carried out on a selected panel of 6 people of median sensitivity to 1-menthol.
  • the following procedure may be used to select a panel.
  • Known quantities of 1 -menthol in solution in petroleum ether (bp. 40-60 0 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.
  • 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 l-menthoj is in the range 0.1 micrograms to IO micrograms and whose average threshold is approximately 0.25 micrograms, this select panel being regarded as the test panel of average sensitivity.
  • 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, desc ⁇ bed in more detail below.
  • U.S. Pat. No. 3,1 11,127 incoiporated herein by reference discloses such monomenthyl esters as monomenthyl succinate, monomenthyl ⁇ -dimethyl succinate and monomenthyl 2- methylmaleate.
  • U.S. Patent No. 4, 150,052 incorporated herein by reference discloses the use of N-ethyl p-menthane-3-carboxamide for its physiological cooling action on rhe skin, and discloses its use in, for example, chewing gum.
  • L -mono menthyl glutarate has been registered as a GRAS flavoring substance, FEMA No. 4006 and, in Smith et a!,, "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.
  • 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.
  • aroma is meant a minty or freshening physiological sensation perceived as a sense of smell.
  • cooling effect is meant a sensation described as cooling by those experiencing it on the skin, oral cavity or mucous membranes.
  • Menthyl ester is meant a class of compounds such as those described in, for instance, U.S. Patent 3, 1 1 1 , 127, U.S. Patent 6,365,215 and U.S. Patent 6,884,906 the disclosures of which are herein incorporated by reference, including monomenthyl succinate, dimenthyl succinate, monomenthyl ⁇ , ⁇ -dim ethyl succinate and monomenthyl 2- methylmaleateraenthyl 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. Patent 6,884,906.
  • menthyl esters also include menthyl acetate, 1-menthyl acetate, d,l- menthyl acetate, homomenthyl acetate, menthyl lactate, and 1-menthyl lactate.
  • 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 isopropyi 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.
  • 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-etb.yl-p-menthane-3-carboxamide, trimethyl isopropyi 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 isopropyi 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.
  • the cooling composition may be a liquid at room temperature (about 25°C).
  • a cooling composition which is liquid at 25 0 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, trimelhyl isopropyl butanamide aod 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.
  • cooling compositions that are liquid at 25 0 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.
  • 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 wei 1 gSh 1 t menthol.
  • 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 0 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 io 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 h ⁇ at. This composition can be formed as a premix at room temperature. Accordingly, an additional solvent is not needed to dissolve the solid cooling agents.
  • cooling agents it may be desirable to heat the combination of cooling agents to melt the cooling agents that are solids at room temperature
  • 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.
  • the following cooling agents have melting points near or above room temperature; menthol (43°C); WS-3 (88 0 C); WS-23 (62- ⁇ 4°C); menthyl lactate (40- 42°C); menthyl succinate (59-61 0 C); and menthyl acetate ester (23-24°C).
  • 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 3O 0 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.
  • 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.
  • compositions including alcoholic and non-alcoholic beverages, confectionery, chewing gum; cachous; ice cream; jellies.
  • 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.
  • 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.
  • tobacco preparations including cigars, cigarettes, pipe tobacco, chewing tobacco and snuff; tobacco filters, especially filter tips for cigarettes.
  • 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.
  • 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.
  • 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.
  • these products can contain other additives according to use.
  • 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.
  • bakery products can comprise wheat flour (base), butter, a raising agent, e.g., baking powder, an emulsif ⁇ er, 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, saccha ⁇ des, e.g., sugar, stabilizers, e.g., carboxymethyl cellulose, acidifiers, e.g., citric acid, and flavorings, e.g., a pineapple flavor.
  • dairy products such as milk and powdered skim milk
  • saccha ⁇ des e.g., sugar
  • stabilizers e.g., carboxymethyl cellulose
  • acidifiers e.g., citric acid
  • flavorings e.g., a pineapple flavor.
  • the cooling compositions are used in chewing gums.
  • Some chewing gum formulations are described in, for instance, U.S. Patents 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.
  • 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; tackif ⁇ ers, 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.
  • abrasives such calcium phosphate, as calcium carbonate, aluminum hydroxide, silica, and calcium pyrophosphate
  • wetting agents such as glycerin, sorbi
  • the cooling compositions are used in chewing gums and confectionaries.
  • Compositions of chewing gum and confectionaries are well known in the art and described in depth in, for instance, U.S. Patents 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.
  • 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.
  • 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 uncoatcd 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • the chewing gum composition may contain a larger or smaller amount of sugar alcohols than conventional chewing gum compositions to facilitate delivery.
  • the cooling compositions are added during the manufacture of the chewing gum composition, that is, with the sweeteners, flavoring agents and the like.
  • the gum base generally comprises elastomers, elastomer plasticizers, waxes, bromine, ethanol, emulsif ⁇ ers, 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, polyvmyiacetate 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.
  • 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.
  • 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.
  • 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, xyhtol. 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 m 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.
  • antioxidants e.g. butylated hydroxyanisole, butylated hydroxytoluene, beta-carotenes, tocopherols
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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 marmitol or dicalcium phosphate.
  • useful anti-adherent compounds which may also function as filler, include talc, magnesium trisilieate and calcium carbonate.
  • These ingredients may be employed in amounts of about 0.5% to 5% by weight of the syrup.
  • 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.
  • 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.
  • 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 Confectioner/ Manufacture (2nd Edition) (1995), E. B. Jackson, Editor, pp. 258-286, the content of which is incorporated herein by reference.
  • confectioner also encompasses confectioner)' 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 confectioner ⁇ ' 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.
  • flavoring agent e.g. peppermint flavor
  • bulking agent such as gum arabic
  • 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.
  • desired mesh size e.g. 12 mesh
  • 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 resisting 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.
  • 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 13O 0 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.
  • 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 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.
  • sweetenings 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, urae, cherry, raspberry, blackberry, tropical fruit, mango, mangosteen, pomegranate, papaya and so forth.
  • 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, urae, 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 perilia flavor, a
  • 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.
  • 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.
  • aldehydes and esters such as cinnamyl acetate, cinnamaldehyde, citral diethylacetal, dihydrocarvyl acetate, eugenyl formate, p-methylamisol, and so forth may be used.
  • 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.
  • 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., melonai (melon), 2,6-
  • flavoring agents are used at levels that provide a perceptible sensory experience i.e. at or above their threshold levels. Iu 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.
  • 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.
  • 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.
  • the flavoring agent may be adsorbed onto silicas, zeolites, and the like.
  • the flavoring agents may be used in many distinct physical forms.
  • such physical forms include free forms, such as spray dried, powdered, beaded forms, encapsulated forms, and mixtures thereof.
  • encapsulation of a component will result in a delay in the release of the predominant amount of the component during consumption of a confectioner ⁇ ' composition that includes the encapsulated component (e.g., as part of a delivery system added as an ingredient to the chewing confectionery composition)
  • the release profile of the ingredient e.g., the flavor, sweetener, etc
  • the release profile of the ingredient 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.
  • 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 deliver)' 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.
  • 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, dipepiide based sweeteners, and protein based sweeteners, including mixtures thereof. Without being limited to particular sweeteners, representative categories and examples include;
  • water-soluble sweetening agents such as dihydrochalcones, monellin, steviosides, Io 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;
  • water-soluble sweetening agents such as dihydrochalcones, monellin, steviosides, Io han quo, glycyrrhizin, dihydroflavenol, and sugar alcohols such as sorbitol, mannitol, maltitol, xylitol, erythritol, and L-aminodicar
  • 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-l ,2,3-oxathiazine-4-one-2,2-dioxide, the potassium salt of 3,4-dihydro- ⁇ - methyl-l ,2,3-oxathiazine-4-one-2,2-dioxide (Acesulfame-K), the free acid form of saccharin, and mixtures thereof;
  • soluble saccharin salts i.e., sodium or calcium saccharin salts, cyclamate salts
  • 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- ⁇ - aspartyl]-L-phenylalanine 1 -methyl ester (Neotame), and mate ⁇ als described in U.S. Pat. No.
  • 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 SplendaTM;
  • chlorodeoxysucrose and chlorodeoxygalactosucrose derivatives include but are not limited to: l-chloro- l '-deoxysucrose; 4-ehloro-4-deoxy-a!pha-D- galactopyranosyl-alpha-D-fructofuranoside, or 4-chloro-4-deoxygalactosucrose; 4-chloro-4- deoxy-alpha-D-galactopyranosyl-l -chloro-l-deoxy-beta-D-fructo-f ⁇ ranoside,
  • protein based sweeteners such as thaumaoccous danielli (Thaumatin I and I ⁇ ) 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.
  • the sweetener is a high intensity sweetener such as aspartame, sucralose, and acesulfame potassium (e.g., Ace-K or acesulfame-K).
  • the sweetener may be a polyoi.
  • Poiyols 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
  • the active component 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).
  • an effective amount of intense sweetener may be utilized to provide the level of sweetness desired, and this amount may van,' 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 compounds can include warming agents, tingling agents, effervescent agents, and combinations thereof.
  • 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.
  • useful warming compounds can include vanillyl alcohol n-butylelher (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-hexyieather, 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.
  • a tingling sensation can be provided.
  • One such tingling sensation is provided by adding jambu, oleoresin, or spilanthol to some examples.
  • alkyJamides extracted from materials such as jambu or sanshool can be included
  • a sensation is created due to effervescence Such effervescence is created by combining an alkaline material with an acidic rnatena!
  • an alkaline matenal can include alkali metal carbonates, alkali metal bicaibonates.
  • an acidic material can include acetic acid, adipic acid, ascorbic acid, butyric acid cit ⁇ c acid, formic acid furna ⁇ c acid, glyconic acid, lactic acid, phosphoric acid, malic acid, oxalic acid, succinic acid, tartaric acid, aspartic acid, benzoic acid, caffeoiannic acid, sso-cit ⁇ c acid, citramahc acid, galacturonic acid, glucuronic acid, glycenc acid, glycolic acid, ketogluta ⁇ c acid, a-ketoglutaric acid, lactoisocitnc acid, oxalacetic acid, pyruvic acid, quimc acid, shikimic acid, succinic acid, tannic acid, hydroxyacctic acid, suberic acid, sebacic acid, azelaic acid, pimehc acid, cap ⁇ c cid,
  • Sensate components may also be referred to as "trigeminal stimulants" such as those disclosed in U S Patent Application No 2005 ⁇ 02021 18, which is incorporated herein by refeience Trigeminal stimulants aie defined as an orally consumed product or agent that stimulates the trigeminal nerve
  • Trigeminal stimulants include menthol, WS-3, N-substituted p-menthane carboxamide, acyclic carboxamidcs including WS-23, VVS-5, WS-14, methyl succinate, and menthone glycerol ketals
  • Trigeminal stimulants can also include flavors tingling agents, Jambu extract, vanillyl alkyl etheis, such as vanillyl n-butyl ether, spilanthol, Echinacea extract, Northern Prickly Ash extract, capsaicin, capsicum oleoresin, red pepper oleorcsm, black pepper oleoresin, pipcnne
  • a cooling sensation can be provided by mate ⁇ als exhibiting a negative heat of solution including, but not limited to polyols such as xylitol, erythntol, dextrose, and sorbitol, and combinations thereof
  • sensat ⁇ components are used at levels that provide a perceptible sensory experience i.e. at or above their threshold levels.
  • sensate components are used at levels below their threshold levels such that they do not provide an independent perceptible sensory experience.
  • the sensates may provide an ancillary benefit such as flavor or sweetness enhancement or potentiation.
  • 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,
  • 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.
  • an effervescing system may include one or more other ingredients such as, for example, carbon dioxide, oral care ingredients, flavorants, etc.
  • 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.
  • potentiators designed to intensify, supplement, modify, or enhance the perception of flavor, sweetness, tartness, umami, kokumi, saltiness and combinations thereof can be included.
  • potentiators also known as taste potentiators include, but are not limited to, neohesperidin dihydrochalcone, optically active S- alkyi 2-methyl butane thioate compounds such as those disclosed in PCT Application Number WO 2007/032262 to Og ⁇ ra et al, which is incorporated in its entirety herein by reference, chlorogenic acid, alapyridaine, cynarin, miraculin, giupyridaine, pyridinium-betain compounds, glutamates, such as monosodium glutamate and monopotassium giutamate, 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
  • 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. Patent 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 TlRs) and taste potentiator compositions that impart kokumi, as disclosed in U.S. Patent 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.
  • exemplary sweetener potentiators include, but are not limited to, monoammonium glycyrrhizinate, licorice glycyrrhizinates, citrus aurantium, alapyridaine, alapyridaine (N-(l-carboxyethyl)-6-(hydroxymethyl)pyridinium-3-ol) inner salt, miraculin.
  • curculin strogin, mabinlin, gymnemic acid, cynarin, giupyridaine, pyridinium- betain compounds, sugar beet extract, neotame, thaumatin, neohespe ⁇ din 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 TI Rs) and combinations thereof.
  • T2Rs and TI Rs G-protein coupled receptors
  • potentiators for the enhancement of salt taste include acidic peptides, such as those disclosed in U.S. Patent No. 6,974,597, herein incorporated by reference.
  • 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, com 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).
  • plant proteins e.g. wheat gluten, com 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
  • microbial proteins e.g., microbial cell protein and polypeptides produced by microorganisms.
  • hydrophobic sweeteners include those of the formulae I-XI as set forth below:
  • X, Y and Z are selected from the group consisting of CH 2 , O and S; wherein X and Y are selected from the group consisting of S and O;
  • X is C or S; R is OH or H and R 1 is OCHj or OH;
  • R, R 2 and R 3 are OH or H and R 1 is H or COOH; VI wherein X is O or CH 2 and R is COOH or H; wherein R is CH 3 CH 2 , OH, N (CH3) 2 or CI;
  • Perillartine may also be added as described in U.S. Patent No. 6, 159,509 also incorporated in its entirety herein by reference,
  • Acids can include, but are not limited to acetic acid, adipic acid, ascorbic acid, butyric acid, citric acid, formic acid, fumaric acid, giyconic acid, lactic acid, phosphoric acid, malic acid, oxalic acid, succinic acid, tartaric acid, aspartic acid, benzoic acid, caffeota ⁇ nic acid, iso-citric acid, citramalic add, 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, pimeiic acid, capric cid, and combinations thereof.
  • Mouth moistcners can include, but are not limited to, saliva stimulators such as acids and salts and combinations thereof.
  • acids can include acetic acid, adipic acid, ascorbic acid, butyric acid, citric acid, formic acid, fumaric acid, giyconic acid, lactic add, phosphoric acid, malic acid, oxalic acid, succinic acid, tartaric acid and combinations thereof.
  • Mouth moisteners can also include hydrocolloid mate ⁇ als 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.
  • 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, tama ⁇ n, bacterial gums, and combinations thereof.
  • modified natural gums such as propylene glycol alginate, carboxymethyl locust bean gum, low methoxyl pectin, and their combinations can be included.
  • modified celluloses can be included such as microcrystalline cellulose, carboxymethlcellulose (CMC), methylcellulose (MC), hydroxypropylmethylcellulose (HPCM), and hydroxypropylcellulose (MPC), and combinations thereof.
  • humectants which can provide a perception of mouth hydration can be included.
  • humectants can include, but are not limited to glycerol, sorbitol, polyethylene glycol, eryth ⁇ tol, and xyiitol.
  • 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-pellito ⁇ n, N-isobutyl-trans-2-trans-4-decadienamide, alkadienamides including N-isobutyl-E2, E4-deeadienamide; N-isobutyl-E2, E4-undecadienamide; N- pyrollidyl-E2, E4-decadienamide; N-pipe ⁇ dl-E2, E4-decadienamdie, or combinations thereof as disclosed in U.S. Patent Application No.
  • 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, Exemplar/ 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.
  • 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 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.
  • the best fit equations (those with the highest R " ) and those with the best predictive ability (lowest residual predictive sum of squares, or residual PRESS) are obtained.
  • 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.
  • cooling compositions can be formulated to contain a menthyi 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.
  • Cooling Composition 0.2 - 1.2%
  • Cooling Composition 0.2-1.2%
  • Cooling Composition 0.2-1,2%
  • Cooling Composition 0.2 - 1.2%
  • chewing gum and confectionanes will be prepared having some of the components provided below in amounts within those amounts recommended by the United States 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.

Abstract

L'invention concerne des compositions rafraîchissantes conférant à la peau ou à une membrane muqueuse une sensation de rafraîchissement physiologique prolongée. Ces compositions rafraîchissantes peuvent se présenter seules ou à l'intérieur d'un produit tel qu'un chewing-gum ou une confiserie. Dans certains modes de réalisation, les compositions selon l'invention contiennent du glutarate de menthyle et au moins un agent rafraîchissant supplémentaire, WS-3 ou WS-23 par exemple, et facultativement du menthol. Ces compositions peuvent se présenter sous forme liquide à température ambiante.
EP08745205.8A 2007-04-05 2008-04-07 Compositions rafraichissantes contenant des esters de menthyle Withdrawn EP2129234A4 (fr)

Applications Claiming Priority (2)

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US11/732,942 US20070221236A1 (en) 2005-10-05 2007-04-05 Cooling compositions including menthyl esters
PCT/US2008/059530 WO2008124667A1 (fr) 2007-04-05 2008-04-07 Compositions rafraichissantes contenant des esters de menthyle

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EP2129234A1 true EP2129234A1 (fr) 2009-12-09
EP2129234A4 EP2129234A4 (fr) 2015-04-22

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Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1962779A2 (fr) * 2005-10-05 2008-09-03 Cadbury Adams USA LLC Compositions de refroidissement comprenant un methylester
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
WO2009111685A1 (fr) 2008-03-06 2009-09-11 Sensient Flavors Llc Extraits végétaux et systèmes d’essences pour des produits oraux et leurs procédés de fabrication
WO2009140783A1 (fr) * 2008-05-22 2009-11-26 Givaudan Sa Composition de refroidissement
US20100018540A1 (en) * 2008-07-28 2010-01-28 David James Doolittle Smokeless tobacco products and processes
RU2517179C2 (ru) 2008-08-15 2014-05-27 Дзе Проктер Энд Гэмбл Компани Синтез производных циклогексана, используемых в потребительских товарах в качестве оказывающих сенсорное воздействие веществ
EP2313070A1 (fr) 2008-08-15 2011-04-27 The Procter & Gamble Company Solution de carboxamides de menthane pour une utilisation dans des produits de consommation
US20100099766A1 (en) * 2008-10-16 2010-04-22 Novartis Ag Topical NSAID compositions having sensate component
US20110237674A1 (en) * 2008-10-16 2011-09-29 Novartis Ag Topical nsaid compositions having sensate component
AU2009318056B2 (en) 2008-11-20 2014-07-24 The Procter & Gamble Company Personal care compositions providing enhanced cooling sensation
PL2375912T3 (pl) * 2009-01-15 2018-01-31 Intercontinental Great Brands Llc Kompozycje i sposoby leczenia uczucia dyskomfortu gardła
EP2398337A4 (fr) * 2009-02-18 2014-10-08 Intercontinental Great Brands Llc Confiseries produisant un rafraîchissement d'humidification de la bouche
US8962057B2 (en) * 2009-04-29 2015-02-24 The Procter & Gamble Company Methods for improving taste and oral care compositions with improved taste
AU2010255540A1 (en) * 2009-06-05 2012-01-19 Edward Tak Wei Treatment of eye discomfort by topical administration of a cooling agent to the external surface of the eyelid
CA2805411C (fr) * 2010-06-18 2016-05-17 Wm. Wrigley Jr. Company Produits de gomme a macher contenant un ester ethylique de n-[[5-methyl-2-(1-methylethyl)-cyclohexyl]carbonyl]glycine
US20130156885A1 (en) * 2010-06-18 2013-06-20 Sonya S. Johnson Chewing gum containing combinations of physiological cooling agents
BR112012030192A2 (pt) * 2010-06-30 2016-09-20 Colgate Palmolive Co liberação de sabor de filme de camadas múltiplas durante o escovamento
BR112014014872B1 (pt) * 2011-12-21 2022-11-16 Wm. Wrigley Jr. Company Composições de goma de mascar que contém éster isopropílico de ácido [(2-isopropil-5-metil-ciclohexanocarbonil)-amino] acético
EP2606746B2 (fr) 2011-12-22 2018-10-24 International Flavors & Fragrances, Inc. Compositions d'amélioration de refroidissement
WO2014005614A1 (fr) * 2012-07-02 2014-01-09 Symrise Ag Procédé pour aromatiser un produit à fumer
ITMI20130685A1 (it) 2013-04-24 2014-10-25 Perfetti Van Melle Spa Gomme da masticare con freschezza prolungata e processo di ottenimento
PL3370547T3 (pl) * 2015-11-05 2024-03-04 Wm. Wrigley Jr. Company Naturalne formulacje chłodzące
PL3768093T3 (pl) * 2018-03-19 2024-03-04 Wm. Wrigley Jr. Company Wyroby cukiernicze o intensywnym początkowym chłodzeniu i przedłużonej stabilności w środowisku o wysokiej wilgotności
WO2020007819A1 (fr) * 2018-07-02 2020-01-09 Performanat Gmbh Additif alimentaire comprenant un modulateur de trp
EP3590354A1 (fr) * 2018-07-02 2020-01-08 PerformaNat GmbH Additif alimentaire contenant un modulateur de trp
US20220062173A1 (en) * 2019-01-08 2022-03-03 Johnson & Johnson Consumer Inc. Liquid compositions
CN110419764A (zh) * 2019-07-26 2019-11-08 深圳雾芯科技有限公司 口香糖、电子烟液及其用途
CN111802499A (zh) * 2020-07-17 2020-10-23 朱远鹏 一种爽口片及其制备方法
CN113133950A (zh) * 2021-03-24 2021-07-20 深圳全棉时代科技有限公司 一种用于醒神和舒解疲劳的组合物、溶液及其应用
US20220354785A1 (en) * 2021-04-22 2022-11-10 Nicoventures Trading Limited Oral lozenge products
IT202100021824A1 (it) * 2021-08-12 2023-02-12 E Liquid Labs S R L Formulazione liquida aromatizzata per sigaretta elettronica

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997007771A1 (fr) * 1995-08-29 1997-03-06 V. Mane Fils S.A. Compositions rafraichissantes
US20040141927A1 (en) * 2002-11-14 2004-07-22 Johnson Sonya S. Oral products containing novel flavor composition
WO2005082154A1 (fr) * 2004-02-26 2005-09-09 Wm. Wrigley Jr. Company Confiserie contenant un mélange d'agents rafraîchissants physiologiques
US20050265930A1 (en) * 2004-05-28 2005-12-01 Erman Mark B Physiological cooling compositions
US20060160713A1 (en) * 2003-06-17 2006-07-20 Takasago International Corporation Shampoo and body detergent composition
WO2007044526A2 (fr) * 2005-10-05 2007-04-19 Cadbury Adams Usa Llc Compositions de refroidissement
WO2007076025A2 (fr) * 2005-12-23 2007-07-05 Cadbury Adams Usa Llc Compositions produisant une sensation substantiellement semblable a celle produite par le menthol
WO2008030274A1 (fr) * 2006-09-08 2008-03-13 Cadbury Adams Usa Llc Compositions de sucrerie et de chewing gum avec fourrage contenant des particules de saccharide en suspension

Family Cites Families (70)

* 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
US4060091A (en) * 1972-01-28 1977-11-29 Wilkinson Sword Limited Tobacco and tobacco-containing manufactures containing an ingredient having physiological cooling activity
US4059118A (en) * 1972-01-28 1977-11-22 Wilkinson Sword Limited Tobacco and tobacco-containing manufactures containing an ingredient having physiological cooling activity
GB1421743A (en) * 1972-04-18 1976-01-21 Wilkinson Sword Ltd Ingestible topical and other compositions
CA1027347A (fr) * 1972-07-20 1978-03-07 David G. Rowsell Composes ayant un effet physiologique de refroidissement et compositions contenant du ehcm
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
US4388328A (en) * 1981-10-15 1983-06-14 Warner-Lambert Company Sorbitol containing mixture encapsulated flavor
JPS5888334A (ja) * 1981-11-20 1983-05-26 Takasago Corp ３−ｌ−メントキシプロパン−１、２−ジオ−ル
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
CA1295874C (fr) * 1986-06-19 1992-02-18 Zdravko Dokuzovic Emulsions aromatisantes et compositions de gomme a macher les renfermant
GB8617222D0 (en) * 1986-07-15 1986-08-20 Tate & Lyle Plc Sweetener
GB8627139D0 (en) * 1986-11-13 1986-12-10 Tate & Lyle Plc Sweetening composition
US4933190A (en) * 1986-12-23 1990-06-12 Warner-Lambert Co. Multiple encapsulated sweetener delivery system
US4981698A (en) * 1986-12-23 1991-01-01 Warner-Lambert Co. Multiple encapsulated sweetener delivery system and method of preparation
US4722845A (en) * 1986-12-23 1988-02-02 Warner-Lambert Company Stable cinnamon-flavored chewing gum composition
US5004595A (en) * 1986-12-23 1991-04-02 Warner-Lambert Company Multiple encapsulated flavor delivery system and method of preparation
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
DE4110973A1 (de) * 1991-04-05 1992-10-08 Haarmann & Reimer Gmbh Mittel mit physiologischem kuehleffekt und fuer diese mittel geeignete wirksame verbindungen
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
JPH08509018A (ja) * 1993-04-16 1996-09-24 マコーミック アンド カンパニー，インク． カプセル化組成物
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
PH31445A (en) * 1994-04-12 1998-11-03 Wrigley W M Jun Co 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
US5556652A (en) * 1994-08-05 1996-09-17 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
DE19607278A1 (de) * 1996-02-27 1997-08-28 Haarmann & Reimer Gmbh Stabilisierter Milchsäurementhylester
US8828432B2 (en) * 1996-10-28 2014-09-09 General Mills, Inc. Embedding and encapsulation of sensitive components into a matrix to obtain discrete controlled release particles
US6159509A (en) * 1996-10-28 2000-12-12 Wm. Wrigley Jr. Company Method of making chewing gum products containing perillartine
GB9707979D0 (en) * 1997-04-21 1997-06-11 Procter & Gamble Confectionery compositions
GB9711643D0 (en) * 1997-06-05 1997-07-30 Janssen Pharmaceutica Nv Glass thermoplastic systems
US6627233B1 (en) * 1997-09-18 2003-09-30 Wm. Wrigley Jr. Company Chewing gum containing physiological cooling agents
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
JP3497466B2 (ja) * 2000-12-12 2004-02-16 高砂香料工業株式会社 温感組成物
JP4454838B2 (ja) * 2000-12-12 2010-04-21 高砂香料工業株式会社 温感組成物
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
DE60213471T2 (de) * 2002-01-10 2007-08-23 Firmenich S.A. Prozess zur herstellung extrudierter abgabesysteme
EP1551367A2 (fr) * 2002-06-25 2005-07-13 Wm. Wrigley Jr. Company Rafraichisseur d'haleine et produit d'hygiene buccale contenant un cinnamaldehyde
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
CN101119643B (zh) * 2004-12-29 2013-07-24 Wm.雷格利Jr.公司 用于糖果的清凉剂的组合
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

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997007771A1 (fr) * 1995-08-29 1997-03-06 V. Mane Fils S.A. Compositions rafraichissantes
US20040141927A1 (en) * 2002-11-14 2004-07-22 Johnson Sonya S. Oral products containing novel flavor composition
US20060160713A1 (en) * 2003-06-17 2006-07-20 Takasago International Corporation Shampoo and body detergent composition
WO2005082154A1 (fr) * 2004-02-26 2005-09-09 Wm. Wrigley Jr. Company Confiserie contenant un mélange d'agents rafraîchissants physiologiques
US20050265930A1 (en) * 2004-05-28 2005-12-01 Erman Mark B Physiological cooling compositions
WO2007044526A2 (fr) * 2005-10-05 2007-04-19 Cadbury Adams Usa Llc Compositions de refroidissement
WO2007076025A2 (fr) * 2005-12-23 2007-07-05 Cadbury Adams Usa Llc Compositions produisant une sensation substantiellement semblable a celle produite par le menthol
WO2008030274A1 (fr) * 2006-09-08 2008-03-13 Cadbury Adams Usa Llc Compositions de sucrerie et de chewing gum avec fourrage contenant des particules de saccharide en suspension

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO2008124667A1 *

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