US20130323388A1 - Flavour composition comprising menthol and menthane carboxamides - Google Patents

Flavour composition comprising menthol and menthane carboxamides Download PDF

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Publication number
US20130323388A1
US20130323388A1 US13/980,760 US201213980760A US2013323388A1 US 20130323388 A1 US20130323388 A1 US 20130323388A1 US 201213980760 A US201213980760 A US 201213980760A US 2013323388 A1 US2013323388 A1 US 2013323388A1
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Prior art keywords
flavour composition
flavour
menthol
amount
flavor
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Paul Alexander Talsma
Tracy Bartholomew
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Givaudan SA
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Givaudan SA
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    • 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
    • A23L1/22664—
    • 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
    • A23L27/203—Alicyclic 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
    • A23L27/205—Heterocyclic 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
    • A23L27/205—Heterocyclic compounds
    • A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
    • 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
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • 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
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/92—Oral administration

Definitions

  • the present invention is concerned with flavour compositions comprising menthol and menthane carboxamides, and in particular, with such compositions containing low levels of menthol.
  • the invention is also concerned with consumable products, in particular oral care products, containing said flavour compositions.
  • menthol particularly I-menthol, which is found naturally in peppermint oil, notably of Mentha arvensis L and Mentha viridis L.
  • I-menthol is found naturally in peppermint oil, notably of Mentha arvensis L and Mentha viridis L.
  • the I-isomer occurs most widely in nature and is typically what is referred by the name menthol having coolant properties.
  • L-menthol has the characteristic peppermint odor, has a clean fresh taste and exerts a cooling sensation when applied to the skin and mucosal surfaces.
  • flavours in particular peppermint flavours, can exceed 50% by weight of menthol and it is not uncommon to find 60% or more.
  • menthol when used alone, has an initial high flavour impact, but the flavour impact drops sharply within a few minutes after use and it tends to distort flavour notes and render the products containing it bitter. Furthermore, as well as bitterness problems, very high levels of menthol can restrict flavour creation and cause additional processing constraints.
  • menthol In order to address some of the drawbacks of menthol use, it has become increasingly common to use it in admixture with other coolant compounds, most notably the N-substituted-p-menthane carboxamides.
  • other coolant compounds most notably the N-substituted-p-menthane carboxamides.
  • GB233873 discloses such mixtures in order to provide different cooling profiles and even longer lasting coolant effects. Menthol-only formulations are compared with mixtures in which the amounts of menthol are reduced and replaced with like amounts of a menthane carboxamide coolant.
  • flavours industry today A challenge faced by the flavours industry today, is the drive from the consumer products companies to reduce the levels of non-active materials contained in their compositions. This is related, obviously to cost, but also to the need for sustainability, and the need to deliver greener products to the marketplace.
  • menthol without the loss of sensorial attributes and consumer liking attendant with its use. If one can reduce or compact the amount of a major component used in a flavour composition, one can, in turn, compact the amount of flavour composition used in consumer products, or alternatively one can exploit the use of lower levels of menthol to permit the use of more flavour ingredients thereby increasing a flavourist's latitude to create new and interesting flavour profiles and drive consumer preference. None of this would be possible, of course, if by reducing menthol one simply replaces it with other coolant materials in like amounts.
  • the invention provides in a first aspect a flavour composition
  • a flavour composition comprising a mixture of coolant compounds consisting of menthol and a menthane carboxamide selected from N-(4-cyanomethylphenyl) p-menthanecarboxamide, 2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide, or a mixture of N-(4-cyanomethylphenyl) p-menthanecarboxamide and 2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide, wherein the total amount of menthane carboxamide is about 0.1 to 10%.
  • a flavour composition comprising a mixture of coolant compounds consisting of menthol and a menthane carboxamide selected from N-(4-cyanomethylphenyl) p-menthanecarboxamide, 2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide, or a mixture of N-(4-cyanomethylphenyl) p-menthanecarboxamide and 2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide, wherein the amount of menthol represents less than 70%, more particularly less than 50% by weight of the total flavour compositions and the total amount of menthane carboxamide is about 0.1 to 10%.
  • menthol is used in admixture with 2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide alone or in combination with N-(4-cyanomethylphenyl) p-menthanecarboxamide.
  • the total amount of menthol used in the flavour compositions of the present invention is an effective amount, when taken in conjunction with the menthane carboxamides, to provide a good cooling and breath freshening perception without bitterness.
  • the exact amount of the menthol employed in the cooling compositions is a matter of preference subject to such factors as the degree of vapour action desired.
  • the amount of menthol may be varied within the limits stated herein in order to obtain the result desired in the final product and such variations are within the capabilities of those skilled in the art without the need for undue experimentation.
  • the amount of menthol in the total flavour is about 1% to 50% by weight, still more particularly 5 to 30% by weight.
  • the total amount of menthane carboxamide in the total flavour is about 0.1 to 10% by weight, still more particularly 0.5 to 8% by weight.
  • the menthane carboxamide consists of N-(4-cyanomethylphenyl) p-menthanecarboxamide in an amount of 0.1 to 3% by weight in the total flavour, more particularly 0.5 to 2% by weight.
  • the menthane carboxamide consists of 2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide in an amount of 0.1 to 10% by weight, more particularly 0.5 to 7% by weight.
  • the menthane carboxamide consists of a mixture of N-(4-cyanomethylphenyl) p-menthanecarboxamide and 2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide, said mixture being provided in an amount of 0.1 to 13% by weight, more particularly 1 to 9% by weight of the total flavour composition.
  • the mixture of N-(4-cyanomethylphenyl) p-menthanecarboxamide and 2-isopropyl-5-methyl-N-(2-(pyridin-4-yl)ethyl)cyclohexanecarboxamide is provided in a ratio of 1:100 to 30:1, more particularly 1:15 to 4:1.
  • flavour compositions of the present invention surprisingly provided cooling and freshening effects that meet with high ratings in consumer preference testing despite reducing or compacting the amount of menthol and not replacing it with a similar amount of the menthane carboxamides.
  • both menthol and the total coolant compounds are compacted.
  • the consumer preference tests do not merely reflect the intensity of cooling, indeed, if a coolant composition is too intense it can be offensive and unpleasant and rate poorly in consumer preference tests. Rather, the tests reflect an overall impression of liking and pleasantness.
  • the coolant properties of a composition can act as a sensorial cue, informing the user of the compositions efficacy, and this can drive preference or liking for these types of products also.
  • Both of the menthane carboxamides employed in the present invention exhibit a rather pronounced tingling sensation when applied to mucosal surfaces, particular the oral mucosa, which is particularly of interest in imparting this sensorial cue.
  • the invention provides in another of its aspects a method of compacting the amount of menthol employed in a flavour composition, comprising the step of adding to said flavour composition a mixture of menthol and menthane carboxamides as hereinabove defined.
  • the invention provides in yet another of its aspects a method of compacting the amount of coolant compounds employed in a flavour composition, comprising the step adding to said flavour composition a mixture of menthol and menthane carboxamides as hereinabove defined.
  • composition comprising menthol against a panel of consumers to determine a first preference score for said composition
  • the consumer test employed may be any of those test designs known and used by market researchers for determining preference or liking for taste of consumer products.
  • the test may be a Sequential Monadic evaluation of a pre-defined balanced Latin Square design wherein all products are tested by respondents. Further particulars of a suitable test are provided in the examples, below.
  • the menthane carboxamides employed in the present invention contain asymmetric carbon atoms. Such diasteromeric mixtures can be separated into their individual diastereomers on the basis of their physical chemical differences by methods known per se, for example, by chromatography and/or fractional crystallization. Enantiomers can be separated by converting the enantiomeric mixtures into a diastereomric mixture by reaction with an appropriate optically active compound separating the diastereomers and converting the individual diastereomers to the corresponding pure enantiomers. All such isomers, including diastereomers mixtures and pure enantiomers are considered as part of the invention.
  • menthane carboxamides are the optical isomers shown below:
  • flavour compositions according to the invention may additionally comprise flavouring agents, sweetening agents and other auxiliaries commonly used in the formulation of such compositions.
  • Flavouring agents include but are not limited to:
  • flavoring agents include synthetic flavor oils and flavoring aromatics and/or oils, oleoresins, essences, distillates, and extracts derived from plants, leaves, flowers, fruits, and so forth, and a combination comprising at least one of the foregoing.
  • Exemplary flavor oils include spearmint oil, cinnamon oil, oil of wintergreen (methyl salicylate), peppermint oil, Japanese mint oil, clove oil, bay oil, anise oil, eucalyptus oil, thyme oil, cedar leaf oil, oil of nutmeg, allspice, oil of sage, mace, oil of bitter almonds, and cassia oil; useful flavoring agents include artificial, natural and synthetic fruit flavors such as vanilla, and citrus oils including lemon, orange, lime, grapefruit, yazu, sudachi, and fruit essences including apple, pear, peach, grape, blueberry, strawberry, raspberry, cherry, plum, prune, raisin, cola, guarana, neroli, pineapple, apricot, banana, melon, apricot, ume, cherry, raspberry, blackberry, tropical fruit, mango, mangosteen, pomegranate, papaya and so forth.
  • useful flavoring agents include artificial, natural and synthetic fruit flavors such as vanilla, and citrus oils including lemon,
  • Additional exemplary flavors imparted by a flavoring agent include a milk flavor, a butter flavor, a cheese flavor, a cream flavor, and a yogurt flavor; a vanilla flavor; tea or coffee flavors, such as a green tea flavor, an oolong tea flavor, a tea flavor, a cocoa flavor, a chocolate flavor, and a coffee flavor; mint flavors, such as a peppermint flavor, a spearmint flavor, and a Japanese mint flavor; spicy flavors, such as an asafetida flavor, an ajowan flavor, an anise flavor, an angelica flavor, a fennel flavor, an allspice flavor, a cinnamon flavor, a chamomile flavor, a mustard flavor, a cardamom flavor, a caraway flavor, a cumin flavor, a clove flavor, a pepper flavor, a coriander flavor, a sassafras flavor, a savory flavor, a Zanthoxyli Fructus flavor, a perilla flavor
  • other flavoring agents include aldehydes and esters such as cinnamyl acetate, cinnamaldehyde, citral diethylacetal, dihydrocarvyl acetate, eugenyl 49 formate, p-methylamisol, and so forth can be used.
  • aldehyde flavorings include acetaldehyde (apple), benzaldehyde (cherry, almond), anisic aldehyde (licorice, anise), cinnamic aldehyde (cinnamon), citral, i.e., alpha-citral (lemon, lime), neral, i.e., beta-citral (lemon, lime), decanal (orange, lemon), ethyl vanillin (vanilla, cream), heliotrope, i.e., piperonal (vanilla, cream), vanillin (vanilla, cream), alpha-amyl cinnamaldehyde (spicy fruity flavors), butyraldehyde (butter, cheese), valeraldehyde (butter, cheese), citronellal (modifies, many types), decanal (citrus fruits), aldehyde C-8 (citrus fruits), aldehyde
  • flavour ingredients useful in the present invention may contain menthol, for example peppermint oil.
  • menthol for example peppermint oil.
  • the amounts of menthol referred to herein relate to the amounts of free menthol added to the flavour composition and it does not relate to any menthol that might be contained in a flavour ingredient, such as a flavour oil.
  • the amount of flavouring agents employed in the flavour formulation may typically be from about 1% to about 99%, and the particular amounts may vary depending on the nature of the flavour formulation created.
  • Sweetening agents include but are not limited:
  • High intensity sweetening agents have a sweetness intensity substantially greater than that of sucrose.
  • Suitable high intensity sweetening agents include water-soluble natural sweetening agents such as dihydrochalcones, monellin, Stevia Rebaudiana (steviosides), glycyrrhizin, and mixtures thereof.
  • Suitable water-soluble artificial sweetening agents include saccharin and its soluble salts, i.e., sodium and calcium saccharin salts, cyclamate and its salts, 3,4-dihydro-6-methyl 1.2,3-oxathiazine4-one-2.2-dioxide (Acesulfame) and the sodium ammonium, and calcium salts thereof, and especially the potassium salt of 3,4-dihydro-6-methyl-1,2,3-oxathiazine4-one-2.2-dioxide (Acesulfame-K).
  • saccharin and its soluble salts i.e., sodium and calcium saccharin salts, cyclamate and its salts, 3,4-dihydro-6-methyl 1.2,3-oxathiazine4-one-2.2-dioxide (Acesulfame) and the sodium ammonium, and calcium salts thereof, and especially the potassium salt of 3,4-dihydro-6-methyl-1,2,3
  • Suitable dipeptide based sweetening agents include L-aspartic acid derived sweetening agents such as L-aspartyl-L-phenvlalanine methyl ester (Aspartame), compounds described in U.S. Pat. No. 3,492,131, L-alpha aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide hydrate (Alitame), methyl esters of L-aspartvl-L-phenylglycerine and L-aspartyl-L-2,5-dihvdrophenylglycine, Laspartyl-2.5-dihydro-L-phenyl-alanine, and L-aspartyl-L-(I-cyclohexen)alanine.
  • L-aspartic acid derived sweetening agents such as L-aspartyl-L-phenvlalanine methyl ester (Aspartame), compounds described in U.S. Pat. No
  • suitable water-soluble sweetening agents include those derived from naturally occurring water-soluble sweetening agents such as chlorinated derivatives of sucrose, e.g., chlorodeoxysugar derivatives such as derivatives of chlorodeoxysucrose and chlorodeoxy-galactosucrose.
  • chlorodeoxysucrose and chlorodeoxygalactosucrose derivatives include but are not limited to I-chloro-I′-deoxysucrose; 4-chloro-4-deoxy-alpha-D-galacto-pyranosyl-alpha-D-fructofuranoside, or 4-chloro-4-deoxygalactosucrose; 4-chloro-4-deoxy-alpha-D-galacto-pyranosyl-1-chloro-I deoxy-beta-D-fructo-ftrranoside, or 4,1′-dichloro-4,1′dideoxygalactosucrose; 1′,6′-dichloro-I′,6′-dideoxysucrose; 4-chloro-4-deoxy-alpha-D-galacto-pyranosyl-1,6-dichloro-I,6-dideoxy-beta-D-fructo-furanoside, or
  • the chlorodeoxysugar derivative is 4,1′,6′ trichloro-4,1′,6′-trideoxygalacto-sucrose, or 4-chloro 4-deoxy-alpha-D-galactopyranosyl-1,6dichloro 1,6dideoxy-beta-D-fructofuranoside, which is commercially available under the tradename Sucralose from McNeil Specialty Products Company, Skillman, N.J.
  • Suitable high intensity sweetening agents include protein based sweetening agents such as talin (thaumaoccous danielli, Thaumatin I and II).
  • the amount of sweetening agent employed in the flavour formulation may typically be from about 0.001% to about 1%, but greater or lesser amounts may be employed depending on the nature of the flavour formulation created.
  • Auxilliaries are materials used in flavour formulations for their attributes and properties other than their ability to impart flavour or sweetening effects.
  • Auxilliaries include additives, surfactants, emulsifiers, superfatting agents, bodying agents, thickeners, polymers, silicone compounds, fats, waxes, stabilizers, preservatives, antioxidants, dyes, antimicrobial agents, solvents and co-solvents; viscosity and rheology modifiers; gelling agents; preservative materials such as fungicides and bactericides; pigments, dyestuffs and colouring matters; extenders, fillers and reinforcing agents; stabilisers against the detrimental effects of heat and light; bulking agents, which may include mineral adjuvants, which may serve as fillers and textural agents. Suitable mineral adjuvants include calcium carbonate, magnesium carbonate, alumina, aluminum hydroxide, aluminum silicate, talc, tricalcium phosphate, tricalcium phosphate and the like, which can serve as
  • Additional bulking agents suitable for use include sweetening agents such as monosaccharides, disaccharides, polysaccharides, sugar alcohols, polydextrose, and maltodextrins; minerals, such as calcium carbonate, talc, titanium dioxide, dicalcium phosphate; and combinations thereof.
  • Fillers modify the texture and aid processing.
  • examples of such fillers include magnesium and aluminum silicates, clay, alumina, talc, titanium oxide, cellulose polymers, and the like.
  • flavour compositions, or particular ingredients thereof may be provided in many distinct physical forms, for example solid, liquid or encapsulated forms. Selection of the particular form may be selected by reason of ease of handling or storage, or in order to achieve a particular effect such as sustained or controlled release.
  • encapsulated form is meant that a material or ingredient is contained within an encapsulating material, which protects and/or retains it and permits its release either gradually or completely. All known methods of encapsulation, may be used, for example, coacervation, spray drying, absorption into a porous substrate and the like. All possible encapsulation materials may also be used, for example, natural fibres, minerals of large surface area and polymeric materials.
  • the amount of flavour composition employed in a consumer product may vary according to the particular effect that is desired. Typically, however, the flavour composition may be used in an amount of about 0.01 to 2% by weight based on the weight of the consumer product, more particularly 0.1 to 1.5% by weight.
  • flavour compositions according to the invention may be used in any manner of consumable products.
  • consumable products is meant any product intended to be applied to the body, or placed in the mouth before discarding (e.g. by rinsing) or ingesting, for the purpose of therapy, treatment, nourishment or enjoyment.
  • Consumable products may be in any physical form such as creams, gels, lotions, alcoholic and aqueous/alcoholic solutions, emulsions, dispersions, stick preparations or the like.
  • Flavour compositions may be employed in consumable products for use in oral care.
  • oral care relates to any product applied to the oral cavity for the purposes of cleaning, freshening, healing, deodorising the cavity or any part thereof.
  • Such compositions include, but are not limited to, toothpastes, toothgels, tooth powders, tooth whitening products, mouthwashes, lozenges, dental floss, tooth picks, anti-plaque and anti-gingivitis compositions, throat lozenges, throat drops, inflammatory compositions, compositions for treatment of nasal symptoms, cold symptoms and upper gastrointestinal tract distress, compositions for cold relief, for alleviating discomfort of hot flash, gargle compositions.
  • Oral care products utilising these compounds may be prepared by blending a flavour composition with one or more of the conventional ingredients normally associated with such products, in standard quantities.
  • standard ingredients include, but are not limited to, Mentha Arvensis, Mentha Piperita, Mentha Spicata, Mentha Cardiaca, Synthetic Mints, Anethole, Methyl Salicylate, Eucalyptol, Cinnamic Aldehyde, Eugenol, Calcium Carbonate, Silica (Precipitates & Xerogels), Dicalcium Phosphate, Alumina, Sodium Lauryl Sulphate, Betaine, Glycerine, Sorbitol, Water, Saccharin, Sodium Cyclamate, Aspartame, Xylitol, Sodium Carboymethyl Cellulose, Methyl Cellulose, Sodium Carageenate, Xanthan Gum, Polyvinyl Pyrrolidone, Sodium Tripolyphosphate, Ethyl Alcohol, Sodium Fluor
  • Some of these materials may be present in encapsulated form, as this term is described above.
  • flavour compositions according to the invention may be used in personal care products such as pharmaceuticals, cosmetics and toiletries.
  • the formulations can be used in any of the “Reported Product Categories” listed by the Cosmetic, Toiletries and Fragrance Association's ‘International Cosmetic Ingredient Dictionary and Handbook’, and with any one or more of the ingredients cited as being used for the reported product categories.
  • the Reported Product Categories are: Aftershave lotions, Baby lotions, oils, powders and creams, Baby products miscellaneous, Baby shampoos, Basecoats and undercoats, Bath capsules, Bath oils, tablets and salts, Bath preparations miscellaneous, Bath soaps and detergents, Beard softeners, Blushers, Body and hand preparations, Bubble baths, Cleaning products, C perfumes and toilet waters, Cuticle softeners, Dentifrices, Deodorants, Depilatories, Douches, Eye lotions, Eye makeup preparations miscellaneous, Eye makeup removers, Eye shadows, Eyebrow pencils, Eyeliners, Face and neck preparations, Face powders, Feminine hygiene deodorants, Foot powders and sprays, foundations, Fragrance preparations miscellaneous, Hair bleaches, Hair colour sprays, Hair colouring preparations miscellaneous, Hair conditioners, Hair dyes and colours, Hair lighteners with colour, Hair preparations, Hair rinses, Hair shampoos, Hair sprays, Hair straighteners
  • Flavour compositions according to the invention may be used in foodstuffs of all kinds, confectionery, baked goods, sweet goods, dairy products and beverages.
  • fectionery includes, but is not limited to:
  • chewing gum which includes sugarized gum, sugar-free gum, functional gum and bubble gum
  • center-fill confections chocolate and other chocolate confectionery, medicated confectionery, lozenges, tablets, pastilles, mints, standard mints, power mints, chewy candies, hard candies, boiled candies, breath and other oral care films or strips, candy canes, lollipops, gummies, jellies, fudge, caramel, hard and soft panned goods, toffee, taffy, liquorice, gelatin candies, gum drops, jelly beans, nougats, fondants, or combinations of one or more of these, or edible compositions incorporating one or more of these.
  • the confectionery compositions can be incorporated into an otherwise conventional hard or soft confectionery format using standard techniques and equipment known to those of ordinary skill in the art.
  • the confectionery compositions can also be center filled and/or coated with hard, soft, or particulate coatings.
  • naked goods includes, but is not limited to:
  • sweet goods includes, but is not limited to:
  • breakfast cereals ready-to-eat (“rte”) cereals, family breakfast cereals, flakes, muesli, other rte cereals, children's breakfast cereals and hot cereals.
  • rte ready-to-eat
  • air products includes, but is not limited to:
  • foodstuff includes, but is not limited to:
  • chilled snacks sweet and savory snacks, fruit snacks, chips/crisps, extruded snacks, tortilla/corn chips, popcorn, pretzels, nuts, other sweet and savory snacks, snack bars, granola bars, breakfast bars, energy bars, fruit bars, other snack bars, meal replacement products, slimming products, convalescence drinks, ready meals, canned ready meals, frozen ready meals, dried ready meals, chilled ready meals, dinner mixes, frozen pizza, chilled pizza, soup, canned soup, dehydrated soup, instant soup, chilled soup, uht soup, frozen soup, pasta, canned pasta, dried pasta, chilled/fresh pasta, noodles, plain noodles, instant noodles, cups/bowl instant noodles, pouch instant noodles, chilled noodles, snack noodles, dried food, dessert mixes, sauces, dressings and condiments, herbs and spices, spreads, jams and preserves, honey, chocolate spreads, nut-based spreads, and yeast-based spreads.
  • beverage means any drinkable liquid or semi-liquid, including for example:
  • ingredients found in such products, used in art-recognised quantities.
  • ingredients include (but are by no means limited to) solvents and co-solvents; surfactants and emulsifiers; viscosity and rheology modifiers; thickening and gelling agents; preservative materials; pigments, dyestuffs and colouring matters; extenders, fillers and reinforcing agents; stabilisers against the detrimental effects of heat and light, bulking agents, flavoring and flavor-enhancing agents, warming agents, breath fresheners, mouth moisteners, coloring agents, acidulants, buffering agents and antioxidants.
  • suitable components include in addition to a water-insoluble gum base portion, a water soluble bulk portion and various additives.
  • the water soluble portion may include sweetening agents, bulking agents, softening agents and/or plasticizers, waxes, emulsifiers, thickening agents, flavor enhancing agents, warming agents, breath fresheners, mouth moisteners, acidulants, coloring agents, buffering agents, antioxidants, nutraceuticals, medicaments and other conventional chewing gum additives that provide desired attributes.
  • Other conventional chewing gum additives known to one having ordinary skill in the art may also be used in the water soluble bulk portion.
  • Softeners and plasticizers may be used to provide a variety of desirable textures and consistency properties.
  • Suitable plasticizers and softeners may include lanolin, palmitic acid, oleic acid, stearic acid, sodium stearate, potassium stearate, glyceryl triacetate, glyceryl lecithin, glyceryl monostearate, propylene glycol monostearate, acetylated monoglyceride, glycerine, and a combination comprising at least one of the foregoing. Because of the low molecular weights of these softeners and plasticizers, they are able to penetrate the fundamental structure of the gum base, making it plastic and less viscous.
  • Waxes may be used in the gum base to soften the elastomer, improve the elasticity of the gum base, and obtain a variety of desirable textures and consistency properties.
  • Suitable waxes may include natural and synthetic waxes, hydrogenated vegetable oils, petroleum waxes such as polyurethane waxes, polyethylene waxes, paraffin waxes, microcrystalline waxes, fatty waxes, sorbitan monostearate, tallow, and propylene glycol.
  • Low melting waxes may be used in the gum compositions. These waxes typically have a melting point below about 60° C., and specifically about 45 to about 55° C.
  • High melting waxes may also be used in the gum base. Such high melting waxes include beeswax, vegetable wax, candelilla wax, camauba wax, most petroleum waxes, and the like, and combinations thereof.
  • Suitable emulsifiers include distilled monoglycerides, acetic acid esters of mono and diglycerides, citric acid esters of mono and diglycerides, lactic acid esters of mono and diglycerides, mono and diglycerides, polyglycerol esters of fatty acids, ceteareth-20, polyglycerol polyricinoleate, propylene glycol esters of fatty acids, polyglyceryl laurate, glyceryl cocoate, gum arabic, acacia gum, sorbitan monostearates, sorbitan tristearates, sorbitan monolaurate, sorbitan monooleate, sodium stearoyl lactylates, calcium stearoyl lactylates, diacetyl tartaric acid esters of mono- and diglycerides, glyceryl tricaprylate-caprate/medium chain triglycerides, glyceryl dioleate, glyceryl o
  • Suitable thickening agents include cellulose ethers (e.g., hydroxyethyl cellulose, hydroxypropylmethyl cellulose, or hydroxypropyl cellulose), methylcellulose, carboxymethylcellulose, and combinations thereof.
  • Additional polymers useful as thickeners include carbomer, polyvinyl pyrrolidone, polyvinyl alcohol, sodium alginate, polyethylene glycol, natural gums like xanthan gum, tragacantha, guar gum, acacia gum, arabic gum, water-dispersible polyacrylates like polyacrylic acid, methyl methacrylate copolymer, and carboxyvinyl copolymers.
  • a chewing gum composition may additionally contain bulking agents and fillers, nutraceuticals, medicaments and flavoring agents, as hereinabove described.
  • the chewing gum composition may be coated or compressed, and be in the form of slabs, sticks, pellets, cubes, trapezoids, rectangles, or balls.
  • the compositions of the different forms of the gum compositions will be similar but may vary with regard to the ratios of the ingredients.
  • Center-filled gum is another common gum form, the center-fill is typically an aqueous liquid or gel, which is injected into the center of the gum during processing.
  • the center-filled gum may also be optionally coated and may be prepared in various forms, such as in the form of a lollipop.
  • flavours were prepared with propylene glycol as a diluent to make the flavours up to 100%:
  • Flavour B containing 10% added menthol and 5% Evercool 190, performed the best for cooling, tingling and freshness and was most preferred.
  • flavours were dosed into typical silica toothpaste according to the following, such that the modified flavours were dosed at a lower, compacted level:
  • the two sets of samples were coded and given to 16 na ⁇ ve volunteers who were asked to brush their teeth for 30 seconds and score (0-10 scale) for cooling, freshness and tingling at 0 minutes, 5 minutes, 10 minutes, 20 minutes, 30 minutes and 60 minutes. Overall preference was also scored for each flavour (0-10 scale). The results are shown in FIGS. 5 through 8 .

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  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Nutrition Science (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
  • Seasonings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Confectionery (AREA)
  • Fats And Perfumes (AREA)
  • Pyridine Compounds (AREA)
US13/980,760 2011-02-23 2012-02-23 Flavour composition comprising menthol and menthane carboxamides Abandoned US20130323388A1 (en)

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WO2020033669A1 (en) 2018-08-10 2020-02-13 Firmenich Incorporated Antagonists of t2r54 and compositions and uses thereof
WO2021043482A1 (de) 2019-09-04 2021-03-11 Fidlock Gmbh Verbindungsvorrichtung zum lösbaren verbinden zweier baugruppen
DE202021103028U1 (de) 2021-06-03 2021-08-16 Fidlock Gmbh Verbindungsvorrichtung mit einem Unterdruckelement
WO2021259512A1 (de) 2020-06-26 2021-12-30 Fidlock Gmbh Verbindungsvorrichtung zum lösbaren verbinden zweier baugruppen

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US10182573B2 (en) * 2011-02-15 2019-01-22 Freshguard Defense Llc Antimicrobial solution for use with dental appliances
US20140271948A1 (en) * 2011-02-15 2014-09-18 Freshguard Defense Llc Antimicrobial solution for use with dental appliances
US10463597B2 (en) * 2012-05-22 2019-11-05 Conopco, Inc. Personal care composition
US9974761B2 (en) 2014-04-23 2018-05-22 The Procter & Gamble Company Medications for deposition on biological surfaces
US10392371B2 (en) 2015-10-01 2019-08-27 Senomyx, Inc. Compounds useful as modulators of TRPM8
EP3929451A1 (de) 2017-11-06 2021-12-29 Fidlock GmbH Verbindungsvorrichtung zum lösbaren verbinden zweier baugruppen
DE102017125846A1 (de) 2017-11-06 2019-05-09 Fidlock Gmbh Verbindungsvorrichtung zum lösbaren Verbinden zweier Baugruppen
US11739786B2 (en) 2017-11-06 2023-08-29 Fidlock Gmbh Connection device for releasably connecting two assemblies
WO2019086648A2 (de) 2017-11-06 2019-05-09 Fidlock Gmbh Verbindungsvorrichtung zum lösbaren verbinden zweier baugruppen
WO2020033669A1 (en) 2018-08-10 2020-02-13 Firmenich Incorporated Antagonists of t2r54 and compositions and uses thereof
EP3943762A1 (de) 2019-09-04 2022-01-26 Fidlock GmbH Verbindungsvorrichtung zum lösbaren verbinden zweier baugruppen
DE202020005647U1 (de) 2019-09-04 2021-11-30 Fidlock Gmbh Verbindungsvorrichtung zum lösbaren Verbinden zweier Baugruppen
DE202020005648U1 (de) 2019-09-04 2021-11-30 Fidlock Gmbh Verbindungsvorrichtung zum lösbaren Verbinden zweier Baugruppen
WO2021043482A1 (de) 2019-09-04 2021-03-11 Fidlock Gmbh Verbindungsvorrichtung zum lösbaren verbinden zweier baugruppen
US11835081B2 (en) 2019-09-04 2023-12-05 Fidlock Gmbh Connecting apparatus for releasably connecting two assemblies
WO2021259512A1 (de) 2020-06-26 2021-12-30 Fidlock Gmbh Verbindungsvorrichtung zum lösbaren verbinden zweier baugruppen
DE102020207983A1 (de) 2020-06-26 2021-12-30 Fidlock Gmbh Verbindungsvorrichtung zum lösbaren Verbinden zweier Baugruppen
DE202021103028U1 (de) 2021-06-03 2021-08-16 Fidlock Gmbh Verbindungsvorrichtung mit einem Unterdruckelement
WO2022253586A1 (de) 2021-06-03 2022-12-08 Fidlock Gmbh Verbindungsvorrichtung mit einem unterdruckelement

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WO2012113873A3 (en) 2013-06-06
JP2014507440A (ja) 2014-03-27
MX363019B (es) 2019-03-05
CN103391764A (zh) 2013-11-13
CN106860034A (zh) 2017-06-20
KR101924664B1 (ko) 2018-12-03
US10299999B2 (en) 2019-05-28
CN106860034B (zh) 2020-05-19
US20160317407A1 (en) 2016-11-03
JP6556811B2 (ja) 2019-08-07
EP2677988A2 (en) 2014-01-01
MX2013008696A (es) 2013-08-21
ZA201306056B (en) 2014-04-30
JP2018070628A (ja) 2018-05-10
BR112013021413A2 (pt) 2016-08-09
JP6262532B2 (ja) 2018-01-17
WO2012113873A2 (en) 2012-08-30
GB201103103D0 (en) 2011-04-06
CN103391764B (zh) 2017-04-12

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