WO2008138162A1 - Compositions and their use - Google Patents
Compositions and their use Download PDFInfo
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- WO2008138162A1 WO2008138162A1 PCT/CH2008/000218 CH2008000218W WO2008138162A1 WO 2008138162 A1 WO2008138162 A1 WO 2008138162A1 CH 2008000218 W CH2008000218 W CH 2008000218W WO 2008138162 A1 WO2008138162 A1 WO 2008138162A1
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- WIPO (PCT)
- Prior art keywords
- cooling
- flavour
- methyl
- menthane
- isopropyl
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Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
- C12G3/00—Preparation of other alcoholic beverages
- C12G3/04—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs
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- 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
- A23L27/88—Taste or flavour enhancing agents
Definitions
- compositions comprising flavour enhancing compounds for use in food products or products placed in the oral cavity, and flavour-enhanced food products comprising said compounds or compositions.
- flavour sensations for example the "cooling" sensation associated with mint oil or menthol, or the warming sensation associated with alcohol (ethanol).
- enhancing is meant the effect of a compound on a particular flavour sensation in food products or products placed in the oral cavity which is found more pronounced (stronger, enhanced) in its taste intensity and/or which is found to last longer when comparing to the product without added enhancing compound and/or which is found to have an earlier onset of the flavour sensation.
- flavour sensations are of great interest and may allow not only to improve/intensify the perceived flavour but also to reach a certain flavour intensity at a reduced concentration of flavour ingredients, for example less ethanol, and/or less mint/cooling ingredient.
- compositions and products (food products, products placed in the oral cavity) can be formed which have an enhanced effect of the associated flavour sensation.
- Aframodial and labda-8(17),12-diene-15,16-dial are known to occur in certain species of the Zingiberaceae plant family, and to have antifungal properties.
- flavour compounds cooling ingredients, and ethanol
- the cooling sensation is intensified and the duration of the cooling sensation and/or mint taste is lengthened.
- the warming sensation caused by ethanol is enhanced in intensity and duration.
- composition comprising one or more flavour enhancers selected from aframodial and labda-
- cooling ingredient it has a concentration that together with the enhancer provides a cooling effect above the detection threshold for the cooling sensation.
- compositions include, for example, flavour compositions, food products, compositions for products placed in the oral cavity, and the latter products.
- flavour enhancer is present in a concentration from 0.25 ppm to 3000 ppm.
- flavour enhancers selected from aframodial and labda-8(17),12-diene-15,16- dial in combination with one or more ingredient selected from a cooling ingredient and ethanol, in food products and products placed in the oral cavity to enhance the flavour sensations associated with cooling compounds or ethanol.
- flavour enhancer selected from aframodial and labda-8(17),12-diene-15,16-dial, and one or more ingredient selected from a cooling compound and ethanol, are mixed to provide a food product or flavour composition for a food product in a sufficient amount to enhance said taste sensations.
- flavour enhancing compound or compounds are added in a total concentration from 0.25 ppm to 3000 ppm.
- the one or more cooling ingredient is selected from the group consisting of mint oil, peppermint oil, spearmint oil, eucalypt oil, 2-l-menthoxyethane-1- ol, 3-l-menthoxypropane-1-ol, and 4-l-menthoxybutane-1-ol, pulegol, cineol, eucalyptol, 2-sec-butylcyclohexanone, (6-isopropyl-9-methyl-1,4-dioxaspiro[4.5]decan-2-yl)methanol, ((6S,9R)-6-isopropyl-9-methyl-1,4- dioxaspiro[4.5]decan-2-yl)methanol, (+)-D-menthone, isopulegol, (-)-isopulegol, (+)-isopulegol, Coolact P®, p- menthane-3,8-diol
- flavour modifying compounds can be easily tested by an organoleptic titration. This technique is well known in the field of sensory analysis.
- a concentration from 0.25 to 3000 ppm is generally useful, with most applications within the range of 5 to 1000 ppm.
- the concentration used will depend on the type of product and concentration of flavour to be modified (cooling ingredient, ethanol), and will vary accordingly.
- the concentration depends on the ethanol concentration and on the desired degree of enhancement of the alcohol sensation.
- Useful concentrations in alcoholic beverages include, for example, 0.25 to 500 ppm for ethanol concentrations of 5% to 100%, for example 60 to 70% ethanol, and 65 to 70% ethanol.
- 0.25 to 250 ppm and 0.5 ppm to 500 ppm may be useful concentrations of aframodial in alcoholic beverages. Higher concentrations of ethanol will need a higher concentration of the alcohol enhancer.
- a concentration from 0.25 to 3000 ppm is generally useful, depending on the type of product and concentration of flavour to be modified (cooling ingredient, ethanol). For example, a concentration of 0.25 to 1000 ppm, 2 to 100 ppm, or 5 to 50 ppm may be useful .
- Useful concentrations in alcoholic beverages include, for example, 0.25 to 500 ppm for ethanol concentrations of 5 to 70%. For example, 0.25 to 250 ppm and 0.5 ppm to 500 ppm for ethanol concentrations of 5 to 70%. Higher concentrations of ethanol will need a higher concentration of the alcohol enhancer.
- Flavour compositions comprise one or more flavour enhancer selected from aframodial and labda-8(17), 12-diene- 15, 16-dial, an ingredient selected from ethanol and a cooling ingredient, and optionally at least one food grade excipient.
- Suitable excipients for flavour compositions are well known in the art and include, for example, without limitation, solvents (including water, alcohol, ethanol, oils, fats, vegetable oil, and miglyol), binders, diluents, disintegranting agents, lubricants, flavoring agents, coloring agents, preservatives, antioxidants, emulsifiers, stabilisers, flavor-enhancers, sweetening agents, anti-caking agents, and the like.
- flavours examples include ..Perfume and Flavor Materials of Natural Origin,,, S. Arctander, Ed., Elizabeth, N.J, 1960; in “Perfume and Flavor Chemicals”, S. Arctander, Ed, Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; in "Flavourings”, E. Ziegler and H. Ziegler (ed.), Wiley- VCH Weinheim, 1998, and "CTFA Cosmetic Ingredient Handbook", J. M. Nikitakis (ed.), 1st ed. The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.
- the flavour composition may contain additional flavour ingredients including flavour compounds, flavours from natural sources including botanical sources and including ingredients made by fermentation.
- the flavour composition may have any suitable form, for example liquid or solid, wet or dried, or in encapsulated form bound to or coated onto carriers/particles or as a powder.
- Cooling ingredients are ingredients that when present in a suitable concentration above their cooling detection threshold provide a cooling taste sensation when placed in the oral cavity. Many of these compounds are agonists of the cooling taste receptor TRP-p8, also known as TRP-m8.
- cooling ingredients include cooling compounds and botanical materials and extracts, for example, without limitation, plant material or oil including spearmint and peppermint plants, for example, without limitation, mint oil, spearmint oil, peppermint oil, and eucalypt oil.
- TRP-p8 also known as TRP-m8
- TRP-m8 including compounds and groups of compounds that are or may be cooling
- WO 2005/002582 including general formulae I to XIII and individual compounds
- WO 2005/020897 general formulae I to VIII, VIII-A to VIII-G and individual compounds including compounds in tables 1A to 1D, 2, and 3.
- Cooling ingredients or compounds include, without limitation, mint oil, peppermint oil, spearmint oil, eucalypt oil, the compounds and groups of compounds described herein-above and 2-l-menthoxyethane-1-ol, 3-I- menthoxypropane-1-ol, and 4-l-menthoxybutane-1-ol, pulegol, cineol, eucalyptol, 2-sec-butylcyclohexanone, (6- isopropyl-9-methyl-1,4-dioxaspiro[4.5]decan-2-yl)methanol, ((6S,9R)-6-isopropyl-9-methyl-1,4- dioxaspiro[4.5]decan-2-yl)methanol, (+)-D-menthone, isopulegol, (-)-isopulegol, (+)-isopulegol, Coolact P®, p- menthane-3,8-diol, ReI-(I
- the absolute stereochemical form (abs) or relative stereochemical form that is currently considered most active to provide a cooling taste is given.
- other forms also exist and may have a similar or better cooling effect.
- the equitorial form like (-)-menthol) is the one considered most active in the literature (for example, WS-3 in the 1R, 2S, 5Rform).
- Useful concentrations for cooling compounds to be enhanced are at least the concentration of their cooling taste detection threshold, or slightly below (to give an above threshold effect in combination with the cooling enhancers).
- the cooling threshold is known for many compounds and can be easily tested.
- Alcoholic products as herein described comprise a minimum ethanol concentration of 1% or more, or 5% or more, for example 5 to 100%, 5 to 70%, 20 to 70%, 30 to 70%, and 40 to 70%, 30 to 52%, and 40 to 52%.
- Products and flavour compositions described herein may be used in food products and any products placed within the oral cavity. Accordingly, where products placed within the oral cavity are not expicitly mentioned, "food product” is used herein in a broad meaning to include any product placed within the oral cavity, for example food, beverages, nutraceuticals and dental care products including mouth wash and dental hygiene articels, and solid flavoured products such as dental floss, drinking straws and other plastic products where flavour can be added to the formulation or that can be coated.
- Food products include, for example, cereal products, rice products, pasta products, ravioli, tapioca products, sago products, baker's products, biscuit products, pastry products, bread products, confectionery products, dessert products, gums, chewing gums, chocolates, ices, honey products, treacle products, yeast products, salt and spice products, savory products, mustard products, vinegar products, sauces (condiments), processed foods, cooked fruits and vegetable products, meat and meat products, meat analogues/substitutes, jellies, jams, fruit sauces, egg products, milk and dairy products, cheese products, butter and butter substitute products, milk substitute products, soy products, edible oils and fat products, medicaments, beverages, food extracts, plant extracts, meat extracts, condiments, nutraceuticals, gelatins, tablets, lozenges, drops, emulsions, elixirs, syrups, and combinations thereof.
- Mint and mint-type flavoured products that have a cooling taste and contain a cooling ingredient
- said mint products comprising, without limitation, confections and/or health care products including hard candies, soft candies, chewing gums, edible films, mouthwash, toothpaste, and dental floss;
- Alcoholic beverages of various ethanol concentrations with a minimum ethanol concentration of 5% or more for example 5 to 100%, 5 to 70%, 20 to 70%, 30 to 70%, and 40 to 70%, 30 to 52%, and 40 to 52%.
- Savory spicy foods including dips and mayonnaise, and salty snacks.
- Alcohol is indicated as "proof, which is converted into % ethanol by dividing by 2. For example, 10 proof alcohol is 5%, 40 proof is 20%, 190 proof is 95%.
- Example 1 general taste evaluation methodology
- Example 2 enhancement of cooling effect of aframodial in mouthwash
- Example 3 enhancement of cooling effect in hard candy
- Example 6 enhancement of cooling effect of WS-3 in water by aframodial
- Example 7 enhancement of cooling effect of WS-3 in water by labda
- test samples were prepared by adding test compounds and tastants to a reference sample.
- the references contained the tastant in the same or a higher concentration, but without the test compound (putative enhancer).
- Test samples and reference samples were prepared fresh and served at room temperature in flavorless, odorless 1 oz souffle cups. Drinking water was used to rinse and clean the palate between samples.
- Each test sample was evaluated by 6 to 10 panelists for its relevant taste intensity and lasting effect of the taste sensation in comparison to each reference sample.
- test samples are in 50 proof ethanol cordial, with higher concentrated reference samples at 60 or 70 proof ethanol.
- the known cooling compound WS-3 N-ethyl p-menthanecarboxamide
- the panelists evaluated the taste of the samples and compared the taste intensity of each sample (cooling effect, alcoholic taste) with one or more reference samples.
- Example 2 The panelists evaluated the taste of the samples and compared the taste intensity of each sample (cooling effect, alcoholic taste) with one or more reference samples.
- the taste evaluation on intensity and duration of a cooling sensation was performed by 8 panelists as described in example 1 subject to the following modifications.
- the panelists were experts on mint flavor creation and health care product applications.
- the test sample contained 25 ppm Aframodial, added in form of a concentrated stock solution to a mouthwash reference sample to provide the test samples.
- the test compound stock solution was prepared by dissolving 1 part Aframodial into 99 parts propylene glycol/Ethanol.
- the mouthwash reference sample was prepared by mixing 5 parts commercially available alcohol free mint flavored mouthwash (Act Alcohol Free Mint Flavored Mouthwash containing menthol (0.06% w/v) with 95 parts distilled water.
- a half mouth test was used to compare samples: Panelists placed a sample in one side of the mouth and rinsed for 10 seconds. Panelists evaluated flavour perceptions and flavour intensities of each sample both in the mouth and after expelling. After rinsing with drinking water, this procedure is repeated for the next sample in the opposite side of the mouth.
- the mint flavor intensity of the Aframodial sample was increased in intensity and longer in duration when compared to the control sample.
- a test compound stock solution was prepared by dissolving 1 part test compound into 99 parts propylene glycol/Ethanol.
- a hard candy mint flavor was prepared by mixing 77.78 parts peppermint oil with 22.22 parts menthol.
- a hard candy base was prepared by dissolving 50 parts sucrose in 9 parts distilled water, then 41 parts of high maltose corn syrup was added and the mixture was heated to boiling. After the temperature reached 300 F (148°C), the control samples were prepared by mixing 100 parts of hard candy base and 0.05 parts of hard candy mint flavor.
- the test sample was prepared as described for the control sample except for the addition of 50 ppm Aframodial to the mint flavored hard candy base. The samples were then poured into candy molds and allowed to cool and harden briefly before packaging into wrapping. Hard candy test samples with and without test compounds were compared by 8 panelists. The samples were tested on their ability to elicit a cooling sensation and for the duration of that cooling sensation.
- a half mouth test was used to compare samples: Panelists placed the candy into one side of the mouth and sucked on the candy for one minute. Afterwards, the panelists expelled the candy sample into a cup. The sample was evaluated in the mouth and after expelling. Drinking water was used to rinse the mouth between samples to cleanse the palate.
- Panelists observed higher intensity and longer lasting sensations of cooling and tingling sensations in the aframodial hard candy sample in comparison with the control sample.
- Test samples contained 25 ppm of Aframodial in a 50 proof ethanol cordial (42.7 parts distilled water, 30 parts medium invert sugar, 26.3 parts 95% ethyl alcohol and 1 part glycerine). Reference samples had the same cordial of 50, 60, 70 and 80 proof with the same sugar and glycerine content.
- Test samples contained 15 ppm of labda-8(7), 12-diene-15, 16-dial in 50 proof ethanol cordial (42.7 parts distilled water, 30 parts medium invert sugar, 26.3 parts 95% ethyl alcohol and 1 part glycerine).
- Reference samples contained ethanol cordial of 60, 70 and 80 proof with the same sugar and glycerine content. All panelists noted an alcohol warming sensation increased in intensity and duration in the test sample in comparison the 50 proof and the 65 proof reference sample. When compared to the 70 proof reference sample, the alcohol intensity was similar.
- Test samples contained 8 ppm of aframodial and 25 ppm WS-3 in water. 25 and 30 ppm WS-3 in water without aframodial served as reference samples.
- WS-3 is a known synthetic cooling compound.
- Test samples contained 0.25 ppm labda-8(7), 12-diene-15, 16-dial and 25 ppm WS-3. 25 and 30 ppm WS-3 samples without labda served as references.
Abstract
Provided are compositions comprising flavour enhancing compounds for use in food products or products placed in the oral cavity, and flavour-enhanced food products or products placed in the oral cavity comprising said compounds or compositions. The flavor enhancers are aframodial and labda-8(17),12-diene-15,16-dial, which when combined with cooling ingredients and/or alcohol (ethanol) enhance the taste of alcohol and a cooling taste sensation in intensity and duration.
Description
COMPOSITIONS AND THEIR USE
TECHNICAL FIELD
Provided are compositions comprising flavour enhancing compounds for use in food products or products placed in the oral cavity, and flavour-enhanced food products comprising said compounds or compositions.
BACKGROUND
It is of interest in the food industry to enhance desired flavour sensations, for example the "cooling" sensation associated with mint oil or menthol, or the warming sensation associated with alcohol (ethanol).
By enhancing is meant the effect of a compound on a particular flavour sensation in food products or products placed in the oral cavity which is found more pronounced (stronger, enhanced) in its taste intensity and/or which is found to last longer when comparing to the product without added enhancing compound and/or which is found to have an earlier onset of the flavour sensation.
Compounds that can enhance certain flavour sensations are of great interest and may allow not only to improve/intensify the perceived flavour but also to reach a certain flavour intensity at a reduced concentration of flavour ingredients, for example less ethanol, and/or less mint/cooling ingredient.
Applicant has now found that by using one or more of a compound selected from the group consisting of aframodial and labda-8(17),12-diene-15,16-dial, in combination with one or more flavour compounds selected from a cooling ingredient and ethanol, compositions and products (food products, products placed in the oral cavity) can be formed which have an enhanced effect of the associated flavour sensation.
The chemical structures of aframodial and labda-8( 17) , 12-d iene- 15,16-d ial are shown below.
Aframodial:
Labda-8( 17),12-diene-15, 16-dial ("labda"):
Aframodial and labda-8(17),12-diene-15,16-dial are known to occur in certain species of the Zingiberaceae plant family, and to have antifungal properties.
However, the enhancing effects in combination with certain flavour compounds (cooling ingredients, and ethanol) that the applicant discovered have not been previously known.
The enhancing effects are discussed in more detail below.
In combination with cooling ingredients, the cooling sensation is intensified and the duration of the cooling sensation and/or mint taste is lengthened.
In combination with ethanol, the warming sensation caused by ethanol is enhanced in intensity and duration.
SUMMARY
Provided is a composition comprising one or more flavour enhancers selected from aframodial and labda-
8(17), 12-diene-15, 16-dial, and one or more ingredient selected from the group consisting of a cooling ingredient, and ethanol, wherein when ethanol is present it has a concentration of at least 1 % (wt/wt), and wherein when one
2008/000218
or more cooling ingredient is present, it has a concentration that together with the enhancer provides a cooling effect above the detection threshold for the cooling sensation.
Such compositions include, for example, flavour compositions, food products, compositions for products placed in the oral cavity, and the latter products.
Provided is a food product as herein described wherein the flavour enhancer is present in a concentration from 0.25 ppm to 3000 ppm.
Provided is the use of one or more flavour enhancers selected from aframodial and labda-8(17),12-diene-15,16- dial in combination with one or more ingredient selected from a cooling ingredient and ethanol, in food products and products placed in the oral cavity to enhance the flavour sensations associated with cooling compounds or ethanol.
Provided is a method of enhancing the taste sensations associated with cooling ingredients or ethanol, wherein one or more flavour enhancer selected from aframodial and labda-8(17),12-diene-15,16-dial, and one or more ingredient selected from a cooling compound and ethanol, are mixed to provide a food product or flavour composition for a food product in a sufficient amount to enhance said taste sensations.
In one embodiment as herein described, the flavour enhancing compound or compounds are added in a total concentration from 0.25 ppm to 3000 ppm.
In certain embodiments of compositions, uses and methods described herein, the one or more cooling ingredient is selected from the group consisting of mint oil, peppermint oil, spearmint oil, eucalypt oil, 2-l-menthoxyethane-1- ol, 3-l-menthoxypropane-1-ol, and 4-l-menthoxybutane-1-ol, pulegol, cineol, eucalyptol, 2-sec-butylcyclohexanone, (6-isopropyl-9-methyl-1,4-dioxaspiro[4.5]decan-2-yl)methanol, ((6S,9R)-6-isopropyl-9-methyl-1,4- dioxaspiro[4.5]decan-2-yl)methanol, (+)-D-menthone, isopulegol, (-)-isopulegol, (+)-isopulegol, Coolact P®, p- menthane-3,8-diol, ReI-(I S,2R,5R)-2-(2-hydroxypropan-2-yl)-5-methylcyclohexanol, (-)-trans p-Menthane-3,8-diol, (+)-cis p-Menthane-3,8-diol, PMD38, menthol, dl-menthol, 1R,3R,4R-(+)-neoisomenthol, 1R,3S,4R-(+)-isomenthol, 1 R,3S,4S-(+)-neomenthol, 1 S,3S,4S-(-)-neoisomenthol, 1 S,3R,4S-(-)-isomenthol, 1 S,3R,4R-(-)-neomenthol, 1S,3S,4R-(+)-menthol, (-)-Menthyl 2-pyrrolidone-5-carboxylate, menthone, dl-menthone, (-)-menthyl lactate, menthyl lactate, monomenthyl glutarate, dl-Menthyl succinate, 4-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)- 4-oxobutanoic acid, monomenthyl dimethyl succinate, (-)-menthoxypropane-1,2-diol, 3-(1-menthoxy)-1,2- propanediol, (2R)-3-(l-menthoxy)propane-1 ,2-diol, (2S)-3-(l-menthoxy) propane- 1 ,2-diol), 3-(l-menthoxy)-2-
methylpropane-1 ,2-diol, N-(4-cyanomethylphenyl)-p-menthanecarboxamide, (1R,2S,5R)-rel- 5-methyl-2-(1- methylethyl)-N-[2-(2-pyridinyl)ethyl]- cyclohexanecarboxamide,
(1 R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(2-methoxyethoxy)acetate, (1 R,2S,5R)-2-isopropyl-5- methylcyclohexyl 2-methoxyacetate, (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(2-(2- methoxyethoxy)ethoxy)acetate, (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(2-hydroxyethoxy)acetate, (1R,2S,5R)- [2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-acetic acid 5-methyl-2-(1-methylethyl)cyclohexyl ester, (-)- cubebol, eutectic mixture of WS-23 and WS-3 (ICE 1500™), 1-[2-hydroxyphenyl]-4-[3-nitrophenyl- ]-1 ,2,3,6- tetrahydropyrimidin-2-one, 1-(2-hydroxyphenyl)-4-(3-methylphenyl)-1,2,3,6-tetrahydropyrimidin-2-one, 4-methyl-3- (1-pyrrolidinyl)-2[5H]-furanone, 4,5-dimethyl-3-(1-pyrrolidinyl)-2[5H]-furanone, 5-methyl-4-(1-pyrrolidinyl)-3-[2H]- furanone, WS-3 (N-ethyl p-menthane-3-carboxamide), WS-4 (ethyleneglycol p-menthane-3-carboxylate), WS-5 (N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine ethyl ester), WS-12 (N-(4-methoxyphenyl)-p-menthane- 3-carboxamide), WS-14 (N-t-butyl-p-menthane-3-caώoxamide, [1R-(1α,2β,5α)]- N-(1,1-dimethylethyl)-5-methyl- 2-(1-methy!ethyl)-cyclohexanecarboxamide), WS-23 (N,2,3-trimethyl-2-isopropylbutanamide), and WS-30 (1- glyceryl p-menthane-3-carboxylate).
DETAILED DESCRIPTION
The appropriate concentration of the flavour modifying compounds can be easily tested by an organoleptic titration. This technique is well known in the field of sensory analysis.
For aframodial, for example, a concentration from 0.25 to 3000 ppm is generally useful, with most applications within the range of 5 to 1000 ppm. The concentration used will depend on the type of product and concentration of flavour to be modified (cooling ingredient, ethanol), and will vary accordingly. For example, in candy a range from 10 to 1000 ppm is useful, chewing gum usually requires higher concentrations from 100 to 2500 ppm. In alcoholic beverages, the concentration depends on the ethanol concentration and on the desired degree of enhancement of the alcohol sensation. Useful concentrations in alcoholic beverages include, for example, 0.25 to 500 ppm for ethanol concentrations of 5% to 100%, for example 60 to 70% ethanol, and 65 to 70% ethanol. For example, 0.25 to 250 ppm and 0.5 ppm to 500 ppm may be useful concentrations of aframodial in alcoholic beverages. Higher concentrations of ethanol will need a higher concentration of the alcohol enhancer.
For labda-8(17), 12-diene-15, 16-dial, for example, a concentration from 0.25 to 3000 ppm is generally useful, depending on the type of product and concentration of flavour to be modified (cooling ingredient, ethanol). For example, a concentration of 0.25 to 1000 ppm, 2 to 100 ppm, or 5 to 50 ppm may be useful .
Useful concentrations in alcoholic beverages include, for example, 0.25 to 500 ppm for ethanol concentrations of 5 to 70%. For example, 0.25 to 250 ppm and 0.5 ppm to 500 ppm for ethanol concentrations of 5 to 70%. Higher concentrations of ethanol will need a higher concentration of the alcohol enhancer.
Flavour compositions comprise one or more flavour enhancer selected from aframodial and labda-8(17), 12-diene- 15, 16-dial, an ingredient selected from ethanol and a cooling ingredient, and optionally at least one food grade excipient. Suitable excipients for flavour compositions are well known in the art and include, for example, without limitation, solvents (including water, alcohol, ethanol, oils, fats, vegetable oil, and miglyol), binders, diluents, disintegranting agents, lubricants, flavoring agents, coloring agents, preservatives, antioxidants, emulsifiers, stabilisers, flavor-enhancers, sweetening agents, anti-caking agents, and the like. Examples of such carriers or diluents for flavours may be found e.g. in ..Perfume and Flavor Materials of Natural Origin,,, S. Arctander, Ed., Elizabeth, N.J, 1960; in "Perfume and Flavor Chemicals", S. Arctander, Ed, Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; in "Flavourings", E. Ziegler and H. Ziegler (ed.), Wiley- VCH Weinheim, 1998, and "CTFA Cosmetic Ingredient Handbook", J. M. Nikitakis (ed.), 1st ed. The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.
The flavour composition may contain additional flavour ingredients including flavour compounds, flavours from natural sources including botanical sources and including ingredients made by fermentation. The flavour composition may have any suitable form, for example liquid or solid, wet or dried, or in encapsulated form bound to or coated onto carriers/particles or as a powder.
Cooling ingredients (or coolants) are ingredients that when present in a suitable concentration above their cooling detection threshold provide a cooling taste sensation when placed in the oral cavity. Many of these compounds are agonists of the cooling taste receptor TRP-p8, also known as TRP-m8.
These cooling ingredients include cooling compounds and botanical materials and extracts, for example, without limitation, plant material or oil including spearmint and peppermint plants, for example, without limitation, mint oil, spearmint oil, peppermint oil, and eucalypt oil.
Agonists of the cooling taste receptor TRP-p8, also known as TRP-m8, including compounds and groups of compounds that are or may be cooling, are described in WO 2005/002582 (including general formulae I to XIII and individual compounds), and in WO 2005/020897 (general formulae I to VIII, VIII-A to VIII-G and individual compounds including compounds in tables 1A to 1D, 2, and 3).
Further general chemical formulae that include cooling compounds are indicated below.
n = 1 ,2 & R = OMe , OEt, Q Pr, O-iPR, OBu Various cooling compounds falling under the above general formula are described in US 7,030,273.
Various cooling compounds that are alkyloxy amides of p-menthane derivates falling under the above general formula are described by Takazawa et al. in JP2004059474.
Various cooling compounds that are p-menthane carboxamides, including N-(4-cyanomethylphenyl) p- menthanecarboxamide, are described by Galopin et al. in WO2005049553.
Various cooling compounds that are menthyl half acid ester derivatives including N,N-Dimethyl menthyl succinamide (or more correctly 2-isopropyl-5-methylcyclohexyl 4-(dimethylamino)-4-oxobutanoate, FEMA No. 4230), are described by Dewis et al. in US 6,884,906.
Various cooling compounds that belong to a family called cyclic alpha-keto enamines are described by T. Hoffmann and co-workers (US 6,592,884, Ottinger et al. 2001 , J. Agric. Food Chem, 49, 5383-5390), which comprises, among others, 4-methyl-3-(1-pyrrolidinyl)-2[5H]-furanone, 5-methyl-4-(1-pyrrolidinyl)-3-[2H]-furanone, and 4,5-dimethyl-3-(1-pyrrolidinyl)-2[5H]-furanone.
Further, various cooling compounds can be found in WO 2005/049553, WO 2006/125334, and WO 2007/019719.
All publications relating to cooling compounds cited above are hereby incorporated herein by reference.
Cooling ingredients or compounds include, without limitation, mint oil, peppermint oil, spearmint oil, eucalypt oil, the compounds and groups of compounds described herein-above and 2-l-menthoxyethane-1-ol, 3-I-
menthoxypropane-1-ol, and 4-l-menthoxybutane-1-ol, pulegol, cineol, eucalyptol, 2-sec-butylcyclohexanone, (6- isopropyl-9-methyl-1,4-dioxaspiro[4.5]decan-2-yl)methanol, ((6S,9R)-6-isopropyl-9-methyl-1,4- dioxaspiro[4.5]decan-2-yl)methanol, (+)-D-menthone, isopulegol, (-)-isopulegol, (+)-isopulegol, Coolact P®, p- menthane-3,8-diol, ReI-(I S,2R,5R)-2-(2-hydroxypropan-2-yl)-5-methylcyclohexanol, (-)-trans p-Menthane-3,8-diol, (+)-cis p-Menthane-3,8-diol, PMD38, menthol, dl-menthol, 1R,3R,4R-(+)-neoisomenthol, 1R,3S,4R-(+)-isomenthol, 1 R,3S,4S-(+)-neomenthol, 1 S,3S,4S-(-)-neoisomenthol, 1 S,3R,4S-(-)-isomenthol, 1 S,3R,4R-(-)-neomenthol, 1S,3S,4R-(+)-menthol, (-)-Menthyl 2-pyrrolidone-5-carboxylate, menthone, dl-menthone, (-)-menthyl lactate, menthyl lactate, monomenthyl glutarate, dl-Menthyl succinate, 4-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)- 4-oxobutanoic acid, monomenthyl dimethyl succinate, (-)-menthoxypropane-1,2-diol, 3-(1-menthoxy)-1,2- propanediol, (2R)-3-(l-menthoxy)propane-1 ,2-diol, (2S)-3-(l-menthoxy) propane- 1 ,2-diol), 3-(l-menthoxy)-2- methylpropane-1 ,2-diol, N-(4-cyanomethylphenyl)-p-menthanecarboxamide, (1 R,2S,5R)-rel- 5-methyl-2-(1- methylethyl)-N-[2-(2-pyridinyl)ethyl]-cyclohexanecarboxamide,
(1 R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(2-methoxyethoxy)acetate, (1 R,2S,5R)-2-isopropyl-5- methylcyclohexyl 2-methoxyacetate, (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(2-(2- methoxyethoxy)ethoxy)acetate, (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(2-hydroxyethoxy)acetate, (1R,2S,5R)- [2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-acetic acid'5-methyl-2-(1-methylethyl)cyclohexyl ester, (-)- cubebol, eutectic mixture of WS-23 and WS-3 (ICE 1500™), 1-[2-hydroxyphenyl]-4-[3-nitrophenyl- ]-1,2,3,6- tetrahydropyrimidin-2-one, 1-(2-hydroxyphenyl)-4-(3-methylphenyl)-1,2,3,6-tetrahydropyrimidin-2-one, 4-methyl-3- (1-pyrrolidinyl)-2[5H]-furanone, 4,5-dimethyl-3-(1-pyrrolidinyl)-2[5H]-furanone, 5- methy l-4-( 1 -pyrrolid inyl)-3- [2H]- furanone, WS-3 (N-ethyl p-menthane-3-carboxamide), WS-4 (ethyleneglycol p-menthane-3-carboxylate), WS-5 (N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine ethyl ester), WS-12 (N-(4-methoxyphenyl)-p-menthane- 3-carboxamide), WS-14 (N-t-butyl-p-menthane-3-carboxamide, [1R-(1α,2β,5α)]- N-( 1 , 1 -dimethylethyl)-5-methyl- 2-(1-methylethyl)-cyclohexanecarboxamide), WS-23 (N,2,3-trimethyl-2-isopropylbutanamide), WS-30 (1-glyceryl p-menthane-3-carboxylate), in a concentration above their threshold for the detection of the cooling taste sensation. EExamples of chemical formulae for various cooling compounds are indicated herein below. The detection threshold concentration for most cooling compounds is known and otherwise can be easily determined by standard procedures well known in the art.
For some compounds, the absolute stereochemical form (abs) or relative stereochemical form that is currently considered most active to provide a cooling taste is given. However, other forms also exist and may have a similar or better cooling effect. In general, the equitorial form (like (-)-menthol) is the one considered most active in the literature (for example, WS-3 in the 1R, 2S, 5Rform).
Useful concentrations for cooling compounds to be enhanced are at least the concentration of their cooling taste detection threshold, or slightly below (to give an above threshold effect in combination with the cooling enhancers). The cooling threshold is known for many compounds and can be easily tested.
Most of the above cooling compounds that have a CAS number indicated are commercially available, and commercial sources include Givaudan, IFF, Symrise, Takasago, Hasegawa, Millenium Specialty Chemicals, Penta, Rhodia, Qarόma, Frutarom, Natural-Advantage. The rest of the compounds can be produced using methods that are well known in the art.
Alcoholic products (including alcoholic beverages) as herein described comprise a minimum ethanol concentration of 1% or more, or 5% or more, for example 5 to 100%, 5 to 70%, 20 to 70%, 30 to 70%, and 40 to 70%, 30 to 52%, and 40 to 52%.
Products and flavour compositions described herein may be used in food products and any products placed within the oral cavity. Accordingly, where products placed within the oral cavity are not expicitly mentioned, "food product" is used herein in a broad meaning to include any product placed within the oral cavity, for example food, beverages, nutraceuticals and dental care products including mouth wash and dental hygiene articels, and solid flavoured products such as dental floss, drinking straws and other plastic products where flavour can be added to the formulation or that can be coated.
Food products include, for example, cereal products, rice products, pasta products, ravioli, tapioca products, sago products, baker's products, biscuit products, pastry products, bread products, confectionery products, dessert products, gums, chewing gums, chocolates, ices, honey products, treacle products, yeast products, salt and spice products, savory products, mustard products, vinegar products, sauces (condiments), processed foods, cooked fruits and vegetable products, meat and meat products, meat analogues/substitutes, jellies, jams, fruit sauces, egg
products, milk and dairy products, cheese products, butter and butter substitute products, milk substitute products, soy products, edible oils and fat products, medicaments, beverages, food extracts, plant extracts, meat extracts, condiments, nutraceuticals, gelatins, tablets, lozenges, drops, emulsions, elixirs, syrups, and combinations thereof.
Of particular interest are the following food products:
Mint and mint-type flavoured products that have a cooling taste and contain a cooling ingredient, said mint products comprising, without limitation, confections and/or health care products including hard candies, soft candies, chewing gums, edible films, mouthwash, toothpaste, and dental floss;
Alcoholic beverages of various ethanol concentrations with a minimum ethanol concentration of 5% or more, for example 5 to 100%, 5 to 70%, 20 to 70%, 30 to 70%, and 40 to 70%, 30 to 52%, and 40 to 52%.
Savory spicy foods including dips and mayonnaise, and salty snacks.
Examples
All percentages given are wt/wt, unless indicated otherwise. Alcohol (ethanol) is indicated as "proof, which is converted into % ethanol by dividing by 2. For example, 10 proof alcohol is 5%, 40 proof is 20%, 190 proof is 95%.
Overview examples:
Example 1 - general taste evaluation methodology
Example 2 - enhancement of cooling effect of aframodial in mouthwash
Example 3 - enhancement of cooling effect in hard candy
Example 4 - enhancement of alcohol by aframodial
Example 5 - enhancement of alcohol by labda
Example 6 - enhancement of cooling effect of WS-3 in water by aframodial
Example 7 - enhancement of cooling effect of WS-3 in water by labda
Example 1 Taste evaluations
For taste evaluations, test samples were prepared by adding test compounds and tastants to a reference sample. The references contained the tastant in the same or a higher concentration, but without the test compound (putative enhancer). Test samples and reference samples were prepared fresh and served at room temperature in flavorless, odorless 1 oz souffle cups. Drinking water was used to rinse and clean the palate between samples. Each test sample was evaluated by 6 to 10 panelists for its relevant taste intensity and lasting effect of the taste sensation in comparison to each reference sample.
To evaluate the enhancement of alcohol, test samples are in 50 proof ethanol cordial, with higher concentrated reference samples at 60 or 70 proof ethanol.
To evaluate the enhancement of cooling, the known cooling compound WS-3 (N-ethyl p-menthanecarboxamide) is used.
The panelists evaluated the taste of the samples and compared the taste intensity of each sample (cooling effect, alcoholic taste) with one or more reference samples.
Example 2
Enhancement of cooling effect /mint intensity of aframodial in mouthwash
The taste evaluation on intensity and duration of a cooling sensation was performed by 8 panelists as described in example 1 subject to the following modifications. The panelists were experts on mint flavor creation and health care product applications.
The test sample contained 25 ppm Aframodial, added in form of a concentrated stock solution to a mouthwash reference sample to provide the test samples. The test compound stock solution was prepared by dissolving 1 part Aframodial into 99 parts propylene glycol/Ethanol. The mouthwash reference sample was prepared by mixing 5 parts commercially available alcohol free mint flavored mouthwash (Act Alcohol Free Mint Flavored Mouthwash containing menthol (0.06% w/v) with 95 parts distilled water.
A half mouth test was used to compare samples: Panelists placed a sample in one side of the mouth and rinsed for 10 seconds. Panelists evaluated flavour perceptions and flavour intensities of each sample both in the mouth and after expelling. After rinsing with drinking water, this procedure is repeated for the next sample in the opposite side of the mouth.
The mint flavor intensity of the Aframodial sample was increased in intensity and longer in duration when compared to the control sample.
Example 3
Enhancement of cooling effect /mint intensity of aframodial in hard candy
As a test compound, 50 ppm Aframodial was evaluated in hard candy.
A test compound stock solution was prepared by dissolving 1 part test compound into 99 parts propylene glycol/Ethanol. A hard candy mint flavor was prepared by mixing 77.78 parts peppermint oil with 22.22 parts menthol. A hard candy base was prepared by dissolving 50 parts sucrose in 9 parts distilled water, then 41 parts of high maltose corn syrup was added and the mixture was heated to boiling. After the temperature reached 300 F (148°C), the control samples were prepared by mixing 100 parts of hard candy base and 0.05 parts of hard candy mint flavor. The test sample was prepared as described for the control sample except for the addition of 50 ppm Aframodial to the mint flavored hard candy base. The samples were then poured into candy molds and allowed to cool and harden briefly before packaging into wrapping.
Hard candy test samples with and without test compounds were compared by 8 panelists. The samples were tested on their ability to elicit a cooling sensation and for the duration of that cooling sensation.
A half mouth test was used to compare samples: Panelists placed the candy into one side of the mouth and sucked on the candy for one minute. Afterwards, the panelists expelled the candy sample into a cup. The sample was evaluated in the mouth and after expelling. Drinking water was used to rinse the mouth between samples to cleanse the palate.
The procedure was repeated afterwards with the control sample in the other half of the mouth.
Panelists were asked to compare the samples and the aframodial sample was found to be of higher mint intensity that the control sample.
Panelists observed higher intensity and longer lasting sensations of cooling and tingling sensations in the aframodial hard candy sample in comparison with the control sample.
Example 4
Enhancement of alcohol taste by aframodial
A taste evaluation on the taste of alcohol was performed as described in example 1. Test samples contained 25 ppm of Aframodial in a 50 proof ethanol cordial (42.7 parts distilled water, 30 parts medium invert sugar, 26.3 parts 95% ethyl alcohol and 1 part glycerine). Reference samples had the same cordial of 50, 60, 70 and 80 proof with the same sugar and glycerine content.
All panelists noted an alcohol warming sensation increased in intensity and duration in the test sample in comparison the 50 proof reference sample. When compared to the 65 proof reference sample, the alcohol intensity was similar.
Example 5
Enhancement of alcohol taste by labda
A taste evaluation on the taste of alcohol was performed as described in example 1. Test samples contained 15 ppm of labda-8(7), 12-diene-15, 16-dial in 50 proof ethanol cordial (42.7 parts distilled water, 30 parts medium invert sugar, 26.3 parts 95% ethyl alcohol and 1 part glycerine). Reference samples contained ethanol cordial of 60, 70 and 80 proof with the same sugar and glycerine content.
All panelists noted an alcohol warming sensation increased in intensity and duration in the test sample in comparison the 50 proof and the 65 proof reference sample. When compared to the 70 proof reference sample, the alcohol intensity was similar.
Example 6
Enhancement of cooling effect of WS-3 by aframodial in water
A taste evaluation on the cooling effect was performed as described in example 1. Test samples contained 8 ppm of aframodial and 25 ppm WS-3 in water. 25 and 30 ppm WS-3 in water without aframodial served as reference samples. WS-3 is a known synthetic cooling compound.
All panelists noted a cooling effect increased in intensity in the test sample in comparison the 25 ppm WS-3 reference sample. When compared to the 30 ppm WS-3 reference sample, the cooling intensity of the test sample was similar.
Example 7
Enhancement of cooling effect of WS-3 by labda in water
A taste evaluation on the cooling effect was performed as described in example 1. Test samples contained 0.25 ppm labda-8(7), 12-diene-15, 16-dial and 25 ppm WS-3. 25 and 30 ppm WS-3 samples without labda served as references.
All panelists noted a cooling effect increased in intensity in the test sample in comparison the 25 ppm WS-3 reference sample. When compared to the 30 ppm WS-3 reference sample, the cooling intensity was similar in the test sample. The panelists also noted that the onset of the cooling sensation is sooner in the test sample than in the 25 ppm WS-3 reference sample.
Claims
1. A composition comprising one or more flavour enhancers selected from aframodial and labda-8(17),12-diene- 15,16-dial, and one or more ingredients selected from the group consisting of a cooling ingredient, and ethanol, wherein when ethanol is present it has a concentration of at least 1 % (wt/wt), and wherein when one or more cooling ingredient is present, it has a concentration that together with the enhancer provides a cooling effect above the detection threshold for the cooling sensation.
2. A composition according to claim 1 which is a food product or product placed in the oral cavity.
3. A composition according to claim 1 which is a flavour composition for a food product or product placed in the oral cavity comprising at least one excipient.
4. Food product or product placed in the oral cavity according to claim 2 wherein the flavour enhancer is present in a concentration from 0.25 ppm to 3000 ppm.
5. Use of one or more flavour enhancers selected from aframodial and labda-8(17),12-diene-15,16-dial in combination with one or more ingredient selected from a cooling ingredient and ethanol, in food products or products placed in the oral cavity to enhance the flavour sensations associated with cooling ingredients or alcohol.
6. A method of enhancing the taste sensations associated with cooling ingredients or alcohol, wherein one or more flavour enhancer selected from aframodial and labda-8(17),12-diene-15,16-dial, and one or more ingredient selected from a cooling ingredient and ethanol, are mixed to provide a food product or product placed in the oral cavity, or flavour composition for a food product or product placed in the oral cavity, in a sufficient amount to enhance said taste sensations.
7. Use or method according to any one of claims 5 or 6 wherein the flavour modifying compound or compounds are added in a total concentration from 0.25 ppm to 3000 ppm.
8. A composition according to any one of claims 1 to 4, wherein the one or more cooling ingredient is selected from the group consisting of mint oil, peppermint oil, spearmint oil, eucalypt oil, 2-l-menthoxyethane-1-ol, 3-I- menthoxypropane-1-ol, and 4-l-menthoxybutane-1-ol, pulegol, cineol, eucalyptol, 2-sec-butylcyclohexanone, (6- isopropyl-9-methyl-1,4-dioxaspiro[4.5]decan-2-yl)methanol, ((6S,9R)-6-isopropyl-9-methyl-1,4- dioxaspiro[4.5]decan-2-yl)methanol, (+)-D-menthone, isopulegol, (-)-isopulegol, (+)-isopulegol, Coolact P®, p- menthane-3,8-diol, ReI-(I S,2R,5R)-2-(2-hydroxypropan-2-yl)-5-methylcyclohexanol, (-)-trans p-Menthane-3,8-diol, (+)-cis p-Menthane-3,8-diol, PMD38, menthol, dl-menthol, 1R,3R,4R-(+)-neoisomenthol, 1R,3S,4R-(+)-isomenthol, 1R,3S,4S-(+)-neomenthol, 1S,3S,4S-(-)-neoisomenthol, 1S,3R,4S-(-)-isomenthol, 1S,3R,4R-(-)-neomenthol, 1S,3S,4R-(+)-menthol, (-)-Menthyl 2-pyrrolidone-5-carboxylate, menthone, dl-menthone, (-)-menthyl lactate, menthyl lactate, monomenthyl glutarate, dl-Menthyl succinate, 4-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)- 4-oxobutanoic acid, monomenthyl dimethyl succinate, (-)-menthoxypropane-1,2-diol, 3-(1-menthoxy)-1,2- propanediol, (2R)-3-(l-menthoxy)propane-1,2-diol, (2S)-3-(l-menthoxy)propane-1,2-diol), 3-(l-menthoxy)-2- methylpropane-1 ,2-diol, N-(4-cyanomethylphenyl)-p-menthanecarboxamide, (1 R,2S,5R)-rel- 5-methyl-2-(1- methylethyl)-N-[2-(2-pyridinyl)ethyl]- cyclohexanecarboxamide,
(1 R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(2-methoxyethoxy)acetate, (1 R,2S,5R)-2-isopropyl-5- methylcyclohexyl 2-methoxyacetate, (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(2-(2- methoxyethoxy)ethoxy)acetate, ( 1 R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(2-hydroxyethoxy)acetate, (1R.2S.5R)- [2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-acetic acid 5-methyl-2-(1-methylethyl)cyclohexyl ester, (-)- cubebol, eutectic mixture of WS-23 and WS-3 (ICE 1500™), 1-[2-hydroxyphenyl]-4-[3-nitrophenyl- ]-1,2,3,6- tetrahydropyrimidin-2-one, 1-(2-hydroxyphenyl)-4-(3-methylphenyl)-1,2,3,6-tetrahydropyrimidin-2-one, 4-methyl-3- (1-pyrrolidinyl)-2[5H]-furanone, 4,5-dimethyl-3-(1-pyrrolidinyl)-2[5H]-furanone, 5-methyl-4-(1-pyrrolidinyl)-3-[2H]- furanone, WS-3 (N-ethyl p-menthane-3-carboxamide), WS-4 (ethyleneglycol p-menthaπe-3-carboxylate), WS-5 (N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine ethyl ester), WS-12 (N-(4-methoxyphenyl)-p-menthane- 3-carboxamide), WS-14 (N-t-butyl-p-menthane-3-carboxamide, [1R-(1α,2β,5α)]- N-(1,1-dimethylethyl)-5-methyl- 2-(1-methylethyl)-cyclohexanecarboxamide), WS-23 (N,2,3-trimethyl-2-isopropylbutanamide), and WS-30 (1- glyceryl p-menthane-3-carboxylate).
9. A use or method according to any one of claims 5, 6 or 7 wherein the one or more cooling ingredient is selected from the group as defined in claim 8.
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| US8242289B2 (en) | 2009-03-06 | 2012-08-14 | Symrise Ag | Alkyl-substituted tetrahydropyrans as flavoring substances |
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| US9585865B2 (en) | 2011-03-08 | 2017-03-07 | B.R.A.I.N. Biotechnology Research And Information Network Ag | Small molecule modulators of the cold and menthol receptor TRPM8 |
| CN103787905A (en) * | 2013-12-11 | 2014-05-14 | 安徽丰乐香料有限责任公司 | Novel synthesis method for L-menthyl-N,N-dimethyl succinamide |
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