WO2008138162A1 - Compositions et leur utilisation - Google Patents

Compositions et leur utilisation Download PDF

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Publication number
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
Authority
WO
WIPO (PCT)
Prior art keywords
cooling
flavour
methyl
menthane
isopropyl
Prior art date
Application number
PCT/CH2008/000218
Other languages
English (en)
Inventor
Xiaogen Yang
Zhonghua Jia
Rongrong Li
Jason Jordan
Original Assignee
Givaudan Sa
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 Givaudan Sa filed Critical Givaudan Sa
Publication of WO2008138162A1 publication Critical patent/WO2008138162A1/fr

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Classifications

    • 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
    • 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.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Confectionery (AREA)
  • Cosmetics (AREA)

Abstract

L'invention porte sur des compositions à base de composés renforçateurs de saveur, utilisables dans des produits alimentaires ou des produits destinés à la cavité buccale, et sur des produits alimentaires à saveur renforcée ou sur des produits destinés à la cavité buccale comprenant lesdits composés. Les renforçateurs de saveur sont l'aframodial et le labda-8 (17), 12-diène-15,16-dial, qui combinés à des ingrédients rafraîchissants et-ou à de l'alcool (éthanol) augmentent le goût de l'alcool et produisent une sensation de fraîcheur intense et durable.
PCT/CH2008/000218 2007-05-16 2008-05-14 Compositions et leur utilisation WO2008138162A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US93827307P 2007-05-16 2007-05-16
US60/938,273 2007-05-16

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WO2008138162A1 true WO2008138162A1 (fr) 2008-11-20

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2168957A2 (fr) 2009-03-06 2010-03-31 Symrise GmbH & Co. KG Tétrahydropyrane substitué par alkyl en tant qu'arome
EP2186506A1 (fr) 2009-10-06 2010-05-19 Symrise GmbH & Co. KG Composition de nettoyage des dents contenant du menthol dotée d'une admission de l'amertume réduite
EP2497458A1 (fr) * 2011-03-08 2012-09-12 B.R.A.I.N. Biotechnology Research And Information Network AG Petits modulateurs de molécule du froid et récepteur trpm8 du menthol
JP2012524764A (ja) * 2009-04-23 2012-10-18 ヴェ．マン・フィス 生理学的効果を有する化合物
US8664261B2 (en) 2009-05-05 2014-03-04 Givaudan S.A. Organic compounds having cooling properties
CN103787905A (zh) * 2013-12-11 2014-05-14 安徽丰乐香料有限责任公司 一种l-薄荷基-n,n-二甲基琥珀酰胺的合成新方法
US9446267B2 (en) 2009-10-06 2016-09-20 Symrise Ag Products comprising a flavoring agent composition

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2701959A1 (fr) * 1993-02-23 1994-09-02 Miclo Michel Procédé d'obtention d'une boisson alcoolisée et boisson ainsi obtenue.
US5523105A (en) * 1993-11-24 1996-06-04 Lotte Company Limited Improved mint composition and method for producing the same
EP1121927A2 (fr) * 2000-02-04 2001-08-08 Takasago International Corporation Composition provocant différentes sensations cutanées
US20030072842A1 (en) * 2001-05-11 2003-04-17 Johnson Sonya S. Chewing gum having prolonged sensory benefits

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2701959A1 (fr) * 1993-02-23 1994-09-02 Miclo Michel Procédé d'obtention d'une boisson alcoolisée et boisson ainsi obtenue.
US5523105A (en) * 1993-11-24 1996-06-04 Lotte Company Limited Improved mint composition and method for producing the same
EP1121927A2 (fr) * 2000-02-04 2001-08-08 Takasago International Corporation Composition provocant différentes sensations cutanées
US20030072842A1 (en) * 2001-05-11 2003-04-17 Johnson Sonya S. Chewing gum having prolonged sensory benefits

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
"8(17),12-labdadiene-15,16-diol", CHEMNETBASE DICTIONARY OF NATURAL PRODUCTS, XP002498052, Retrieved from the Internet <URL:http://dnp.chemnetbase.com/entry.do?id=KHC00&method=view&si=> [retrieved on 20081001] *
"Gingembre - Zingiber officinalis", TOIL'D'ÉPICES, XP002498117, Retrieved from the Internet <URL:http://www.toildepices.com/fr/plantes/angio_mon/zingiberacee/zingiber/officinale.php> [retrieved on 20081001] *
ABE MASAKO ET AL: "Labdane-type diterpene dialdehyde, pungent principle of myoga, Zingiber mioga Roscoe.", BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, vol. 66, no. 12, December 2002 (2002-12-01), pages 2698 - 2700, XP002498045, ISSN: 0916-8451 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 15 December 2003 (2003-12-15), JANG, KI-CHANG ET AL: "Isolation and structure identification of antibacterial substances from the rhizome of Zingiber mioga Roscoe", XP002498047, retrieved from STN Database accession no. 2003:978819 *
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KIMBU S F ET AL: "NEW LABDANE DITERPENOID FROM THE SEEDS OF AFRAMOMUM DANIELLII", JOURNAL OF NATURAL PRODUCTS, AMERICAN CHEMICAL SOCIETY, US, vol. 50, no. 2, 1 January 1987 (1987-01-01), pages 230/231, XP000891749, ISSN: 0163-3864 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2168957A2 (fr) 2009-03-06 2010-03-31 Symrise GmbH & Co. KG Tétrahydropyrane substitué par alkyl en tant qu'arome
US8242289B2 (en) 2009-03-06 2012-08-14 Symrise Ag Alkyl-substituted tetrahydropyrans as flavoring substances
JP2012524764A (ja) * 2009-04-23 2012-10-18 ヴェ．マン・フィス 生理学的効果を有する化合物
US8664261B2 (en) 2009-05-05 2014-03-04 Givaudan S.A. Organic compounds having cooling properties
EP2186506A1 (fr) 2009-10-06 2010-05-19 Symrise GmbH & Co. KG Composition de nettoyage des dents contenant du menthol dotée d'une admission de l'amertume réduite
EP2364689A2 (fr) 2009-10-06 2011-09-14 Symrise AG Composition de nettoyage des dents contenant du menthol dotée d'une admission de l'amertume réduite
US9446267B2 (en) 2009-10-06 2016-09-20 Symrise Ag Products comprising a flavoring agent composition
EP2497458A1 (fr) * 2011-03-08 2012-09-12 B.R.A.I.N. Biotechnology Research And Information Network AG Petits modulateurs de molécule du froid et récepteur trpm8 du menthol
WO2012120099A3 (fr) * 2011-03-08 2013-08-01 B.R.A.I.N. Biotechnology Research And Information Network Ag Modulateurs à petites molécules du froid et récepteur au menthol trpm8
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 (zh) * 2013-12-11 2014-05-14 安徽丰乐香料有限责任公司 一种l-薄荷基-n,n-二甲基琥珀酰胺的合成新方法

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