WO2001035768A1 - Exhausteurs de fraicheur de flaveur - Google Patents

Exhausteurs de fraicheur de flaveur Download PDF

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Publication number
WO2001035768A1
WO2001035768A1 PCT/US2000/031267 US0031267W WO0135768A1 WO 2001035768 A1 WO2001035768 A1 WO 2001035768A1 US 0031267 W US0031267 W US 0031267W WO 0135768 A1 WO0135768 A1 WO 0135768A1
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WO
WIPO (PCT)
Prior art keywords
optionally substituted
alkyl
cycloalkyl
hydrogen
alkenyl
Prior art date
Application number
PCT/US2000/031267
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English (en)
Inventor
Lawrence L. Buckholz, Jr.
Brian Byrne
Original Assignee
J.Manheimer, Inc.
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 J.Manheimer, Inc. filed Critical J.Manheimer, Inc.
Priority to AU16077/01A priority Critical patent/AU1607701A/en
Publication of WO2001035768A1 publication Critical patent/WO2001035768A1/fr

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Classifications

    • 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
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3526—Organic compounds containing nitrogen
    • 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
    • A23L27/202—Aliphatic compounds
    • A23L27/2022—Aliphatic compounds containing sulfur
    • 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
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3481—Organic compounds containing oxygen
    • A23L3/3499—Organic compounds containing oxygen with doubly-bound oxygen
    • 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
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3481—Organic compounds containing oxygen
    • A23L3/3508—Organic compounds containing oxygen containing carboxyl groups

Definitions

  • glycosides a family of bound flavor materials, known as glycosides.
  • the contribution of these materials to the generation of flavor has been studied, as well as, the use of enzymes to free more of the sugar bound flavor molecules. The purpose of doing this is to enhance the flavor of juices by increasing the volatile flavor molecules. From those studies, it appears that many of the flavor molecules in ripening foods liberate upon enzymatic action during the ripening process.
  • glycosides upon the taste impression of a flavor has not been studied at length in the art. While not wishing to be bound by theory, we have speculated that flavor molecules, similar to the glycosides, are bound up as addition products to amino acids and proteins. Some of the amino acid bound flavor molecules remain bound material during the ripening process similar to the glycosides. Upon thermal processing these materials, which are far more delicate than glycosides, decompose to give volatile flavor molecules and the parent amino acid or protein. It is believed that during the ripening process the amino acid bound flavor materials are enzymatically converted into volatile sulfur flavor compounds.
  • U.S. 5,128,194 uses this strategy to make natural sulfur chemicals.
  • the adduct obtained from the reaction of cysteine, its salt and esters with an unsaturated flavor component, imparts freshness and flavors to foodstuffs and tobacco products when the adduct is added to these components. Furthermore, we have discovered that the inventive adducts enhance the flavor of flavoring agents, which then are used in foodstuffs, tobacco products, pharmaceutical, and oral care products.
  • This invention provides for a flavoring composition which comprises optionally a flavoring agent and a cysteine adduct obtainable by the reaction of cysteine, or a salt or ester thereof, with an , ⁇ -unsaturated carbonyl-containing compound.
  • This invention further provides for food products, tobacco products, oral care products, pharmaceuticals, confectioneries and flavoring agents which contain the inventive flavoring compositions.
  • this invention provides for foodstuffs, tobacco products, oral care products, pharmaceuticals and flavoring agents which comprise a flavor enhancing composition comprising a cysteine adduct obtainable by the reaction of cysteine, or a salt or ester thereof, with an ⁇ , ⁇ -unsaturated carbonyl-containing compound as well as a method of enhancing the flavor of these products.
  • a flavor enhancing composition comprising a cysteine adduct obtainable by the reaction of cysteine, or a salt or ester thereof, with an ⁇ , ⁇ -unsaturated carbonyl-containing compound as well as a method of enhancing the flavor of these products.
  • the cysteme adducts of the present invention relate to compounds of the formula
  • R is hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted aryl or optionally substituted heterocycle
  • R 3 is hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted aryl or optionally substituted heterocycle
  • R 4 is hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted aryl or optionally substituted heterocycle; or
  • R 1 , R 2 , R 3 or R 4 together with one another form an optionally substituted cycloalkyl or cycloalkenyl ring, or an ester or salt of the compound.
  • adducts of the present invention are obtainable by the reaction of cysteine (I) , or a salt or ester thereof,
  • an ⁇ , ⁇ -unsaturated carbonyl compound which include, for example compounds of the formula
  • the optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl and aryl groups contain 1 to 20 carbon atoms with alkyl and alkenyl groups having from 1 to 10 carbon atoms and cycloalkyl groups having 3 to 10 carbon atoms being most preferred.
  • Preferred substituted aryl groups are those containing 6 to 14 carbon atoms, with phenyl and naphthyl being the most preferred.
  • the optionally substituted heterocyclic groups are preferably for example, cycloalkyl, cycloalkenyl, or aryl groups in which at least one carbon atom is replaced by S, N or O.
  • Examples of such groups include piperdine, thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole,
  • 1,2,3-triazole, 1,2,3,4-tetrazole benzo[b]thiophene, benzo[b]furan, indole, benzo[c]thiophene, benzo[c] furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine,
  • Substituents for the alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, and heterocycle groups are those typically found in flavors. These substituents include functional groups such as alcohols, ketones, aldehydes, acids, esters, amines, etc.
  • substituents are C ⁇ -C 20 alkyl, -OR 5 or - NR 6 R 7 , wherein R 5 R 6 and
  • R 7 each independently are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted aryl or optionally substituted heterocycle wherein the optionally substituents are those identified above.
  • Especially preferred adducts are those where:
  • -R 1 is -CH 2 CH 2 CH 3 , R 2 , R 3 , R 4 are -H; --R J R 2 is -CH 3 , R 3 is -H and R 4 is -CH 3 ;
  • R 1 and R 2 is -CH 3
  • R 3 is -CH 2 CH 2 CH(CH 3 )CH 2 - connected to the R 4 position.
  • the corresponding basic and acid addition salts and the ester derivatives of these adducts are also contemplated. These salts are formed from the corresponding organic and inorganic acids and bases and include the customary hydrohahde, such as the hydrochloride salt, and phosphate salts.
  • Esters formed from the corresponding alcohol or carboxylic acid moiety include alkyl esters having 1 to 20 carbon atoms with the acetate, proprionate and butyrate esters being most preferred.
  • flavoring adducts used in the inventive flavoring compositions are prepared by the following reaction:
  • amino acid section of the compounds of formula III are derived from cysteine, its esters and salts.
  • This reaction is known in the art and is described, for example, in U.S. Patent No. 5,182,194.
  • Cysteine is an amino acid used extensively in beef and chicken flavors, particularly for reaction flavors and Maillard products.
  • Cysteine, as well as its salts and esters derivatives is well known in the art and is described, for example in "The Merck Index", 10th ed., M. Wildholz, ed., Merck & Co., Inc., Rahway, NJ (1983).
  • Processes for its syntheses are described, for example, in U.S. Patent 2,376,186; 2,406,362; and 2,449,303.
  • cysteine hydrochloride is especially preferred.
  • carbocyclic acid alkyl esters of cysteine with the methyl, ethyl, propyl, isopropyl, butyl and isobutyl esters being most preferred.
  • These sources of cysteine are either commercially available or are obtained by processes known in the art.
  • 7 the hydrochloride salt, and phosphate salts.
  • Esters formed from the corresponding alcohol or carboxylic acid moiety include alkyl esters having 1 to 20 carbon atoms with the acetate, proprionate and butyrate esters being most preferred.
  • flavoring adducts used in the inventive flavoring compositions are prepared by the following reaction:
  • amino acid section of the compounds of formula III are derived from cysteine, its esters and salts.
  • This reaction is known in the art and is described, for example, in U.S. Patent No. 5,182,194.
  • Cysteine is an amino acid used extensively in beef and chicken flavors, particularly for reaction flavors and Maillard products.
  • Cysteine, as well as its salts and esters derivatives is well known in the art and is described, for example in "The Merck Index", 10th ed., M. Wildholz, ed., Merck & Co., Inc., Rahway, NJ (1983).
  • Processes for its syntheses are described, for example, in U.S. Patent 2,376,186; 2,406,362; and 2,449,303.
  • cysteine hydrochloride is especially preferred.
  • carbocyclic acid alkyl esters of cysteine are particularly preferred.
  • these sources of cysteine are either commercially available or are obtained by processes known in the art.
  • ⁇ , ⁇ -unsaturated carbonyl-containing compounds of formula II are also well known in the art and are either obtained commercially or by process known in the art. Examples of such compounds include:
  • the flavors contemplated in the present invention are any of the oils, flavors, or aromas known in the flavoring art. These oils, flavors, and aromas may be derived from natural sources or produced synthetically. These oils, flavors and aromas are obtained commercially or by known technique. Preferred flavors include citrus oils, such as lemon and orange oil, natural orange flavors, spearmint oil, peppermint oil, other mint oils and artificial reconstituted flavors.
  • flavor and aroma compositions may be used in a wide range of products and fragrances such as of foodstuffs, tobacco products, pharmaceuticals, oral care products, sweeteners and cosmetics. Such products, as well as the amount of flavor or aroma to add to these products would be well known to one skilled in the art.
  • Especially preferred food products include beverages, such as orange juice or lemonade, confectioneries and chewing gums.
  • Especially preferred oral care products include mouthwashes or toothpastes.
  • Example 3 The pulegone-cysteine adduct of Example #1 was diluted in one part to ninety-nine parts rectified Scotch Spearmint Oil. The resultant mixture was tasted at 10 ppm in sweetened water against a control containing 10 ppm rectified Scotch Spearmint Oil, only. All panelists selected the adduct as having a more "fresh picked" mint flavor, as well as having a stronger more intense flavor.
  • Example 3 trans-2-Hexenal 98.15 g
  • the 1 -cysteine hydrochloride and sodium bicarbonate were dissolved in water.
  • the trans-2-Hexenal was dissolved in ethanol.
  • the water and ethanol solutions were mixed together for 16 hours at room temperature, filtered and evaporated to dryness in vacuum.
  • Example 4 The trans-2-hexenal-cysteine adduct of Example #3 was diluted 0.1 part in 99.9 parts propylene glycol. To 100 grams tomato soup (Campbell Soup Company, Camden, NJ 08103) 0.10 grams of the propylene glycol solution was added. The resultant soup was 12 tasted against the untreated soup. All panelists selected the adduct containing soup as being stronger in tomato flavor. Additionally, comments were made as to "vine ripened" character and greater mouthfeel created by the adduct.
  • the piperine-cysteine adduct was tasted against pipeline both at 0.1 ppm in instant mashed potatoes (Potato Buds, General Mills, Minneapolis, MN 55440).
  • the adduct had a stronger warming effect with an overall mouth warming, whereas piperine had more of a tongue biting effect.
  • the mashed potatoes with the adduct were deemed by the panelists to be more like freshly prepared rather than instant.
  • the 1 -cysteine hydrochloride and sodium bicarbonate (2 equivalents) were dissolved in water.
  • the citral was dissolved in ethanol.
  • the water and ethanol solutions were mixed 13 together at room temperature for 16 hours and filtered.
  • the resultant red-black solution of the citral-cysteine sodium salt adduct was used as is.
  • Flavor (Treated and Control) 9.0 ml

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Fats And Perfumes (AREA)
  • Seasonings (AREA)

Abstract

L'invention concerne des compositions aromatisantes contenant un adduit de cystéine pouvant être obtenues par la réaction d'un ester ou d'un sel de celui-ci et d'un composé contenant du carbonyle à insaturation α, β. Cette invention concerne également des produits alimentaires, des produits de soin buccal, des produits de tabac, des agents pharmaceutiques, des confiseries et des agents aromatisants pouvant contenir les produits de l'invention.
PCT/US2000/031267 1999-11-15 2000-11-14 Exhausteurs de fraicheur de flaveur WO2001035768A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU16077/01A AU1607701A (en) 1999-11-15 2000-11-14 Flavor freshness enhancers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US44059199A 1999-11-15 1999-11-15
US09/440,591 1999-11-15

Publications (1)

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WO2001035768A1 true WO2001035768A1 (fr) 2001-05-25

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006084186A2 (fr) * 2005-02-04 2006-08-10 Senomyx, Inc. Composes comportant des groupes fonctionnels d'heteroaryle lies et leur utilisation en tant que nouveaux modificateurs de saveur, agents gustatifs et exhausteurs de gout umami pour des compositions alimentaires
WO2008154765A1 (fr) * 2007-06-19 2008-12-24 Givaudan Sa Dérivés de cystéine agissant contre les mauvaises odeurs
US7476399B2 (en) 2003-08-06 2009-01-13 Senomyx Inc. Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
US7842324B2 (en) 2005-06-15 2010-11-30 Senomyx, Inc. Bis-aromatic amides and their uses as sweet flavor modifiers, tastants, and taste enhancers
JP2011094044A (ja) * 2009-10-30 2011-05-12 Ogawa & Co Ltd 持続性香気賦与剤
US9072313B2 (en) 2006-04-21 2015-07-07 Senomyx, Inc. Comestible compositions comprising high potency savory flavorants, and processes for producing them
US20150272907A1 (en) * 2014-04-01 2015-10-01 The Procter & Gamble Company Methods And Compositions For Modifying Sensorial Perception
CN107334139A (zh) * 2017-08-04 2017-11-10 北京工商大学 烃基化修饰谷胱甘肽类衍生物
WO2020217553A1 (fr) * 2019-04-25 2020-10-29 小川香料株式会社 AGENT D'AMÉLIORATION D'ARÔME PERSISTANT COMPRENANT DU p-MENTHA-8-S-GLUTATHIONYLE-3-ONE
WO2020224767A1 (fr) 2019-05-07 2020-11-12 Givaudan Sa Composés organiques
US11879215B2 (en) 2016-10-25 2024-01-23 The Procter & Gamble Company Fibrous structures
US11970818B2 (en) 2016-10-25 2024-04-30 The Procter & Gamble Company Fibrous structures

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DATABASE ACS [online] TOMINAGA T. ET AL.: "A new type of flavor precursors in vitis vinifera L. cv. sauvignon blanc: S-cysteine conjugates", XP002937621, Database accession no. 130:65569 *
DATABASE ACS [online] TOMINAGA T. ET AL.: "A S-cysteine conjugate, precursor of aroma of white Sauvignon", XP002937622, Database accession no. 124:230538 *
J. AGRIC. FOOD CHEM., vol. 46, no. 12, 1998, pages 5215 - 5219 *
J. INT. SCI. VIGNE VIN, vol. 29, no. 4, 1995, pages 227 - 232 *

Cited By (33)

* Cited by examiner, † Cited by third party
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US8895050B2 (en) 2003-08-06 2014-11-25 Senomyx, Inc. Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
US11268952B2 (en) 2003-08-06 2022-03-08 Firmenich Incorporated Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
US10352929B2 (en) 2003-08-06 2019-07-16 Senomyx, Inc. T1R hetero-oligomeric taste receptors, cell lines that express said receptors, and taste compounds
US7476399B2 (en) 2003-08-06 2009-01-13 Senomyx Inc. Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
US9459250B2 (en) 2003-08-06 2016-10-04 Senomyx, Inc. Use of T1R3 venus flytrap region polypeptide to screen for taste modulators
US10060909B2 (en) 2003-08-06 2018-08-28 Senomyx, Inc. Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
US10557845B2 (en) 2003-08-06 2020-02-11 Firmenich Incorporated Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
US7888470B2 (en) 2003-08-06 2011-02-15 Senomyx, Inc. Chimeric T1R taste receptor polypeptides and nucleic acid sequences encoding and cell lines that express said chimeric T1R polypeptides
US9091686B2 (en) 2003-08-06 2015-07-28 Senomyx, Inc. Chimeric T1R taste receptor polypeptides and nucleic acid sequences encoding and cell lines that express said chimeric T1R polypeptides
US8124121B2 (en) 2003-08-06 2012-02-28 Senomyx, Inc. Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
US8404455B2 (en) 2003-08-06 2013-03-26 Senomyx, Inc. Chimeric T1R taste receptor polypeptides and nucleic acid sequences encoding and cell lines that express said chimeric T1R polypeptides
WO2006084186A2 (fr) * 2005-02-04 2006-08-10 Senomyx, Inc. Composes comportant des groupes fonctionnels d'heteroaryle lies et leur utilisation en tant que nouveaux modificateurs de saveur, agents gustatifs et exhausteurs de gout umami pour des compositions alimentaires
US8784782B2 (en) 2005-02-04 2014-07-22 Senomyx, Inc. Compounds comprising linked heteroaryl moieties and their use as novel umami flavor modifiers, tastants and taste enhancers for comestible compositions
KR101340859B1 (ko) 2005-02-04 2013-12-13 세노믹스, 인코포레이티드 연결형 헤테로 아릴 잔기를 포함한 화합물, 및 식용조성물을 위한 신규의 우마미 향미 개선제, 맛 촉진물질 및맛 향상제로서의 그의 용도
US8968708B2 (en) 2005-02-04 2015-03-03 Senomyx, Inc. Compounds comprising linked heteroaryl moieties and their use as novel umami flavor modifiers, tastants and taste enhancers for comestible compositions
WO2006084186A3 (fr) * 2005-02-04 2007-02-22 Senomyx Inc Composes comportant des groupes fonctionnels d'heteroaryle lies et leur utilisation en tant que nouveaux modificateurs de saveur, agents gustatifs et exhausteurs de gout umami pour des compositions alimentaires
US7842324B2 (en) 2005-06-15 2010-11-30 Senomyx, Inc. Bis-aromatic amides and their uses as sweet flavor modifiers, tastants, and taste enhancers
US9072313B2 (en) 2006-04-21 2015-07-07 Senomyx, Inc. Comestible compositions comprising high potency savory flavorants, and processes for producing them
US7846887B2 (en) 2007-06-19 2010-12-07 Givaudan Sa Cysteine derivatives which counteract malodour
JP2010530373A (ja) * 2007-06-19 2010-09-09 ジボダン エス エー 悪臭を防止するシステイン誘導体
WO2008154765A1 (fr) * 2007-06-19 2008-12-24 Givaudan Sa Dérivés de cystéine agissant contre les mauvaises odeurs
JP2011094044A (ja) * 2009-10-30 2011-05-12 Ogawa & Co Ltd 持続性香気賦与剤
US9427415B2 (en) * 2014-04-01 2016-08-30 The Procter & Gamble Company Methods and compositions for modifying sensorial perception
US20150272907A1 (en) * 2014-04-01 2015-10-01 The Procter & Gamble Company Methods And Compositions For Modifying Sensorial Perception
US11879215B2 (en) 2016-10-25 2024-01-23 The Procter & Gamble Company Fibrous structures
US11970818B2 (en) 2016-10-25 2024-04-30 The Procter & Gamble Company Fibrous structures
CN107334139A (zh) * 2017-08-04 2017-11-10 北京工商大学 烃基化修饰谷胱甘肽类衍生物
WO2020217553A1 (fr) * 2019-04-25 2020-10-29 小川香料株式会社 AGENT D'AMÉLIORATION D'ARÔME PERSISTANT COMPRENANT DU p-MENTHA-8-S-GLUTATHIONYLE-3-ONE
JP2020180205A (ja) * 2019-04-25 2020-11-05 小川香料株式会社 ｐ−メンタ−８−Ｓ−グルタチオニル−３−オンからなる持続性香味増強剤
WO2020224767A1 (fr) 2019-05-07 2020-11-12 Givaudan Sa Composés organiques
CN113795479A (zh) * 2019-05-07 2021-12-14 奇华顿股份有限公司 有机化合物
JP2022537631A (ja) * 2019-05-07 2022-08-29 ジボダン エス エー 有機化合物
JP7405868B2 (ja) 2019-05-07 2023-12-26 ジボダン エス エー 有機化合物

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