WO2001077096A3 - Preparation of natural thioacetates and derivatives - Google Patents

Preparation of natural thioacetates and derivatives Download PDF

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Publication number
WO2001077096A3
WO2001077096A3 PCT/EP2001/003279 EP0103279W WO0177096A3 WO 2001077096 A3 WO2001077096 A3 WO 2001077096A3 EP 0103279 W EP0103279 W EP 0103279W WO 0177096 A3 WO0177096 A3 WO 0177096A3
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WO
WIPO (PCT)
Prior art keywords
thioacetates
preparation
derivatives
natural
food
Prior art date
Application number
PCT/EP2001/003279
Other languages
French (fr)
Other versions
WO2001077096A2 (en
Inventor
Rhlid Rachid Bel
Yvette Fleury
Laurent Bernard Fay
Marcel Alexandre Juillerat
Original Assignee
Nestle Sa
Rhlid Rachid Bel
Yvette Fleury
Laurent Bernard Fay
Marcel Alexandre Juillerat
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 Nestle Sa, Rhlid Rachid Bel, Yvette Fleury, Laurent Bernard Fay, Marcel Alexandre Juillerat filed Critical Nestle Sa
Priority to AU63799/01A priority Critical patent/AU6379901A/en
Publication of WO2001077096A2 publication Critical patent/WO2001077096A2/en
Publication of WO2001077096A3 publication Critical patent/WO2001077096A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • 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
    • A23L23/00—Soups; Sauces; Preparation or treatment thereof
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/203—Alicyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/204—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/26—Meat flavours
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/02—Thiols having mercapto groups bound to acyclic carbon atoms
    • C07C321/04—Thiols having mercapto groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/02—Thiols having mercapto groups bound to acyclic carbon atoms
    • C07C321/08—Thiols having mercapto groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/22—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
    • C07C323/02—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/06—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
    • C07C323/08—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/17—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/28—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/64—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P11/00—Preparation of sulfur-containing organic compounds
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Abstract

This invention relates to a process for the preparation of thioacetates addition of thioacetic acid or a salt thereof on α-,β-, or η-unsaturated alcohols, carbonyl compounds or cyclic or acyclic alkenes or by nucleophilic substitution of the hydroxyl group or a halogen with S-acetyl group in food-grade organic solvent. These thioacetates can be used as enhancers or intensifiers of flavour in food products or as aromas in compounded flavours. A number of individual compounds is also claimed.
PCT/EP2001/003279 2000-04-06 2001-03-23 Preparation of natural thioacetates and derivatives WO2001077096A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU63799/01A AU6379901A (en) 2000-04-06 2001-03-23 Preparation of natural thioacetates and derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP00201251.6 2000-04-06
EP00201251 2000-04-06

Publications (2)

Publication Number Publication Date
WO2001077096A2 WO2001077096A2 (en) 2001-10-18
WO2001077096A3 true WO2001077096A3 (en) 2002-01-24

Family

ID=8171313

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/EP2001/003278 WO2001077359A2 (en) 2000-04-06 2001-03-23 Preparation of thiols and derivatives by bio-conversion
PCT/EP2001/003279 WO2001077096A2 (en) 2000-04-06 2001-03-23 Preparation of natural thioacetates and derivatives

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PCT/EP2001/003278 WO2001077359A2 (en) 2000-04-06 2001-03-23 Preparation of thiols and derivatives by bio-conversion

Country Status (2)

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AU (2) AU4250501A (en)
WO (2) WO2001077359A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103926353A (en) * 2014-05-06 2014-07-16 国家烟草质量监督检验中心 Method for measuring content of glyceryl triacetate
JP6824926B2 (en) * 2018-04-27 2021-02-03 長谷川香料株式会社 Food and beverage flavor improver
JP7027677B2 (en) * 2018-07-26 2022-03-02 曽田香料株式会社 A citrus fragrance that imparts a pericarp feeling or enhances the pericarp feeling

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US4031256A (en) * 1975-02-19 1977-06-21 International Flavors & Fragrances Inc. Foodstuff flavor compositions comprising 3-furyl alkyl sulfides and processes
US4041186A (en) * 1976-03-12 1977-08-09 International Flavors & Fragrances Inc. Flavoring with (2-methyl-3-furyl)(methylthiomethyl) sulfide
US4620945A (en) * 1983-08-01 1986-11-04 International Flavors & Fragrances Inc. Mixtures of one or more t-mercapto terpene isomers and α-terpineol, β-phenylethyl alcohol, 3-methyl-1-phenyl-pentanol-5 and/or butanoyl cyclohexane derivatives, organoleptic uses thereof and process for preparing same
NL8700240A (en) * 1987-01-30 1988-08-16 Tno METHOD FOR PREPARING THIOL COMPOUNDS.
CA1318627C (en) * 1988-07-14 1993-06-01 Jeffrey M. Howell Enzymatic resolution process
JP2836269B2 (en) * 1991-03-07 1998-12-14 三菱マテリアル株式会社 Optical switch
JPH0751092A (en) * 1993-08-10 1995-02-28 Tanabe Seiyaku Co Ltd Production of optically active pyrrolidine derivative
EP0770686A1 (en) * 1995-10-25 1997-05-02 Societe Des Produits Nestle S.A. Process for the production of thiols
EP0951840A1 (en) * 1997-12-23 1999-10-27 Societe Des Produits Nestle S.A. Process for the preparation of flavouring compositions and use of these compositions in foodstuffs
EP0963706A1 (en) * 1998-05-07 1999-12-15 Societe Des Produits Nestle S.A. Aroma precursor mixture

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Title
B.A. GILBERT, ET AL.: "Structure-activity studies on the retinal rod outer segment isoprenylated protein methyltransferase", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 114, no. 10, 6 May 1992 (1992-05-06), American Chemical Society, Washington, DC, US, pages 3966 - 3973, XP002160253, ISSN: 0002-7863 *
B.M. TROST, ET AL.: "Stereochemistry of desulphurisation of thietane derivatives", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 93, no. 3, 10 February 1971 (1971-02-10), American Chemical Society, Washington, DC, US, pages 676 - 684, XP002160252, ISSN: 0002-7863 *
E.L. GUSTUS: "Oxygen-sensitive reactions of proteins and peptides. III. Chromogenicity and cystine-related structures", JOURNAL OF ORGANIC CHEMISTRY, vol. 32, no. 11, 15 November 1967 (1967-11-15), American Chemical Society, Washington, DC, US, pages 3425 - 3430, XP002160255, ISSN: 0022-3263 *
G.R. DAVLETSHINA, ET AL.: "Reaction of monoterpenes with thioacetic S-acid", RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, vol. 29, no. 8, part 2, August 1993 (1993-08-01), Consultants Bureau, New York, US, pages 1359 - 1360, XP002175329, ISSN: 1070-4280 *
J.S. SHOWELL, ET AL.: "Preparation of sulphonic acids from unsaturated compounds", JOURNAL OF ORGANIC CHEMISTRY, vol. 27, no. 8, 7 August 1962 (1962-08-07), American Chemical Society, Washington, DC, US, pages 2853 - 2858, XP002160303, ISSN: 0022-3263 *
K.N. GURUDUTT, ET AL.: "Nucleophilic substitution of SN1-active halides using zinc salts: preparation of thiolacetates", TETRAHEDRON, vol. 51, no. 10, 6 March 1995 (1995-03-06), Elsevier Science Publishers, Amsterdam, NL, pages 3045 - 3050, XP004104790, ISSN: 0040-4020 *
S. UEMURA, ET AL.: "The reaction of alkyl halides with mercury(II) and potassium thioacetates and selenocyanates", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 51, no. 6, June 1978 (1978-06-01), Japan Publications Trading Co., Tokyo, JP, pages 1818 - 1820, XP002160256, ISSN: 0009-2673 *
S.C. WELCH, ET AL.: "Syntheses and activities of sulphur and selenium isostearate substitution analogues of retinol", JOURNAL OF MEDICINAL CHEMISTRY, vol. 22, no. 12, December 1979 (1979-12-01), American Chemical Society, Washington, DC, US, pages 1532 - 1534, XP002160254, ISSN: 0022-2623 *

Also Published As

Publication number Publication date
AU6379901A (en) 2001-10-23
AU4250501A (en) 2001-10-23
WO2001077359A2 (en) 2001-10-18
WO2001077359A3 (en) 2002-04-18
WO2001077096A2 (en) 2001-10-18

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