WO1984000542A1 - 1-(1-methylthio-3-oxo-butyl)-2,6,6-trimethyl-cyclohexenes et leur utilisation comme arome ou comme parfum - Google Patents

1-(1-methylthio-3-oxo-butyl)-2,6,6-trimethyl-cyclohexenes et leur utilisation comme arome ou comme parfum Download PDF

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Publication number
WO1984000542A1
WO1984000542A1 PCT/EP1983/000202 EP8300202W WO8400542A1 WO 1984000542 A1 WO1984000542 A1 WO 1984000542A1 EP 8300202 W EP8300202 W EP 8300202W WO 8400542 A1 WO8400542 A1 WO 8400542A1
Authority
WO
WIPO (PCT)
Prior art keywords
aroma
methylthio
general formula
compound
oxo
Prior art date
Application number
PCT/EP1983/000202
Other languages
German (de)
English (en)
Inventor
Ernst-Joachim Brunke
Erich Klein
Willi Rojahn
Original Assignee
Dragoco Gerberding Co Gmbh
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 Dragoco Gerberding Co Gmbh filed Critical Dragoco Gerberding Co Gmbh
Publication of WO1984000542A1 publication Critical patent/WO1984000542A1/fr

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Classifications

    • 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
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • 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
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the invention relates to the compounds of the general formula - the thiomethyl ether of. ⁇ -Jonon or ß-Jonon - and their use as a fragrance or flavoring.
  • Compounds 1a, b have extremely fresh taste properties in the fruity direction and are therefore advantageous in numerous different aroma compositions of the fruity type let it work in, which gives it a natural freshness and roundness even at concentrations of 0.1 ppm.
  • the compounds la, b produce fresh, fruity taste aspects on weak-tasting smoking tobacco in concentrations of 0.5 ppb.
  • the compounds 1a, b can also be used advantageously in perfume compositions to which they give natural radiation even at low doses.
  • Compounds 1a, b are prepared in a manner known per se by reacting ⁇ - or ⁇ -ionone (2) with methyl mercaptan in the presence of organic bases, preferably triethylamine, at temperatures from 0 to 20 ° C. An excess is preferred
  • organic bases preferably triethylamine
  • the isolation and purification of the compound obtained is likewise carried out in a manner known per se, preferably by taking up in a suitable solvent, washing and stripping off the solvent, if appropriate followed by careful distillation, although it is not absolutely necessary to add water, ie to prepare a two-phase mixture so that most of the organic base can already be removed at this stage. Removal with sulfuric acid, if necessary with cooling in the next washing stage, is generally sufficient.
  • FIG. 1 1 H-NMR spectrum: FIG. 1 mass spectrum: FIG. 2
  • Compounds 1a and 1b were sensory-assessed in a concentration of 1 g / 100 kg sugar solution (10%) by a test panel.
  • the irritation threshold is approx. 0.1 g / 100 kg sugar solution and the detection threshold is approx. 0.3 g / 100 kg sugar solution.
  • Mixture a is a typical raspberry flavor concentrate.
  • the taste impression in sugar solution (1 g / 100 kg 10% sugar Isg.) Is clearly raspberry-like.
  • ß-Jonon is replaced by compound 1b (mixture b)
  • the taste impression becomes more natural, fuller and pronounced of fully ripe raspberries.
  • the mixture c exchange of ß-Jonon for 1a
  • Mixture a corresponds to the main part of Bulgarian rose oil and has a strong fragrance complex in the direction of "rose”.
  • 1b mixture b
  • waxy green aspects are emphasized and the smell impression becomes more similar to that of Bulgarian rose oil.
  • the mixture c appears more harmonious and more rounded than a.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)

Abstract

Les nouveaux thiométhyl éther 1a- et 1b répondent à la formule suivante et s'utilisent comme arome ou comme parfum
PCT/EP1983/000202 1982-07-29 1983-07-29 1-(1-methylthio-3-oxo-butyl)-2,6,6-trimethyl-cyclohexenes et leur utilisation comme arome ou comme parfum WO1984000542A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19823228289 DE3228289A1 (de) 1982-07-29 1982-07-29 1-(1-methylthio-3-oxo-butyl)-2,6,6-trimethyl- cyclohexene und deren verwendung als riech- und aromastoff

Publications (1)

Publication Number Publication Date
WO1984000542A1 true WO1984000542A1 (fr) 1984-02-16

Family

ID=6169581

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1983/000202 WO1984000542A1 (fr) 1982-07-29 1983-07-29 1-(1-methylthio-3-oxo-butyl)-2,6,6-trimethyl-cyclohexenes et leur utilisation comme arome ou comme parfum

Country Status (3)

Country Link
EP (1) EP0116061A1 (fr)
DE (1) DE3228289A1 (fr)
WO (1) WO1984000542A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1984003508A1 (fr) * 1983-03-05 1984-09-13 Dragoco Gerberding Co Gmbh 1- ad(3-methylthio)-1-oxo-butyl bd-cyclohexene methyl substitue, son procede de fabrication et son utilisation comme parfum et aromate
US7723286B2 (en) 2001-12-13 2010-05-25 Firmenich Sa Compounds for a controlled release of active molecules
WO2022084437A1 (fr) * 2020-10-21 2022-04-28 Firmenich Sa Compositions conférant une fraîcheur améliorée

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107881011B (zh) * 2017-12-12 2021-02-26 江西中烟工业有限责任公司 一种复合水果浸膏的制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2159924A1 (fr) * 1970-12-08 1972-06-22
DE2808710A1 (de) * 1977-03-03 1978-09-14 Int Flavors & Fragrances Inc 1-eckige klammer auf 3-methylthio) butyryl eckige klammer zu -2,6,6-trimethylcyclohexen und das 1,3-cycdohexadien-analoge, verfahren zu deren herstellung und deren verwendung

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2159924A1 (fr) * 1970-12-08 1972-06-22
DE2808710A1 (de) * 1977-03-03 1978-09-14 Int Flavors & Fragrances Inc 1-eckige klammer auf 3-methylthio) butyryl eckige klammer zu -2,6,6-trimethylcyclohexen und das 1,3-cycdohexadien-analoge, verfahren zu deren herstellung und deren verwendung

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1984003508A1 (fr) * 1983-03-05 1984-09-13 Dragoco Gerberding Co Gmbh 1- ad(3-methylthio)-1-oxo-butyl bd-cyclohexene methyl substitue, son procede de fabrication et son utilisation comme parfum et aromate
US7723286B2 (en) 2001-12-13 2010-05-25 Firmenich Sa Compounds for a controlled release of active molecules
WO2022084437A1 (fr) * 2020-10-21 2022-04-28 Firmenich Sa Compositions conférant une fraîcheur améliorée

Also Published As

Publication number Publication date
DE3228289A1 (de) 1984-02-09
EP0116061A1 (fr) 1984-08-22

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