EP0829529B1 - Agents parfumants ou aromatisants - Google Patents

Agents parfumants ou aromatisants Download PDF

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Publication number
EP0829529B1
EP0829529B1 EP97115444A EP97115444A EP0829529B1 EP 0829529 B1 EP0829529 B1 EP 0829529B1 EP 97115444 A EP97115444 A EP 97115444A EP 97115444 A EP97115444 A EP 97115444A EP 0829529 B1 EP0829529 B1 EP 0829529B1
Authority
EP
European Patent Office
Prior art keywords
fragrance
perfuming
aroma
fruity
acid
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
EP97115444A
Other languages
German (de)
English (en)
Other versions
EP0829529A2 (fr
EP0829529A3 (fr
Inventor
Wilhelm Dr. Pickenhagen
Axel Dr. Schöning
Sabine Dr. Widder
Dirk Lauven
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Symrise AG
Original Assignee
Dragoco Gerberding and 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 and Co GmbH filed Critical Dragoco Gerberding and Co GmbH
Publication of EP0829529A2 publication Critical patent/EP0829529A2/fr
Publication of EP0829529A3 publication Critical patent/EP0829529A3/fr
Application granted granted Critical
Publication of EP0829529B1 publication Critical patent/EP0829529B1/fr
Anticipated expiration legal-status Critical
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Classifications

    • 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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • 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
    • C11B9/0007—Aliphatic compounds
    • C11B9/0011—Aliphatic compounds containing S

Definitions

  • the invention relates to the use of the known thiocarboxylic acids of the general formula I as a fragrance and / or flavoring (flavor).
  • R methyl, ethyl, propyl, phenyl
  • the invention further relates to fragrance and / or flavoring compositions, which by a content of thiocarboxylic acids of the general formula I Marked are.
  • the thiocarboxylic acids according to the invention can used both individually and in any combination with each other become.
  • Fragrances are said to have pleasant, as close to natural fragrances as possible have sufficient intensity and be able to smell cosmetic or to influence technical consumer goods. flavorings should be well tolerated, more popular with typical flavor components Remember food or even be identical to it and contribute to it can, the taste of food, orally administered medication and positively influence the like. Finding Fragrance and aroma substances that meet these requirements have proven to be Proven relatively expensive and regularly requires extensive Investigations, especially when interesting new fragrance notes or Flavors are aimed for.
  • Thioacetic acid is in the literature (Römpp Chemie Lexikon, Thieme Verlag Stuttgart, 9th edition, volume 6, p. 4585) as colorless to yellow air-smoking liquid described with a pungent, unpleasant smell, their vapors the eyes, the respiratory tract and the lungs as well as the Irritate and damage skin.
  • the other thiocarboxylic acids according to the invention have similar properties.
  • Thioacetic acid has so far been widely used as a reagent for introduction of sulfur in organic substances and was therefore also used in the synthesis of fragrances and flavors; in EP 369 668, US 4,886,897 and For example, US 4,285,984 is the synthesis of a fragrance or aroma described with the help of thioacetic acid. Given the noticeable unpleasant properties of thioacetic acid (see above) and given it was due to their considerable reactivity towards organic compounds but far from using it yourself as a fragrance or aroma.
  • the thiocarboxylic acids according to the invention are in each case coordinated low concentration - excellently suitable for use in flavors of all kinds Art. They have a sulphurous, tart or fruity fresh-fruity taste and are therefore particularly suitable for Use in fruit flavors, especially tropical fruit flavors such as grapefruit, Guava, mango, pineapple, passion fruit and the like. thioacetic is particularly suitable for use in grapefruit oil; here one can clear typification in the direction of tart, peeled, fruity (see also example 1 below).
  • Thiobutyric acid gives certain fragrance compositions a strawberry-like note
  • thiobenzoic acid conveys in certain fragrance compositions a fresh, fruity note with grapefruit accents.
  • the thiocarboxylic acids according to the invention can be mixed with the constituents customarily used for fragrance and flavoring compositions or added to such compositions.
  • the aim is always to set a proportion by weight (or correspondingly: an adjusted concentration) of the thiocarboxylic acid within the overall composition that is adapted to the desired olfactory or sensory effect.
  • a proportion by weight or correspondingly: an adjusted concentration
  • Favorable proportions by weight ( mass contents) are usually below 10 -4 and often in the range between 10 -6 and 5 x 10 -4 , but in particularly stored cases they can also exceed 10 -4 .
  • Flavor composition grapefruit A B para-cymene 0.30 0.30 beta-pinene 0.40 0.40 octanal 0.50 0.50 decanal 0.70 0.70 carveol 0.90 0.90 Grapefruit juice aroma oil 3 times 100.00 100.00 Orange oil terpenes 120.00 120.00 ethanol 777.20 769.20 Thioacetic acid 1% in ethanol 8.00 1,000.00 1,000.00
  • the aroma of the basic flavor composition (column A) is characterized by the addition of thioacetic acid (column B; 8 parts by weight of a 1% Solution in ethanol) significantly tart and fruity and therefore more typical the natural aroma of a grapefruit.
  • Perfume composition guava A B C D Aldehyde C 14 70,00 70,00 allyl caproate 8.00 8.00 Cassis Bourgeons Abs. 30% Migliol 5.00 5.00 coumarin 20.00 20.00 dihydromyrcenol 30.00 30.00 dimethylbenzylcarbinyl butyrate 65,00 65,00 Ethyl maltol 5.00 5.00 Frambinon crist.
  • the overall impression of the composition is more complex and can be described as softer / more voluminous.
  • Mango flavor composition A B Sulphurol 0.05 0.05 phenylethyl 2.00 2.00 cis-3-Hexenol 3.00 3.00 cis-3-hexenyl acetate 3.00 3.00
  • the aroma of the basic flavor composition A is obtained by adding Thioacetic acid (column B; 10 parts by weight of a 1% solution in triacetin) terpene, peel and tart fruity influenced.
  • the aroma of the basic composition A is due to the addition of thioacetic acid (Column B; 3 parts by weight of a 1% solution in ethanol) more sulphurous, terpene-fruity and more tropical.

Landscapes

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

Claims (3)

  1. Emploi d'acides thiocarboniques de formule générale I comme agents parfumants et/ou aromatisants.
    Figure 00100001
       R = méthyle, éthyle, propyle, phényle
  2. Composition parfumante et/ou aromatisante caractérisée en ce qu'elle présente une teneur en un ou plusieurs acides thiocarboniques de formule générale I.
  3. Composition parfumante et/ou aromatisante selon la revendication 2 caractérisée en ce que la concentration en acides thiocarboniques de formule générale I est inférieure à 10-4 en poids.
EP97115444A 1996-09-17 1997-09-06 Agents parfumants ou aromatisants Expired - Lifetime EP0829529B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19637781A DE19637781A1 (de) 1996-09-17 1996-09-17 Riech- und/oder Aromastoffe
DE19637781 1996-09-17

Publications (3)

Publication Number Publication Date
EP0829529A2 EP0829529A2 (fr) 1998-03-18
EP0829529A3 EP0829529A3 (fr) 2000-04-19
EP0829529B1 true EP0829529B1 (fr) 2002-05-08

Family

ID=7805830

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97115444A Expired - Lifetime EP0829529B1 (fr) 1996-09-17 1997-09-06 Agents parfumants ou aromatisants

Country Status (4)

Country Link
US (1) US6025005A (fr)
EP (1) EP0829529B1 (fr)
DE (2) DE19637781A1 (fr)
ES (1) ES2173360T3 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030078186A1 (en) * 2001-10-18 2003-04-24 Christopher W. Denver Method and composition for the prevention of the auto-oxidation of flavors and fragrances
US20030147972A1 (en) * 2002-02-05 2003-08-07 Christopher W. Denver Method and composition for diminishing loss of color in flavors and fragrances
US7368143B2 (en) * 2003-08-22 2008-05-06 Cumberland Packing Corporation Low-calorie low-fat butter-flavored topping compositions and methods of preparation
WO2006091245A2 (fr) 2004-10-22 2006-08-31 Dow Global Technologies Inc. Articles composites en plastique et leurs procedes de production
CN101070509B (zh) * 2006-05-10 2010-09-08 上海百润香精香料股份有限公司 番石榴香精
JP5016274B2 (ja) * 2006-08-24 2012-09-05 花王株式会社 香料組成物
US20100258140A1 (en) * 2009-04-13 2010-10-14 Creed Sharon H Portable bidet system
CN103005700B (zh) * 2012-12-19 2014-10-22 云南瑞升烟草技术（集团）有限公司 番石榴香精
WO2014130649A1 (fr) 2013-02-21 2014-08-28 Mars, Incorporated Compositions d'arôme de mangue
WO2025114409A1 (fr) * 2023-11-28 2025-06-05 Eurofragance Sl Bis(acétylthio)méthane en tant qu'ingrédient de parfum, parfum et produits parfumés le comprenant

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE790912A (fr) * 1971-11-04 1973-05-03 Int Flavors & Fragrances Inc Compositions et methodes d'aromatisation
US3984573A (en) * 1976-01-06 1976-10-05 Givaudan Corporation Foodstuffs containing 2-mercaptobenzoic acid and derivatives thereof
US4983579A (en) * 1988-11-18 1991-01-08 International Flavors & Fragrances Inc. Cyano-substituted sulfur containing compounds, compositions containing same, processes for preparing same and organoleptic uses thereof
EP0369668A3 (fr) * 1988-11-18 1990-09-26 INTERNATIONAL FLAVORS & FRAGRANCES INC. Composés contenant du soufre, substitués par des groupement hydroxyles et cyano, compositions les contenant, procédé pour les préparer et leur emploi comme organoleptiques
US4886897A (en) * 1988-11-18 1989-12-12 International Flavors & Fragrances Inc. S(4-hydroxy-1-isopropyl-4-methylhexyl) thioacetate
US4883884A (en) * 1988-11-18 1989-11-28 International Flavors & Fragrances Inc. Tetrahydro-5-isopropyl-2-methyl-2-thiophene acetonitrile, organoleptic uses thereof and process for preparing same
DE69630361T2 (de) * 1996-01-25 2004-07-22 Firmenich S.A. Verwendung von S,S'-Ethylidendiacetat als Duft- und Aromastoff

Also Published As

Publication number Publication date
US6025005A (en) 2000-02-15
DE19637781A1 (de) 1998-03-19
DE59707207D1 (de) 2002-06-13
ES2173360T3 (es) 2002-10-16
EP0829529A2 (fr) 1998-03-18
EP0829529A3 (fr) 2000-04-19

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