EP0178532B1 - Ethyl-2-acetyl-4-methyl-4-pentenoat enthaltende Duftzusammensetzungen und parfümierte Waren - Google Patents

Ethyl-2-acetyl-4-methyl-4-pentenoat enthaltende Duftzusammensetzungen und parfümierte Waren Download PDF

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Publication number
EP0178532B1
EP0178532B1 EP85112461A EP85112461A EP0178532B1 EP 0178532 B1 EP0178532 B1 EP 0178532B1 EP 85112461 A EP85112461 A EP 85112461A EP 85112461 A EP85112461 A EP 85112461A EP 0178532 B1 EP0178532 B1 EP 0178532B1
Authority
EP
European Patent Office
Prior art keywords
pentenoate
acetyl
methyl
ethyl
perfuming
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
EP85112461A
Other languages
English (en)
French (fr)
Other versions
EP0178532A2 (de
EP0178532A3 (en
Inventor
Charles Dr. Fehr
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.)
Firmenich SA
Original Assignee
Firmenich 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 Firmenich SA filed Critical Firmenich SA
Publication of EP0178532A2 publication Critical patent/EP0178532A2/de
Publication of EP0178532A3 publication Critical patent/EP0178532A3/fr
Application granted granted Critical
Publication of EP0178532B1 publication Critical patent/EP0178532B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes

Definitions

  • the present invention relates to the field of perfumery. It relates more particularly to the use of an aliphatic keto-ester of formula or ethyl 2-acetyl-4-methyl-4-pentenoate.
  • Ethyl 2-acetyl-4-methyl-4-pentenoate is used to develop a fruity-floral, aromatic and natural, slightly herbaceous odor; odor that evokes an aspect of the chamomile decoction as well as the fruity character of the pineapple.
  • the keto-ester of the invention can lend itself to the scent of various articles such as soaps, cosmetics, shampoos, air fresheners, fabric softeners or liquid or cationic solid detergents , anionic, nonionic or zwitterionic. It has been found that ethyl 2-acetyl-4-methyl-4-pentenoate exhibits good stability even in relatively aggressive media as well as good substantivation on various fabrics, both natural and artificial.
  • the proportions of which it can be used to produce the desired perfuming effects vary within a fairly wide range of values. Concentrations of the order of 1 or 2-5% by weight, based on the weight of the composition in which it is incorporated, can be used when the compound of the invention is used as a shade. Such concentrations, or even lower, are perfectly suitable when perfuming articles such as cosmetics, creams or shampoos, soaps or detergents. These values, of course, should not be interpreted restrictively; from experience, those skilled in the art can indeed determine the appropriate proportion according to the desired effect or the nature of the co-ingredients in a given composition.
  • the compound of the invention can be used as a single ingredient, but preferably it is used in admixture with perfume coingredients and solvents customary in the art (for example, mention may be made for this purpose natural or synthetic compounds mentioned in the European patent application published under the number 0096243).
  • the keto-ester of the invention is a chemical compound of known structure. It has in fact been described, as a synthesis intermediary, by TF Wood et al. [J. Org. Chem. 28, 2248 (1963)] in a study relating to the preparation of certain aromatic musks. Its odorous properties, however, have remained unknown to this day.
  • ethyl 2-acetyl-4-methyl-4-pentenoate is obtained by an addition reaction, in basic medium, between ethyl acetoacetate and methallyl chloride according to the reaction scheme that here:
  • the reaction is preferably carried out in a medium consisting of an aqueous, aqueous-alcoholic or alcoholic solvent, preferably in ethyl alcohol.
  • aqueous, aqueous-alcoholic or alcoholic solvent preferably in ethyl alcohol.
  • Other inert organic solvents such as acetone or an aromatic hydrocarbon, such as benzene, toluene or xylene, can also be used.
  • an alkali metal alkoxide can be used, for example sodium ethylate, sodium carbonate, lithium or potassium carbonate or a hydroxide, such as potassium hydroxide.
  • potassium carbonate is preferably used and the reaction is carried out in ethanol. Under these conditions, the operation is carried out at the boiling temperature of the reaction mixture, ie at approximately 75 ° C.
  • the reaction temperature can be between approximately 50 and 110 ° C. It is at such temperatures that reaction times are relatively short, while the formation of side products is reduced.
  • the process for the preparation of ethyl 2-acetyl-4-methyl-4-pentenoate will be illustrated in detail in the examples which follow; also illustrated will be its use. In the said examples, the temperatures are indicated in degrees centigrade and the abbreviations have the usual meaning in the art.
  • the crude product (740 g) is distilled under nitrogen on a filled column packed with stainless steel propellers using a distillation head with total reflux. 555.8 g of the desired keto-ester having Eb are thus obtained. 115 ° / 2.66x10 3 Pa (yield by weight 107%, theoretic 75%).
  • a perfuming composition for shampoos was by mixing the following ingredients (parts by weight):
  • Ethyl 2-acetyl-4-methyl-4-pentenoate has been used to flavor various products, the nature of which is given in the table below. In this table also appear the concentration values respective of the ester used in the finished product as well as the indication as to the stability of the odor obtained.

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)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
  • Fats And Perfumes (AREA)

Claims (3)

1. Eine Parfümkomposition, die Aethyl 2-Acetyl-4-methyl-4-pentenoat als aktiven Bestandteil, zusammen mit anderen Parfümbestandteilen, Lösungsmitteln, Trägern oder Füllstoffen enthält.
2. Eine parfümiertes Produkt, das Aethyl 2-Acetyl-4-methyl-4-pentenoat als aktiver Parfümbestandteil enthält.
3. Als parfümiertes Produkt gemäß Anspruch 2, ein flüssiges oder festes Waschmittel.
EP85112461A 1984-10-18 1985-10-02 Ethyl-2-acetyl-4-methyl-4-pentenoat enthaltende Duftzusammensetzungen und parfümierte Waren Expired - Lifetime EP0178532B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH498584 1984-10-18
CH4985/84 1984-10-18

Publications (3)

Publication Number Publication Date
EP0178532A2 EP0178532A2 (de) 1986-04-23
EP0178532A3 EP0178532A3 (en) 1989-02-08
EP0178532B1 true EP0178532B1 (de) 1990-06-06

Family

ID=4285949

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85112461A Expired - Lifetime EP0178532B1 (de) 1984-10-18 1985-10-02 Ethyl-2-acetyl-4-methyl-4-pentenoat enthaltende Duftzusammensetzungen und parfümierte Waren

Country Status (4)

Country Link
US (1) US4647407A (de)
EP (1) EP0178532B1 (de)
JP (1) JPS6197214A (de)
DE (1) DE3578082D1 (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1090624A3 (de) * 1997-10-21 2003-12-03 Givaudan SA Beta- Ketoester
SG74666A1 (en) 1997-10-21 2000-08-22 Givaudan Roure Int Beta-ketoester
ES2228355T3 (es) 1999-07-14 2005-04-16 Firmenich Sa Esteres alifaticos y su utilizacion a titulo de ingredientes perfumantes.
FR2805991B1 (fr) * 2000-03-13 2003-03-21 Rhodia Chimie Sa Procede d'obtention de compositions parfumantes et de produits parfumes et produits ainsi obtenus
WO2018196988A1 (de) * 2017-04-28 2018-11-01 Symrise Ag Ethyl-2-acetyl-2,4-dimethyl-pent-4-enoat als riechstoff

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4245122A (en) * 1979-12-05 1981-01-13 International Flavors & Fragrances Inc. Process for the production of allyl acetone
US4348416A (en) * 1980-08-07 1982-09-07 International Flavors & Fragrances Inc. Flavoring with 1-ethoxy-1-ethanol acetate - acetaldehyde mixtures
US4357316A (en) * 1980-12-18 1982-11-02 International Flavors & Fragrances Inc. Use of 1-n-butoxy-1-ethanol acetate for augmenting or enhancing the taste of toothpaste
DE3360520D1 (en) * 1982-06-03 1985-09-12 Givaudan & Cie Sa Cyclohex(en)yl methanols and their esters, with perfuming properties
DE3306560A1 (de) * 1983-02-25 1984-08-30 Henkel KGaA, 4000 Düsseldorf Neue 2-methylpentansaeureester, deren herstellung und verwendung als riechstoffe sowie diese enthaltende riechstoff-kompositionen

Also Published As

Publication number Publication date
JPH0347678B2 (de) 1991-07-22
US4647407A (en) 1987-03-03
EP0178532A2 (de) 1986-04-23
DE3578082D1 (de) 1990-07-12
JPS6197214A (ja) 1986-05-15
EP0178532A3 (en) 1989-02-08

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