EP0178532A2 - 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
EP0178532A2
EP0178532A2 EP85112461A EP85112461A EP0178532A2 EP 0178532 A2 EP0178532 A2 EP 0178532A2 EP 85112461 A EP85112461 A EP 85112461A EP 85112461 A EP85112461 A EP 85112461A EP 0178532 A2 EP0178532 A2 EP 0178532A2
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.)
Granted
Application number
EP85112461A
Other languages
English (en)
French (fr)
Other versions
EP0178532B1 (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 cationic liquid or solid detergents , anionic, nonionic or zwitterionic. It has been found that ethyl 2-acetyl-4-methyl-4-pentenoate has good stability even in relatively aggressive media as well as good substantivity on different fabrics, both natural and artificial.
  • the proportions in which it can be used to produce the desired fragrance effects vary within a fairly wide range of values. Concentrations of the order of 1 or 2-5% by weight, relative to 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 for 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 perfuming co-ingredients and solvents customary in the art (by way of 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 and 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 alcoholate 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 about 50 and 110 ° C. It is at such temperatures that the 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 his 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%, theor. 7596).
  • a perfuming composition for shampoos was prepared by mixing the following ingredients (parts by weight):
  • Two powdered detergent bases were prepared 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 the said table also appear the respective concentration values 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)
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 true EP0178532A2 (de) 1986-04-23
EP0178532A3 EP0178532A3 (en) 1989-02-08
EP0178532B1 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)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2805991A1 (fr) * 2000-03-13 2001-09-14 Rhodia Chimie Sa Procede d'obtention de compositions parfumantes et de produits parfumes et produits ainsi obtenus
US6509312B1 (en) 1999-07-14 2003-01-21 Firmenich Sa Aliphatic esters and their utilization as perfuming ingredients

Families Citing this family (3)

* 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
WO2018196988A1 (de) * 2017-04-28 2018-11-01 Symrise Ag Ethyl-2-acetyl-2,4-dimethyl-pent-4-enoat als riechstoff

Citations (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
EP0048545A2 (de) * 1980-08-07 1982-03-31 INTERNATIONAL FLAVORS & FRAGRANCES INC. 1-Äthoxy äthyl-acetat und dessen Verwendung zur Verstärkung oder Erhöhung des Aromas oder Geschmackes von konsumierbaren Waren
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
EP0096243A1 (de) * 1982-06-03 1983-12-21 L. GIVAUDAN & CIE Société Anonyme Cyclohex(en)ylmethanole und ihre Ester, mit Riechstoffeigenschaften
EP0120274A1 (de) * 1983-02-25 1984-10-03 Henkel Kommanditgesellschaft auf Aktien Neue 2-Methylpentansäureester, deren Herstellung und Verwendung als Riechstoffe sowie diese enthaltende Riechstoff-Kompositionen

Patent Citations (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
EP0048545A2 (de) * 1980-08-07 1982-03-31 INTERNATIONAL FLAVORS & FRAGRANCES INC. 1-Äthoxy äthyl-acetat und dessen Verwendung zur Verstärkung oder Erhöhung des Aromas oder Geschmackes von konsumierbaren Waren
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
EP0096243A1 (de) * 1982-06-03 1983-12-21 L. GIVAUDAN & CIE Société Anonyme Cyclohex(en)ylmethanole und ihre Ester, mit Riechstoffeigenschaften
EP0120274A1 (de) * 1983-02-25 1984-10-03 Henkel Kommanditgesellschaft auf Aktien Neue 2-Methylpentansäureester, deren Herstellung und Verwendung als Riechstoffe sowie diese enthaltende Riechstoff-Kompositionen

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6509312B1 (en) 1999-07-14 2003-01-21 Firmenich Sa Aliphatic esters and their utilization as perfuming ingredients
FR2805991A1 (fr) * 2000-03-13 2001-09-14 Rhodia Chimie Sa Procede d'obtention de compositions parfumantes et de produits parfumes et produits ainsi obtenus
WO2001068049A1 (fr) * 2000-03-13 2001-09-20 Rhodia Chimie Procede d'obtention de compositions parfumantes et de produits parfumes et produits ainsi obtenus

Also Published As

Publication number Publication date
EP0178532B1 (de) 1990-06-06
US4647407A (en) 1987-03-03
JPS6197214A (ja) 1986-05-15
DE3578082D1 (de) 1990-07-12
JPH0347678B2 (de) 1991-07-22
EP0178532A3 (en) 1989-02-08

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