EP0115278B1 - Utilisation de l'acide 1-cyclopenténylacétique en tant qu'ingrédient parfumant, composition parfumante le contenant et produits parfumés - Google Patents

Utilisation de l'acide 1-cyclopenténylacétique en tant qu'ingrédient parfumant, composition parfumante le contenant et produits parfumés Download PDF

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Publication number
EP0115278B1
EP0115278B1 EP84100217A EP84100217A EP0115278B1 EP 0115278 B1 EP0115278 B1 EP 0115278B1 EP 84100217 A EP84100217 A EP 84100217A EP 84100217 A EP84100217 A EP 84100217A EP 0115278 B1 EP0115278 B1 EP 0115278B1
Authority
EP
European Patent Office
Prior art keywords
perfuming
acid
cyclopentenylacetic
composition containing
ingredient
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
Application number
EP84100217A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0115278A2 (fr
EP0115278A3 (en
Inventor
Arnoldus Dr. Uijttewaal
Dietrich Dr. Kastner
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 EP0115278A2 publication Critical patent/EP0115278A2/fr
Publication of EP0115278A3 publication Critical patent/EP0115278A3/fr
Application granted granted Critical
Publication of EP0115278B1 publication Critical patent/EP0115278B1/fr
Expired 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms

Definitions

  • the present invention relates to the field of perfumery and more particularly it relates to the use of an unsaturated cycloaliphatic acid as a perfuming ingredient for the preparation of perfumes and perfumed products.
  • 1-cyclopentenylacetic acid of the formula could be used to impart or improve the honey-like fragrant note of perfumes and scented products without having the specific secondary characteristics of phenylacetic acid.
  • the 1-cyclopentenylacetic acid of the invention finds a very wide use both in fine perfumery and in technical applications, for example in the perfume of soaps, detergents, powder or liquids, cleaning articles or cosmetics, shampoos or beauty creams.
  • the proportions in which the compound of the invention is used to develop the desired odorous effects can vary within a fairly wide range of values. Its power is such that quantities of the order of 1-10 r oo by weight relative to the weight of the composition or of the scented article may already be sufficient to obtain a positive effect. Concentrations of 0.1-2% are preferably used in the manufacture of concentrated compositions or "hearts".
  • 1-cyclopentenylacetic acid can be added either directly to the product which one wishes to perfume, or, more often, in the form of a solution mixed with other perfuming ingredients.
  • the co-ingredients, the solvents or the usual supports, the use of which is well known to those skilled in the art, are perfectly suitable for this purpose.
  • the acid of the invention is a known chemical entity. Its preparation can be carried out according to the methods described [see for this purpose US Pat. No. 1,965,762] or from cyclopentylidene-methyl acetate [see US Pat. No. 4,280,934] by hydrolysis thereof according to the scheme that is here :
  • reaction mixture was kept at 70 ° C overnight, then 2.5 l of water was added thereto and the methanol was evaporated. After acidification with HCl, separation of the organic phase, followed by re-extraction with ether of the aqueous phase, the two combined organic phases were distilled under reduced pressure.
  • the desired product was obtained with a yield of 82.3% at Eb. 96 ° C / approx. 6.65 Pa. Traces of the isomeric compound of formula were also present in the product obtained, but their presence has no practical influence on the quantity of the main product.
  • the 2-cyclopentenylacetic acid in solution at 25% in diethyl phthalate was added at a rate of 2% in a commercial soap paste with neutral odor and, according to the usual techniques, the resulting paste was used for the manufacture of bars of toilet soaps.
  • the odor of the article thus obtained was judged by a group of experts who defined it as being characterized by a separate note of the “honey” type.
  • a basic pink-type composition was prepared by mixing the following ingredients (parts by weight):
  • a basic perfuming composition intended to be incorporated into a shampoo was prepared by mixing the following ingredients (parts by weight):
  • the olfactory stability was also confirmed by tests of prolonged ultraviolet irradiation of the products 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)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
EP84100217A 1983-01-26 1984-01-11 Utilisation de l'acide 1-cyclopenténylacétique en tant qu'ingrédient parfumant, composition parfumante le contenant et produits parfumés Expired EP0115278B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH41983 1983-01-26
CH419/83 1983-01-26

Publications (3)

Publication Number Publication Date
EP0115278A2 EP0115278A2 (fr) 1984-08-08
EP0115278A3 EP0115278A3 (en) 1986-03-19
EP0115278B1 true EP0115278B1 (fr) 1988-03-02

Family

ID=4186596

Family Applications (1)

Application Number Title Priority Date Filing Date
EP84100217A Expired EP0115278B1 (fr) 1983-01-26 1984-01-11 Utilisation de l'acide 1-cyclopenténylacétique en tant qu'ingrédient parfumant, composition parfumante le contenant et produits parfumés

Country Status (4)

Country Link
US (1) US4584127A (enrdf_load_stackoverflow)
EP (1) EP0115278B1 (enrdf_load_stackoverflow)
JP (1) JPS59144714A (enrdf_load_stackoverflow)
DE (1) DE3469562D1 (enrdf_load_stackoverflow)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5164364A (en) * 1986-09-30 1992-11-17 Givaudan Corporation Ethyl campholenates and dihydro derivatives thereof as flavorants and odorants
EP0394810B1 (fr) * 1989-04-27 1993-10-13 Firmenich Sa Procédé de parfumage
US6720295B2 (en) * 2001-08-27 2004-04-13 Firmenich Sa Use of tertiary alcohols or esters as perfuming ingredients
JP4486549B2 (ja) * 2005-06-06 2010-06-23 三菱重工業株式会社 ガスタービンの燃焼器
EP2474301B1 (de) * 2011-12-14 2014-04-16 Symrise AG Riechstoffmischungen enthaltend Cyclopent-2-Enyl-Essigsäureethylester
EP3416612B1 (de) * 2016-02-15 2022-12-28 Symrise AG Riechstoffmischungen enthaltend ester und ketone

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1965792A (en) * 1931-03-06 1934-07-10 Cie De Bethune Esters of unsubstituted and alphasubstituted cyclopentenylacetic acid and their production
US4031132A (en) * 1974-07-19 1977-06-21 Givaudan Corporation Isopropenyl cyclopentene carboxylic acids
CH616077A5 (enrdf_load_stackoverflow) * 1976-06-30 1980-03-14 Firmenich & Cie

Also Published As

Publication number Publication date
EP0115278A2 (fr) 1984-08-08
US4584127A (en) 1986-04-22
JPS6127368B2 (enrdf_load_stackoverflow) 1986-06-25
JPS59144714A (ja) 1984-08-18
DE3469562D1 (en) 1988-04-07
EP0115278A3 (en) 1986-03-19

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