EP0115278A2 - Verwendung der 1-Cyclopentenylessigsäure als Riechstoff, diesen enthaltende Duftzusammensetzung und parfumierte Produkte - Google Patents

Verwendung der 1-Cyclopentenylessigsäure als Riechstoff, diesen enthaltende Duftzusammensetzung und parfumierte Produkte Download PDF

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Publication number
EP0115278A2
EP0115278A2 EP84100217A EP84100217A EP0115278A2 EP 0115278 A2 EP0115278 A2 EP 0115278A2 EP 84100217 A EP84100217 A EP 84100217A EP 84100217 A EP84100217 A EP 84100217A EP 0115278 A2 EP0115278 A2 EP 0115278A2
Authority
EP
European Patent Office
Prior art keywords
perfuming
acid
cyclopentenylacetic
ingredient
composition containing
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
EP84100217A
Other languages
English (en)
French (fr)
Other versions
EP0115278A3 (en
EP0115278B1 (de
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/de
Publication of EP0115278A3 publication Critical patent/EP0115278A3/fr
Application granted granted Critical
Publication of EP0115278B1 publication Critical patent/EP0115278B1/de
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

  • 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 as in technical applications, for example in the perfuming of soaps, detergents, powder or liquids, maintenance articles or cosmetics, shampoos or beauty creams.
  • the proportions in which the compound of the invention serves 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 o / 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 suited for this purpose.
  • the acid of the invention is a known chemical entity. Its preparation can be carried out in accordance with the methods described [see for this purpose US patent 1,965,792] or from cyclopentylidene-methyl acetate [see US patent 4,280,934] by hydrolysis thereof here following the diagram that here:
  • reaction mixture was kept at 70 ° C overnight, then 2.5 lt 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 does not have a practical influence on the quality 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 perfume 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 Verwendung der 1-Cyclopentenylessigsäure als Riechstoff, diesen enthaltende Duftzusammensetzung und parfumierte Produkte Expired EP0115278B1 (de)

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 true EP0115278A2 (de) 1984-08-08
EP0115278A3 EP0115278A3 (en) 1986-03-19
EP0115278B1 EP0115278B1 (de) 1988-03-02

Family

ID=4186596

Family Applications (1)

Application Number Title Priority Date Filing Date
EP84100217A Expired EP0115278B1 (de) 1983-01-26 1984-01-11 Verwendung der 1-Cyclopentenylessigsäure als Riechstoff, diesen enthaltende Duftzusammensetzung und parfumierte Produkte

Country Status (4)

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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017140336A1 (de) * 2016-02-15 2017-08-24 Symrise Ag Riechstoffmischungen enthaltend ester und ketone

Families Citing this family (5)

* 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 (de) * 1989-04-27 1993-10-13 Firmenich Sa Verfahren zum Parfümieren
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

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2729121A1 (de) * 1976-06-30 1978-01-12 Firmenich & Cie Verfahren zum verbessern, verstaerken oder modifizieren der geruchtragenden eigenschaften von parfuemen oder parfuemierten produkten

Family Cites Families (2)

* 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

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2729121A1 (de) * 1976-06-30 1978-01-12 Firmenich & Cie Verfahren zum verbessern, verstaerken oder modifizieren der geruchtragenden eigenschaften von parfuemen oder parfuemierten produkten

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
S. ARCTANDER: "Perfume and flavor chemicals", 1969, Montclair, N.J. (US) *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017140336A1 (de) * 2016-02-15 2017-08-24 Symrise Ag Riechstoffmischungen enthaltend ester und ketone
US10876067B2 (en) 2016-02-15 2020-12-29 Symrise Ag Fragrant mixtures containing esters and ketones

Also Published As

Publication number Publication date
US4584127A (en) 1986-04-22
EP0115278A3 (en) 1986-03-19
JPS59144714A (ja) 1984-08-18
DE3469562D1 (en) 1988-04-07
EP0115278B1 (de) 1988-03-02
JPS6127368B2 (de) 1986-06-25

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