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

Info

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
EP0178532A3 (en
EP0178532A2 (de
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

Links

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
EP0911315B1 (de) * 1997-10-21 2003-06-11 Givaudan SA Beta-Ketoester
SG74666A1 (en) 1997-10-21 2000-08-22 Givaudan Roure Int Beta-ketoester
EP1069176B1 (de) 1999-07-14 2004-09-08 Firmenich Sa Aliphatische Ester und Ihre Verwendung als Duftstoff
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
EP0096243B1 (de) * 1982-06-03 1985-08-07 L. GIVAUDAN & CIE Société Anonyme Cyclohex(en)ylmethanole und ihre Ester, mit Riechstoffeigenschaften
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
EP0178532A3 (en) 1989-02-08
EP0178532A2 (de) 1986-04-23
DE3578082D1 (de) 1990-07-12
JPS6197214A (ja) 1986-05-15
US4647407A (en) 1987-03-03
JPH0347678B2 (de) 1991-07-22

Similar Documents

Publication Publication Date Title
EP0472966B1 (de) Ester und ihre Anwendung in der Parfümerie
EP0392258B1 (de) Aromatische Aldehyde, ihre Derivate und ihre Verwendung als Bestandteil in Riechstoffen, Herbiziden und Fungiziden
EP2566838B1 (de) Verbindungen mit einer holzigen note
EP0178532B1 (de) Ethyl-2-acetyl-4-methyl-4-pentenoat enthaltende Duftzusammensetzungen und parfümierte Waren
EP0694605A2 (de) Cyclische Diestern und Verwendung derselben als Duftstoffe
EP2203417B1 (de) Substituierte octan(en)nitrile, verfahren zu deren synthese und deren anwendungen in der duftstoffherstellung
EP0167709B1 (de) 1,2,3,4,4a,5,8,8a-Octahydro-2,2,6,8-tetramethyl-1-naphthalenol, seine Anwendung als Riechstoff und sein Herstellungsverfahren
EP0004968B1 (de) Norbornen(-an)Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Riechstoffe
EP0378825B1 (de) Alicyclische Ester und ihre Anwendung als Riechstoffkomponenten
EP0457022B1 (de) Optisch aktive aliphatische Alkohole und deren Anwendung als Riechstoffbestandteile
CH644341A5 (fr) Composes tricycliques hydroxyles et leur utilisation en tant qu'ingredients parfumants.
US4601851A (en) Cyclododec-2-enyl ethers in fragrance compositions
JPH05262757A (ja) 環状イソロンギホラノン−ケタール類、その製法及び使用法
JPS60243014A (ja) 香料組成物
US4661285A (en) Balsamic fragrance composition and process for preparation
EP0181475B1 (de) Ungesättigtes aliphatisches Keton und seine Verwendung als Parfümierungsbestandteil
CA1167049A (en) Terpene derivatives and perfume compositions containing them
EP0282798B1 (de) Aliphatische bicyclische Alkohole und ihre Anwendung als Riechstoffe
EP0052115B1 (de) Bicyclische verbindungen und ihre verwendung als riechstoffe
WO1992003402A1 (fr) Compose cetonique polycyclique et son utilisation a titre d'ingredient parfumant
EP0056500A2 (de) Ester der 2,2,-Dimethyl-Propionsäure, ihre Verwendung als Riechstoffe und eine sie enthaltende Zusammensetzung
CH620361A5 (de)
EP0558928B1 (de) Furanether und ihre Anwendung als Riechstoffe
EP0148399B1 (de) Polycyclischer Alkohol, Verfahren zu seiner Herstellung als duftender Bestandteil und eine diesen enthaltende Zusammensetzung
EP0643958A2 (de) Verwendung in Parfumerie vom optisch aktiven Isomeren des (E)-3,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): CH DE FR GB LI NL

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): CH DE FR GB LI NL

17P Request for examination filed

Effective date: 19890110

17Q First examination report despatched

Effective date: 19890906

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): CH DE FR GB LI NL

REF Corresponds to:

Ref document number: 3578082

Country of ref document: DE

Date of ref document: 19900712

GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19971031

Year of fee payment: 13

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19990501

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 19990501

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20040913

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20040916

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20040917

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 20041102

Year of fee payment: 20

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20051001

REG Reference to a national code

Ref country code: GB

Ref legal event code: PE20

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL