EP0838215A2 - Verwendung von ungesättigten aliphatischen Estern in der Parfümerie - Google Patents

Verwendung von ungesättigten aliphatischen Estern in der Parfümerie Download PDF

Info

Publication number
EP0838215A2
EP0838215A2 EP97116147A EP97116147A EP0838215A2 EP 0838215 A2 EP0838215 A2 EP 0838215A2 EP 97116147 A EP97116147 A EP 97116147A EP 97116147 A EP97116147 A EP 97116147A EP 0838215 A2 EP0838215 A2 EP 0838215A2
Authority
EP
European Patent Office
Prior art keywords
perfume
dimethyl
pentenoate
ethyl
composition
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
EP97116147A
Other languages
English (en)
French (fr)
Other versions
EP0838215A3 (de
EP0838215B1 (de
Inventor
Charles Fehr
José Galindo
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 EP0838215A2 publication Critical patent/EP0838215A2/de
Publication of EP0838215A3 publication Critical patent/EP0838215A3/de
Application granted granted Critical
Publication of EP0838215B1 publication Critical patent/EP0838215B1/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

Definitions

  • the present invention relates to the field of perfumery. It relates more particularly to the use as a perfuming ingredient of a compound of formula having a double bond in one of the positions indicated by the dotted lines.
  • esters of formula (I) The structure of the esters of formula (I) is known.
  • ethyl 2,4-dimethyl-2-pentenoate and its cis and trans configuration isomers have been described in the literature, in particular in the context of organic syntheses (see, for example, VJ Lee, AR Branfman, TR Herrin, and KL Rinehart, JACS, vol. 100, 1978 , 4229-4234 or also O. Miyata, T. Shinada, I. Ninomiya, T. Naito, Synthesis, 1990 , 1123-1124).
  • the compounds of formula (I) according to the invention are capable of imparting to the perfume compositions or perfumes in which are integrated a pleasant and fresh scent.
  • the unsaturated aliphatic esters according to the invention have distinct olfactory properties, and in particular that the 2,4-dimethyl-2-pentenoate of ethyl exhales a flower note-chamomile well marked, having a slight tagete-like character, while 2,4-dimethyl-3-pentenoate ethyl has a slightly camomile, anise-fennel and fruity character a honey sub-note, and a nice top note reminiscent of the apple particularly refreshing.
  • ethyl 2,4-dimethyl-2-pentenoate and its isomers of configuration (E) and (Z) have distinct olfactory notes, the two isomers exhaling very powerful scents in which the top note of the chamomile type is very powerful and is accompanied by a very natural fruity character.
  • ethyl (Z) -2,4-dimethyl-2-pentenoate is also an ingredient useful fragrance developing a fruity, chamomile, pleasant and fresh scent, very natural, just as elegant as that of the (E) isomer.
  • mixtures of these isomers in all of their possible relative proportions, also turn out to be ingredients useful perfumers.
  • the mixtures in which the (E) isomer predominates are high-performance perfume ingredients according to the invention, having the characteristics typical fragrances of this compound.
  • ethyl (E) -2,4-dimethyl-2-pentenoate is ready for use in perfumery in compositions of various nature. This is how he can be very beneficial in a floral arrangement, for example, where it develops a significantly more powerful, fruity and more complex camomile smell than, for example, that of 1,3-dimethyl-3-butenyl-isobutyrate (see, for example, US 4,387,047), and thereby gives a new olfactory effect to the perfume.
  • an ester according to the invention constitutes a perfuming ingredient which can be very advantageous both in the isolated state and in mixture with others fragrant ingredients.
  • the perfumes or toilet waters, the soaps, the gels shower or bath, shampoos or other hair care products, cosmetic preparations, body or room air fresheners, detergents or fabric softeners, or cleaning products are examples of the perfumes or toilet waters, the soaps, the gels shower or bath, shampoos or other hair care products, cosmetic preparations, body or room air fresheners, detergents or fabric softeners, or cleaning products.
  • the proportions in which the compounds according to the invention can be incorporated in the aforementioned miscellaneous products vary in a range of values very extent. These values are dependent on the nature of the article or product that we want perfume and the desired olfactory effect, as well as the nature of the co-ingredients in a composition given when a compound of the invention is used in mixture with perfume co-ingredients, solvents or adjuvants commonly used in the art. Good understood, a compound according to the invention can also be added to the compositions and scented articles either alone or in solution in commonly used solvents.
  • perfuming composition is meant here a composition consisting of a mixture of perfuming ingredients which can be chosen from various chemical classes, comprising for example esters, aldehydes, alcohols, ethers, ketones, acetals, nitriles, terpene hydrocarbons, heterocyclic compounds nitrogen or sulfur, as well as essential oils of natural or synthetic origin.
  • a basic perfume composition was prepared by mixing the following ingredients: Ingredient Parts by weight Benzyl acetate 170 Cyclanol acetate 20 Verdyl acetate 20 Citronellol 40 Ethyl vanillin 10% 20 Exaltex ® 140 Heliotropin 40 Iralia ® 100 Lilial ® 100 Linalol 120 Phenethylol 40 Amyl salicylate 40 Benzyl salicylate 120 970
  • Ingredient Parts by weight Benzyl acetate 170 Cyclanol acetate 20 Verdyl acetate 20 Citronellol 40 Ethyl vanillin 10% 20 Exaltex ® 140 Heliotropin 40 Iralia ® 100 Lilial ® 100 Linalol 120 Phenethylol 40 Amyl salicylate 40 Benzyl salicylate 120 970
  • a basic perfume composition with a powdery-floral, woody connotation was prepared by mixing the following ingredients: Ingredient Parts by weight Cyclanol acetate 30 Verdyl acetate 80 Anisde aldehyde 30 Dihydromyrcenol 30 P-tert-butyl-cyclohexyl acetate 210 Exaltex ® 150 Isoraldeine ® 80 Jasmal ® 80 Amyl salicylate 60 Tonalid ® 60 Vertofix heart 80 Essence of violet 80 Total 970 The addition of 30 parts by weight of (E) -2,4-dimethyl-2-pentenoate to this floral base composition gives it a strong fruity connotation while imparting to it, in a more marked manner, a pleasant character. fresh.
  • a basic perfume composition with a fern-lavender-floral odor was prepared by mixing the following ingredients: Ingredient Parts by weight Benzyl acetate 45 Linalyl acetate 60 Styrallyl acetate 30 Verdyl acetate 80 Essence of Aspic 80 Benzophenone 60 Coumarin 30 Cyclomethylene citronellol 60 Eugenol 45 Exaltex ® 30 Lilial ® 45 Linalol 110 Iralia ® 80 Methylhexylketone 45 Methylnaphthylketone 80 Verdyl propionate 45 Amyl salicylate 45 ⁇ -Undecalactone 15 Total 985 The addition of 15 parts by weight of ethyl (E) -2,4-dimethyl-2-pentenoate to this very classic fern-type composition gives it an enriching chamomile note, giving it a particularly modern and camomile appearance .
  • E ethyl

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)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP97116147A 1996-10-23 1997-09-17 Verwendung von ungesättigten aliphatischen Estern in der Parfümerie Expired - Lifetime EP0838215B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH258996 1996-10-23
CH2589/96 1996-10-23
CH258996 1996-10-23

Publications (3)

Publication Number Publication Date
EP0838215A2 true EP0838215A2 (de) 1998-04-29
EP0838215A3 EP0838215A3 (de) 2000-05-10
EP0838215B1 EP0838215B1 (de) 2004-04-28

Family

ID=4237184

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97116147A Expired - Lifetime EP0838215B1 (de) 1996-10-23 1997-09-17 Verwendung von ungesättigten aliphatischen Estern in der Parfümerie

Country Status (5)

Country Link
US (1) US5814598A (de)
EP (1) EP0838215B1 (de)
JP (1) JP3759670B2 (de)
DE (1) DE69728837T2 (de)
ES (1) ES2219717T3 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0921186A2 (de) * 1997-12-08 1999-06-09 Firmenich Sa Verwendung des Ethyl 3-methyl-2-oxopnetanoate als Riechstoff
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

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018196988A1 (de) * 2017-04-28 2018-11-01 Symrise Ag Ethyl-2-acetyl-2,4-dimethyl-pent-4-enoat als riechstoff

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4000327A (en) * 1974-07-22 1976-12-28 International Flavors & Fragrances Inc. Flavoring with cis esters of 2-methyl-3-pentenoic acid
EP0034334A2 (de) * 1980-02-13 1981-08-26 Firmenich Sa 1,3-Dimethyl-but-3-en-1-yl-Ester, deren Verwendung als Parfüm- und Aromabestandteil; Parfüm- und Aromazusammensetzung mit mindestens einem dieser Ester
EP0446759A1 (de) * 1990-03-13 1991-09-18 BASF Aktiengesellschaft Verfahren zur Herstellung von Cyclopentenonen

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3953377A (en) * 1970-12-22 1976-04-27 Firmenich S.A. Ethyl-2-trans-4-cis undecadienoate, ethyl-2-trans-4-cis dodecadienoate and ethyl-2-decadienoate perfume compositions
US4094823A (en) * 1975-04-08 1978-06-13 International Flavors & Fragrances Inc. Ethyl-2-methyl-3,4-pentadienoate perfume compositions
DE2626142A1 (de) * 1976-06-11 1977-12-22 Henkel Kgaa Verwendung von aliphatischen 2-methyl- 2-alkyl-alkansaeureestern als riechstoffe sowie diese enthaltende riechstoffkompositionen
DE2757559C2 (de) * 1977-12-23 1986-10-30 Henkel KGaA, 4000 Düsseldorf Verwendung der 3,5,5-Trimethylhexansäureester als Riechstoffe sowie diese enthaltende Riechstoffkompositionen
DE3013565A1 (de) * 1980-04-09 1981-10-15 Consortium für elektrochemische Industrie GmbH, 8000 München Neue (beta) - a -ungesaettigte ketone und isoprenoide 2,6-dienone, verfahren zu deren herstellung und ihre verwendung als geruchs- und geschmacksstoffe

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4000327A (en) * 1974-07-22 1976-12-28 International Flavors & Fragrances Inc. Flavoring with cis esters of 2-methyl-3-pentenoic acid
EP0034334A2 (de) * 1980-02-13 1981-08-26 Firmenich Sa 1,3-Dimethyl-but-3-en-1-yl-Ester, deren Verwendung als Parfüm- und Aromabestandteil; Parfüm- und Aromazusammensetzung mit mindestens einem dieser Ester
EP0446759A1 (de) * 1990-03-13 1991-09-18 BASF Aktiengesellschaft Verfahren zur Herstellung von Cyclopentenonen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
VING J.L. ET AL : "synthesis of 3-dienoyl tetamic acid" JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 100, 1978, pages 4225-4236, XP002132656 WASHINGTON, DC.; US *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0921186A2 (de) * 1997-12-08 1999-06-09 Firmenich Sa Verwendung des Ethyl 3-methyl-2-oxopnetanoate als Riechstoff
EP0921186A3 (de) * 1997-12-08 2000-04-26 Firmenich Sa Verwendung des Ethyl 3-methyl-2-oxopnetanoate als Riechstoff
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
ES2219717T3 (es) 2004-12-01
EP0838215A3 (de) 2000-05-10
DE69728837T2 (de) 2005-02-03
US5814598A (en) 1998-09-29
DE69728837D1 (de) 2004-06-03
JP3759670B2 (ja) 2006-03-29
JPH10130688A (ja) 1998-05-19
EP0838215B1 (de) 2004-04-28

Similar Documents

Publication Publication Date Title
EP2566838B1 (de) Verbindungen mit einer holzigen note
EP0180885A2 (de) Verwendung eines cycloaliphatischen Carbinols als Riechstoff
EP0694605B1 (de) Cyclischer Diester und Verwendung desselben als Duftstoff
EP0584477B1 (de) Verwendung einer Cyclopentadecenone als Parfümszutat
EP0621892B1 (de) Verwendung von Furanonen wie Duftstoffe
EP0694520B1 (de) Campholen-Aldehyd-Derivate und ihre Anwendung in der Parfümerie
EP0902024B1 (de) 7-propyl-benzodiosepin-3-one und dessen Verwendung in Parfümerie
EP0465936B1 (de) Decalinylketonen, ihre Verwendung in der Parfümerie und Verfahren zu deren Herstellung
EP0504592B1 (de) Campholenstruktureinheit enthaltender Tertiäralkohol und dessen Anwendung als Duftstoff
EP0501031B1 (de) Riechstoff
EP0838215B1 (de) Verwendung von ungesättigten aliphatischen Estern in der Parfümerie
EP1022265B1 (de) 2-Indanmethanolderivate und ihre Verwendung als Riechstoffe
EP0544110A1 (de) Tertiäre cyclische Alkohole und ihre Anwendung als Riechstoffbestandteile
EP0115278B1 (de) Verwendung der 1-Cyclopentenylessigsäure als Riechstoff, diesen enthaltende Duftzusammensetzung und parfumierte Produkte
EP1069176B1 (de) Aliphatische Ester und Ihre Verwendung als Duftstoff
EP0707575A1 (de) Verwendung von dihydrobenzofuranonen als parfüminhaltstoffe
EP0921186B1 (de) Verwendung des Ethyl 3-methyl-2-oxopnetanoate als Riechstoff
EP0080600B1 (de) Verwendung des 2-hydroxy-3,4,4-trimethyl-cyclopent-2-ene-1-ons als Riechstoffbestandteil
EP0676393B1 (de) Cyclische Ketone und deren Verwendung als Riechstoffe
EP0572797B1 (de) Ungesättigte cyclische Alkohole, ihre Anwendung als Riechstoffbestandteile und deren Zwischenprodukte
EP0200890B1 (de) Verwendung von einem Spirolacton als Riechstoff
EP0694604A2 (de) Verwendung des 1,3-Undecadien-5-yne als Duftstoff
EP0504563B1 (de) Geruchsstoff mit einer Spiranstruktur
WO1992003402A1 (fr) Compose cetonique polycyclique et son utilisation a titre d'ingredient parfumant
EP0916650A2 (de) Von 3-Isopropenyl-1,2-dimethyl-1-cyclopentanol abgeleitete Nitrile und Aldehyde und ihre Verwendung in der Parfümerie

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 ES FR GB IT LI NL

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

RIC1 Information provided on ipc code assigned before grant

Free format text: 7A 61K 7/46 A, 7C 11B 9/00 B

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

17P Request for examination filed

Effective date: 20001110

AKX Designation fees paid

Free format text: CH DE ES FR GB IT LI NL

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

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

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

Free format text: NOT ENGLISH

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REF Corresponds to:

Ref document number: 69728837

Country of ref document: DE

Date of ref document: 20040603

Kind code of ref document: P

GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)

Effective date: 20040726

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2219717

Country of ref document: ES

Kind code of ref document: T3

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

Effective date: 20050131

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

Ref country code: NL

Payment date: 20070817

Year of fee payment: 11

Ref country code: IT

Payment date: 20070820

Year of fee payment: 11

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: 20090401

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

Effective date: 20090401

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

Ref country code: IT

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

Effective date: 20080917

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

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: 20160913

Year of fee payment: 20

Ref country code: CH

Payment date: 20160913

Year of fee payment: 20

Ref country code: GB

Payment date: 20160914

Year of fee payment: 20

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

Ref country code: FR

Payment date: 20160816

Year of fee payment: 20

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

Ref country code: ES

Payment date: 20160811

Year of fee payment: 20

REG Reference to a national code

Ref country code: DE

Ref legal event code: R071

Ref document number: 69728837

Country of ref document: DE

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

REG Reference to a national code

Ref country code: GB

Ref legal event code: PE20

Expiry date: 20170916

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: 20170916

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20180507

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

Ref country code: ES

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20170918