EP0838215B1 - Verwendung von ungesättigten aliphatischen Estern in der Parfümerie - Google Patents

Verwendung von ungesättigten aliphatischen Estern in der Parfümerie Download PDF

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Publication number
EP0838215B1
EP0838215B1 EP97116147A EP97116147A EP0838215B1 EP 0838215 B1 EP0838215 B1 EP 0838215B1 EP 97116147 A EP97116147 A EP 97116147A EP 97116147 A EP97116147 A EP 97116147A EP 0838215 B1 EP0838215 B1 EP 0838215B1
Authority
EP
European Patent Office
Prior art keywords
dimethyl
pentenoate
ethyl
perfuming
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.)
Expired - Lifetime
Application number
EP97116147A
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English (en)
French (fr)
Other versions
EP0838215A3 (de
EP0838215A2 (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
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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

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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

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 even 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 perfuming compositions or perfumes in which they are incorporated a pleasant and fresh scent.
  • the unsaturated aliphatic esters according to the invention have distinct olfactory properties, and in particular that ethyl 2,4-dimethyl-2-pentenoate exhales a well-marked floral-chamomile note, having a slight character.
  • taget type while ethyl 2,4-dimethyl-3-pentenoate has a slightly camomile, anise-fennel fruity character accompanied by a honey sub-note, and a nice top note reminiscent of the particularly refreshing apple.
  • 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 chamomile type is very powerful and is accompanied by a very natural fruity character.
  • (E) -2,4-dimethyl-2-pentenoate turns out to be a perfuming ingredient of choice, its odor having a fruity, herbaceous character with strong Roman chamomile connotation, as well as a sub - honey note evoking the characteristic smell of phenylacetic acid. It is a pretty camomile olfactory note with a fruity character, very distinct and natural, recalling the smell of the esters of angelic acid, without however possessing the fatty butyric character of these compounds.
  • (Z) -2,4-dimethyl-2-pentenoate is also a useful perfuming ingredient developing a fruity, chamomile, pleasant and fresh scent, very natural, just as elegant as that of the isomer (E).
  • mixtures of these isomers in all their possible relative proportions, also prove to be ingredients useful perfumers.
  • the mixtures in which the (E) isomer predominates are effective perfuming ingredients according to the invention, possessing the odorous characteristics typical of this compound.
  • ethyl (E) -2,4-dimethyl-2-pentenoate is suitable for use in perfumery in compositions of various nature. This is how it can prove to be very advantageous in a floral composition, for example, where it develops a camomile smell clearly more powerful, more fruity and more complex 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.
  • US4000327 describes the use of ethyl 2-methyl-3-pentenoate as a fuel ingredient.
  • an ester according to the invention constitutes a perfuming ingredient which can prove to be very advantageous both in the isolated state and in mixture with other odorous ingredients.
  • perfumes or eau de toilette soaps, shower or bath gels, shampoos or other hair care products, cosmetic preparations, body or room air fresheners, detergents or fabric softeners, or cleaning products.
  • 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 nitrogen or sulfur compounds, 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 ® 1) 140 heliotrope 40 Iralia ® 2) 100 Lilial ® 3) 100 linalool 120 Phénéthylol 40 Amyl salicylate 40 Benzyl salicylate 120 970 ⁇ * in dipropylene glycol 1) pentadecanolide; origin: Firmenich SA, Geneva, Switzerland 2) methyl ionone; origin: Firmenich SA, Geneva, Switzerland 3) 2-methyl-3- (4-tert-butyl-1-phenyl) -propanal; origin: Givaudan-Roure, Vernier, Switzerland
  • 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 1) 30 P-tert-butyl-cyclohexyl acetate 210 Exaltex ® 2) 150 Isoraldeine ® 3) 80 Jasmal ® 4) 80 Amyl salicylate 60 Tonalid ® 5) 60 Vertofix heart 6) 80 Essence of violet 80 Total 970 ⁇ 1) 2,6-dimethyl-7-octen-2-ol; origin: International Flavors & Fragrances, USA 2) pentadecanolide; origin: Firmenich SA, Geneva, Switzerland 3) origin: Givaudan-Roure, Vernier, Switzerland 4) 4-phenyl-1,3-dioxolane; origin: International Flavors & Fragrances, USA 5) (5,6,7,8-tetrahydro
  • 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 ® 1) 30 Lilial ® 2) 45 linalool 110 Iralia ® 3) 80 methyl hexyl 45 methyl naphthyl ketone 80 Verdyle propionate 45 Amyl salicylate 45 ⁇ -undecalactone 15 Total 985 ⁇ 1) pentadecanolide; origin: Firmenich SA, Geneva, Switzerland 2) 2-methyl-3- (4-tert-butyl-1-phenyl) -propanal; origin: Givaudan-Roure, Vernier, Switzerland 3) methyl ionone; origin: Firmenich SA, Geneva, Switzerland

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)

Claims (7)

  1. Verwendung einer Verbindung der Formel die in einer der durch die gepunktete Linie angegebenen Stellungen eine Doppelbindung besitzt, als Duftbestandteil.
  2. Verwendung nach Anspruch 1 von 2,4-Dimethyl-2-pentensäureethylester.
  3. Verwendung nach Anspruch 2, dadurch gekennzeichnet, daß der 2,4-Dimethyl-2-pentensäureethylester in Form eines seiner (Z)- oder (E)-Konfigurationsisomeren vorliegt.
  4. Duftzusammensetzung oder parfümierter Artikel, enthaltend als Duftbestandteil eine Verbindung der Formel die in einer der durch die gepunktete Linie angegebenen Stellungen eine Doppelbindung besitzt.
  5. Duftzusammensetzungen oder parfümierter Artikel nach Anspruch 4, enthaltend 2,4-Dimethyl-2-pentensäureethylester.
  6. Duftzusammensetzung oder parfümierter Artikel nach Anspruch 5, dadurch gekennzeichnet, daß der 2,4-Dimethyl-2-pentensäureethylester in Form eines seiner (E)- oder (Z)-Konfigurationsisomeren vorliegt.
  7. Parfümierter Artikel nach irgendeinem der Ansprüche 4 bis 6 in Form eines Parfums oder eines Eau-de-Toilette, einer Seife, eines Dusch- oder Badegels, eines Shampoos oder eines anderen Haarpflegeprodukts, eines Kosmetikpräparats, eines Körper- oder Raumluftdeodorants, eines Waschmittels oder Textilweichspülers oder eines Pflegemittels.
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 EP0838215A2 (de) 1998-04-29
EP0838215A3 EP0838215A3 (de) 2000-05-10
EP0838215B1 true 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)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2232910T3 (es) * 1997-12-08 2005-06-01 Firmenich Sa Utilizacion del 3-metil-2-oxopentanoato de etilo como ingrediente perfumante.
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 (8)

* 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
US4000327A (en) * 1974-07-22 1976-12-28 International Flavors & Fragrances Inc. Flavoring with cis esters of 2-methyl-3-pentenoic acid
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
US4387047A (en) * 1980-02-13 1983-06-07 Firmenich Sa Esters of 1,3-dimethyl-but-3-en-1-yl, their utilization as perfuming and flavoring ingredients and compositions containing same
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
DE4007925A1 (de) * 1990-03-13 1991-09-19 Basf Ag Verfahren zur herstellung von cyclopentenonen

Also Published As

Publication number Publication date
JP3759670B2 (ja) 2006-03-29
ES2219717T3 (es) 2004-12-01
US5814598A (en) 1998-09-29
DE69728837T2 (de) 2005-02-03
DE69728837D1 (de) 2004-06-03
EP0838215A3 (de) 2000-05-10
EP0838215A2 (de) 1998-04-29
JPH10130688A (ja) 1998-05-19

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