EP0838215A2 - Verwendung von ungesättigten aliphatischen Estern in der Parfümerie - Google Patents
Verwendung von ungesättigten aliphatischen Estern in der Parfümerie Download PDFInfo
- 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
Links
- YFQCMUXWZKZTGX-HWOCKDDLSA-N CCOC(C1C(C)[C@@H](C)C(C)(C)C1)=O Chemical compound CCOC(C1C(C)[C@@H](C)C(C)(C)C1)=O YFQCMUXWZKZTGX-HWOCKDDLSA-N 0.000 description 1
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)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH2589/96 | 1996-10-23 | ||
CH258996 | 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)
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)
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)
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)
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 |
-
1997
- 1997-09-17 DE DE69728837T patent/DE69728837T2/de not_active Expired - Lifetime
- 1997-09-17 ES ES97116147T patent/ES2219717T3/es not_active Expired - Lifetime
- 1997-09-17 EP EP97116147A patent/EP0838215B1/de not_active Expired - Lifetime
- 1997-09-23 US US08/936,196 patent/US5814598A/en not_active Expired - Lifetime
- 1997-10-22 JP JP28966497A patent/JP3759670B2/ja not_active Expired - Lifetime
Patent Citations (3)
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)
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)
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 |
---|---|
EP0838215B1 (de) | 2004-04-28 |
EP0838215A3 (de) | 2000-05-10 |
US5814598A (en) | 1998-09-29 |
JPH10130688A (ja) | 1998-05-19 |
ES2219717T3 (es) | 2004-12-01 |
JP3759670B2 (ja) | 2006-03-29 |
DE69728837D1 (de) | 2004-06-03 |
DE69728837T2 (de) | 2005-02-03 |
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