EP0339299B1 - Parfümierter bicyclischer Ester - Google Patents

Parfümierter bicyclischer Ester Download PDF

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Publication number
EP0339299B1
EP0339299B1 EP89105777A EP89105777A EP0339299B1 EP 0339299 B1 EP0339299 B1 EP 0339299B1 EP 89105777 A EP89105777 A EP 89105777A EP 89105777 A EP89105777 A EP 89105777A EP 0339299 B1 EP0339299 B1 EP 0339299B1
Authority
EP
European Patent Office
Prior art keywords
hexahydro
indenyl
ethyl acetate
tetramethyl
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
EP89105777A
Other languages
English (en)
French (fr)
Other versions
EP0339299A2 (de
EP0339299A3 (de
Inventor
Wolfgang Klaus Giersch
Karl-Heinrich Schulte-Elte
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 EP0339299A2 publication Critical patent/EP0339299A2/de
Publication of EP0339299A3 publication Critical patent/EP0339299A3/de
Application granted granted Critical
Publication of EP0339299B1 publication Critical patent/EP0339299B1/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
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
    • C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms

Definitions

  • the present invention relates to the field of perfumery; more precisely it relates to the use of a bicyclic ester of formula or 2- (2,3,4,5,6,7-hexahydro-1,1,4,4, -tetramethyl-2 (1H) -indenyl) -ethyl acetate, as a perfuming ingredient in perfuming bases , perfumes or scented products.
  • the invention also relates to perfuming bases, perfumes or perfumed products resulting from such use. It is defined as indicated in the claims.
  • ester of the invention is generally used in admixture with other perfuming ingredients, solvents, diluents or carriers.
  • ester of the invention is used to produce the desired perfuming effects vary within a fairly wide range of values. As often in such a case, those skilled in the art know from experience that such concentrations can vary as a function of the specific effects sought as well as according to the nature of the co-ingredients present in a given composition and the nature of the product to be perfumed.
  • Concentrations of the order of 5-30% by weight relative to the weight of the composition in which it is incorporated can be used in many cases. These values can of course be lower, for example of the order of 0.1-0.5, or even 1%, when perfuming articles such as soaps, detergents or cosmetics.
  • Any common co-ingredient used in perfumery can be used in admixture with the ester of the invention, the usual criteria of chemical-physical stability and olfactory compatibility having to be retained.
  • 2- (2,3,4,5,6,7-hexahydro-1,1,4,4, -tetramethyl-2 (1H) -indenyl) -ethyl acetate is a product described in scientific literature. It can be obtained from isolongifolene by treatment with hydrobromic or hydroiodic acid followed by esterification. The process for obtaining it can be illustrated by the following reaction scheme [see Tetrahedron 42 , 4533 (1986)]: The invention is illustrated in more detail by the following examples.
  • a base consisting of a commercial detergent powder with a neutral odor was perfumed using 2- (2,3,4,5,6,7-hexahydro-1,1,4,4, -tétraméthyl-2 (1H) -indenyl) -ethyl acetate in an amount of 0.1 and 0.2% by weight relative to the weight of the base.
  • the scent base obtained was used for ordinary washing of laundry using an automatic washing machine at 60 ° C. After a washing and drying cycle, the laundry had a fresh and persistent character, a very elegant woody, amber and musky odor.
  • a "fern” type fragrance base was prepared by mixing the following ingredients (parts by weight): Benzyl salicylate 180 Essence of Bourbon Geranium 180 Linalyl acetate 160 Lemon essence 160 Cyclosia (registered trademark) base 1) 120 Amyl salicylate 120 Essence of ylang-ylang at 10% * 100 Sweet orange essence 90 Lavender essence 90 2) at 50% * 80 Vanillin 10% * 80 Anisde aldehyde 75 Tarragon essence 60 Heliotropin 60 Linalol 60 Benzyl acetate 50 Essence of patchouli 45 Oriental sandalwood essence 45 50% oak moss absolute * 40 Phenylethanol 40 Citronellol 25 Bourbon vetyver essence 20 Coumarin 10 Methylnaphthylketone 10 1900 * in diethyl phthalate 1) Firmenich SA: hydroxycitronellal 2) Schiff hydroxycitronellal base / methyl anthranilate
  • a perfuming base for a male line was prepared as follows (part by weight): p-tert-Butyl-cyclohexyl acetate 200 Absolute 10% oak moss * 180 Bergamot essence synth. 140 Alpha-hexylcinnamic aldehyde 80 Iralia (registered trademark) 1) 4) 60 Hedione (registered trademark) 2) 4) 20 Resinoid galbanum 20 Lavender absolute 20 Dihydromircenol 20 Essence of synthetic neroli 20 Essence of synthetic basil 20 10% methyl nonyl aldehyde * 20 Olibanum resinoid 20 Pine absolute at 20% * 10 Essence of synthetic angelica roots 10 Eugenol 10 50% Resinoid Labdanum * 10 Rosemary essence 10 Cypress essence 10 Mayol (registered trademark) 3) 4) 10 Isoeugenol 5 Benzoin Siam 50% resinoid * 5 Total 900 * in diethyl phthalate 1) alpha-methylionone 2) methyl

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)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)

Claims (5)

  1. Verwendung von 2-(2,3,4,5,6,7-Hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl)-ethyl-acetat als Riechstoffbestandteil.
  2. Riechstoffkomposition enthaltend als aktiven Riechstoffbestandteil das 2-(2,3,4,5,6,7-Hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl)-ethyl-acetat.
  3. Parfümierter Artikel, dadurch gekennzeichnet, dass er als aktiven Riechstoffbestandteil das 2-(2,3,4,5,6,7-Hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl)-ethyl-acetat enthält.
  4. Als parfümierter Artikel gemäss Anspruch 3 ein Detergent, gebildet aus einer Seife oder einem pulverförmigen oder flüssigen Detergent.
  5. Verfahren zur Schaffung, Verbesserung oder Verstärkung der Geruchseigenschaften eines Grundmaterials, gebildet aus einer Riechstoffkomposition, einem Parfüm oder einem Artikel, ausgewählt unter den Seifen, Kosmetika, Detergentien, Textilweichspülern oder Raumluftverbesserern, dadurch gekennzeichnet, dass man zu diesem Grundmaterial eine wirksame Menge des 2-(2,3,4,5,6,7-Hexahydro-1,1,4,4-tetramethyl-2(1H)-indenyl) -ethyl-acetats hinzufügt.
EP89105777A 1988-04-27 1989-04-01 Parfümierter bicyclischer Ester Expired - Lifetime EP0339299B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1575/88 1988-04-27
CH157588 1988-04-27

Publications (3)

Publication Number Publication Date
EP0339299A2 EP0339299A2 (de) 1989-11-02
EP0339299A3 EP0339299A3 (de) 1991-06-26
EP0339299B1 true EP0339299B1 (de) 1994-11-30

Family

ID=4213623

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89105777A Expired - Lifetime EP0339299B1 (de) 1988-04-27 1989-04-01 Parfümierter bicyclischer Ester

Country Status (4)

Country Link
US (1) US4929599A (de)
EP (1) EP0339299B1 (de)
JP (1) JPH0214291A (de)
DE (1) DE68919517T2 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5501805A (en) * 1989-06-19 1996-03-26 Lever Brothers Company, Division Of Conopco, Inc. Fragrance compositions and their use in detergent products
US5482635A (en) * 1989-06-19 1996-01-09 Lever Brothers Company Fabric conditioner with deodorant perfume composition
EP0545556B1 (de) * 1991-11-08 1997-07-23 Quest International B.V. Parfumzusammenstellung
US5312570A (en) * 1992-02-21 1994-05-17 Poly-Optical Products, Inc. System and method for preparing fiber optic ribbons
US5374768A (en) * 1992-08-19 1994-12-20 Chisso Corporation Cyclohexene derivatives
GB0031047D0 (en) * 2000-12-20 2001-01-31 Quest Int Perfume compositions
KR101001867B1 (ko) * 2010-05-19 2010-12-17 주식회사 스킨바이오 사이프러스 에센셜 복합 오일을 유효 성분으로 함유하는 기억력 증진 및 인지 기능 장애 개선을 위한 화장료 조성물

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1256535A (de) * 1968-09-27 1971-12-08
GB1519443A (en) * 1974-08-09 1978-07-26 Bush Boake Allen Ltd Isolongifolene derivatives
JPS6051139A (ja) * 1983-08-31 1985-03-22 Kuraray Co Ltd 二環式アルコ−ル及びそのエステル，それらの製造方法並びにそれらを含む香料組成物
US4608194A (en) * 1985-08-08 1986-08-26 International Flavors & Fragrances Inc. Oxobicyclononane derivatives, process for producing same and organoleptic uses thereof
US4673533A (en) * 1985-08-08 1987-06-16 International Flavors & Fragrances Inc. Oxobicyclononane derivatives, process for producing same and organoleptic uses thereof

Also Published As

Publication number Publication date
EP0339299A2 (de) 1989-11-02
US4929599A (en) 1990-05-29
DE68919517D1 (de) 1995-01-12
DE68919517T2 (de) 1995-04-20
EP0339299A3 (de) 1991-06-26
JPH0214291A (ja) 1990-01-18

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