EP0826764B1 - Compositions parfumantes contenant des 2-acétylbenzofuranes substitués - Google Patents

Compositions parfumantes contenant des 2-acétylbenzofuranes substitués Download PDF

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Publication number
EP0826764B1
EP0826764B1 EP97114337A EP97114337A EP0826764B1 EP 0826764 B1 EP0826764 B1 EP 0826764B1 EP 97114337 A EP97114337 A EP 97114337A EP 97114337 A EP97114337 A EP 97114337A EP 0826764 B1 EP0826764 B1 EP 0826764B1
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EP
European Patent Office
Prior art keywords
alkyl
formula
bond
dotted line
represent hydrogen
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
EP97114337A
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German (de)
English (en)
Other versions
EP0826764A3 (fr
EP0826764A2 (fr
Inventor
Steffen Dr. Sonnenberg
Peter Wörner
Ulrich Dr. Harder
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.)
Dragoco Gerberding and Co GmbH
Symrise AG
Original Assignee
Haarmann and Reimer GmbH
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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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms

Definitions

  • the invention relates to substituted 2-carbonylbenzofurans and substituted 2-carbonyl-2,3-dihydrobenzofurans in fragrance compositions.
  • the compounds (I) are either known or can be prepared analogously to known processes.
  • the 2-carbonylbenzofurans (IV) can be prepared according to the following scheme:
  • crown ethers as phase transfer catalysts gives similar 2-carbonylbenzofurans in yields of about 53% (RB Gammill and SA Nash, J. Org. Chem. 51 (1985), 3116).
  • Another method for preparing the 2-carbonylbenzofurans (IV) is the gentle acylation of 2- (trimethylsilyl) benzofuran compounds starting from the corresponding benzofuran derivatives according to M. Gill in Tetrahedron 40 (1984), 621.
  • the 2-carbonyl-2,3-dihydrobenzofurans of the formula can be prepared by reduction from the above-mentioned 2-carbonylbenzofurans (IV), for example by hydrogenation in ethanol using hydrogen in the presence of a Pd catalyst and subsequent oxidation with pyridinium chlorochromate in dichloromethane.
  • the compounds (I) to be used according to the invention have interesting ones Fragrance properties:
  • 2-acetylbenzofuran in addition to the usual, is almond and flowery Smell also has a fine anthranil-like and coumarin note, which in Compositions through their fullness and softness an excellent harmonization causes.
  • the 2-carbonyl-2,3-dihydrobenzofurans are generally related to their olfactory Properties similar to the 2-carbonylbenzofurans used. Yet the 2-carbonyl-2,3-dihydrobenzofurans have further grades: for example with 2-acetyl-2,3-dihydrobenzofuran also a green, melon-like and light floral smell present.
  • the 2-acetyl-2,3-dihydro-3-methylbenzofuran has a lily of the valley smell and has a high diffusion, which has a great impact in compositions generated.
  • the compounds (I) are notable for high stability towards the various acidic, neutral and acalic media.
  • a Solution of the compounds (I) in toluene in hydrochloric acid or in sodium hydroxide solution higher temperatures are stirred largely undamaged.
  • the compounds (I) to be used according to the invention are readily compatible with other fragrances in different, different proportions combine novel, interesting fragrance compositions, the amount 0.01 to 10 wt .-%, based on the whole Composition.
  • compositions can be used for perfuming of cosmetics such as creams, lotions, aerosols, toilet soaps, household products, such as cleaning agents and detergents, fabric softeners, disinfectants and textile treatment agents, the amount of fragrance compositions 0.1 to 40 wt .-%, preferably 0.5 to 20 wt .-%, based on the whole product.
  • compositions, application examples 1 to 4 are suitable preferably for fine perfuming of cosmetics such as creams, lotions, aerosols and toilet soaps.
  • Application example 1 Surname Parts by weight Linalylacet2011 70 lemon 50 Lemon oil Formosa / Java 3 Lavandin oil 30/32% Abrialis 70 Hydroxycitronellal 30 Geranium Ident Oil (African type) 50 Geraniol 70 30 benzyl 15 ⁇ -hexyl cinnamic aldehyde 15 Ylang ylang oil II 10 benzyl 100 isoamyl 100 anethole 2 anisalcohol 35 anisaldehyde 25 Ethyl vanillin (10% in DEP) 5 coumarin 30 Vetiver oil bourbon 10 Patchoulyöl 25 Sandel H&R 40 Mousse C Abs. Verit. (50% in TEC) 15 tonalide 20 Galaxolid (50% in DEP) 40 dipropylene 190 2-propionyl-3-methylbenzofuran 20 total 1000
  • TEC triethyl citrate
  • DPG dipropylene glycol
  • Phenylacetaldehyde 50% in DPG
  • lyral 270 Hydroxycitronellal 150 phenylethyl
  • Citronellol 60 ⁇ -hexyl cinnamic aldehyde 310 indole

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)
  • Furan Compounds (AREA)

Claims (9)

  1. Procédé pour parfumer des compositions cosmétiques ou des produits ménagers, caractérisé en ce que l'on ajoute à ces compositions ou produits une composition de parfum qui contient 0,01 à 10 % en poids, par rapport à la composition de parfum totale, d'un composé de formule (I)
    Figure 00190001
    dans laquelle le trait interrompu représente une liaison présente ou non et
    R1 à R4
    représentent chacun, indépendamment les uns des autres, l'hydrogène, un groupe alkyle en C1-C3 ou alcoxy en C1-C3 et
    R5 et R6
    représentent chacun, indépendamment l'un de l'autre, l'hydrogène, un groupe alkyle en C1-C4 ou alcényle en C2-C4.
  2. Procédé selon la revendication 1, caractérisé en ce que les produits parfumés sont des crèmes, des lotions, des aérosols, des savons de toilette, des produits de nettoyage, des produits de lavage, des produits de rinçage adoucissants, des produits désinfectants ou des , produits pour le traitement des matières textiles.
  3. Procédé selon la revendication 1, le trait interrompu de la formule (I) représentant une liaison et R1 à R6 chacun, indépendamment les uns des autres, l'hydrogène ou un groupe alkyle en C1-C2.
  4. Procédé selon la revendication 1, le trait interrompu de la formule (I) ne représentant pas une liaison et R1 à R6 représentant chacun, indépendamment les uns des autres, l'hydrogène ou un groupe alkyle en C1-C2.
  5. Procédé selon la revendication 1, le trait interrompu de la formule (I) représentant une liaison et R1 à R4 l'hydrogène, R5 et R6 représentant chacun, indépendamment l'un de l'autre, l'hydrogène ou un groupe alkyle en C1-C2.
  6. Procédé selon revendication la 1, le trait interrompu de la formule (I) ne représentant pas une liaison, R1 à R4 représentant l'hydrogène et R5 et R6, chacun, indépendamment l'un de l'autre, l'hydrogène ou un groupe alkyle en C1-C2.
  7. Procédé selon revendication 1, le trait interrompu de la formule (I) représentant une liaison, R1 à R4 l'hydrogène et R5 et R6, chacun, indépendamment l'un de l'autre, un groupe alkyle en C1-C2.
  8. Procédé selon revendication 1, le trait interrompu de la formule (I) représentant une liaison, R1 à R4 l'hydrogène, R5 un groupe alkyle en C1-C2 et R6 l'hydrogène ou un groupe alkyle en C1-C4.
  9. Composition de parfum contenant 0,01 à 10 % en poids d'un composé de formule (I) selon revendication 1.
EP97114337A 1996-09-03 1997-08-20 Compositions parfumantes contenant des 2-acétylbenzofuranes substitués Expired - Lifetime EP0826764B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19635655 1996-09-03
DE19635655A DE19635655A1 (de) 1996-09-03 1996-09-03 Verwendung substituierter 2-Acetylbenzofurane als Riechstoffe

Publications (3)

Publication Number Publication Date
EP0826764A2 EP0826764A2 (fr) 1998-03-04
EP0826764A3 EP0826764A3 (fr) 2000-04-19
EP0826764B1 true EP0826764B1 (fr) 2003-02-26

Family

ID=7804455

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97114337A Expired - Lifetime EP0826764B1 (fr) 1996-09-03 1997-08-20 Compositions parfumantes contenant des 2-acétylbenzofuranes substitués

Country Status (4)

Country Link
US (1) US5972878A (fr)
EP (1) EP0826764B1 (fr)
JP (1) JPH1088181A (fr)
DE (2) DE19635655A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7763238B2 (en) * 2002-01-16 2010-07-27 Monell Chemical Senses Center Olfactory adaptation and cross-adapting agents to reduce the perception of body odors
DE602004029453D1 (de) * 2003-03-21 2010-11-18 Pho Derma Inc Auf licht reagierende duftstoffe
CN104066828B (zh) * 2012-01-18 2017-06-06 宝洁公司 香料体系
CN103508987A (zh) * 2012-06-27 2014-01-15 中国科学院大连化学物理研究所 一种合成2,3-二取代苯并二氢呋喃的方法
US9212336B2 (en) * 2013-10-18 2015-12-15 International Flavors & Fragrances Inc. 3-methyl-benzofuran-5-ol and its use in perfume compositions
CN104672247A (zh) * 2013-11-28 2015-06-03 中国科学院大连化学物理研究所 一种合成2,3-二取代苯并二氢呋喃的方法
DE102013226600A1 (de) * 2013-12-19 2015-06-25 Henkel Ag & Co. Kgaa Luftpflege- und Reinigungsmittel enthaltend CNGA2-Antagonisten
DE102013226602A1 (de) * 2013-12-19 2015-06-25 Henkel Ag & Co. Kgaa Verwendung von CNGA2-Agonisten zur Verstärkung der olfaktorischen Wirkung eines Riechstoffs
CA2956623C (fr) 2014-07-30 2020-10-27 Georgia-Pacific Consumer Products Lp Distributeurs d'assainisseur d'air, cartouches, systemes et procedes associes

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE553621A (fr) * 1956-12-21 1960-01-15 Laboratoires Labaz Soc D Coumarones substitutees et procedes pour leur preparation.
FR1377324A (fr) * 1963-07-24 1964-11-06 Ct De Rech S De Pont A Mousson Procédé et dispositif pour former un emboîtement à l'extrémité d'un tuyau et tuyau en résultant
DE1492403A1 (de) * 1965-03-30 1969-12-04 Merck Ag E UV-Lichtschutzmittel fuer kosmetische Zwecke
US3513239A (en) * 1967-03-15 1970-05-19 Smithkline Corp Pharmaceutical compositions containing 2-aminoalkyl coumaran derivatives and methods of treating depression therewith
BE795672A (fr) * 1972-02-21 1973-08-20 Ugine Kuhlmann Nouveaux composes utilisables comme medicaments
US3917871A (en) * 1972-04-13 1975-11-04 Firmenich & Cie Flavoring agent
US4006234A (en) * 1974-12-18 1977-02-01 American Cyanamid Company Substituted 2-benzofuranyl propenones as anti-tubercular agents
DE3017068A1 (de) * 1980-05-03 1981-11-05 Haarmann & Reimer Gmbh, 3450 Holzminden Verwendung von di- und tetrahydrobenzofuranderivaten als riech- und aromastoffe sowie diese enthaltende riech- und aromastoffkompositionen
FR2634203A1 (fr) * 1988-07-13 1990-01-19 Inst Rech Controles Techn Dihydro-2,3-benzofurannes a odeur musquee et parfums et produits parfumes les contenant
US5250441A (en) * 1993-01-08 1993-10-05 Vogt Peter F Method for kit for estimating the amount of methyl anthranilate
WO1995030667A1 (fr) * 1994-05-09 1995-11-16 Firmenich S.A. Utilisation de dihydrobenzofuranones a titre d'ingredients parfumants

Also Published As

Publication number Publication date
DE59709372D1 (de) 2003-04-03
EP0826764A3 (fr) 2000-04-19
DE19635655A1 (de) 1998-03-05
JPH1088181A (ja) 1998-04-07
US5972878A (en) 1999-10-26
EP0826764A2 (fr) 1998-03-04

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