EP0826764A2 - Utilisation de 2-acétylbenzofuranes comme agents parfumants - Google Patents

Utilisation de 2-acétylbenzofuranes comme agents parfumants Download PDF

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Publication number
EP0826764A2
EP0826764A2 EP97114337A EP97114337A EP0826764A2 EP 0826764 A2 EP0826764 A2 EP 0826764A2 EP 97114337 A EP97114337 A EP 97114337A EP 97114337 A EP97114337 A EP 97114337A EP 0826764 A2 EP0826764 A2 EP 0826764A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
hydrogen
bond
acetyl
mol
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
EP97114337A
Other languages
German (de)
English (en)
Other versions
EP0826764A3 (fr
EP0826764B1 (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
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 Haarmann and Reimer GmbH filed Critical Haarmann and Reimer GmbH
Publication of EP0826764A2 publication Critical patent/EP0826764A2/fr
Publication of EP0826764A3 publication Critical patent/EP0826764A3/fr
Application granted granted Critical
Publication of EP0826764B1 publication Critical patent/EP0826764B1/fr
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
    • C11B9/0069—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 as fragrances.
  • the compounds (I) are either known or can be prepared analogously to known processes.
  • the 2-carbonylbenzofurans (IV) can be produced 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 anthranilate and coumarin note, which is 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 the 2-aceryl-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 50 wt .-%, preferably 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, where 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 Linalyl acetate 70 Lemon oil 50 Lemon oil Formosa / Java 3rd Lavandin oil 30/32% Abrialis 70 Hydroxycitronellal 30th Geranium Ident Oil (African type) 50 Geraniol 70 30th Benzyl acetate 15 ⁇ -hexyl cinnamaldehyde 15 Ylang ylang oil II 10th Benzyl salicylate 100 Isoamyl salicylate 100 Anethole 2nd Anise alcohol 35 Anisaldehyde 25th Ethyl vanillin (10% in DEP) 5 Coumarin 30th Vetiver oil bourbon 10th Patchouly oil 25th Sandel H&R 40 Mousse C Abs.
  • Example of use 2 Surname Parts by weight Styrolylacetate 4th Dihydromyrcenol 4th Lemon oil 20th ⁇ -undecalactone 2nd Linalool 10th Phenylethyl alcohol 8th Citronellol 6 Benzyl acetate 15 Hedion 20th ⁇ -hexyl cinnamaldehyde 100 Jasmine base # 151 25th Ylangbase # 10372MT 18th Isoraldein 70 50 Eugenol 4th Isoeugenol 1 Vanillin 10th Coumarin 10th Oryclone 30th Patchouly oil 3rd Sandel 80 50 Galaxolid (50% in DEP) 20th Bergamott Identöl 100 Diethyl phthalate 465 2-acetylbenzofuran 25th total 1000 In this feminine composition, the use of 2-acetylbenzofuran increases the volume, the diffusion and increases the fixation.
  • 2-acetyl-3-methylbenzofuran increases the adhesion and gives the composition a constant floral impression in the aftertaste.
  • DPG dipropylene glycol
  • Example of use 4 Surname Parts by weight Phenylacetaldehyde (50% in DPG) 20th Lyral 270 Hydroxycitronellal 150 Phenylethyl alcohol 60 Citronellol 60 ⁇ -hexyl cinnamaldehyde 310 Indole 120 2-acetyl-2,3-dihydrobenzofuran 10th total 1000
  • the use of 2-acetyl-2,3-dihydrobenzofuran adds a fresh neroli-like note to the fragrance and enhances the natural character of this lily of the valley composition.

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)
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 true EP0826764A2 (fr) 1998-03-04
EP0826764A3 EP0826764A3 (fr) 2000-04-19
EP0826764B1 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)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004084853A2 (fr) * 2003-03-21 2004-10-07 Pho Derma, Inc. Parfums photosensibles
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
EP2862918A1 (fr) * 2013-10-18 2015-04-22 International Flavors & Fragrances Inc. 3-methyl-benzofuran-5-ol et son utilisation dans des compositions de parfum
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
WO2015091055A1 (fr) * 2013-12-19 2015-06-25 Henkel Ag & Co. Kgaa Produits désodorisants d'intérieur et nettoyants contenant des antagonistes de cnga2
WO2015091056A1 (fr) * 2013-12-19 2015-06-25 Henkel Ag & Co. Kgaa Utilisation d'agonistes de cnga2 pour renforcer l'effet olfactif d'une matière odorante

Families Citing this family (3)

* 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
CN104066828B (zh) * 2012-01-18 2017-06-06 宝洁公司 香料体系
CA2956623C (fr) 2014-07-30 2020-10-27 Georgia-Pacific Consumer Products Lp Distributeurs d'assainisseur d'air, cartouches, systemes et procedes associes

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1063158A (en) * 1965-03-30 1967-03-30 Merck Ag E Aroyl benzofuran derivatives
US3917871A (en) * 1972-04-13 1975-11-04 Firmenich & Cie Flavoring agent
EP0041122A2 (fr) * 1980-05-03 1981-12-09 Haarmann & Reimer Gmbh Agents parfumants contenant de dérivés des di- et tétrahydrofuranes
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
WO1995030667A1 (fr) * 1994-05-09 1995-11-16 Firmenich S.A. Utilisation de dihydrobenzofuranones a titre d'ingredients parfumants

Family Cites Families (6)

* 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
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
US4006234A (en) * 1974-12-18 1977-02-01 American Cyanamid Company Substituted 2-benzofuranyl propenones as anti-tubercular agents
US5250441A (en) * 1993-01-08 1993-10-05 Vogt Peter F Method for kit for estimating the amount of methyl anthranilate

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1063158A (en) * 1965-03-30 1967-03-30 Merck Ag E Aroyl benzofuran derivatives
US3917871A (en) * 1972-04-13 1975-11-04 Firmenich & Cie Flavoring agent
EP0041122A2 (fr) * 1980-05-03 1981-12-09 Haarmann & Reimer Gmbh Agents parfumants contenant de dérivés des di- et tétrahydrofuranes
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
WO1995030667A1 (fr) * 1994-05-09 1995-11-16 Firmenich S.A. Utilisation de dihydrobenzofuranones a titre d'ingredients parfumants

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004084853A2 (fr) * 2003-03-21 2004-10-07 Pho Derma, Inc. Parfums photosensibles
WO2004084853A3 (fr) * 2003-03-21 2005-02-24 Pho Derma Inc Parfums photosensibles
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
EP2862918A1 (fr) * 2013-10-18 2015-04-22 International Flavors & Fragrances Inc. 3-methyl-benzofuran-5-ol et son utilisation dans des compositions de parfum
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
WO2015091055A1 (fr) * 2013-12-19 2015-06-25 Henkel Ag & Co. Kgaa Produits désodorisants d'intérieur et nettoyants contenant des antagonistes de cnga2
WO2015091056A1 (fr) * 2013-12-19 2015-06-25 Henkel Ag & Co. Kgaa Utilisation d'agonistes de cnga2 pour renforcer l'effet olfactif d'une matière odorante

Also Published As

Publication number Publication date
DE59709372D1 (de) 2003-04-03
EP0826764A3 (fr) 2000-04-19
DE19635655A1 (de) 1998-03-05
EP0826764B1 (fr) 2003-02-26
JPH1088181A (ja) 1998-04-07
US5972878A (en) 1999-10-26

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