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WO1998009933A1 - 2-cyclohexyl-propan-1-ol substitue et son utilisation dans des compositions pour parfums - Google Patents

2-cyclohexyl-propan-1-ol substitue et son utilisation dans des compositions pour parfums Download PDF

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Publication number
WO1998009933A1
WO1998009933A1 PCT/GB1997/002342 GB9702342W WO9809933A1 WO 1998009933 A1 WO1998009933 A1 WO 1998009933A1 GB 9702342 W GB9702342 W GB 9702342W WO 9809933 A1 WO9809933 A1 WO 9809933A1
Authority
WO
WIPO (PCT)
Prior art keywords
propan
alcohol
odour
cyclohexyl
perfume
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.)
Ceased
Application number
PCT/GB1997/002342
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English (en)
Other versions
WO1998009933A8 (fr
Inventor
David Munro
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.)
Givaudan Nederland Services BV
Original Assignee
Quest International BV
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 Quest International BV filed Critical Quest International BV
Priority to AU40268/97A priority Critical patent/AU4026897A/en
Priority to EP97937748A priority patent/EP0925269A1/fr
Priority to JP10512333A priority patent/JP2001500854A/ja
Priority to PCT/GB1997/002342 priority patent/WO1998009933A1/fr
Priority to BR9711654A priority patent/BR9711654A/pt
Publication of WO1998009933A1 publication Critical patent/WO1998009933A1/fr
Anticipated expiration legal-status Critical
Publication of WO1998009933A8 publication Critical patent/WO1998009933A8/fr
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/13—Monohydroxylic alcohols containing saturated rings
    • C07C31/133—Monohydroxylic alcohols containing saturated rings monocyclic
    • C07C31/135—Monohydroxylic alcohols containing saturated rings monocyclic with a five or six-membered rings; Naphthenic alcohols
    • 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • This invention concerns a novel substituted 2 -cyclohexyl - propan-1-ol and its use in perfumes and perfumed products.
  • CH 652 113 (Firmenich) describes 2- (4-ter .butyl-cyclohexyl) -propan-1-ol and its use in perf mes.
  • the compound has musky, woody and sandalwood odour notes and has a heavy and oriental character.
  • the 4-isopropyl analogue is described in S. Arctander, Perfume and Flavor Chemicals as having a rosy, balsamic, mild, floral and woody odour.
  • Dialkyl-substituted 2-cyclohexyl-propan-l-ols in which the alkyl groups are Cl- C4 are described in EP 0 328 116 as compounds with a woody, floral, vetiverol-like odour.
  • 1- (4 -tert . alkyl -cyclohexyl) -ethanols and propan-1-ols are known from GB 1 476 720 as compounds with a sandalwood odour. It is noted therein that the lowest homologue 1- (4-tert .butyl-cyclohexyl) -ethanol (having 12 carbon atoms) has the highest odour strength and intensity and that the odour diminishes with increasing molecular weight. Compounds with more than 15 carbon atoms were considered to be too weak to have a detectable sandalwood odour .
  • the present invention provides 2- (4-tert . amylcyclohexyl) - propan-1-ol of the formula below as well as perfumes and perfumed products comprising this compound in olfactively effective amounts.
  • the novel substituted 2-cyclohexyl-propan-l-ol of the invention is a powerful fragrance material with an odour which has the unusual combination of strong sandalwood and muguet odour notes.
  • the odour is much fresher and less heavy than the odour of its tert. butyl homologue known from CH 652 113.
  • the odour is unexpectedly strong in spite of the fact that the compound has 14 carbon atoms.
  • the unusual combination of odour notes provides new creative opportunities in perfumery.
  • the alcohol according to the invention may be used as such to impart, strengthen or improve the odour of a wide variety of products, or it may be used as a component of a perfume to contribute its odour character to the overall odour of such perfume.
  • a perfume is intended to mean a mixture of fragrance materials, if desired mixed with or dissoved in a suitable solvent or mixed with a solid substrate, which is used to impart a desired odour to the skin and/or any product for which an agreeable odour is indispensible or desirable.
  • Such products are: fabric washing powders, washing liquids, fabric softeners and other fabric care products; detergents and household cleaning, scouring and disinfection products; air fresheners, room sprays and pomanders; soaps, bath and shower gels, shampoos, hair conditioners and other personal cleansing products; cosmetics such as creams, ointments, toilet waters, preshave, aftershave, skin and other lotions, talcum powders, body deodorants and antiperspirants, etc.
  • fragrance materials which can be advantageously combined with the alcohol according to the invention in a perfume are, for example, natural products such as extracts, essential oils, absolutes, resinoids, resins, concretes etc., but also synthetic materials such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ketals, nitriles, etc., including saturated and unsaturated compounds, aliphatic, carbocyclic and heterocyclic compounds.
  • fragrance materials are mentioned, for example, in S. Arctander, Perfume and Flavor Chemicals (Montclair, N.J., 1969) , in S. Arctander, Perfume and Flavor Materials of Natural Origin (Elizabeth, N.J., 1960) and in "Flavor and Fragrance Materials - 1991", Allured Publishing Co. Wheaton, 111. USA.
  • fragrance materials which can be used in combination with the alcohol according to the invention are: geraniol, geranyl acetate, linalol, linalyl acetate, tetrahydrolinalol, citronellol, citronellyl acetate, dihydromyrcenol , dihydromyrcenyl acetate, tetrahydro- myrcenol, terpineol, terpinyl acetate, nopol, nopyl acetate, 2-phenylethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate, benzyl benzoate, amyl salicylate, dimethylbenzyl-carbinol, trichloromethylphenylcarbinyl acetate, p-tert-butyl- cyclohexyl acetate, isononyl
  • Solvents which can be used for perfumes which contain the alcohol according to the invention are, for example: ethanol, isopropanol, diethyleneglycol monoethyl ether, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.
  • the quantities in which the alcohol according to the invention can be used in perfumes or in products to be perfumed may vary within wide limits and depend, inter alia, on the nature of the product, on the nature and the quantity of the other components of the perfume in which the compound is used and on the olfactive effect desired. It is therefore only possible to specify wide limits, which, however, provide sufficient information for the specialist in the art to be able to use the alcohol according to the invention for his specific purpose.
  • an amount of 0.01% by weight or more of the alcohol according to the invention will generally have a clearly perceptible olfactive effect.
  • the amount is 0.1 - 80% by weight, more preferably at least 1% .
  • the amount of the alcohol according to the invention present in products will generally be at least 10 ppm by weight, preferably at least 100 ppm, more preferably at least 1000 ppm.
  • levels of up to about 20% by weight may be used in particular cases, depending on the product to be perfumed.
  • the alcohol occurs in a cis and a trans isomer, and the invention covers both separately as well as all mixtures thereof.
  • the alcohol may be conveniently prepared from 4-tert.amyl- cyclohexanone by reaction with triethyl-2-phosphono- propionate followed by catalytic reduction and reduction with LiAlH 4 .
  • it may be prepared by Friedel- Crafts alkylation of benzene with isoamylene followed by alkylation of tert . amylbenzene with propylene oxide and catalytic reduction of 2- (4-tert .amylphenyl) -propan-1-ol .
  • the reaction products consist of a mixture of the cis and trans isomers, which may be separated by routine methods. However, for the use as fragrance material such separation is unnecessary.
  • reaction mixture was stirred for a further hour.
  • a 1ml aliquot was quenched in 4ml of a l/l diethyl ether/water mixture, and the organic layer analysed by both TLC (silica stationary phase, chloroform eluent) , and by packed-column glc [SE52; 100-200C, 4C/min] .
  • TLC sica stationary phase, chloroform eluent
  • glc packed-column glc [SE52; 100-200C, 4C/min] .
  • glc recorded a 94.6% : 4.2% mixture of isomers, assigned cis- and trans-ethyl 2- (4- ertiary-amyl- cyclohexylidenyl) -propionate .
  • Most ethanol was removed under reduced pressure.
  • Ethyl 2- (4- tertiary-amylcyclohexylidenyl) propionate (60. Og , 0.238 moles) was dissolved in ethanol (250ml), within a 1 litre Buchi autoclave, and 5% Pd/C (6g) added.
  • the reaction mixture was stirred at ambient temperature under a hydrogen pressure of 6bar for 6 hours, monitoring the reaction by packed-column glc (SE52; 100-200°C, 4C/minute) .
  • ethyl 2- (4- tertiary-amylcyclohexyl) propionate (llOg, 0.43 moles) was added dropwise under nitrogen to a stirred suspension of lithium aluminium hydride (30g, 0.79 moles) in tetrahydrofuran (300ml) , maintaining the temperature below 30°C by ice-water cooling. After complete addition, the reaction mixture was cooled to 0°C and 50ml ethyl acetate was carefully added dropwise.
  • a sandalwood base with a fresh floral note was prepared according to the following recipe: relative amounts by volume

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne le nouveau composé 2-(4-tert.butylcyclohexyl)-propan-1-ol et des parfums ainsi que certains produits parfumés contenant ce composé. Il s'agit d'une matière odorante puissante dégageant de fortes effluves de bois de Santal et de muguet. Les parfums en question contiennent de préférence au moins 0,01 % en poids de ce composé.
PCT/GB1997/002342 1996-09-02 1997-08-29 2-cyclohexyl-propan-1-ol substitue et son utilisation dans des compositions pour parfums Ceased WO1998009933A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU40268/97A AU4026897A (en) 1996-09-02 1997-08-29 Substituted 2-cyclohexyl-propan-1-ol and its use in perfume compositions
EP97937748A EP0925269A1 (fr) 1996-09-02 1997-08-29 2-cyclohexyl-propan-1-ol substitue et son utilisation dans des compositions pour parfums
JP10512333A JP2001500854A (ja) 1996-09-02 1997-08-29 置換２―シクロヘキシル―プロパン―１―オールおよび香料組成物におけるその用途
PCT/GB1997/002342 WO1998009933A1 (fr) 1996-09-02 1997-08-29 2-cyclohexyl-propan-1-ol substitue et son utilisation dans des compositions pour parfums
BR9711654A BR9711654A (pt) 1996-09-02 1997-08-29 Alcool perfume e produto de perfume

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP96306332 1996-09-02
EP96306332.6 1996-09-02
PCT/GB1997/002342 WO1998009933A1 (fr) 1996-09-02 1997-08-29 2-cyclohexyl-propan-1-ol substitue et son utilisation dans des compositions pour parfums

Publications (2)

Publication Number Publication Date
WO1998009933A1 true WO1998009933A1 (fr) 1998-03-12
WO1998009933A8 WO1998009933A8 (fr) 1999-06-10

Family

ID=8225071

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1997/002342 Ceased WO1998009933A1 (fr) 1996-09-02 1997-08-29 2-cyclohexyl-propan-1-ol substitue et son utilisation dans des compositions pour parfums

Country Status (5)

Country Link
EP (1) EP0925269A1 (fr)
JP (1) JP2001500854A (fr)
AU (1) AU4026897A (fr)
BR (1) BR9711654A (fr)
WO (1) WO1998009933A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0976714A1 (fr) * 1998-07-06 2000-02-02 Quest International B.V. Addition de cétones à des alcénes
EP1029845A1 (fr) * 1999-02-15 2000-08-23 Quest International B.V. 2-(4-Tert-pentylcyclohexyl)acétaldehyde et son utilisation comme agent parfumant
EA017534B1 (ru) * 2009-08-04 2013-01-30 Общество С Ограниченной Ответственностью "Домодедовский Опытный Машиностроительный Завод" Насадка гидромонитора устройства нижнего слива для устройства разогрева и слива высоковязких и застывших продуктов методом замещения

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH652113A5 (en) * 1982-05-03 1985-10-31 Firmenich & Cie Cycloaliphatic alcohol and its use as a perfuming ingredient
EP0328116A1 (fr) * 1988-02-10 1989-08-16 Kao Corporation Propan-1-ol-2-(alkyle-cyclohexyle), procédé pour sa fabrication et composition de parfum le contenant
JPH02188549A (ja) * 1988-09-06 1990-07-24 Kao Corp ２−（アルキルシクロヘキシル）−１−プロパナール類及びこれを含有する香料組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH652113A5 (en) * 1982-05-03 1985-10-31 Firmenich & Cie Cycloaliphatic alcohol and its use as a perfuming ingredient
EP0328116A1 (fr) * 1988-02-10 1989-08-16 Kao Corporation Propan-1-ol-2-(alkyle-cyclohexyle), procédé pour sa fabrication et composition de parfum le contenant
JPH02188549A (ja) * 1988-09-06 1990-07-24 Kao Corp ２−（アルキルシクロヘキシル）−１−プロパナール類及びこれを含有する香料組成物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 014, no. 459 (C - 0767) 4 October 1990 (1990-10-04) *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0976714A1 (fr) * 1998-07-06 2000-02-02 Quest International B.V. Addition de cétones à des alcénes
WO2000001648A3 (fr) * 1998-07-06 2000-04-13 Quest Int Preparation de cetones macrocycliques par addition des cetones a des alcenes
EP1029845A1 (fr) * 1999-02-15 2000-08-23 Quest International B.V. 2-(4-Tert-pentylcyclohexyl)acétaldehyde et son utilisation comme agent parfumant
EA017534B1 (ru) * 2009-08-04 2013-01-30 Общество С Ограниченной Ответственностью "Домодедовский Опытный Машиностроительный Завод" Насадка гидромонитора устройства нижнего слива для устройства разогрева и слива высоковязких и застывших продуктов методом замещения

Also Published As

Publication number Publication date
BR9711654A (pt) 1999-08-24
WO1998009933A8 (fr) 1999-06-10
JP2001500854A (ja) 2001-01-23
EP0925269A1 (fr) 1999-06-30
AU4026897A (en) 1998-03-26

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