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WO2011073843A1 - Alcools odorants - Google Patents

Alcools odorants Download PDF

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Publication number
WO2011073843A1
WO2011073843A1 PCT/IB2010/055578 IB2010055578W WO2011073843A1 WO 2011073843 A1 WO2011073843 A1 WO 2011073843A1 IB 2010055578 W IB2010055578 W IB 2010055578W WO 2011073843 A1 WO2011073843 A1 WO 2011073843A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
methyl
formula
hydrogen atom
cyclohexanol
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/IB2010/055578
Other languages
English (en)
Inventor
Robert Moretti
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 WO2011073843A1 publication Critical patent/WO2011073843A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/06—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
    • C07C35/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings with unsaturation only outside the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/647—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring
    • 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
    • C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
    • 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
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • 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

  • the present invention relates to the field of perfumery. More particularly, it concerns the use of some derivatives of 2-isobutyl-cyclohexanol or cyclopentanol as defined herein below. These derivatives are useful to confer odor notes of the white flower type.
  • the present invention concerns some of the compounds as well as the compositions or articles containing said compounds.
  • n 0 or 1 ;
  • R 1 represents a hydrogen atom or a methyl or ethyl group
  • R 2 represents a hydrogen atom or a methyl or ethyl group
  • R 3 represents a hydrogen atom or a linear Ci_3 alkyl group .
  • each R 4 represents a hydrogen atom or a methyl or ethyl group; provided that both R 4 have in total, i.e. all together, 0, 1 or 2 carbon atoms ;
  • n is 1.
  • the dotted line represents a carbon-carbon single bond.
  • R 1 represents a hydrogen atom or a methyl group.
  • R represents a hydrogen atom or a methyl group.
  • R 3 represents a a methyl, ethyl or n-propyl group, preferably a methyl or ethyl group.
  • each R 4 represents a hydrogen atom or a methyl group.
  • said compound (I) has an even total number of carbon atoms, in particular are Cio, C1 2 or C14, compounds.
  • the invention's compound when n is 0 the invention's compound is preferably do, while when n is 1 the invention's compound is preferably C 12 or C 14 .
  • the invention's compound has also the advantage of conferring also odor notes of the indol/naphthalene type.
  • n the dotted line, R 1 , R 2 and R 4 have the meaning indicated in formula (I), and R 5 represents a hydrogen atom or a methyl or ethyl group;
  • the invention's compound (II) has a even total number of carbon atoms, in particular are do, C 12 or C 14 , compounds.
  • the invention's compound when n is 0 the invention's compound is preferably do, while when n is 1 the invention's compound is preferably C 12 or C 14 .
  • 2-(l,2-dimethylbutyl)-cyclohexanol which possesses a jasmine/lily of the valley odor, with a very natural indole/naphthalene character.
  • the overall odor is in between that of linalool (Arctander N° 1803) and that of indole (Arctander N° 1772).
  • the odor of this compound is devoid of the herbaceous aspect of the rose or waxy/oily notes.
  • This compound is quite interesting since it allies together the natural floral aspect of linalool and a well balanced indole/jasminic note, the latter having an animal character much less pronounced than the note of indole itself.
  • 2-[(2E)-2-methyl-2-butenyl]cyclopentanol which possesses a floral, lilac/liUy of the valley type of odor with a bottom note of the indole, peppery type.
  • the compounds of formula (I) are : 2-(l,2-dimethylbutyl)-cyclohexanol or 2-[(2E)-2-methyl-2- butenyl] cyclopentanol.
  • the odor of the invention's compounds when compared with that of the prior art compounds, distinguishes itself by having a white flower character, as well as by lacking the herbaceous aspect of the rose or waxy/oily notes of the prior art compounds, despite the peculiar teaching of the prior art cited above. Said differences lend the invention's compounds and the prior art compounds to be each suitable for different uses, i.e. to impart different organoleptic impressions. Moreover, the invention's compounds have the great advantage of allowing to impart indole type notes without the coloring problems typical of indole itself, and this even at very high concentrations.
  • the invention concerns the use of a compound of formula (I) as perfuming ingredient.
  • it concerns a method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of at least a compound of formula (I).
  • use of a compound of formula (I) it has to be understood here also the use of any composition containing compound (I) and which can be advantageously employed in perfumery industry as active ingredients.
  • compositions which in fact can be advantageously employed as perfuming ingredient, are also an object of the present invention.
  • Another object of the present invention is a perfuming composition
  • a perfuming composition comprising :
  • the perfuming ingredient is of formula (I), wherein R 1 , R 2 , R 3 and R 4 are as defined above, and when n is 0 the invention's compound is preferably do, while when n is 1 the invention's compound is preferably C 12 or C 14 .
  • Said perfuming ingredient in particular, can be also a compound of formula (II).
  • perfumery carrier we mean here a material which is practically neutral from a perfumery point of view, i.e. that does not significantly alter the organoleptic properties of perfuming ingredients.
  • Said carrier may be a liquid or a solid.
  • liquid carrier one may cite, as non-limiting examples, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery.
  • a solvent and a surfactant system i.e. a solvent and a surfactant system
  • a solvent commonly used in perfumery A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive.
  • solvents such as dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2- ethoxyethoxy)-l-ethanol or ethyl citrate, which are the most commonly used.
  • ethanol can also be commonly used as solvent.
  • solid carrier one may cite, as non-limiting examples, absorbing gums or polymers, or yet encapsulating materials.
  • examples of such materials may comprise wall- forming and plasticizing materials, such as mono, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins, or yet the materials cited in reference texts such as H. Scherz, Hydrokolloids : Stabilisatoren, Dickungs- und Geherstoff in Struktur, Band 2 der committee Strukturchemie, claritat, Behr's VerlagGmbH & Co., Hamburg, 1996.
  • the encapsulation is a well known process to a person skilled in the art, and may be performed, for instance, using techniques such as spray-drying, agglomeration or yet extrusion ; or consists of a coating encapsulation, including coacervation and complex coacervation techniques.
  • perfumery base we mean here a composition comprising at least one perfuming co-ingredient.
  • perfuming co-ingredient is not of the formula (I).
  • perfuming co-ingredient it is meant here a compound, which is used in perfuming preparation or composition to impart a hedonic effect.
  • co-ingredient to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor.
  • perfuming co-ingredients present in the base do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of its general knowledge and according to intended use or application and the desired organoleptic effect.
  • these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S.
  • compositions which comprise both a perfumery carrier and a perfumery base can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol (origin: Dow Chemical Company).
  • Isopar oil/ethanol mixtures
  • glycol ethers and glycol ether esters such as those known under the trademark Dowanol (origin: Dow Chemical Company).
  • perfumery adjuvant we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc.
  • additional added benefit such as a color, a particular light resistance, chemical stability, etc.
  • An invention's composition consisting of at least one compound of formula (I) and at least one perfumery carrier represents a particular embodiment of the invention as well as a perfuming composition comprising at least one compound of formula (I), at least one perfumery carrier, at least one perfumery base, and optionally at least one perfumery adjuvant.
  • any mixture resulting directly from a chemical synthesis e.g. a reaction medium without an adequate purification, in which the compound of the invention would be involved as a starting, intermediate or end-product could not be considered as a perfuming composition according to the invention as far as said mixture do not provide the inventive compound in a suitable form for perfumery.
  • Unpurified reaction mixtures are generally excluded from the present invention unless otherwise specified.
  • the invention's compound can also be advantageously used in all the fields of modern perfumery, i.e. fine or functional perfumery, to positively impart or modify the odor of a consumer product into which said compound (I) is added. Consequently, a perfumed consumer product comprising :
  • a perfumed consumer product comprises the functional formulation, as well as optionally additional benefit agents, corresponding to a perfume compatible consumer product, e.g. a detergent or an air freshener, and an olfactive effective amount of at least one invention's compound.
  • Non-limiting examples of suitable fragrance goods can be a perfume, such as a fine perfume, a cologne or an after-shave lotion; a fabric care product, such as a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, papers, or a bleaches ; a body-care product, such as a hair care product (e.g. a shampoo, a coloring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream or a deodorant or antiper spirant), or a skin-care product (e.g.
  • a hair care product e.g. a shampoo, a coloring preparation or a hair spray
  • a cosmetic preparation e.g. a vanishing cream or a deodorant or antiper spirant
  • a skin-care product e.g.
  • a perfumed soap, shower or bath mousse, oils or gel, or an hygiene product such as a perfumed soap, shower or bath mousse, oils or gel, or an hygiene product
  • an air care product such as a an air freshener or a "ready to use” powdered air freshener
  • a home care product such as a wipe, a dish detergent or hard-surface detergent.
  • consumer product bases may represent an aggressive medium for the invention's compound, so that it may be necessary to protect the latter from premature decomposition, for example by encapsulation or by chemically bound it to another chemical which is suitable to release the invention ingredient upon a suitable external stimulus, such as an enzyme, light or a change of pH.
  • the proportions in which the compounds according to the invention can be incorporated into the various aforementioned articles or compositions vary within a wide range of values. These values are dependent on the nature of the article to be perfumed and on the desired organoleptic effect as well as the nature of the co -ingredients in a given base when the compounds according to the invention are mixed with perfuming co- ingredients, solvents or additives commonly used in the art.
  • concentrations are in the order of 0.1 % to 25 % by weight, or even more, of the compounds of the invention based on the weight of the composition into which they are incorporated. Concentrations lower than these, such as in the order of 0.01 % to 15% by weight, can be used when these compounds are incorporated into perfumed articles, percentage being relative to the weight of the article.
  • the invention's compounds can be prepared according to a method a described in
  • the ketone obtained in the previous step (5.00 g, 27.7 mmol) was dissolved in dry diethyl ether (10 ml) and added drop wise to a slurry of lithium aluminum hydride (1.32 g; 34.7 mmol) in dry diethyl ether (50 ml) under nitrogen, while cooling in an ice- water bath. After stirring for one more hour at 5°C, water (5 ml) was slowly added, followed by 5% aqueous sodium hydroxide (15 ml) and again water (5 ml). The mixture was warmed up to room temperature and stirred until a white slurry was obtained (15 minutes). Solid anhydrous sodium sulfate was added in order to dry the reaction mixture.
  • the alcohol obtained in the previous step (1 g; 5.5 mmol) was dissolved in methanol (20 ml) and hydrogenated at room temperature and 20-40 bar of hydrogen in presence of 5 % palladium on carbon (0.15 g) for 18 hours.
  • the catalyst was then filtered off, rinsed with methanol and the filtrate concentrated on the rotavapor.
  • the product was purified by bulb-to-bulb distillation.
  • Lithium aluminum hydride 2.85 g; 0.075 mol
  • Lithium aluminum hydride 3 g, 0.075 mol
  • the unsaturated ketone 2-(l,2-dimethyl-2-propenyl)cyclopentanone (14 g; 0.092 mol) was hydrogenated at room temperature and 30 bar hydrogen in cyclohexane (20 ml) in presence of 5 % palladium on carbon (0.3 g) for 5h30.
  • the product was isolated by bulb-to-bulb distillation.
  • Lithium aluminum hydride 1.64 g; 0.041 mol
  • Lithium aluminum hydride 2.9 g; 0.073 mol
  • a perfuming composition of the lilac type, was prepared by admixing the following ingredients :
  • a detergent's perfuming composition of the flowery, woody and musky type, was prepared by admixing the following ingredients : Ingredient Parts by weight

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne l'utilisation en tant que composant parfumant, visant à conférer des notes odorantes de type fleur blanche, de certains dérivés de 2-isobutyl-cyclohexanol ou cyclopentanol de formule (I) sous la forme de l'un quelconque de ses stéréoisomères ou un mélange de ceux-ci, et où le trait pointillé représente une simple ou double liaison carbone-carbone ; n est 0 ou 1 ; et R1 représente un atome d'hydrogène ou un groupe méthyle ou éthyle ; R2 représente un atome d'hydrogène ou un groupe méthyle ou éthyle ; R3 représente un atome d'hydrogène ou un groupe alkyle en C1-3 linéaire ; et chaque R4 représente un atome d'hydrogène ou un groupe méthyle ou éthyle ; à condition que les deux R4 aient au total, c'est-à-dire conjointement, 0, 1 ou 2 atomes de carbone.
PCT/IB2010/055578 2009-12-17 2010-12-03 Alcools odorants Ceased WO2011073843A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP09179706 2009-12-17
EP09179706.8 2009-12-17

Publications (1)

Publication Number Publication Date
WO2011073843A1 true WO2011073843A1 (fr) 2011-06-23

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ID=42197697

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2010/055578 Ceased WO2011073843A1 (fr) 2009-12-17 2010-12-03 Alcools odorants

Country Status (1)

Country Link
WO (1) WO2011073843A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104710283A (zh) * 2013-12-11 2015-06-17 国际香料和香精公司 新型环戊醇化合物
WO2020189670A1 (fr) 2019-03-18 2020-09-24 花王株式会社 PROCÉDÉ DE PRODUCTION DE CYCLOALCANONE α-ALLYLÉE
US11840542B2 (en) 2018-09-28 2023-12-12 Kao Corporation Method for producing cyclic enol ether compound

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2376105A (en) 1944-03-06 1945-05-15 Shell Dev Esters of thiocyano-substituted organic acids
EP0262388A2 (fr) * 1986-08-30 1988-04-06 BASF Aktiengesellschaft Dérivés du 2-tert.-butyl-4-méthyl-cyclohexanol, leur préparation et leur utilisation comme agents parfumants
JPH02131405A (ja) 1988-07-08 1990-05-21 T Hasegawa Co Ltd ゴキブリ忌避剤
WO2002014255A1 (fr) * 2000-08-14 2002-02-21 Quest International B.V. Production de 3-alkylcycloalcanols
US20030087775A1 (en) * 2001-08-27 2003-05-08 Koenraad Vanhessche Use of tertiary alcohols or esters as perfuming ingredients
DE10308047A1 (de) * 2003-02-26 2004-09-09 Symrise Gmbh & Co. Kg 4-Cyclohexyl-2-butanol als Riechstoff
WO2009093175A1 (fr) * 2008-01-22 2009-07-30 Firmenich Sa Composants parfumants conférant des notes de type sève et terre

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2376105A (en) 1944-03-06 1945-05-15 Shell Dev Esters of thiocyano-substituted organic acids
EP0262388A2 (fr) * 1986-08-30 1988-04-06 BASF Aktiengesellschaft Dérivés du 2-tert.-butyl-4-méthyl-cyclohexanol, leur préparation et leur utilisation comme agents parfumants
JPH02131405A (ja) 1988-07-08 1990-05-21 T Hasegawa Co Ltd ゴキブリ忌避剤
WO2002014255A1 (fr) * 2000-08-14 2002-02-21 Quest International B.V. Production de 3-alkylcycloalcanols
US20030087775A1 (en) * 2001-08-27 2003-05-08 Koenraad Vanhessche Use of tertiary alcohols or esters as perfuming ingredients
DE10308047A1 (de) * 2003-02-26 2004-09-09 Symrise Gmbh & Co. Kg 4-Cyclohexyl-2-butanol als Riechstoff
WO2009093175A1 (fr) * 2008-01-22 2009-07-30 Firmenich Sa Composants parfumants conférant des notes de type sève et terre

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
H. SCHERZ: "Hydrokolloids : Stabilisatoren, Dickungs- und Gehermittel in Lebensmittel", vol. 2, 1996, VERLAGGMBH & CO
J. O. C., vol. 62, 1997, pages 1523
PERFUMER & FLAVORIST, vol. 8, 1983, pages 68
S. ARCTANDER: "Perfume and Flavor Chemicals", 1969, MONTCLAIR

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104710283A (zh) * 2013-12-11 2015-06-17 国际香料和香精公司 新型环戊醇化合物
EP2902468A3 (fr) * 2013-12-11 2015-09-16 International Flavors & Fragrances Inc. Nouveaux composés cyclopentanol
US11840542B2 (en) 2018-09-28 2023-12-12 Kao Corporation Method for producing cyclic enol ether compound
WO2020189670A1 (fr) 2019-03-18 2020-09-24 花王株式会社 PROCÉDÉ DE PRODUCTION DE CYCLOALCANONE α-ALLYLÉE
US11685705B2 (en) 2019-03-18 2023-06-27 Kao Corporation Method for producing α-allylated cycloalkanone

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