[go: up one dir, main page]

EP3880163A1 - Utilisation de dérivés de 1-éthyl-4,4-diméthyl-cyclohexane comme substances odoriférantes - Google Patents

Utilisation de dérivés de 1-éthyl-4,4-diméthyl-cyclohexane comme substances odoriférantes

Info

Publication number
EP3880163A1
EP3880163A1 EP18807003.1A EP18807003A EP3880163A1 EP 3880163 A1 EP3880163 A1 EP 3880163A1 EP 18807003 A EP18807003 A EP 18807003A EP 3880163 A1 EP3880163 A1 EP 3880163A1
Authority
EP
European Patent Office
Prior art keywords
dimethylcyclohexyl
oil
ethyl acetate
compound
fragrance
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.)
Pending
Application number
EP18807003.1A
Other languages
German (de)
English (en)
Inventor
Bernd HÖLSCHER
Vijayanand CHANDRASEKARAN
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.)
Symrise AG
Original Assignee
Symrise AG
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 Symrise AG filed Critical Symrise AG
Publication of EP3880163A1 publication Critical patent/EP3880163A1/fr
Pending legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/37—Esters of carboxylic acids
    • 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
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • 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
    • C07C31/1355—Monohydroxylic alcohols containing saturated rings monocyclic with a five or six-membered rings; Naphthenic alcohols with a six-membered ring
    • 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
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/29—Saturated compounds containing keto groups bound to rings
    • C07C49/303—Saturated compounds containing keto groups bound to rings to a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12—Acetic acid esters
    • C07C69/14—Acetic acid esters of monohydroxylic compounds
    • 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
    • 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
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • 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 primarily to the use of 1- (4,4-dimethylcyclohexyl) ethanone, 1- (4,4-dimethylcyclohex-1-en-1-yl) ethanone, 1- (4,4-dimethylcyclohexyl) etha - nol, 1- (4,4-dimethylcyclohexyl) ethyl acetate and 1- (2-hydroxy-4,4-dimethylcyclohexyl) ethanone as an odorant, in particular with a floral and / or fruity odor characteristic.
  • the present invention also relates to fragrance mixtures and perfumed products comprising the compounds listed above.
  • the present invention also relates to a process for the production of perfumed products and a process for the production of 1- (4,4-dimethylcyclohexyl) ethanol or 1- (4,4-dimethylcyclohexyl) ethyl acetate.
  • the invention further relates to the compounds 1- (4,4-dimethylcyclohexyl) ethyl acetate, 1- (4,4-dimethylcyclohexyl) ethanol and 1- (2-hydroxy-4,4-dimethylcyclohexyl) ethanone.
  • fragrances with a floral and / or fruity fragrance are used in many fragrance mixtures and are of great interest to the fragrance industry, especially if they have a rose or violet note.
  • EP2474301A1 describes the use of cyclopent-2-enyl-acetic acid ethyl ester in fragrance mixtures. Cyclopent-2-enyl-acetic acid ethyl ester has a floral smell.
  • WO2018171865A1 describes the use of 5-bicyclo [2.2.1] hept-2-enyl acetate as a fragrance and / or flavoring.
  • 5-Bicyclo [2.2.1] hept-2-enyl acetate has a woody, fruity and / or floral odor.
  • DE1923223A1 describes derivatives of 1-ethyl-3,3-dimethyl-cyclohexane, for example 1- (3,3-dimethylcyclohexyl) ethyl acetate.
  • 1- (3,3-dimethylcyclohexyl) ethyl acetate is added to an odor composition to give the odor composition "warmth and a pleasant natural musky nuance”.
  • the smell of 1- (3,3-dimethylcyclohexyl) ethyl acetate is "intense, flowery-woody”.
  • DE102004047536A1 describes the use of 4-isoamylcyclohexanol as a floral fragrance.
  • fragrances not all compounds that have a (desired) odor are suitable for use as fragrances, since they are, for example, toxic or not sufficiently stable.
  • fragrances in particular fragrances with a floral and / or fruity odor characteristic.
  • Such fragrances should preferably be suitable for scenting or perfuming certain products.
  • fragrances should preferably meet one, more or preferably all of the following requirements: easy access, high effectiveness in low concentration, extensive or complete colorlessness, high stability in various mixtures or preparations, in particular no discoloration and / or separation and / or cloudiness should occur, inert behavior, - no toxic and / or allergenic effect on humans.
  • perfumed products and processes for producing such products should also be specified.
  • the present invention was intended, in particular, to provide new, advantageous fragrance mixtures which contain such fragrances.
  • the primary object of the present invention is achieved by the use of a compound selected from the group comprising 1- (4,4-dimethylcyclohexyl) ethanone, 1- (4,4-dimethylcyclohex-1-en-1-yl) ethanone, 1- (4,4-dimethylcyclohexyl) ethanol, 1 - (4,4-dimethylcyclohexyl) ethyl acetate and 1- (2-hydroxy-4,4-dimethylcyclohexyl) ethanone as a fragrance.
  • the use of 1- (4,4-dimethylcyclohexyl) ethyl acetate as a fragrance is particularly preferred.
  • the compounds 1- (4,4-dimethylcyclohexyl) ethanone, 1- (4,4-dimethylcyclohex-1-en-1-yl) ethanone, 1- (4,4-dimethylcyclohexyl) ethanol, 1- (4,4- Dimethylcyclohexyl) ethyl acetate and 1- (2-hydroxy-4,4-dimethylcyclohexyl) ethanone or the stereoisomers described below of these compounds are also referred to in this text as the compounds to be used according to the invention.
  • X is hydrogen or hydroxy
  • Y is oxygen, hydroxy or acetate (in particular ethyl acetate) and the bonds shown in corrugated form, independently of one another, represent single bonds or double bonds.
  • X is hydrogen and Y is ethyl acetate.
  • X is hydrogen, both corrugated bonds are single bonds and X is hydroxy (OH).
  • X is hydroxy (OH)
  • the corrugated bond within the cyclohexyl is a single bond
  • Y is oxygen (O) and the corrugated bond between Y. and carbon is a double bond
  • X is hydrogen
  • the corrugated bond within the cyclohexyl is a single bond
  • Y is oxygen (O) and the corrugated bond between Y and the carbon is a double bond.
  • Compound A1 is (R) -1- (4,4-dimethylcyclohexyl) ethyl acetate and compound A2 is (S) -1- (4,4-dimethylcyclohexyl) ethyl acetate.
  • compound A2 is (S) -1- (4,4-dimethylcyclohexyl) ethyl acetate.
  • Another aspect of the present invention is the compound 1- (4,4-dimethylcyclohexyl) ethanol.
  • 1- (4,4-Dimethylcyclohexyl) ethanol has the following structure (B):
  • Compound B1 is (S) -1- (4,4-dimethylcyclohexyl) ethanol and compound A2 is (R) -1- (4,4-dimethylcyclohexyl) ethanol.
  • compound A2 is (R) -1- (4,4-dimethylcyclohexyl) ethanol.
  • Another aspect of the present invention is the compound 1- (2-hydroxy-4,4-dimethylcyclohexyl) ethanone.
  • 1- (2-Hydroxy-4,4-dimethylcyclohexyl) ethanone has the following structure (C):
  • Compound C1 is 1 - ((1S, 2R) -2-hydroxy-4,4-dimethylcyclohexyl) ethanone
  • compound C2 is 1 - ((1 R, 2S) -2-hydroxy -4,4-dimethylcyclohexyl) ethanone
  • compound C3 by 1 - ((1 R, 2R) -2-hydroxy-4,4-dimethylcyclohexyl) ethanone
  • compound C4 by 1 - ((1S , 2S) -2-hydroxy-4,4-dimethylcyclohexyl) ethanone.
  • fragrance mixtures comprising a compound selected from the group consisting of 1- (4,4-dimethylcyclohexyl) ethanone, 1- (4,4-dimethylcyclohex-1-en-1-yl) ethanone , 1- (4,4-dimethylcyclohexyl) ethanol, 1- (4,4-dimethylcyclohexyl) ethyl acetate and 1- (2-hydroxy-4,4-dimethylcyclohexyl) ethanone.
  • a fragrance mixture is preferred, additionally comprising one or more further odorants.
  • the additional or one, several or all of the additional odorants is or are particularly preferably selected from the group consisting of alcohols, aldehydes, ketones, ethers, esters and carboxylates, preferably alcohols and aldehydes, in particular those with a molecular weight in the range from 150 to 285 g / mol, preferably from 210 g / mol or less.
  • the general rule is that the fragrances optionally additionally contained in a fragrance mixture according to the invention have a molar mass in the range from 150 to 285 g / mol, preferably from 210 g / mol or less. Fragrances to be used with particular preference are described below.
  • a fragrance mixture is preferred, additionally comprising 1 - (3,3-dimethylcyclohexyl) ethyl acetate.
  • fragrance mixtures are preferred according to the invention, the molar ratio between the compound used according to the invention and 1- (3,3-dimethylcyclohexyl) ethyl acetate being 1: 199 to 1: 4, preferably 1: 199 to 1: 9, especially is preferably 2: 99 to 1:19, more preferably 1:49 to 1:24.
  • a fragrance mixture is preferred according to the invention, the compound used according to the invention being 1- (4,4-dimethylcyclohexyl) ethyl acetate.
  • a fragrance mixture comprising 1- (4,4-dimethylcyclohexyl) ethyl acetate and one or more further odorous substances is preferred.
  • a fragrance mixture comprising 1- (4,4-dimethylcyclohexyl) ethyl acetate and 1- (3,3-dimethylcyclohexyl) ethyl acetate and optionally one or more further odorous substances is preferred.
  • fragrance mixtures are preferred according to the invention, the molar ratio between 1- (4,4-dimethylcyclohexyl) ethyl acetate and 1- (3,3-dimethylcyclohexyl) ethyl acetate being 1: 199 to 1: 4, preferably 1: 199 to 1: 9, particularly preferably 2: 99 to 1:19, more preferably 1:49 to 1:24.
  • fragrances which can in principle be used advantageously as a constituent of a fragrance mixture according to the invention can be found e.g. in S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, NJ, 1969, Dverlag or H. Surburg, J. Panten, Common Fragrance and Flavor Materials, 5th Ed., Wiley-VCH, Weinheim 2006.
  • the other odorants used according to the invention can also be ethereal oils, concretes, absolutes, resins, resinoids, balms and / or tinctures.
  • Preferred essential oils, concretes, absolutes, resins, resinoids, balms and / or tinctures, which can be part of a fragrance mixture according to the invention, are preferably to be selected from the group consisting of:
  • Preferred fragrances are selected from the group of hydrocarbons, preferably 3-carene; a-pinene; b-pinene; a-terpinene; g-terpinene; p-cymene; Bisabolene; Camphene; Caryophyllene; Cedren; Farnese; Lime; Longifolen; Myrcene; Ocimen; Valencene; (E, Z) -1, 3,5-undecatriene; Styrene; Diphenylmethane; aliphatic alcohols, preferably hexanol; Octanol; 3-octanol; 2,6-dimethyl-heptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexenol; (E) - and (Z) -3-hexenol; 1-oc
  • 3-cyclohexen-1-yl) ketone the ester of cyclic alcohols, preferably 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; 3,3,5-trimethylcyclohexyl acetate; Decahydro-2-naphthylacetate; 2-cyclopentylcyclopentylcrotonate; 3-pentyltetrahydro-2H-pyran-4-ylacetate; Decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, or 6-indenyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, or 6-
  • Fragrance mixtures according to the invention are usually liquid at 25 ° C. and 1013 hPa and are generally homogeneous solutions. Fragrance mixtures often comprise synthetic or natural (preferably) tasteless and odorless carrier oils which contain the fragrances (as artificial or natural substances) in highly concentrated form (and, if appropriate, perfume-based solvents and / or auxiliaries).
  • Perfume oils (as a preferred embodiment of fragrance mixtures according to the invention) often serve fragrance applications.
  • Perfume oils are used, for example, to produce perfumes by adding them to (e.g. alcoholic) solutions that "carry away" the fragrance or fragrance substances when they evaporate and thus to the user's olfactory organ, i.e. of humans to convey the sensory impression of a certain smell.
  • Such mixtures can be, for example, a perfume, eau de perfume or eau de toilette.
  • Perfume oils also serve to produce a specific fragrance in living rooms, such as for example in use in fragrance lamps, atomizers or diffusers.
  • perfume oils can also be used in countless other articles or preparations, for example from shoe creams to hair shampoos, sanitary napkins to toilet cleaners, face creams to washing powder and cat stones.
  • Another aspect of the present invention relates to perfumed products comprising a compound selected from the group comprising 1- (4,4-dimethylcyclohexyl) ethanone, 1- (4,4-dimethylcyclohex-1-en-1-yl) ethanone , 1- (4,4-dimethylcyclohexyl) ethanol, 1- (4,4-dimethylcyclohexyl) ethyl acetate and 1- (2-hydroxy-4,4-dimethylcyclohexyl) ethanone.
  • the compounds used according to the invention are preferably present in the perfumed product in a sensorially effective amount.
  • “sensorically effective amount” means that the perfumed product according to the invention reveals the sensory properties of the fragrance mixture according to the invention in operation or when in use.
  • Preferred products are, for example, perfume extras, eau de perfumes, eau de toilets, aftershaves, eau de colognes, pre-shave products, splash colognes and scented refreshing wipes as well as scented or to be scented acidic, alkaline and neutral cleaning agents, such as, for example Floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring milk, solid and liquid toilet cleaners, toilet sticks, toilet stones (liquid or solid), powder and foam-shaped carpet cleaners, liquid detergents, powder detergents, laundry pretreatment agents such as bleach , Soaking agents and stain removers, fabric softeners, washing soap, washing tablets, disinfectants, surface disinfectants and air fresheners in liquid, gelatinous or solid form, especially for deodorising exhaust air from air conditioning systems and industrial processes, as well as air freshen
  • a perfumed product is particularly preferred, the product being selected from the group consisting of perfume extras, eau de perfumes, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, perfumed refreshing wipes, acidic , alkaline and neutral detergents, textile fresheners, ironing aids, liquid detergents, powder detergents, laundry pretreatment agents, fabric softeners, laundry soaps, washing tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, body care products, hand creams, foot creams and lotion lotions, depilatory creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair care products, deodorants and antiperspirants, decorative cosmetic products, candles, lamp oils, incense sticks, insecticides, repellents and fuels.
  • perfumed products according to the invention are selected from the following list:
  • Acidic, alkaline and neutral cleaning agents especially in the household sector, preferably floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring milk, solid and liquid toilet cleaners, powdered and foam-shaped carpet cleaners, liquid detergents, powdered detergents, fabric softeners, surface disinfectants, especially for hard surface cleaner;
  • Body care products preferably solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams;
  • cosmetic emulsions of the oil-in-water, water-in-oil and water-in-oil-in-water type preferably skin creams and lotions, face creams and lotions, sun protection creams and lotions, anus -sun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, skin tanning creams and lotions,
  • Hair care products preferably hair sprays, hair gels, setting hair lotions, hair rinses, permanent and semi-permanent hair colorants, hair lotions, hair creams and lotions;
  • Deodorants and antiperspirants preferably armpit sprays, roll-ons (preferably as an alcoholic or non-alcoholic solution, as a gel or (micro) emulsion, deodorant sticks (deodorant sticks), deodorant creams.
  • perfumed products according to the invention are washing and cleaning agents, hygiene or care products, in particular in the field of body and hair care, cosmetics and household.
  • Preferred perfumed products according to the invention are also those in which the proportion of the fragrance mixture according to the invention in the perfumed product is 0.01 to 10% by weight, preferably 0.1 to 5% by weight, particularly preferably 0.25 to 3% by weight. %, is in each case based on the total mass of the perfumed product.
  • a product according to the invention can also be based on a product which can be improved in odor by reducing an unpleasant odor or by enhancing a pleasant odor aspect (in particular as described herein).
  • the compounds to be used according to the invention or corresponding mixtures thereof or fragrance mixtures (as described herein) are adsorbed on a carrier which ensures both a fine distribution of the compounds in the product and a controlled release during use.
  • a carrier can be porous inorganic materials such as silica gels, zeolites, gypsum, clays, clay granules, gas concrete etc. or organic materials such as woods and cellulose-based substances.
  • the compounds to be used according to the invention or corresponding mixtures thereof or fragrance mixtures (as described here) can also be microencapsulated, spray-dried, present as inclusion complexes or as extrusion products and added to a product in this form. If necessary, the properties of such modified compounds to be used according to the invention or corresponding mixtures thereof or fragrance mixtures (as described herein) can be further optimized by so-called “coating” with suitable materials with a view to a more targeted release, for which purpose wax-like plastics such as polyvinyl alcohol are preferably used will.
  • the compounds to be used according to the invention or corresponding mixtures thereof or fragrance mixtures (as described herein) can be microencapsulated, for example, by the so-called coacervation process with the aid of capsule materials, for example made of polyurethane-like substances or soft gelatin.
  • Spray-dried compounds to be used according to the invention can, for example, by spray drying a substance to be used according to the invention or a Corresponding mixture containing emulsion or dispersion are prepared, modified starches, proteins, dextrin and / or vegetable gums can be used as the carrier.
  • Inclusion complexes can be prepared, for example, by introducing dispersions which are or comprise corresponding compounds to be used according to the invention or corresponding mixtures thereof, and cyclodextrins or urea derivatives in a suitable solvent, for example water.
  • Extrusion products can be made by fusing the compounds to be used according to the invention or corresponding mixtures with a suitable waxy substance and by extrusion with subsequent solidification, if appropriate in a suitable solvent, for example isopropanol.
  • the compounds to be used according to the invention or corresponding mixtures thereof or fragrance mixtures can be used in many preparations or products, they preferably being combined with one or more of the following auxiliaries or active ingredients: preservatives, abrasives, anti-acne agents, Anti-aging agents, anti-bacterial agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, anti-irritant agents, anti-irritant agents, antimicrobial agents, antioxidants, additive agents, antiperspirant agents, antiseptic agents, antistatic agents, binders, buffers, carrier agents, chelating agents, cell , cleaning agents, care agents, depilatory agents, surface-active substances, deodorants, antiperspirants, plasticizers, emulsifiers, enzymes, essential oils, fibers, fixatives, foaming agents, foam stabilizers, substances to prevent the build-up umens, foam boosters, fungicides, gelling agents, gel-forming agents, hair care products, hair shaping agents,
  • Antimicrobial substances that inhibit the development of the microorganisms responsible for the smell of sweat; for example triclosana (5-chloro-2- (2,4-dichlorophenoxy) phenol), triclocarbane, chlorhexidine, chlorhexidine hydrochloride,
  • Chlorhexidine diacetate, chlorhexidine digluconate, 2-phenoxyethanol, farnesol, glycerol esters and ethers such as glycerol monolaurate, glycerol monocaprinate, hexoxyglycerol, octoxyglycerol ( ethylhexylglycerol, 3- (2-ethylhexyloxy-1, 2-propanediol) & Sen (siva) SC & (Sen- siva®) 50 Mayr), aliphatic 1, 2-diols such as 1, 2-decanediol (EP 1 269 983), araliphatic alcohols as described for example in EP 799
  • 174 preferably 4-methyl-4-phenyl-2-pentanol (Vetikol; WO 03/024907) or 2-methyl-4-phenyl-2-butanol (1, 1-dimethyl-3-phenylpropanol, alpha, alpha-dimethyl - phenethylcarbinol), I-menthyl methyl ether as described in WO 02/41861, 2-benzylheptan-1-ol (Jasmol; 2-n-pentyl-3-phenylpropan-1-ol), 2,2-dimethyl-3-phe- nylpropanol (muguet alcohol; see US 4,091,090), antimicrobial secondary
  • enzyme inhibiting substances that inhibit the action of enzymes involved in the formation of sweat odor; for example citric acid esters and metal chelating substances such as EDTA (ethylenediaminetetraacetic acid), EGTA [ethylenebis (oxyethylenenitrilo) tetraacetic acid] and DTPA (diethylenetriamine-pentaacetic acid, pentetic acid); (3) odor-absorbing substances that absorb substances responsible for the smell of sweat; for example zinc ricinoleate, cyclodextrins;
  • Antiperspirants which inhibit sweat secretion and thus remove the nutrient medium from the bacteria responsible for body odor.
  • the preferred antiperspirants used are astringent metal salts, particularly inorganic and organic metal salts of the elements aluminum, zinc, magnesium, tin and zircon and mixtures thereof, in particular using halides such as aluminum chloride, basic aluminum hydroxychloride, zirconyloxychloride and zirconylhydroxychloride and mixtures thereof will.
  • halides such as aluminum chloride, basic aluminum hydroxychloride, zirconyloxychloride and zirconylhydroxychloride and mixtures thereof will.
  • These aluminum and zirconium salts and their mixtures are often also used in a complexed form, propylene glycol, polyethylene glycol or glycine preferably being used as the complexing agent.
  • the compounds to be used according to the invention in a composition, preferably a perfume oil, which contains one or more (further) pleasant and / or unpleasant smelling substances, the unpleasant odor impression of which is masked or reduced by the mixture according to the invention and / or whose pleasant smell impression is enhanced by the mixture according to the invention, this (r) pleasant and / or unpleasant smelling substance or a several or all of these pleasant and / or unpleasant smelling substances are selected from the group consisting of alcohols, aldehydes, ketones, ethers, esters and carboxylates, preferably ketones and esters, and / or a molar mass in the range from 150 to 285 g / mol has or have.
  • a method is also described in this context
  • the amount of the fragrance mixture according to the invention or on the compound to be used according to the invention is sufficient to (a) intensify the pleasant odor impression (s) of the pleasantly smelling substance and / or (b) reduce the unpleasant odor impression (s) of the unpleasant smelling substance (s) or to mask.
  • a further aspect of the present invention is a method for producing a perfumed product, in particular a perfumed product according to the invention (as described herein), comprising the following steps: i) providing a compound to be used according to the invention or a fragrance mixture according to the invention, ii) providing one or more further components of the perfumed product to be produced, and iii) contacting or mixing the further components provided in step ii) with a sensorially effective amount of the components provided in step i).
  • Another aspect of the present invention is a process for the preparation of 1- (4,4-dimethylcyclohexyl) ethanol or 1- (4,4-dimethylcyclohexyl) ethyl acetate, comprising the following reaction step:
  • the ketone is preferably reduced by a hydride, preferably lithium aluminum hydride, sodium borohydride or sodium hydride, particularly preferably sodium borohydride.
  • a hydride preferably lithium aluminum hydride, sodium borohydride or sodium hydride, particularly preferably sodium borohydride.
  • the acetylation is preferably carried out with acetyl chloride or acetic anhydride, preferably with acetyl chloride.
  • acetyl chloride or acetic anhydride preferably with acetyl chloride.
  • a 31% strength aqueous hydrogen peroxide solution (15.8 ml) was added to a solution of A /, A / -diethylgeranylamine (10 g, 0.048 mol) in methanol (50 ml) at room temperature. The mixture was stirred for 48 hours and then approximately 30 mg MnCh was added to decompose the excess oxidizing agent. The reaction mixture was filtered through Celite and rinsed with methanol. The filtrate was freed from the methanol under reduced pressure. The crude N-oxide (2a) is obtained. 50% H2SO4 aq. (V / v 9.8 mL) was added to this colorless aqueous solution.
  • Example 5 Synthesis of 1- (4,4-dimethylcclohexylethyl acetate (A): Under a nitrogen atmosphere, a mixture of 9.6 g (61.4 mmol) of 1- (4,4-dimethylcyclohexyl) ethanol (B), cyclohexane (150 ml) and pyridine (7.4 ml) and 6.3 g of acetyl chloride were added dropwise at a temperature between 0 and 5 ° C.
  • Example 7 Combination of 1- (4,4-dimethylcvclohexyl) ethyl acetate with 1- (3,3-dimethylcvc-lohexyl ethyl acetate):
  • Example 9 Actates from the Dihvdromyrcenol Process:

Landscapes

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

Abstract

La présente invention concerne l'utilisation de 1-(4,4-diméthylcyclohexyl)éthanone, -(4,4-dimethylcyclohex-1-én-1-yl)éthanone, 1-(4,4-diméthylcyclohexyl)éthanol,1-(4,4-diméthylcyclohexyl)éthylacétate et 1-(2-hydroxy-4,4-diméthylcyclohexyl)éthanone comme substances odoriférantes, présentant notamment une caractéristique olfactive florale et/ou fruitée. La présente invention concerne en outre des mélanges de substances odoriférantes et des produits parfumés comprenant les composés mentionnés ci-dessus. La présente invention concerne également un procédé de fabrication de produits parfumés et un procédé de préparation de 1-(4,4-diméthylcyclohexyl)éthanol ou de 1-(4,4-diméthylcyclohexyl)éthylacétate. L'invention concerne en outre les composés 1-(4,4-diméthylcyclohexyl)éthylacétate, 1-(4,4-diméthylcyclohexyl)éthanol et 1-(2-hydroxy-4,4-diméthylcyclohexyl)éthanone.
EP18807003.1A 2018-11-12 2018-11-12 Utilisation de dérivés de 1-éthyl-4,4-diméthyl-cyclohexane comme substances odoriférantes Pending EP3880163A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2018/080899 WO2020098901A1 (fr) 2018-11-12 2018-11-12 Utilisation de dérivés de 1-éthyl-4,4-diméthyl-cyclohexane comme substances odoriférantes

Publications (1)

Publication Number Publication Date
EP3880163A1 true EP3880163A1 (fr) 2021-09-22

Family

ID=64402179

Family Applications (3)

Application Number Title Priority Date Filing Date
EP18807003.1A Pending EP3880163A1 (fr) 2018-11-12 2018-11-12 Utilisation de dérivés de 1-éthyl-4,4-diméthyl-cyclohexane comme substances odoriférantes
EP19798325.7A Active EP3681463B1 (fr) 2018-11-12 2019-11-12 Synthèse et utilisation de 2-éthyl-5,5-diméthyl-cyclohexanol en tant que parfum et matériau aromatique
EP21160197.6A Active EP3868358B1 (fr) 2018-11-12 2019-11-12 Synthèse et utilisation de 2-éthyl-5,5-diméthyl-cyclohexanol en tant que parfum et substance aromatisée

Family Applications After (2)

Application Number Title Priority Date Filing Date
EP19798325.7A Active EP3681463B1 (fr) 2018-11-12 2019-11-12 Synthèse et utilisation de 2-éthyl-5,5-diméthyl-cyclohexanol en tant que parfum et matériau aromatique
EP21160197.6A Active EP3868358B1 (fr) 2018-11-12 2019-11-12 Synthèse et utilisation de 2-éthyl-5,5-diméthyl-cyclohexanol en tant que parfum et substance aromatisée

Country Status (4)

Country Link
US (2) US12031106B2 (fr)
EP (3) EP3880163A1 (fr)
CN (1) CN112969444A (fr)
WO (2) WO2020098901A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020098901A1 (fr) 2018-11-12 2020-05-22 Symrise Ag Utilisation de dérivés de 1-éthyl-4,4-diméthyl-cyclohexane comme substances odoriférantes
KR102820284B1 (ko) 2019-08-30 2025-06-16 다우 글로벌 테크놀로지스 엘엘씨 폴리에테르 폴리올 및 폴리우레탄 폼에서 알데히드 방출을 감소시키는 방법
EP4132901A1 (fr) * 2020-04-08 2023-02-15 Symrise AG Esters en tant que composés de parfum
CN111333509B (zh) * 2020-04-14 2022-06-10 东莞波顿香料有限公司 苹果风味化合物及其制备方法和食品添加剂
CN115701973A (zh) * 2020-06-18 2023-02-14 西姆莱斯有限公司 含有1-(4,4-二甲基环己烯-1-基)乙酮的香料混合物
WO2023021063A1 (fr) * 2021-08-20 2023-02-23 Basf Se Utilisation de 1-(4-tert-butyl cyclohexyl) propyl-acétate comme ingrédient aromatique
WO2025108540A1 (fr) 2023-11-22 2025-05-30 Symrise Ag 5-méthylcyclohexanols et dérivés utilisés en tant que parfums

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE732205A (fr) * 1968-05-09 1969-10-28
AU513753B2 (en) 1974-07-08 1980-12-18 Johnson & Johnson Antimicrobial composition
US4187251A (en) 1976-12-16 1980-02-05 Schleppnik Alfred A Malodor counteractants
EP0081699B1 (fr) * 1981-12-10 1985-01-23 Firmenich Sa Nouveaux composés alicycliques, leur utilisation à titre d'ingrédients parfumants ou aromatisants, procédé pour leur préparation
DE4447361A1 (de) 1994-12-21 1996-06-27 Schuelke & Mayr Gmbh Biozide Alkohole, ihre Herstellung und ihre Verwendung
WO1998013447A1 (fr) 1996-09-27 1998-04-02 Firmenich S.A. Utilisation de cetones cycliques en parfumerie
DE10058459A1 (de) 2000-11-24 2002-06-06 Haarmann & Reimer Gmbh Rhinologica
ATE249200T1 (de) 2001-06-22 2003-09-15 Dragoco Gerberding Co Ag Verwendung von 1,2-decandiol gegen körpergeruch verursachende keime
DE10143434A1 (de) 2001-09-05 2003-03-20 Dragoco Gerberding Co Ag Antimikrobiell wirksame 4-Methyl-4-aryl-2-pentanole, deren Herstellung und Verwendung
DE10214675A1 (de) * 2002-04-03 2003-10-16 Haarmann & Reimer Gmbh Neue alicyclische Ester mit Moschusgeruch
DE10330697A1 (de) 2003-07-08 2005-02-03 Symrise Gmbh & Co. Kg Sekundäre Alkohole als antimikrobielle Wirkstoffe
DE102004047536A1 (de) 2004-09-30 2006-04-13 Symrise Gmbh & Co. Kg 4-Isoamylcyclohexanol als Riechstoff
WO2009144136A1 (fr) 2008-05-28 2009-12-03 Dsm Ip Assets B.V. Synthèse de mono-cétones à partir de 1,3-dicétones
WO2010043522A1 (fr) 2008-10-15 2010-04-22 Dsm Ip Assets B.V. Synthèse d'intermédiaire de cétone verte
EP2474301B1 (fr) 2011-12-14 2014-04-16 Symrise AG Mélanges de parfum comprenant du cyclopent-2-ényl-éthylester d'acide acétique
EP3601508B1 (fr) 2017-03-21 2020-09-02 Symrise AG 5-bicyclo[2.2.1]hept-2-ényl-acétate utilisé comme parfum et/ou arôme
WO2020098901A1 (fr) 2018-11-12 2020-05-22 Symrise Ag Utilisation de dérivés de 1-éthyl-4,4-diméthyl-cyclohexane comme substances odoriférantes

Also Published As

Publication number Publication date
CN112969444A (zh) 2021-06-15
US20210395639A1 (en) 2021-12-23
US11946019B2 (en) 2024-04-02
WO2020099372A1 (fr) 2020-05-22
EP3868358A1 (fr) 2021-08-25
WO2020098901A1 (fr) 2020-05-22
US12031106B2 (en) 2024-07-09
EP3681463B1 (fr) 2021-03-03
US20210395640A1 (en) 2021-12-23
EP3868358B1 (fr) 2025-05-21
EP3681463A1 (fr) 2020-07-22

Similar Documents

Publication Publication Date Title
EP3197987B1 (fr) Utilisation de cis- ou trans-(2-isobutyl-4-méthyl-tétrahydropyrane-4-yl) acétate isomèrique pur ou très enrichi en isomères
EP2662434B2 (fr) Utilisation de certaines liaisons pour augmenter des odeurs
US12031106B2 (en) Use of 1-ethyl-4,4-dimethyl-cyclohexane derivatives as fragrances
DE102006043587A1 (de) 2-Methyl-2-alkenyl-substituierte 1,3-Dioxane als Riechstoffe
EP1682230A1 (fr) 4,8-dimethyl-7-nonen-2-one et 4,8-dimethylnonan-2-one en tant que substances odorantes
EP1492759A2 (fr) Nouveaux esters alicycliques a odeur de musc
EP3167031B1 (fr) Mélanges d'isomères de composés musqués macrocyliques insaturés
EP2072083B1 (fr) Utilisation de 2,4'-diméthyl-propiophénone en tant que parfum
DE202005021550U1 (de) 3-Methylbenzylisobutyrat
EP3612620B1 (fr) 4-éthyl-octène-2/3-nitrile s'utilisant comme substance odorante
EP4045490B1 (fr) De nouveaux monothiocétals aromatiques comme parfums
EP1599434A1 (fr) 4-cyclohexyl-2-butanol servant de parfum
DE102008000275A1 (de) Alkenacetale und ihre Verwendung als Riechstoffe
EP2966159B1 (fr) Mélanges d'isomères E enrichis de composés musqués macrocycliques insaturées
WO2021008696A1 (fr) Mélange de parfums contenant du 1,3-propandiol
EP3853199B1 (fr) 2-(5-isopropyl-2-méthyl-cyclohex-2-én-1-yl-)acétaldéhyde et 2-(6-isopropyl-3-méthyl-cyclohex-2-én-1-yl-)acétaldéhyde en tant que nouveaux parfums
EP1648526B1 (fr) Esters cis-3,3,5-trimethylcyclohexyliques
EP1923389A1 (fr) 2-Isopropyl-5-méthyloxépane et son utilisation comme composé de fragrance
WO2004002930A1 (fr) Nouvelles substances odorantes et procede de fabrication
WO2003097629A1 (fr) Oxalactones macrocycliques insaturees servant de parfums
DE10325628A1 (de) 2-Methyl-5-phenylpentanal als Rosenriechstoff

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: UNKNOWN

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20210614

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

17Q First examination report despatched

Effective date: 20241115