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
  • C11B9/0007—Aliphatic compounds
  • C11B9/0023—Aliphatic compounds containing nitrogen as the only heteroatom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/32—Oximes
  • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
  • C07C251/36—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms
  • C07C251/40—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C255/00—Carboxylic acid nitriles
  • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
  • C07C255/06—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and unsaturated carbon skeleton
  • C07C255/07—Mononitriles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
  • C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
  • C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
  • C07C33/03—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond in beta-position, e.g. allyl alcohol, methallyl alcohol
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
  • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
  • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
  • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
  • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
  • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C47/00—Compounds having —CHO groups
  • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
  • C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
• • 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
  • C11B9/0007—Aliphatic compounds
  • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom

Definitions

• the present invention relates to new trimethyldecene compounds of special structure, and to their use as fragrances.
• fragrance industry has a constant need for new fragrances with interesting fragrance notes.
• the range of naturally available fragrances can be supplemented, on the other hand it is possible to make the necessary adjustments to changing fashionable tastes. It also makes it possible to meet the ever-increasing need for odor improvers for everyday products such as cosmetics and cleaning agents.
• the present invention initially relates to trimethyldecene compounds of the general structure (I)
• the invention relates to the use of trimethyldecene compounds of the general structure (I) specified above as fragrances.
• the compounds (I) according to the invention are distinguished by an odor characteristic in which tangerine notes and fruity aspects dominate. They have excellent stability in cosmetic and consumer perfume formulas.
• the compounds (I) can be prepared by known synthetic methods of organic chemistry.
• the compounds (I) enhance the harmony and charisma as well as the naturalness and also the adhesion, the dosage being matched to the desired fragrance note, taking into account the other components of the composition.
• the compounds of formula (I) are particularly suitable for modifying and reinforcing known compositions due to their scent profile.
• their extraordinary smell strength should be emphasized, which generally contributes to the refinement of the composition.
• the compounds of formula (I) can be combined with numerous known fragrance ingredients, for example other fragrances of natural, synthetic or partially synthetic origin, essential oils and plant extracts.
• the range of natural fragrances can include both volatile, medium and low volatile components.
• the range of synthetic fragrances can include representatives from practically all classes of substances.
• suitable substances with which the compounds (I) can be combined are in particular: (a) Natural products such as tree moss absolute, basil oil, agricultural oils such as bergamot oil, mandarin oil, etc., mastic absolute, myrtle oil, palmarosa oil, patchouli oil, petitgrain oil, wormwood oil, myrrh oil, olibanum oil
• aldehydes such as citral, helional, ⁇ -hexylcinnamaldehyde, hydroxycitronellal, linear ⁇ - [p-tert-butyl- ⁇ -methyldihydrocinnamaldehyde], methylnonylacetaldehyde,
• ketones such as allyl ionone, ⁇ -ionone, ⁇ -ionone, isoraldein, methyl ionone,
• esters such as allylphenoxyacetate, benzyl salicylate, cinnamyl propionate, citronellyla acetate, decyl acetate, dimethylbenzylcarbinylacetate, ethyl acetoacetate, hexenyl isobutyrate, linalyl acetate, methyl dihydrojasmonate, vetiveryl acetate, cycloatylsylate, cycloatylsilate
• Lactones such as gamma-undecalactone, l-oxaspiro [4.4] nonan-2-one, as well as various other components often used in perfumery such as musk and sandalwood fragrances, indole, p-menthan-8-thiol-3- on, methylleugenol and ambroxan.
• the usable proportions of the compounds (I) according to the invention or their mixtures in fragrance compositions range from about 1-70% by weight, based on the mixture as a whole.
• Mixtures of the compounds (I) according to the invention and compositions of this type can be used for perfuming cosmetic preparations such as lotions, creams, shampoos, soaps, ointments, powders, aerosols, toothpastes, mouthwashes, deodorants as well as in alcoholic perfumery (e.g. Eau de Cologne, Eau de Toilette, Extraits) can be used.
• perfuming technical products such as detergents and cleaning agents, fabric softeners and textile treatment agents.
• compositions are added to them in an olfactory effective amount, in particular in a concentration of 0.05-2% by weight, based on the entire product.
• these values are not limiting limits, since the experienced perfumer can still achieve effects with even lower concentrations or build up novel complexes with even higher doses.
• Equipment 1 L three-necked flask with stirrer, thermometer and water separator.
• Apparatus 2 L four-necked flask with stirring apparatus and dropping funnel.
• the crude product was distilled on a 15 cm Vigreux column, 99 g of orange main run were obtained at 119-136 ° C./0.15-0.12 mbar with a GC purity of 94%.
• Odor characteristics Metallic in the smell, wet fur, orange, mandarin, and in the after smell of mandarin.
• Equipment 2 L four-necked flask with stirrer, PT 100 thermometer, 250 ml dropping funnel and reflux condenser, ice water bath for cooling, oil bath for heating.
• the crude product was distilled on a 15 cm Vigreux column, 59.2 g of the main run went over at 79-80 ° C./0.08-0.06 mbar.
• the GC purity was 98.6%.
• Odor characteristic Tridecen-2-nitrile, mandarin, wet fur, metallic in the smell; after smell of nitrile, tangerine.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (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)
• Steroid Compounds (AREA)
• Color Television Systems (AREA)

Priority Applications (6)

Applications Claiming Priority (2)

Publications (1)

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ID=7640991

Family Applications (1)

Country Status (8)

Cited By (2)

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Citations (2)

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• 2000
  • 2000-05-06 DE DE10022076A patent/DE10022076A1/de not_active Withdrawn
• 2001
  • 2001-04-28 IL IL15263201A patent/IL152632A0/xx unknown
  • 2001-04-28 US US10/275,724 patent/US6867175B2/en not_active Expired - Fee Related
  • 2001-04-28 AT AT01927928T patent/ATE254099T1/de not_active IP Right Cessation
  • 2001-04-28 WO PCT/EP2001/004817 patent/WO2001085672A1/de not_active Ceased
  • 2001-04-28 ES ES01927928T patent/ES2210152T3/es not_active Expired - Lifetime
  • 2001-04-28 DE DE50100972T patent/DE50100972D1/de not_active Expired - Lifetime
  • 2001-04-28 EP EP01927928A patent/EP1280763B1/de not_active Expired - Lifetime
  • 2001-04-28 JP JP2001582273A patent/JP4386612B2/ja not_active Expired - Fee Related

Patent Citations (2)

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