WO1996041853A1 - Cyclohexyl-substituierte alkanole - Google Patents
Cyclohexyl-substituierte alkanole Download PDFInfo
- Publication number
- WO1996041853A1 WO1996041853A1 PCT/EP1996/002388 EP9602388W WO9641853A1 WO 1996041853 A1 WO1996041853 A1 WO 1996041853A1 EP 9602388 W EP9602388 W EP 9602388W WO 9641853 A1 WO9641853 A1 WO 9641853A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- cyclohexyl
- hydrogen
- alkyl group
- radical
- carbon atoms
- Prior art date
Links
Classifications
-
- 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/19—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings
-
- 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/175—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of an oxo group
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- 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 invention relates to the use of cyclohexyl-substituted alkanols of the structure given below as fragrances.
- fragrance industry has a constant need for new fragrances with interesting fragrance notes in order to supplement the range of naturally available fragrances and to make the necessary adaptations to changing fashionable tastes, as well as the constantly increasing need for odor improvers for everyday products To cover needs such as cosmetics and cleaning agents.
- the compounds of the general formula (I) meet the above requirements excellently in all respects and can advantageously be used as fragrances with differently nuanced odor notes with good adhesive strength.
- the compounds of the formula (I) have an improved odor intensity over compounds of the prior art which are structurally close to them, i.e. develop their effect at lower concentrations.
- the present invention relates to the use of aromatic carbonyl compounds of the general formula (I)
- radicals R 1 to R 3 independently of one another are hydrogen or an alkyl group having 1 to 4 carbon atoms
- radical R 4 is hydrogen or an alkyl group having 1 to 4 carbon atoms and
- Cy is a cyclohexyl group
- fragrances mean as fragrances.
- the radical * is methyl.
- the radicals R2 and R3 are hydrogen. Again, those compounds are preferred in which R 4 is hydrogen, methyl or ethyl. Of these latter compounds (I), 4-cyclohexyl-hexan-2-ol is very particularly preferred. It is characterized by an olfactory characteristic, in which rose, damascone and woody notes dominate and excellent stability in formulations of cosmetics and perfumery.
- the compounds (I) are prepared by known synthetic organic chemical methods.
- the compounds (I) are preferably produced in a 2-stage process.
- Carroll reaction in the context of the present invention means the conversion of allyl alcohols into gam a-delta-unsaturated ketones.
- the allyl alcohol is converted into the corresponding allyl acetoacetate by reaction with acetoacetic ester, from which the alpha-allylacetoacetic acid is formed by [3,3] sigmatropic rearrangement (Claisen rearrangement) thermal decarboxylation gives the desired gamma-delta unsaturated ketone (I).
- the allyl acetoacetate can be used in bulk or formed in situ.
- allyl alcohols are reacted with 2-alkoxyalkenes, in particular 2-methoxypropene, in the Carroll reaction.
- 2-alkoxyalkenes in particular 2-methoxypropene
- the intermediate allyl vinyl ether can be isolated or subjected directly to the subsequent [3,3] sigmatropic rearrangement to the corresponding ketone (I) in situ.
- the [3,3] -sigmatropic rearrangement via the Allyl vinyl ether takes place and in which the allyl alcohol used at the beginning of the synthesis is reacted with a 2-alkoxyalkene, preferred since this type of production ensures a particularly high product purity and thus the desired high olfactory quality of the compounds (I) is ensured.
- the compounds (I) in which R 1 denotes a methyl group are distinguished by a floral, fruity odor which gains intensity from fresh wood notes.
- the compounds (I) enhance the harmony and charisma as well as the adhesion, the dosage being matched to the desired fragrance note taking into account the other constituents of the composition.
- the compounds of the formula (I) are particularly suitable for modifying and enhancing known compositions. Particularly to be emphasized is their extraordinary olfactory strength, 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 and moderately volatile components and that of synthetic fragrances include representatives from practically all classes of substances. Examples are:
- 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, lilial R [p-tert.-butyl- ⁇ -methyldihydrocinnamaldehyde], methylnonyl acetaldehyde,
- ketones such as allyl ionone, ⁇ -ionone, ⁇ -ionone, isoraldein, methyl ionone,
- esters such as allylphenoxyacetate, benzyl salicylate, cinna yl propionate, citronelly acetate, decyl acetate, dimethylbenzylcarbinylacetate, ethyl acetoacetate, hexenyl isobutyrate, linalyl acetate, methyl dihydrojasmonate, viethyl acetate, cyclohexyl acetate, cyclohexyl acetate, cyclohexyl acetate, cyclohexyl acetate
- lactones such as gam a-undecalactone, l-0xaspiro [4.4] nonan-2-one,
- perfumery such as musk, indole, p-menthan-8-thiol-3-one, methyleugenol, ambroxan.
- the compounds according to the invention contain centers of chirality, so that these compounds can exist in different spatial forms.
- the compounds according to the invention are obtained as mixtures of the corresponding isomers and are used as such as fragrances.
- the usable proportions of the compounds according to the invention or their mixtures in fragrance compositions range from 1 to 70% by weight. percent, based on the total mixture.
- 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 (eg Eaux de Cologne , Eau de toilette, extras) can be used.
- perfuming technical products such as washing 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 to 2 percent by weight, based on the entire product.
- these values are not intended to represent any limit values, since the experienced perfumer can achieve effects with even lower concentrations or can build up novel complexes with even higher doses.
- Cinnamon alcohol 98% (Riedel de Haen) Isopropenyl methyl ether: 2-methoxypropene, 92% (Janssen) Cinnamaldehyde: 98% (Fluka)
- Perfume concentrate for perfuming soap (floral-fresh fantasy composition):
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9502566A JPH11507681A (ja) | 1995-06-12 | 1996-06-03 | シクロヘキシル置換されたアルカノール |
EP96918659A EP0833883A1 (de) | 1995-06-12 | 1996-06-03 | Cyclohexyl-substituierte alkanole |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19521364A DE19521364A1 (de) | 1995-06-12 | 1995-06-12 | Cyclohexyl-substituierte Alkanole |
DE19521364.5 | 1995-06-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996041853A1 true WO1996041853A1 (de) | 1996-12-27 |
Family
ID=7764200
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1996/002388 WO1996041853A1 (de) | 1995-06-12 | 1996-06-03 | Cyclohexyl-substituierte alkanole |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0833883A1 (de) |
JP (1) | JPH11507681A (de) |
DE (1) | DE19521364A1 (de) |
WO (1) | WO1996041853A1 (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6172016B1 (en) * | 1999-07-12 | 2001-01-09 | Bush Boakes Allen Inc. | Fragrance materials |
US6187727B1 (en) * | 1999-07-12 | 2001-02-13 | Bush Boake Allen, Inc. | Fragrance materials |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1569424A (en) * | 1974-07-08 | 1980-06-18 | Johnson & Johnson | Topical medicaments |
DE4304467A1 (de) * | 1993-02-15 | 1994-08-18 | Henkel Kgaa | Hexanol-Derivate, deren Herstellung und Verwendung |
-
1995
- 1995-06-12 DE DE19521364A patent/DE19521364A1/de not_active Withdrawn
-
1996
- 1996-06-03 JP JP9502566A patent/JPH11507681A/ja active Pending
- 1996-06-03 WO PCT/EP1996/002388 patent/WO1996041853A1/de not_active Application Discontinuation
- 1996-06-03 EP EP96918659A patent/EP0833883A1/de not_active Withdrawn
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1569424A (en) * | 1974-07-08 | 1980-06-18 | Johnson & Johnson | Topical medicaments |
DE4304467A1 (de) * | 1993-02-15 | 1994-08-18 | Henkel Kgaa | Hexanol-Derivate, deren Herstellung und Verwendung |
Non-Patent Citations (2)
Title |
---|
G.B.BENNET: "The Claisen rearrangement in organic synthesis", SYNTHESIS, 1977, STUTTGART DE, pages 589 - 606, XP002011814 * |
M.F.CARROLL: "Addition of beta gamma-unsaturated alcohols to the active methylene group.Part II.The action of ethyl acetoacetate on cinnamyl alcohol and phenylvinylcarbinol.", JOURNAL OF THE CHEMICAL SOCIETY, 1940, LETCHWORTH GB, pages 1266 - 1268, XP000578878 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6172016B1 (en) * | 1999-07-12 | 2001-01-09 | Bush Boakes Allen Inc. | Fragrance materials |
US6187727B1 (en) * | 1999-07-12 | 2001-02-13 | Bush Boake Allen, Inc. | Fragrance materials |
Also Published As
Publication number | Publication date |
---|---|
EP0833883A1 (de) | 1998-04-08 |
JPH11507681A (ja) | 1999-07-06 |
DE19521364A1 (de) | 1996-12-19 |
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