- Process for the preparation of 1-(2,2,6-trimethylcyclohexyl)-hexan-3-ol
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A process for the preparation of 1-(2,2,6-trimethylcyclohexyl)-hexan-3-ol of the formula A having a content of at least 30 wt. % of the corresponding trans isomer, based on the total amount of 1-(2,2,6-trimethylcyclohexyl)-hexan-3-ol of the formula A, wit
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Page/Page column 4
(2008/06/13)
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- Method for producing trimethylcyclohexyl-3-alkanols with a high portion of trans-isomers
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Production of 1-(2,2,6-trimethylcyclohexyl)-3-alkanols containing trans isomers (D) comprises hydrogenating corresponding enones (B) in the presence of a nickel catalyst in the absence of copper chromite. Production of 1-(2,2,6-trimethylcyclohexyl)-3-alka
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- Amber-woody scent: Alcohols with divergent structure present common olfactory characteristics and sharp enantiomer differentiation
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Only one out of the four possible trans isomers of the important perfumery alcohol Norlimbanol (1) possesses a very strong amber-woody smell, the isomer 1A with (1′ R,3S,6'S) absolute configuration. Its enantiomer 1B is almost odorless and devoid of amber-woody character, whereas the diastereoisomers 1C and 1D are considerably weaker and perceptible only by the most-sensitive persons. The same is true for a whole series of perceptual analogs of 1, including β-alkoxy alcohols. These ethers belong to two structural classes: [(2,2,6-trimethylcyclohexyl)oxy]- (see 3, 4, and 16) or {[2-(tert-butyl)cyclohexyl]oxy)alkan-2-ol derivatives (see 19 and 20; Table). A superimposition model allowing for good overlap of the respective hydroxylated side chains offers a tentative explanation for the shared perceptual characteristics of the two classes (Fig. 5). The lipophilic cyclohexane moieties present only a minimal overlap in this model, suggesting that quite larger molecules might possess the same smell. (S)-Configured β-alkoxy alcohols can conveniently be obtained on a larger scale by enantioselective reduction of the corresponding ketones (Scheme 9).
- Margot, Christian,Simmons, Dana P.,Reichlin, Daniel,Skuy, David
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p. 2662 - 2684
(2007/10/03)
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- Optically active aliphatic alcohols and their use as perfuming ingredients
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The optically active compounds of formula wherein R1 represents a hydrogen atom or a methyl radical, or of formula are useful as perfuming ingredients for the preparation of perfuming compositions and perfumed articles to which they impart woody-amber notes.
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- Enzyme-mediated preparation of the single enantiomers of the olfactory active components of the woody odorant Timberol
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Enantiomerically pure (3S)-3a and -3b, the olfactory active forms of 1- (2,2,6-trimethylcyclohexyl)hexan-3-ol, components of the commercial woody odorant Timberol, are obtained by lipase-PS-mediated enantioselective acetylation of the allylic alcohols 6 a
- Brenna, Elisabetta,Fronza, Giovanni,Fuganti, Claudio,Righetti, Annalisa,Serra, Stefano
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p. 1762 - 1773
(2007/10/03)
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- Propanol derivatives and perfumes containing the same
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An optically active 3-[6(S)-2,2,6-trimethylcyclohexan-1-yl]propanol derivative represented by formula (I): STR1 wherein R1 represents a lower alkyl group, and a perfume containing the same as an active ingredient are disclosed.
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- Composition essentially consisting of trans-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol
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Composition consisting of from less than 100% to more than about 80% of trans-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol and a definite amount, but not more than about 20%, of cis-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol. Process for preparing same from β-cyclocitral via a three-, optionally, four-step pathway. Utilization of the said composition as effective perfume ingredient.
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- 208. Diastereoselektivitaet der Geruchswahrnehmung von Alkoholen der Iononreihe
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The characteristic odor of the diastereoisomers 1 and 2 of 1-(2,2,6-trimethylcyclohexyl)-3-hexanol is configuration dependent, the trans-alcohol 1 being identified as the sensorily active component.Structure modifications of model 1/2, for example substitution on C(2), C(13), and C(14) (ionon numbering) by CH3 groups, introduction of double bonds in the 3- or 4-position, and isosteric substitution of C(7) by an O-atom, leads to analogues revealing an unequivocal relation between stereochemistry and odor.The specific odor of alcohol 1 is generally released when all substituents are in an equatorial position; the resulting analogy with the molecular size and shape of odoriferous steroids suggests that the release of the particular scent can be correlated with a steroid-resembling receptor event.
- Schulte-Elte, Karl H.,Giersch, Wolfgang,Winter, Beat,Pamingle, Herve,Ohloff, Guenther
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p. 1961 - 1985
(2007/10/02)
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