265094-58-4Relevant articles and documents
Amber-woody scent: Alcohols with divergent structure present common olfactory characteristics and sharp enantiomer differentiation
Margot, Christian,Simmons, Dana P.,Reichlin, Daniel,Skuy, David
, p. 2662 - 2684 (2007/10/03)
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).
