362044-49-3

Upstream product

• 64-17-5 ethanol 
• 7757-82-6 sodium sulfate 
• 362044-52-8 (+)-(3S)-2,2,3,6-tetramethylcyclohexanone 
• 130693-79-7 (+)-(3S,6S)-2,2,3,6-tetramethyl-1-cyclohexanone 

Relevant academic research and scientific papers

Amber-woody scent: Alcohols with divergent structure present common olfactory characteristics and sharp enantiomer differentiation

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).

Optically active, oxygenated, alicyclic compounds and their use as perfuming ingredients

The compounds of the formula wherein R1 and R2 represent, independently from each other, a hydrogen atom or a methyl group and R3 represents a linear or branched, saturated or unsaturated, lower alkyl radical, in the form of an optically active isomer of the formula wherein the wavy line indicates one or other of the two possible orientations of the OH group, and mixtures of these isomers can be used to impart fragrances of the woody and amber-scented type, devoid of any animal/perspiration characteristics, to consumer products.