Diastereoselektivität der Geruchswahrnehmung von Alkoholen der Iononreihe

Diastereoselective Odor Perception of Alcohols in the Ionone Series 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 modification of model 1 / 2 , for example substitution on C(2), C(13), and C(14) (ionon numbering) by CH 3 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.