208. Diastereoselektivitaet der Geruchswahrnehmung von Alkoholen der Iononreihe

Article abstract of DOI:10.1002/hlca.19850680722

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.