Helvetica Chimica Acta p. 1961 - 1985 (1985)
Update date:2022-09-26
Topics:
Schulte-Elte, Karl H.
Giersch, Wolfgang
Winter, Beat
Pamingle, Herve
Ohloff, Guenther
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.
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Doi:10.1016/S0040-4039(00)81454-9
(1983)Doi:10.1021/jo00217a025
(1985)Doi:10.1021/ja00542a059
(1980)Doi:10.1055/s-2007-980383
(2007)Doi:10.1016/S0040-4039(01)90896-2
(1963)Doi:10.1021/jm00148a015
(1985)