Synthesis and olfactoric activity of side-chain modified beta-santalol analogues.
Three osmophoric points have been postulated to be necessary for the sandalwood scent of beta-santalol derivatives. One of these points, close to the hydroxyl group, is highly specific on the stereochemistry and, in particular, on the molecular shape. The role of the 2-methyl group in the side chain of beta-santalol derivatives was studied by replacement through a hydrogen atom, an ethyl or an isopropyl group. It turns out that any change at the 2-methyl substituent leads to the complete loss of sandalwood odour.
Buchbauer
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G
Institute of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, A-1090, Vienna, Austria. gerhard.buchbauer@univie.ac.at
Sunara
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A
Weiss-Greiler
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Wolschann
P
P
D003374:Coumarins / Q000737:chemistry*; D006801:Humans; D008968:Molecular Conformation; D015394:Molecular Structure; D009812:Odorants / Q000032:analysis*; D010938:Plant Oils; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D012903:Smell; D013329:Structure-Activity Relationship
D003374:Coumarins; D010938:Plant Oils; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C043206:santalol; C076763:sandalwood oil