Structure-activity relationships of sandalwood odorants: total synthesis and fragrance properties of cyclopropano-beta-santalol.
The synthesis and odor properties of cyclopropano-beta-santalol, a new santalol analogue, are described. The exocyclic double bond of the original molecule, beta-santalol, is replaced by a cyclopropane ring. Despite the analogies in the binding properties between the double bond and cyclopropane this change in the bulky hydrophobic part of the molecule leads to the complete loss of the characteristic sandalwood odor: in an olfactory evaluation the (Z)-product appears spicy and sweet, the (E)-isomer woody, but neither of them exhibits the typical sandalwood character.
Stappen
Iris
I
Department of Clinical Pharmacy and Diagnostics, Center of Pharmacy, University of Vienna, Vienna, Austria. iris.stappen@univie.ac.at
Höfinghoff
Joris
J
Friedl
Susanne
S
Pammer
Claudia
C
Wolschann
Peter
P
Buchbauer
Gerhard
G
D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D009812:Odorants; D000081223:Polycyclic Sesquiterpenes; D032123:Santalum / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C532281:cyclopropano-beta-santalol