Some Aspects of the Molecular Surface of Sandalwood Odour Molecules. Conformational Calculations on Sandalwood Odour VII

Abstract

The molecular surfaces of five different sandalwood odour molecules were investigated and subsequently used as a basis for a mean surface and compared to each other. It was possible to find a specific surface part with a significant pattern, which seems to be necessary for evoking the typical odour.

Structure-activity-relationships of someexo-isocamphanylcyclohexanols. Conformational calculations on sandalwood odour IX

“…This fact seems to be reasonable, because an association at a peptide or a protein may be performed via an hydrogen bridge. In addition, this result is in agreement with investigations on other Sandalwood compounds [8,9]. For the search of further important surface regions the comparisons in other octants have to be performed.…”

Structure−Odor Relationships

“…The discovery of the above new synthetic sandalwood odorant assisted Buchbauer and his co-workers in the conformational analysis of several sandalwood compounds. − 8- tert -Butylbicyclo[4.4.0]decanol (BBD) is an extremely rigid molecule: only the tert -butyl group and the hydroxyl group are free to rotate. Both of these rotations can be neglected because rotation of the symmetrical tert -butyl group leads to identical conformations and rotation of the hydroxyl group does not significantly change the shape of the molecule.…”

“…(3) The surface region around the hydroxyl group and a part of the hydrophobic bulky group seem to be very important in determining the sandalwood odor of a molecule. Other parts of the molecular surface can tolerate greater surface variations. − …”

“…(4) Although androstenol is much larger than other sandalwood odor molecules, 70% of its surface coincides with the “sandalwood” mean surface …”

“…Other parts of the molecular surface can tolerate greater surface variations. [251][252][253] (4) Although androstenol is much larger than other sandalwood odor molecules, 70% of its surface coincides with the "sandalwood" mean surface. 252 This may explain why androstenol is perceived by some human subjects as sandalwood.…”