Queensland Sandalwood - Cropwatch

Buchbauer G., Winiwarter S. & Wolschann P. (1992) "Surface comparisons of some odour
molecules: conformational calculations on sandalwood odour V.” J. Comput. Aided Mol. Des.
6(6), 583-592. Abstract: Molecular surface comparison seems to be a very suitable tool for the
investigation of small differences between biologically active and inactive compounds of the same
structural type. A fast method for such comparisons, based on volume matching followed by the
estimation of comparable surface dots, is presented and applied on a few selected sandalwood
odour molecules.
Demole E., Demole C. & Enggist P. (1976) “A chemical investigation of volatile constituents of
volatile constituents of East Indian sandalwood oil (Santalum album L.)” Helv. Chim. Acta 59,
737.
Dimoglo A.S., Beda A.A., Shvets N.M., Gorbachov M.Yu., Kheifits L.A. & Aulchenko S. (1995)
"Investigation of the relationship between sandalwood odour & chemical structure: electron
topological approach.” New J of Chemistry 19(2), 149-154.
Kovatcheva A., Buchbauer G., Golbraikh A. & Wolschann P. (2003) “QSAR modeling of alphacampholenic
derivatives with sandalwood odor.” J Chem Inf Comput Sci. 43(1), 259-66. Abstract.
Three-dimensional quantitative structure-activity relationship (3D-QSAR) models were developed
for a series of 44 synthetic alpha-campholenic derivatives with sandalwood odor. These
compounds have complex stereochemistry as they contain up to five chiral atoms. To address
stereospecificity of odor intensity, a 3D-QSAR method was developed, which does not require
spatial alignment of molecules. In this method, compounds are represented as derivatives of
several common structural templates with several substituents, which are numbered according to
their relative spatial positions in the molecule. Both wholistic and substituent descriptors
calculated with the TSAR software were used as independent variables. Based on published
experimental data of sandalwood odor intensities, two discrete scales of the odor intensity with
equal or unequal intervals between the threshold values were developed. The data set was
divided into a training set of 38 compounds and a test set of six compounds. To build QSAR
models, a stepwise multiple linear regression method was used. The best model was obtained
using the unequal scale of odor intensity: for the training set, the leave one out cross-validated
R(2) (q(2)) was 0.80, the correlation coefficient R between actual and predicted odor intensities
was 0.93, and the correlation coefficient for the test set was 0.95. The QSAR models developed
in this study contribute to the better understanding of structural, electronic, and lipophilic
properties responsible for sandalwood odor. Furthermore, the QSAR approach reported herein
can be applied to other data sets that include compounds with complex stereochemistry.
Hatt H.H. & Schoenfeld R. (1956) “Some seed fats of the Santalaceae family.” J. Sci Food Agric
7(2), 130-133. Cropwatch comments. The drying oil from the hard-shelled seeds (50-60% fixed
oil) contains 30-35% santalbic acid and 1% stearolic acid. Tthese acetylenic compounds inhibit
lipoenzymes in experimental animals.
CH 3
(CH 2
) 5
CH C
H
(CH 2
) 7
COOH
santalbic acid
Hayashi K., Haseegawa T., Machiguchi T. & Yoshida T. (2005) “"Isolation and structure of a new
aroma constituent from Indian Sandalwood, Santalum album L." Nippon Kagakkai Koen Yokoshu
85(2), 863. Abstract. This work presents the isolation and structural elucidation of a new aroma
compound in the major component from Indian sandalwood tree, Santalum album L., not from
sandalwood oil obtained through steam distillation. We have found that the compound has a
novel hemiacetal structure and has sandalwood odor stronger than those of.alpha.- and.beta.-
santalols (the major components of sandalwood oil). (author abst.)
Heissler D. & Riehl J.-J. (1980) “Synthesis with benzenesulfenyl chloride. On the structure of a
C 12 H 18 hydrocarbon from East Indian sandalwood oil” Tetrahedron Letters 21(49), 4711-4714.
Abstract: The tetracyclic hydrocarbon was synthesized by means of the electrophilic addition of
benzenesulfenyl chloride to an appropriately substituted methylenenorbornene. The synthetic