Sandalwood Biblio - Cropwatch

Jirovetz L. et al. (1988). “Differentiation of double bond isomers of sesquiterpene alcohols in East
Indian sandalwood oil by means of GC-MS and GC-FTIR: Dihydrosantalols.” Spectroscopy 6(5-
6), 283-294.
John M.D., Paul T.M. & Jaiswal P.K. (1991) “Detection of adulteration of polyethylene glycol in oil
of sandalwood” Indian Perfumer 35(4), 186-187..
Kim T.H., Ito H., Hayashi K., Hasegawa T., Machguchi T., & Yoshida T. (2005) "Aromatic
constituents from the heartwood of Santalum album." Chem Bull Pharm (Tokyo) 53(6), 641-646.
Abstract: A phytochemical investigation of the polar constituents in the heartwood of Indian
Santalum album L. resulted in the isolation of three new neolignans (1-3) and a new aromatic
ester (4), along with 14 known components. The structures of the new compounds (1-4) were
established using spectroscopic methods.
Kim T.H., Ito H., Hatano T., Haswegawa T., Akiba A., Machiguchi T., Yoshida T. (2005)
"Bisabolane & santalane-type sequiterpemoids from Santalum album of East Indian origin" J. Nat
Products 68(12), 1805-1808. Abstract: Six new bisabolane-type (1-3) and santalane-type (4-6)
sesquiterpenoids, together with (+)-alpha-nuciferol, (+)-citronellol, and geraniol, were isolated
from the heartwood of Santalum album of Indian origin. Their structures, including two bisabolol
diastereomers (1, 2), were established on the basis of spectroscopic data interpretation.
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.
Kretschmar H.C., Barneis Z.J. & Erman W.F. (1970) “The isolation & synthesis of a novel
tetracyclic ether from East Indian sandalwood oil. A facile intramolecular Prins reaction.”
Tetrahedron Letters 11(1), 37-40.
Kuttan R. & Radhakrishnan A.N. (1972) "Studies on the biosynthesis of sym-homospermidine in
sandal (Santalum album L.)." Biochem J. 127(1), 61-67. Abstract. The biosynthesis of the newly
isolated polyamine, sym-homospermidine (NH2–[CH2]4–NH–[CH2]4 –NH2), was studied by
using radioactive amino acids. Arginine was the most effective precursor, being about 10 times as
active as ornithine. Unlabelled agmatine and putrescine markedly inhibited the incorporation of
[14C]arginine into homospermidine. Similarly the incorporation of ornithine was inhibited by
unlabelled arginine and putrescine. γ-Aminobutyraldehyde, the oxidation product of putrescine,
was considered to be one of the intermediates in the biosynthesis of homospermidine. The
biosynthesis may involve a Schiff-base formation of putrescine with γ-aminobutyraldehyde and
subsequent reduction. A limited synthesis of spermidine also takes place under these conditions.
36