Isolation and chiral GC analysis of (beta)-bisabolols--trace constituents from the essential oil of Santalum album L. (Santalaceae)
Journal of Essential Oil Research: JEOR, Mar/Apr 2003 by Braun, Norbert A, Meier, Manfred, Pickenhagen, Wilhelm
Abstract
The essential oil produced from the heartwood of Santalurn album L. was analyzed using GC/MS. Forty-four constituents were identified: one monoterpene and 43 sesquiterpenes. 2,10-Bisabola(lien-6-ol (= 0-bisabolol/epi-0bisabolol) was one of the trace compounds found in east Indian sandalwood oil. Chiral GC analysis showed that besides the main stereoisomer, which possessed an (R,R)-configuration, all three other isomers were -also present. Key Word Index
Santalum album, Santalaceae, essential oil composition, cls-alpha-santalol, cis-beta-santalol, beta-bisabolo/epi-beta-bisabolo, chiral GC analysis.
Introduction
Acknowledgments
We are especially grateful to Georg Frdter, Givaudan AG, Dubendorf(Switzerland), for providing us with samples of enantiopure beta-bisabolols. The authors are indebted to Birgit Kohlenberg, Anja Reimers and Franz-Joseph Hanwrschnidt, Dragoco Gerberding dr Co. AG, Holzrtinden, Gerany, for the oil analysis and helpful discussions.
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Norbert A. Braun,* Manfred Meier and Wilhelm Pickenhagen
Dragoco Gerberding, Co. AG, Corporate Research Division, 37601 Holzminden, Gennany
*Address for correspondence
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