A Chemical Investigation of the Volatile Constituents of East Indian Sandalwood Oil (SantalumalbumL.)

Distillation foreruns from East Indian sandalwood oil (Santalum album L .), representing 5–8% of the oil, have been investigated using fractional distillation, preparative column chromatography, gas liquid chromatography (GLC.), and chemical treatments. This allowed the isolation and characterization by their spectral data of 46 compounds. 32 of them were newly identified sandalwood oil constituents including 4 novel substances: santalone ( 2 ), 4-methylcyclohexa-1,3-dien-1-yl methyl ketone ( 4 ), 5,6-dimethyl-5-norbornen-exo-2-ol ( 7 ), and (E)-5-(2,3-dimethyl-3-nortricyclyl)-pent-3-en-2-one ( 20 ). The other constituents identified were 1-furfuryl-pyrrole ( 10 ) and 10 phenols accompanied by 17 terpene and sesquiterpene derivatives. Endo-2,endo-3-dimethyl-norbornan-exo-2-ol ( 6 ), an α-santenol ( z ), precursor, was present in the last group of constituents. The compounds 2, 4, 6, 7, 20 have been synthesized as well as another novel constituent, endo-2-mythyl-3-methylidene-norbornan-exo-2-ol ( 5 ).