Constituents of Haitian vetiver oil

Abstract

155 constituents in the neutral part of commercial Haitian vetiver oil were identified. Their structures were assigned mainly by 1H- and 13C-NMR spectra, as reported previously. Furthermore, the following new compounds are described: acora-2,4-diene (7) and its 10-epimer (8), 3-isopropyl-2-(3-methylcyclopent-2-enyl)-tetrahydrofuran (4), 3-isopropyl-6-methyl-2-(3-methylcyclopent-2-enyl)-3,4-dihydro-2H-pyran (15) and its precursor 6-hydroxy-3-isopropyl-6-methyl-2-(3-methycyclopent-2-enyl)-3,4,5,6-tetrahydr-2H-opyran (D), 12,13-di-nor-6(7←8)-abeo-eremophil-1(10)-en-7-one (16), 8α-methyl-11,12,13-tri-nor-eremophil-1(10)-en-7-one (20), eudesma-5,7-dien-4-ol (cascarilladienol, 50), 13-nor-7,8-epoxy-eremophil-1(10)-en-11-one (98), eremophil-7(11)-en-10β-ol (111), 7,11-epoxy-eremophila-1,9-dien-8α-ol (124), two epimers of 6,12;7,11-diepoxy-eudesm-4-ene (125, 128) and of 7,11;8,12-diepoxy-eremophil-9-ene (129, 137). NMR data of β-vetispirene (18), γ-amorphene (22), β-vetivenene (48), elema-1,3-dien-6α-ol (6-epi-shyobunol, 32), eudesm-4(15)-en-5β-ol (69), trans-eudesma-4(15),7-dien-12-yl formate (vetiselinenyl formate, 127), ziza-6(13)-en-12-yl acetate (142), preziza-7(15)-en-12-yl acetate (143), methyl (E)-eremophila-1(10),7(11)-dien-12-oate (139) and (E)-eremophila-1(10),7(11)-dien-12-yl (isovalencenyl acetate, 144) are described. The contribution of some constituents to the very complex odour of vetiver oil is discussed. Copyright © 2000 John Wiley & Sons, Ltd.