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Constituents of Haitian vetiver oil
Author(s) -
Weyerstahl Peter,
Marschall Helga,
Splittgerber Ute,
Wolf Dietmar,
Surburg Horst
Publication year - 2000
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/1099-1026(200011/12)15:6<395::aid-ffj930>3.0.co;2-9
Subject(s) - chemistry , epimer , stereochemistry , isopropyl , carbon 13 nmr , organic chemistry
155 constituents in the neutral part of commercial Haitian vetiver oil were identified. Their structures were assigned mainly by 1 H‐ and 13 C‐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.