Analysis of the polar fraction of Haitian vetiver oil

• Published in: Flavour and fragrance journal 2000-05, Vol.15 (3), p.153-173
• Main Authors: Weyerstahl, Peter, Marschall, Helga, Splittgerber, Ute, Wolf, Dietmar
• Format: Article
• Language: English
• Subjects: Applied sciences; b-Vetivone; Chemical industry and chemicals; essential oil; Essential oils, perfumes; Exact sciences and technology; methyl ether derivatives; NMR; sesquiterpene alcohols; sesquiterpenes; vetiver oil; Vetiveria zizanioides (L.) Nash; Washing products. Cosmetics and toiletries. Perfumes
• ISSN: 0882-5734; 1099-1026
• DOI: 10.1002/1099-1026(200005/06)15:3<153::AID-FFJ885>3.0.CO;2-5

The polar part of commercial Haitian vetiver oil was converted to the methyl ethers, and this product separated by distillation and repeated flash chromatography (FC). The following new (nor‐) sesquiterpene alcohols were isolated as their methyl ethers and identified by their 1H‐ and 13C‐NMR spectra: 12‐nor‐ziza‐6(13)‐en‐2β‐ (2) and ‐2α‐ol (3), eudesma‐4(15),7‐dien‐3β‐ (7) and ‐2β‐ol (18), eudesma‐3,5‐dien‐1α‐ol (26), eremophila‐1(10),4(15)‐dien‐2α‐ol (31), eremophila‐1(10),11‐dien‐2α‐ol (nootkatol, 38), guaia‐1(5),11‐dien‐3‐ol (11), spirovetiva‐3,7(11)‐dien‐12‐ol (42), preziza‐7(15)‐en‐3α‐ol (14) and helifol‐1‐en‐14‐ol (syn. khusien‐14‐ol, 12). Furthermore, the hemi‐acetal 7,10‐epoxy‐salvialan‐10‐ol (8) was identified. The structure of some artefacts formed by alkylation of β‐vetivone 52 (→M 39, M 43) and of 11,12,13‐tri‐nor‐eudesmenone (→16, 17) was also elucidated. Copyright © 2000 John Wiley & Sons, Ltd.