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Mono‐ and sesquiterpenoids of the volatile oil of Bursera graveolens
Author(s) -
Yukawa Chiyoki,
Iwabuchi Hisakatsu,
Komemushi Sadao,
Sawabe Akiyoshi
Publication year - 2005
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/ffj.1523
Subject(s) - chemistry , limonene , monoterpene , sesquiterpene , cyclopentene , aroma , terpene , essential oil , stereochemistry , ether , organic chemistry , chromatography , food science , catalysis
The characteristic spicy, sweet and balsamic aroma components of the woods of Bursera graveolens (palo santo) were measured using GC‐MS. The characteristic four compounds, 1–4, were isolated from the diethyl ether extract. The structure of compounds 1 and 2 was elucidated by means of NMR studies, and confirmed to be 1‐acetyl‐4‐isopropenyl‐1‐cyclopentene (1) and 2‐methyl‐5‐isopropenyl‐1‐cyclopenten‐1‐carboxaldehyde (2) by synthesis from limonene oxide derivatives. The structure of compounds 3 and 4 was determined to be 6,10‐epoxy‐7(14)‐isodaucane (3) and 10‐hydroxy‐6,10‐epoxy‐7(14)‐isodaucane (4) by NMR experiments. Of these, compound 4 is a new sesquiterpenoid with a weak woody note, and the presence of compounds 1–4 in B. graveolens is reported here for the first time. Copyright © 2005 John Wiley & Sons, Ltd.