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Reduction of cis ‐ and trans ‐1,2‐epithio‐ p ‐menth‐8‐ene: preparation of new fragrant terpenoid thiols
Author(s) -
Candela Karine,
Fellous Roland,
Joulain Daniel,
Faure Robert
Publication year - 2002
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.1153
Subject(s) - chemistry , monoterpene , terpenoid , limonene , epoxide , terpene , organic chemistry , sesquiterpene , stereochemistry , essential oil , chromatography , catalysis
The synthesis of 2‐mercapto‐ p ‐menth‐8‐ene ( 3 ) and 1‐mercapto‐ p ‐menth‐8‐ene ( 4 ) are described, starting, respectively, from thioepoxydation of (+)‐ trans ‐limonene 1,2‐epoxide ( 1a ) and (+)‐ cis ‐limonene 1,2‐epoxide ( 1b ) via hydride reduction of episulphides 2a and 2b . Structural determination of these sulphur‐containing terpenoids was achieved by one‐ and two‐dimensional NMR spectroscopy. The odours of these two new monoterpene thiols were described, respectively, as reminescent of grapefruit juice and as being typically alliaceous. Copyright © 2002 John Wiley & Sons, Ltd.