Reduction ofcis- andtrans-1,2-epithio-p-menth-8-ene: preparation of new fragrant terpenoid thiols

Autor:	Daniel Joulain, Robert Faure, Roland Fellous, Karine Candela
Rok vydání:	2003
Předmět:	food.ingredient Chemistry Monoterpene General Chemistry Nuclear magnetic resonance spectroscopy Chemical synthesis Grapefruit juice Terpenoid food Organic chemistry Stereoselectivity Ene reaction Cis–trans isomerism Food Science
Zdroj:	Flavour and Fragrance Journal. 18:52-56
ISSN:	1099-1026 0882-5734
DOI:	10.1002/ffj.1153
Popis:	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.
Databáze:	OpenAIRE
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