STEREOISOMERIC FLAVOR COMPOUNDS .75. SYNTHESIS AND STRUCTURE-FUNCTIONRELATIONSHIP OF 3-METHYLTHIOBUTANAL ENANTIOMERS

Authors
WEBER B MOSANDL A
Citation
B. Weber et A. Mosandl, STEREOISOMERIC FLAVOR COMPOUNDS .75. SYNTHESIS AND STRUCTURE-FUNCTIONRELATIONSHIP OF 3-METHYLTHIOBUTANAL ENANTIOMERS, ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG A-FOOD RESEARCH AND TECHNOLOGY, 204(3), 1997, pp. 194-197
Citations number
14
Categorie Soggetti
Food Science & Tenology
Journal title
ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG A-FOOD RESEARCH AND TECHNOLOGY → ACNP
ISSN journal
14314630
Volume
204
Issue
3
Year of publication
1997
Pages
194 - 197
Database
ISI
SICI code
1431-4630(1997)204:3<194:SFC.SA>2.0.ZU;2-K
Abstract
The synthesis of enantiopure 3-methylthioalkanals, in particular of 3- methylthiobutanal enantiomers, is described. Elucidation of the struct ure was achieved by aldehyde-evoked reduction to 3-methylthiobutanol o f a known absolute configuration. The odour characteristics of the ena ntiomers were determined by enantioselective gas chromatography/olfact ometry using yl-6-O-tert-butyldimethylsilyl)-gamma-cyclodextrin as the chiral stationary phase. Exclusively, the (R)-configured 3-methylthio butanal exhibits the odour typical of cooked potatoes, whereas the (S) -configured stereoisomer is odourless.