Stereoisomeric flavour compounds LXXV: synthesis and structure–function relationship of 3-methylthiobutanal enantiomers |
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| Authors: | Bernhard Weber and A. Mosandl |
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| Affiliation: | (1) Institut für Lebensmittelchemie, Johann Wolfgang Goethe-Universit?t Frankfurt, Marie-Curie-Strasse 9, D-60439 Frankfurt/Main, Germany, DE |
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| Abstract: | The synthesis of enantiopure 3-methylthioalkanals, in particular of 3-methylthiobutanal enantiomers, is described. Elucidation of the structure was achieved by aldehyde-evoked reduction to 3-methylthiobutanol of a known absolute configuration. The odour characteristics of the enantiomers were determined by enantioselective gas chromatography/ olfactometry using octakis(2,3-di-O-butyryl-6-O-tert-butyldimethylsilyl)-γ-cyclodextrin as the chiral stationary phase. Exclusively, the (R)-configured 3-methylthiobutanal exhibits the odour typical of cooked potatoes, whereas the (S)-configured stereoisomer is odourless. Received: 24 May 1996 |
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| Keywords: | Stereoisomeric flavour compounds Enantioselective GC/olfactometry analysis Chirality and odour Sulphur-containing volatiles |
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