ISSN:
1431-4630
Keywords:
Key words Enantiomerseparation
;
4-tert-butyl-α-methyldihydrocinnamaldehyde
;
Flavour compounds
;
Gas chromatography/olfactometry
Source:
Springer Online Journal Archives 1860-2000
Topics:
Process Engineering, Biotechnology, Nutrition Technology
Notes:
Abstract Using enantioselective gas chromatography and heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin (DIAC-TBDMS-β-CD) as the chiral stationary phase, the direct enantioseparation of 4-tert-butyl-α-methyldihydrocinnamaldehyde was achieved. The threshold values and odour characteristics of the enantiomers were investigated by enantioselective gas chromatography/olfactometry. In order to elucidate stereochemical features, the carbonyl-function was oxidized to the corresponding acid and diastereomeric amides were generated with (S)-2-amino-2-phenyl-ethanol [L(+)-α-phenylglycinol] as the enantiopure reagent. After separation and isolation by high-performance liquid chromatography, absolute configurations were deduced from X-ray structure elucidation of a pure stereoisomer. Amide cleavage, reduction and selective oxidation yielded the enantiomers of 4-tert-butyl-α-methyldihydrocinnamaldehyde.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/s002170050127
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