Stereoisomeric flavor compounds LXXVII: 3-Butylhexahydrophthalides: Simultaneous enantioselective analysis, structure elucidation, and sensorial properties of the stereoisomers
✍ Scribed by Bartschat, Dietmar ;Wüst, Matthias ;Mosandl, Armin ;Hanssum, Helmut
- Publisher
- John Wiley and Sons
- Year
- 1997
- Tongue
- English
- Weight
- 532 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0935-6304
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✦ Synopsis
Abstract
Using heptakis‐(2,3‐di‐O‐acetyl‐6‐O‐tert‐butyldimethylsilyl)‐β‐cy‐clodextrin as the chirul stationary phase in enantioselective gas chromatography, the simultaneous enantioselective analysis of all eight 3‐butylhexahydrophthalide Stereoisomers was achieved. Fur‐thermore, the odor characteristics and odor thresholds were investigated by enantioselective gas chromatography/olfactometry. Racemic standards were synthesized via hydrogenation and subsequent base catalyzed epimerization. Starting from racemic 3‐butylphthalide. After separation by high performance liquid chromatography. Relative configurations of the pure diastereoisom‐ers were determined by means of NOE‐difference spectroscopy. The absolute configuration at C‐3 was determined starting from (3S)‐butylphthalide as an educt for hydrogenation and epimerization. Absolute configurations of all eight 3‐butylhexahydrophtbalide stereoisomers are unambiguously concluded from the NOE‐experi‐ments in connection with the determination of the absolute configuration at C‐3.