ISSN:
0935-6304
Keywords:
Enuntioselective GC
;
Structure elucidation
;
3-Butylhexahydrophthalide stercoisomers
;
Odor thresholds
;
Celery oil
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jhrc.1240200502
