STEREOISOMERIC FLAVOR COMPOUNDS LI - ENANTIOSELECTIVE CGC-ANALYSIS AND ORIGIN ASSIGNMENT OF CHIRAL FURANONES - SCOPE AND LIMITATIONS

The chirospecific CGC analysis of 2,5-dimethyl-4-hydroxy-3[2H]-furanone has been carried out without any racemization, using heptakis (2,6-di-O-isopentyl-3-O-allyl)-beta-cyclodextrin as the chiral stationary phase. Both compounds were detected as racemates in strawberries, pineapples, grapes and wines therefore, chirospecific analysis cannot be applied to assign their origin. On the other hand, 4,5-dimethyl-3-hydroxy-2[5H]-furanone (sotolone) was separated into its mirror images by extreme chiral resolution (R triple-over-dot S = 5.8), suggesting a new method to evaluate the quality of wines and sherries made from grapes affected by botrytis.