ENANTIOMERIC RATIOS OF PANTOLACTONE, SOLERONE, 4-CARBOETHOXY-4-HYDROXY-BUTYROLACTONE AND OF SOTOLON, A FLAVOR IMPACT COMPOUND OF FLOR-SHERRY AND BOTRYTIZED WINES

The enantiomers of sotolon (2), a flavour impact compound of flor-sherry and botrytized wines, were synthesized to determine the chromatographic behaviour of the enantiomers (R)-2 and (S)-2 on permethylated beta-cyclodextrin as the chiral stationary phase. Using enantioselective multidimensional gas chromatography (column combination: DB 1701/permethyl-beta-cyclodextrin) the enantiomeric ratios of the chiral gamma-lactones pantolactone (1), sotolon (2), solerone (3) and 4-carboethoxy-4-hydroxy butyrolactone (4) in flor-sherry and botrytized wines were evaluated. High enantiomeric excess in favour of the (4R)-configurated mirror images was detected for lactones 1 and 4. The measured enantiomeric ratios of sotolon (2) and solerone (3) were too low and unspecific to be useful in authenticity control of 2 and 3.