Enantioselective analysis of 2-methy1-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-enol,2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-enal and #alpha#-campholene aldehyde by capillary gas chromatography

摘要

2-Methyl-4-(2,2,3,-trimethylcyclopent-3-en-1-yl)-but-2-enol is a synthetic fragrance with a strong sandalwood-like odor.It was found that the (R)-enantiomer is exclusively responsible for the sandalwood-like odor,whilst the (S)-enantiomer has only a faint,non-specificodor.Consequently,enantioselective analysis is a powerful tool in sensory quality control of 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-enol.The industrial synthesis starts form #alpha#-campholene aldehyde via 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-enal.This is whythe enantimericpurity of 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-enol depends on the purity of #alpha#-campholene aldehyde as starting material.Hence,anenantioselective analysis of #alpha#-campholene aldehyde,2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-enal,and 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-enol was achieved by enantioselective gas chromatography using tert-butyldimethylsilylated-cyclodextrin derivative as chiral GC phases.