S. Bilke, A. Mosandl
Nov 1, 2001
Citations
0
Influential Citations
5
Citations
Journal
Journal of Separation Science
Abstract
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-specific odor. 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 from u-campholene aldehyde via 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-enal. This is why the enantiomeric purity of 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-enol depends on the purity of u-campholene aldehyde as starting material. Hence, an enantioselective analysis of u-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 derivatives as chiral GC phases.