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Enantioselective analysis of 2‐methyl‐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 α‐campholene aldehyde by capillary gas chromatography
Author(s) -
Bilke Steffi,
Mosandl Armin
Publication year - 2001
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/1615-9314(20011101)24:10/11<819::aid-jssc819>3.0.co;2-y
Subject(s) - enantioselective synthesis , enol , aldehyde , chemistry , enantiomer , odor , sandalwood , stereochemistry , gas chromatography , enantiomeric excess , organic chemistry , chromatography , catalysis , archaeology , history
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 α‐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 α‐campholene aldehyde as starting material. Hence, an enantioselective analysis of α‐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.