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Stereoisomeric flavour compounds. LII: Separation and structure elucidation of the furanoid linalool oxide stereoisomers using chirospecific capillary gas chromatography and nuclear magnetic resonance spectroscopy
Author(s) -
Askari Christiane,
Mosandl Armin
Publication year - 1991
Publication title -
phytochemical analysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 72
eISSN - 1099-1565
pISSN - 0958-0344
DOI - 10.1002/pca.2800020506
Subject(s) - chemistry , linalool , gas chromatography , nuclear magnetic resonance spectroscopy , chromatography , capillary gas chromatography , oxide , organic chemistry , essential oil
Using heptakis(2,3,6‐tri‐ O ‐methyl)‐β‐cyclodextrin as the chiral stationary phase in capillary gas chromatography, the direct stereodifferentiation of the four furanoid linalool oxide stereoisomers has been achieved. The structure elucidation of the two geometrical isomers by 1 H NMR spectroscopy (including intramolecular nuclear Overhauser effects of the separated diastereomers) is now reported. The elution order of the optical isomers is ascertained by synthesis and chromatography of the (2 R )‐configured diastereomers, starting from ( R )‐linalool.