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Stereoisomeric flavour compounds XXXV: Chiral aroma compounds of sherry I. Optically pure stereoisomers of solerone and solerole
Author(s) -
Mosandl Armin,
Hollnagel Angelika
Publication year - 1989
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530010408
Subject(s) - chemistry , diastereomer , aroma , enantiomer , lactone , chiral stationary phase , flavour , absolute configuration , stereochemistry , stereoselectivity , organic chemistry , catalysis , food science
The enantioseparation of the sherry aroma components 5‐oxo‐4‐hydroxyhexanoic acid γ‐lactone (solerone) and 4,5‐dihydroxyhexanoic acid γ‐lactone (solerole) is achieved, using Chiraspher (Merck) as the chiral HPLC phase and the optical purity ascertained directly by HRGC with heptakis(3‐ O ‐acetyl‐2,6‐di‐ O ‐pentyl)‐β‐cyclodextrin (Lipodex D) as the chiral stationary phase. The absolute configurations of 4,5‐dihydroxyhexanoic acid γ‐lactones are assigned by 1 H‐NMR spectral data of diastereomeric α‐methoxy‐α‐trifluoromethylphenylacetic acid (MTPA) esters, according to Mosher's model. Sensory qualities of the isomers are given.