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Determination of optical purity and absolute configuration of natural 12‐hydroxystearic acid by the 1 H NMR anisotropy method
Author(s) -
Murakami Satoshi,
Satou Kazuhiro,
Kijima Taturo,
Watanabe Masataka,
Izumi Taeko
Publication year - 2011
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201000348
Subject(s) - diastereomer , chemistry , enantiopure drug , absolute configuration , elution , enantiomer , silica gel , enantiomeric excess , high performance liquid chromatography , proton nmr , chromatography , diol , nmr spectra database , organic chemistry , stereochemistry , enantioselective synthesis , spectral line , catalysis , physics , astronomy
The enantiopure of ( R )‐(−) MαNPA was allowed to react with racemic 18‐( tert ‐butyldimethylsilyloxy)‐5‐octadecayne‐7‐ol which was derived from dodecane‐1,12‐diol, yielding diastereomeric esters mixture. These racemic esters were easily separated by HPLC on silica‐gel. The absolute configurations of the first‐eluted diastereomeric esters from the separated esters were determined using 1 H NMR anisotropy method. Analysis on 1 H NMR spectra and HPLC elution time of the synthesized esters and those of MαNP ester derived from natural methyl‐12‐hydroxystealate showed that the absolute configuration of natural 12‐hydroxystearic acid was R form, and the enantiomeric excess was over 99%.