Determination of optical purity and absolute configuration of natural 12-hydroxystearic acid by the 1H NMR anisotropy method

被引：8
|
作者：
Murakami, Satoshi [1 ]
Satou, Kazuhiro [1 ]
Kijima, Taturo [1 ]
Watanabe, Masataka [1 ]
Izumi, Taeko [1 ]
机构：
[1] Yamagata Univ, Grad Sch Sci & Engn, Yonezawa, Yamagata 9928510, Japan
来源：
EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY | 2011年 / 113卷 / 04期
关键词：
Absolute configuration; Anisotropy method; Chiral; 12-Hydroxystearic acid; NMR; 2-METHOXY-2-(1-NAPHTHYL)PROPIONIC ACID; ACETYLENE ALCOHOLS; ENANTIORESOLUTION;
D O I：
10.1002/ejlt.201000348
中图分类号：
TS2 [食品工业];
学科分类号：
0832 ;
摘要：
The enantiopure of (R)-(-) M alpha NPA 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 H-1 NMR anisotropy method. Analysis on H-1 NMR spectra and HPLC elution time of the synthesized esters and those of M alpha NP 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%.
引用
收藏
页码：450 / 458
页数：9
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