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Determination of Absolute Configuration of Hydroxyl Group of Long
Chain Alcohols, and Discrimination of E- / Z-isomers of Double Bond
Kusakari Miho1, Murakami Satoshi 1, Sato Ei-ichi 3, Kato Akane1, Matsumoto Takatoshi 2,
Hatano Bunpei1, Izumi Taeko1, Watanabe Masataka1, Kijima Tatsuro1
Yamagata University1, 992-8510, Yonezawa, Japan
Tohoku University 2, 980-8577, Sendai, Japan
Kusumoto Chemicals Ltd.3, 340-0004, Souka, Japan
It is well known that configuration of double bond (E or Z) depends on their 1H NMR
coupling constant.
We reinvestigated configuration of double bond and absolute
configuration of hydroxyl group of methyl ricinoleate 1 to have Z-configuration and
R-configuration of hydroxyl group by 1H NMR spectrum and 2D NMR spectrum using
(S)-(+)- and (R)-(‐)-2-methoxy-2-(1-naphthyl) propionic acid (MαNP acid) 2 as a chiral
auxiliaries.
However configuration of double bond of oleic acid 3 could not be determined by 1H
NMR spectrum. We will also reported that double bond of configuration of 3 has Zconfiguration by 2D NMR spectrum.
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