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Optical resolution of (±)‐ Threo ‐9,10,16‐trihydroxy hexadecanoic acid using (−)brucine
Author(s) -
Malkar Navdeep B.,
Kumar V. G.
Publication year - 1998
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-998-0202-9
Subject(s) - brucine , chemistry , crystallization , enantiomer , hydrolysis , reagent , diastereomer , fractional crystallization (geology) , resolution (logic) , organic chemistry , biochemistry , geochemistry , artificial intelligence , basalt , computer science , strychnine , geology
The optical resolution of (±) threo ‐9,10,16‐trihydroxy hexadecanoic acid was achieved by fractional crystallization using (−)brucine. Formation of an estolide during decomposition of the (−)brucine complex was observed to interfere with the separation of the optically pure material. This was corrected by converting the estolide to (+)‐ threo ‐9,10,16‐trihydroxy hexadecanoic acid via alcoholic alkaline hydrolysis followed by neutralization. Enantiomeric purity was determined by chiral lanthanide nuclear magnetic resonance shift reagent.