Optical resolution of (±)-Threo-9,10,16-trihydroxy hexadecanoic acid using (−)brucine

  title={Optical resolution of (±)-Threo-9,10,16-trihydroxy hexadecanoic acid using (−)brucine},
  author={Navdeep B. Malkar and V. Ganesh Kumar},
  journal={Journal of the American Oil Chemists' Society},
  • N. B. MalkarV. Kumar
  • Published 1 October 1998
  • Chemistry
  • Journal of the American Oil Chemists' Society
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… 
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