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Article: Synthesis of Sodium (+)-(12S,13R)-Epoxy-cis-9-octadecenyl Sulfonate from Vernonia Oil
- Article from:
- JAOCS, Journal of the American Oil Chemists' Society
- Article date:
- July 1, 2009
- Author:
CopyrightCopyright AOCS Press Jul 2009. Provided by ProQuest LLC. (Hide copyright information)
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Abstract
A water-soluble, foaming epoxyalkene sulfonate, sodium (+)-(12S,13R)-epoxy-cis-9-octadecenyl sulfonate, was synthesized from vernonia oil (VO) by a series of simple reactions that include transesterification, metal hydride reduction, tosylation, and S^sub N^2 reactions. Conversion of VO into vernonia oil methyl esters (VOME) using sodium methoxide was quantitative. Subsequent reduction of VOME with lithium aluminum hydride yielded (+)-(12S,13R)-epoxy-cis-9-octadecenol (94%), along with minor amounts of hexadecenol, octadecenol, cis-9-octadecenol, and cis-9,12-octadecandienol. The (+)-(12S,13R)-epoxy-cis-9-octadecenol, was tosylated with p-toluenesulfonyl chloride to give ...