Article: Synthesis of Sodium (+)-(12S,13R)-Epoxy-cis-9-octadecenyl Sulfonate from Vernonia Oil

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 ...

Related newspaper, magazine, and journal articles:

 
 
Newsweek Harper's Magazine The Washington Post Chicago Tribune Crain's Chicago Business PRNewswire Pediatric News The Nation Advertising Age The Economist (US) A FREE trial gives you access to over 80 million articles! Access over 6,500 publications with a FREE trial!