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Preparative chromatographic isolation of hydroxy acids from lesquerella fendleri and lesquerella gordonii seed oils

Preparative chromatographic isolation of hydroxy acids from lesquerella fendleri and lesquerella gordonii seed oils

Journal of the American Oil Chemists' Society 67(8): 495-498

ISSN/ISBN: 0003-021X

To conduct product development research on Lesquerella seed oils, we explored methods to obtain > 100 g quantities of lesquerolic (14-hydroxy-cis-11-eicosenoic) acid. Preliminary experiments with open-column silica gel chromatography showed that L. fendleri oil could be separated into 3 triglyceride (TG) fractions. The first (10%) contained nonhydroxy 16-(13%) and 18-carbon acids (65% 18:1,2,3). The second fraction (15%) contained monolesquerolins (39% lesquerolic acid). The major TG fraction (73%) was mainly dilesquerolins (66% lesquerolic acid) showing that a hydroxy acid-enriched TG oil was obtainable by this procedure. Silica gel chromatography easily separated L. fendleri fatty acid methyl esters (FAME) into hydroxy-free ester fraction (40-44%) consisting largely of 18:1 (39%), 18:2 (19%) and 18:3 (31%), and a hydroxy ester fraction (56-60%) that was largely methyl lesquerolate (94%) with small amounts of auricolate (5%) (14-hydroxy-cis-11,cis-17-eicosadienoate) and traces of 18-carbon hydroxy esters. This process for isolating the hydroxy FAME of Lesquerella oil was scaled up 15- to 100-fold with a preparative high performance liquid chromatograph. Thirty-gram samples of L. gordonii FAME were dissolved in eluting solvent, pumped onto the high performance liquid chromatography (HPLC) silica column and eluted with 97:3 hexane/ethyl acetate. In an 8-hr period, up to 200 g of methyl lesquerolate could be obtained with a purity > 98%, the only contaminants being methyl auricolate and methyl ricinoleate.

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Accession: 007681915

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