Synthesis of 6-hydroxy δ-lactones and 5,6-dihydroxy eicosanoic/docosanoic acids from meadowfoam fatty acids via a lipase-mediated self-epoxidation |
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Authors: | Hans B Frykman Terry A Isbell |
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Affiliation: | (1) New Crops Research, NCAUR, ARS, USDA, 1815 North University St., 61604 Peoria, IL |
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Abstract: | Meadowfoam fatty acids were reacted with hydrogen peroxide in a lipase-catalyzed autocatalytic system, forming a mixture of
5,6-epoxyeicosanoic, 13,14-epoxydocosanoic, 5,6-epoxydocosanoic, and 5,6-13,14-diepoxydocosanoic acids in 98% yield. The 5,6-epoxy
acids were cyclized to 6-hydroxy δ-eicosanoic/docosanoic lactones by sulfuric acid catalysis in high yield (99%). 5,6-Dihydroxy
acids could be obtained from 6-hydroxy δ-lactones by a simple alkaline work-up procedure. Meadowfoam fatty acids were converted
(77% yield) in a one-pot reaction to 6-hydroxy δ-lactones by in situ performic acid epoxidation and subsequent addition of sulfuric acid. |
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Keywords: | 5 6-13 14-Diepoxydocosanoic acid dihydroxy eicosanoic acid 5 13-docosadienoic acid δ -eicosanolactone 5-eicosenoic acid epoxidation 5 6-epoxyeicosanoic acid formic acid hydrogen peroxide 6-hydroxy-δ -lactones lactonization lipase performic acid sulfuric acid |
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