Synthesis of Polyunsaturated Fatty Acid L-Menthyl Esters through Lipase-Catalyzed Esterification in an Organic Solvent-Free System

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Synthesis of L-menthyl eicosapentaenoate was achieved through lipase-catalyzed esterification of eicosapentaenoic acid (EPA) with L-menthol in an organic solvent-free system. A suitable enzyme was a lipase from Candida rugosa (Lipase-AY, Amano Enzyme Inc., Aichi) when L-menthol was esterified at 30°C in a mixture of L-menthol/EPA (1.2/1, mol/mol), 20 wt% water and 1600 U/g-mixture of lipase. The reaction reached equilibrium after 3 d at ca. 75% esterification. L-Menthyl γ-linolenate and arachidonate could also be synthesized under the same conditions as those in synthesis of L-menthyl eicosapentaenoate, although the degrees of esterification after 4 d were 54 and 41%, respectively. Synthesis of L-menthyl eicosapentaenoate greatly depended on the water content, and reaction rate significantly decreased in the presence of < 20% of water.<br>

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