Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract only
Publication Acceptance Date: 2/1/2005
Publication Date: 4/7/2005
Citation: Piazza, G.J., Foglia, T.A. 2005. Increased diol formation by hydrolysis of fatty epoxides formed by oat peroxygenase [abstract]. Annual Meeting and Expo of the American Oil Chemists' Society. p. 64. Interpretive Summary:
Technical Abstract: We have been studying the synthesis of fatty polyols by the hydrolysis of fatty epoxides. The fatty epoxides were prepared using a peroxygenase enzyme found in oat seeds. Epoxidation procedures were developed for aqueous and organic solvent reaction media using commonly available organic hydroperoxides such as tert-butyl hydroperoxide, which is prepared by the addition of oxygen to iso-butane. In recent research, we used ground oat seeds as an inexpensive source of peroxygenase, and epoxide derivatives were prepared using fatty amides and fatty acids because these are not affected by the lipase activity present in oat seeds. The synthesis of nonadjacent epoxides was favored by limited oxidant or limited reaction time. Thus for example from linoleic acid or its amide derivative, the monoepoxides are obtained under these conditions. From linolenic acid or its amide derivative, a diepoxide is obtained in which the epoxides are found at the ends of the former methylene-interrupted triene system. When we hydrolyze these epoxides by the addition of water under acidic conditions, diols or tetrols are obtained. In contrast when fully epoxided linoleic acid, linolenic acid, or their respective amide derivatives are hydrolyzed, cyclic tetrahydrofuran derivatives are obtained. Thus partial epoxidation by peroxygenase followed by hydrolysis leads to higher amounts of diols and tetrols, resulting in a more polar and potentially more reactive product.