The oxidation of oleic acid by means of hydrogen peroxide with and without the addition of copper sulphate: a possible analogy with its oxidation in vivo

Abstract

In the action of H2O2 on oleic acid in the presence of a Cu catalyst (CuSOi), oxidation occurs first at the 9th and 10th C atoms. On further oxidation the 8 terminal C atoms are broken off and the rest of the chain broken up; succinic, carbonic, formic, acetic, glycollic and oxalic acids were identified. The 8 carbon acid was assigned the formula 4-keto-7-hydroxycaprylie acid. Under similar conditions the same keto acid and succinic acid were obtained from the oxidation of caprylic acid. The use of cupric salts with H2O2 apparently resulted in [gamma]-oxidation of oleic and caprylic acids. The theory of [beta]-oxidation is discussed.