Fat oxidation. I.—Preparation of <i>Trans‐trans</i> methyl linoleate hydroperoxide

Abstract

Abstract A method is described for the preparation of methyl linoleate hydroperoxide by the oxidation of methyl linoleate in solution in light petroleum, followed by partition of the product between light petroleum (b.p. 60–80°) and 85% aqueous methanol which gave material with an extinction coefficient ( E ) (1%, 1 cm.) of 810 at 231.5 mμ in ethanol ( c = 26,400). This hydroperoxide was found to be a mixture of cis‐trans and trans‐trans conjugated dienes, from which the latter was isolated by low‐temperature precipitation from light petroleum (b.p. 40–60°) followed by low‐temperature crystallisation from ethanol. This product had an E (1%, 1 cm.) of 890 at 231.5 mμ ( ϵ = 29,000).