Fatty acid allene oxides. II. Formation of two macrolactones from 12,13(S)-epoxy-9(Z),11-octadecadienoic acid.
An unstable fatty acid allene oxide, 12,13(S)-epoxy-9(Z),11-octadecadienoic acid, was recently identified as the product formed from 13(S)-hydroperoxy-9(Z), 11(E)-octadecadienoic acid in the presence of corn (Zea mays L.) hydroperoxide dehydrase (M. Hamberg (1987) Biochim. Biophys. Acta 920, 76-84). The present paper is concerned with the spontaneous decomposition of 12,13(S)-epoxy-9(Z),11-octadecadienoic acid in acetonitrile solution. Two major products were isolated and characterized, i.e. macrolactones 12-keto-9(Z)-octadecen-11-olide and 12-keto-9(Z)-octadecen-13-olide.
Hamberg
M
M
Department of Physiological Chemistry, Karolinska Institutet, Stockholm, Sweden.
D005231:Fatty Acids, Unsaturated; D008041:Linoleic Acids; D009829:Oleic Acids
D005231:Fatty Acids, Unsaturated; D008041:Linoleic Acids; D009829:Oleic Acids; C055941:12-keto-9(2)-octadecen-11-olide; C055943:12-keto-9(2)-octadecen-13-olide; C055944:12,13-epoxy-9(2),11-octadecadienoic acid; C027369:octadecadienoic acid