Formation of<i>trans</i>‐12,13‐epoxy‐9‐hydroperoxy‐<i>trans</i>‐10‐octadecenoic acid from 13‐L‐hydroperoxy‐<i>cis</i>‐9,<i>trans</i>‐11‐octadecadienoic acid catalyzed by either a soybean extract or cysteine‐FeC1₃

Abstract

Abstract A soybean extract or an ethanolic solution of cysteine and ferric chloride catalyzed the conversion of 13‐L‐hydroperoxy‐ cis ‐9, trans ‐11‐octadecadienoic acid to numerous products among which was trans ‐12,13‐epoxy‐9‐hydroperoxy‐ trans ‐10‐octadecenoic acid. When this fatty acid was treated further with the cysteine‐ferric chloride solution, 9‐hydroxy‐12,13‐epoxy‐10‐octadecenoic and 9‐oxo‐12,13‐epoxy‐10‐octadecenoic acids were formed. Thus, trans ‐12,13‐epoxy‐9‐hydroperoxy‐ trans ‐10‐octadecenoic acid probably is an intermediate in the formation of the latter two compounds. Additionally, the erythro and threo isomers of trans ‐12,13‐epoxy‐11‐hydroperoxy‐ cis ‐9‐octadecenoic acid tenatatively were identified as products.