Abstract
AbstractTwo epimers of methyl (12S,13S)‐(E)‐12,13‐epoxy‐9‐hydroperoxy‐10‐octadecenoate were isolated after esterification of a mixture of fatty acids obtained from decomposition of (13S)‐(9Z,11E)‐13‐hydroperoxy‐9,11‐octadecadienoic acid by an Fe++‐cysteine catalyst. These epimeric epoxyhydro‐peroxyoctadecenoates were decomposed by heat (210 C) in the injection port of a gas chromatograph, and the cleavage fragments were subsequently separated by gas chromatography (GC) and identified by mass spectrometry (MS). Among the scission products obtained, the most prominent in the GC peak profile were methyl octanoate and methyl 9‐oxononanoate. Other peaks were identified as pentane, 1‐pentanol, hexanal, 2‐heptanone, 2‐pentylfuran, methyl heptanoate, 2‐octenal, 4,5‐epoxy‐2‐decenal, methyl 8‐(2‐furyl)‐octanoate, 11‐oxo‐9‐undecenoate and methyl 13‐oxo‐9,11‐tridecadienoate. In addition, 3,4‐epoxynonanal, methyl 8‐oxooctanoate, 3‐hydroxy‐2‐pentyl‐2,3‐dihydrofuran and methyl 10‐oxodecanoate were tentatively identified. Except for the furan compounds, the formation of the fragmentation products could be explained by conventional free‐radical scission mechanisms.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
