Detail of "1931-63-1"

Reference

Photosensitized oxidation of methyl linoleate monohydroperoxides: hydroperoxy cyclic peroxides, dihydroperoxides, keto esters and volatile thermal decomposition products

Photosensitized oxidation of methyl linoleate monohydroperoxides: hydroperoxy cyclic peroxides, dihydroperoxides, keto esters and volatile thermal decomposition products. Neff, W. E.; Frankel, E. N.; Selke, E.; Weisleder, D. (North. Reg. Res. Cent., U. S. Dep. Agric., Peoria, IL 61604, USA). Lipids, 18(12), 868-76 (English) 1983. CODEN: LPDSAP. ISSN: 0024-4201. DOCUMENT TYPE: Journal CA Section: 17 (Food and Feed Chemistry) Previous studies of lipid secondary oxidn. products were extended to 6-membered hydroperoxy cyclic peroxides from the singlet oxygenation of a mixt. of 9- and 13-hydroperoxides from autoxidized methyl linoleate. The oxidn. product was fractionated by silicic acid chromatog. with Et2O-hexane mixts., and selected fractions were sepd. by polar phase high-performance liq. chromatog. Products characterized by TLC, gas chromatog., UV, IR, NMR, and mass spectrometry included: 6-membered cyclic peroxides (13-hydroperoxy-9,12-epidioxy-10- and 9-hydroperoxy-10,13-epidoxy-11-octadecenoates), dihydroperoxides (8,13- and 9,14-dihydroperoxyoctadecadienoates) and keto dienes (9- and 13-oxooctadecadienoates). 3777-69-3 and 38199-50-7 which are cas registry numbers of substances are two of reagents here. The 6-membered hydroperoxy cyclic peroxides are apparently formed by 1,4-addn. of singlet O to 9- and 13-hydroperoxides with trans, trans-conjugated diene systems. Thermal decompn. of the 6-membered hydroperoxy cyclic peroxides at 200° produced methyl 9-oxononanoate [1931-63-1] and hexanal [66-25-1] as the major volatiles. Other volatiles included 2-pentylfuran [3777-69-3], pentane [109-66-0], 4-oxo-2-nonenal [89186-13-0], methyl furan-2-octanoate [38199-50-7] and methyl 9,12-dioxo-10-dodecenoate [89186-12-9]. .

Volatiles from thermal decomposition of isomeric methyl (12S,13S)-(E)-12,13-epoxy-9-hydroperoxy-10-octadecenoates

Volatiles from thermal decomposition of isomeric methyl (12S,13S)-(E)-12,13-epoxy-9-hydroperoxy-10-octadecenoates. Gardner, H. W.; Selke, E. (North. Reg. Res. Cent., Agric. Res. Serv., Peoria, IL 61604, USA). Lipids, 19(6), 375-80 (English) 1984. CODEN: LPDSAP. ISSN: 0024-4201. DOCUMENT TYPE: Journal CA Section: 17 (Food and Feed Chemistry) Two epimers of Me (12S,13S)-(E)-12,13-epoxy-9-hydroperoxy-10-octadecenoate were isolated after esterification of a mixt. of fatty acids obtained from decompn. of (13S)-(9Z,11E)-13-hydroperoxy-9,11-octadecadienoic acid by an Fe++-cysteine catalyst. These epimeric epoxyhydroperoxyoctadecenoates were decompd. by heat (210°) in the injection port of a gas chromatograph, and the cleavage fragments were subsequently sepd. by gas chromatog.(GC) and identified by mass spectrometry. Among the scission products obtained, the most prominent in the GC peak profile were Me octanoate [111-11-5] and Me 9-oxononanoate [1931-63-1]. Other peaks were identified as pentane [109-66-0], 1-pentanol [71-41-0], hexanal [66-25-1], 2-heptanone [110-43-0], 2-pentylfuran [3777-69-3], Me heptanoate [106-73-0], 2-octenal [2363-89-5], 4,5-epoxy-2-decenal [73528-44-6], Me 8-(2-furyl)-octanoate [38199-50-7], 11-oxo-9-undecenoate [79868-91-0] and Me 13-oxo-9,11-tridecadienoate [86153-27-7]. In addn. 3,4-epoxynonanal [91795-92-5], Me 8-oxooctanoate [3884-92-2], 3-hydroxy-2-pentyl-2,3-dihydrofuran [91795-93-6] and Me 10-oxodecanoate [14811-73-5] were tentatively identified. Except for the furan compds., the formation of the fragmentation products could be explained by conventional free-radical scission mechanisms.