38199-50-7Relevant academic research and scientific papers
A detailed identification study on high-temperature degradation products of oleic and linoleic acid methyl esters by GC-MS and GC-FTIR
Berdeaux, Olivier,Fontagné, Stéphanie,Sémon, Etienne,Velasco, Joaquin,Sébédio, Jean Louis,Dobarganes, Carmen
experimental part, p. 338 - 347 (2012/06/29)
GC-MS and GC-FTIR were complementarily applied to identify oxidation compounds formed under frying conditions in methyl oleate and linoleate heated at 180 °C. The study was focused on the compounds that originated through hydroperoxide scission that remain attached to the glyceridic backbone in fats and oils and form part of non-volatile molecules. Twenty-one short-chain esterified compounds, consisting of 8 aldehydes, 3 methyl ketones, 4 primary alcohols, 5 alkanes and 1 furan, were identified. In addition, twenty non-esterified volatile compounds, consisting of alcohols, aldehydes and acids, were also identified as major non-esterified components. Furanoid compounds of 18 carbon atoms formed by a different route were also identified in this study. Overall, the composition of the small fraction originated from hydroperoxide scission provides a clear idea of the complexity of the new compounds formed during thermoxidation and frying.
Epoxyoxoene fatty esters: key intermediates for the synthesis of long-chain pyrrole and furan fatty esters
Hidalgo, Francisco J.,Zamora, Rosario
, p. 1 - 12 (2007/10/02)
The reaction of epoxyoxoene fatty esters, methyl (Z)-9,10-epoxy-13-oxo-(E)-11-octadecenoate (1) and methyl (Z)-12,13-epoxy-9-oxo-(E)-10-octadecenoate (2), with glycine methyl ester in the presence of a basic resin was studied to establish if these compounds might be useful intermediates in the preparation of long-chain pyrrole fatty esters.Production of C18 pyrrole fatty esters and fragmentation products with the pyrrole ring were isolated and identified in the reaction.In addition, furanoid derivatives with analogous structures were also detected and identified.Formation of these last compounds was induced by the basic resin and the same compounds were also produced in a reaction mixture incubated in the absence of the amino acid.The results found in this study show that epoxyoxoene fatty esters 1 and 2 may be used in the preparation of both long-chain pyrrole and furan fatty acids.Although their existence in nature is as yet unclear, the mass spectra results obtained in this study provide the basis for detection and identification of this type of long-chain pyrrole and furan fatty acids by gas chromatography coupled with mass spectrometry.Keywords: Long-chain pyrrole fatty esters; Long-chain furanoid fatty acids; Carbonyl-amine reactions; Oxidized lipids/amino acids reactions; Lipid peroxidation products; Non-enzymatic browning reactions
