title: Mechanisms of lipid peroxidation: iron catalyzed decomposition of fatty acid hydroperoxides as the basis of hydrocarbon evolution in vivo.
abstract: Ethane and pentane are evolved during peroxidation of tissue lipids in vivo and are believed to be derived from omega3 and omega6 fatty acids respectively. We present evidence supporting a scission mechanism as the means of forming these hydrocarbons during hydroperoxide decomposition. A fatty acid omega6 hydroperoxide (methyl 13-hydroperoxy-6,9,11-octatrienoate), when incubated with a ferrous ion, yielded pentane as the major hydrocarbon (98%). Reaction with ferrous ion results in an alkoxy capable of undergoing scission to an aldehydic fatty acid and a hydrocarbon.
mesh_terms: D002384:Catalysis; D004980:Ethane / Q000378:metabolism; D005227:Fatty Acids / Q000378:metabolism*; D066298:In Vitro Techniques; D007501:Iron; D010084:Oxidation-Reduction; D010420:Pentanes / Q000378:metabolism; D010545:Peroxides
chemical_list: D005227:Fatty Acids; D010420:Pentanes; D010545:Peroxides; D007501:Iron; D004980:Ethane