Aliphatic hydroxylamines as lipid antioxidants

It was previously noted that N,N-dioctylhydroxylamine is formed from the oxidation of trioctylamine in oxidizing fats and that N,N-dioctyl- and N,N-diethylhydroxylamine preparations have antioxidant activity. In this paper we summarize some additional observations with these and some other N-substituted hydroxylamines. ESR spectra indicate that nitroxides are present in oxidized preparations of hydroxylamines. Since some stable nitroxides have been shown to be exceptionally effective antioxidants, we hypothesize that the antioxidant effectiveness of the hydroxylamines is accounted for by their conversion to nitroxides during the inital stages of oxidation.