Ned Porter
Faculty Member
Last active: 5/29/2014

Peroxidation of polyunsaturated fatty acid methyl esters catalyzed by N-methyl benzohydroxamic acid: a new and convenient method for selective synthesis of hydroperoxides and alcohols.

Punta C, Rector CL, Porter NA
Chem Res Toxicol. 2005 18 (2): 349-56

PMID: 15720142 · DOI:10.1021/tx049685x

A new catalytic system, based on N-methyl benzohydroxamic acid (NMBHA), was developed for the selective synthesis of lipid hydroperoxides and alcohols by aerobic oxidation of lipid precursors. The reactions were carried out under mild conditions with air at atmospheric pressure and 37 degrees C. The products were isolated in much better yields (50-60%) as compared to previously reported procedures. NMBHA can be recovered at the end of the reaction and recycled. The putative reactive intermediate, a nitroxyl radical, readily abstracts a hydrogen atom from polyunsaturated lipid precursors such as linoleate esters, and NMBHA itself is an excellent hydrogen atom donor, thus conferring high selectivity to oxidations catalyzed by this reagent.

MeSH Terms (8)

Alcohols Catalysis Esters Fatty Acids, Unsaturated Hydroxamic Acids Molecular Structure Peroxides Time Factors

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