Related Experiment Videos
Ozonation of PC in ethanol: separation and identification of a novel ethoxyhydroperoxide
Misako Tagiri-Endo1, Kaori Ono, Kiyotaka Nakagawa
1Food & Biodynamic Chemistry Laboratory, Graduate School of Life Science and Agriculture, Tohoku University, Sendai, Japan.
Abstract:
The product of the ozonolysis of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine in ethanol-containing solvent was analyzed by chemiluminescence detection-HPLC with on-line electrospray MS, and characterized on the basis of NMR spectroscopy and MS in high-resolution fast atom bombardment mode. The reaction yielded a large amount of a novel ethoxyhydroperoxide compound [1-palmitoyl-2-(9-ethoxy-9-hydroperoxynonanoyl)-sn-glycero-3-phosphcholinel. In addition to a structural analysis, we speculate on the reaction pathway and discuss the possibility of ethoxyhydroperoxide as a potentially reactive ozonized lipid in food and biological materials.