title: Ozonation of PC in ethanol: separation and identification of a novel ethoxyhydroperoxide.
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.
authors.affiliation: Food & Biodynamic Chemistry Laboratory, Graduate School of Life Science and Agriculture, Tohoku University, Sendai, Japan.
authors.forename: Misako
authors.initials: M
authors.lastname: Tagiri-Endo
authors.forename: Kaori
authors.initials: K
authors.lastname: Ono
authors.forename: Kiyotaka
authors.initials: K
authors.lastname: Nakagawa
authors.forename: Mari
authors.initials: M
authors.lastname: Yotsu-Yamashita
authors.forename: Teruo
authors.initials: T
authors.lastname: Miyazawa
mesh_terms: D002851:Chromatography, High Pressure Liquid; D000431:Ethanol / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification*; D015394:Molecular Structure; D010126:Ozone / Q000737:chemistry*; D010713:Phosphatidylcholines / Q000737:chemistry*
chemical_list: D010713:Phosphatidylcholines; D000431:Ethanol; D010126:Ozone; D006861:Hydrogen Peroxide