Ozonation of PC in ethanol: separation and identification of a novel ethoxyhydroperoxide |
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| Authors: | Tagiri-Endo Misako Ono Kaori Nakagawa Kiyotaka Yotsu-Yamashita Mari Miyazawa Teruo |
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| Affiliation: | (1) Food & Biodynamic Chemistry Laboratory, Graduate School of Life Science and Agriculture, Tohoku University, 1-1, Tsutsumidori Amamiyamachi, 981-8555 Sendai, Japan;(2) Present address: Industrial Technology Institute, Miyagi Prefectural Government, 981-3206 Sendai, Japan |
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| 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-phosphocholine]. 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. |
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