A Chromatographic and Spectrophotometric Study of the Products of the Reaction of Osmium Tetroxide with Unsaturated Lipids

Thin films of methyl oleate, oleic acid, and di-octadecenoyl phosphatidylcholine were reacted with a 2% solution of OsO(4) in water for 1 hr at 0 degrees . As controls, methyl 9,10-dihydroxystearate and 9,10-dihydroxystearic acid were reacted with OsO(4) in 0.25 N NaOH in methanol for 1 hr at room temperature. The reaction products were isolated, purified, and analyzed by thin-layer chromatography, gas-liquid chromatography, and infrared and visible spectroscopy. In all cases, the products were identified as diesters of osmic acid in which two molecules of fatty acids are linked through 1 molecule of osmic acid.