A CHROMATOGRAPHIC AND SPECTROPHOTOMETRIC STUDY OF THE PRODUCTS OF THE REACTION OF OSMIUM TETROXIDE WITH UNSATURATED LIPIDS

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Abstract
Thin films of methyl oleate, oleic acid, and di-octadecenoyl phosphatidylcholine were reacted with a 2% solution of OsO4 in water for 1 hr at 0°. As controls, methyl 9,10-dihydroxystearate and 9,10-dihydroxystearic acid were reacted with OsO4 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.