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Journal of Lipid Research, Vol. 4, 385-391, October 1963
Copyright © 1963 by Lipid Research, Inc.

Studies on the composition of glyceryl ethers and their preparation from diacyl glyceryl ethers in liver oils

Kenneth E. Guyer , William A. Hoffman , Lloyd A. Horrocks , and David G. Cornwell

Department of Physiological Chemistry, The Ohio State University, Columbus, Ohio and Department of Neurochemistry, Cleveland Psychiatric Institute and Hospital, Cleveland, Ohio

Procedures are described for the preparation of alkyl iodides from fatty alcohols and glyceryl ethers. Alkyl iodides were separated directly by gas-liquid chromatography (GLC) on ethylene glycol succinate columns and do not require calibration factors in their analysis with a thermal conductivity detector. Iodide derivatives have absolute retention times on GLC similar to the corresponding fatty alcohol acetates. Alkyl iodides were converted to alcohol acetates with silver acetate or to hydrocarbons with lithium aluminum hydride and these derivatives were separated by GLC. The elimination of hydriodic acid from secondary iodides during GLC is described. The resulting monoene iodides are readily separated from saturated iodides by GLC. Alkoxy structures have been assigned by comparison of the retention time data of iodide derivatives with standard alcohol derivatives. Unsaturation was confirmed by catalytic hydrogenation. Branched components were identified as the alkanes.

Glyceryl ethers were prepared from diacyl glyceryl ethers by hydrogenolysis with lithium aluminum hydride. The glyceryl ether-fatty alcohol mixture was separated quantitatively by thin-layer chromatography (TLC) and sufficient material obtained from one TLC plate for the preparation of alkyl iodide derivatives.

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