The glyceryl ethers in the liver oils of elasmobrach fish

The glyceryl ethers from the liver oils of the grey dogfish, the Greenland shark, and the ratfish were isolated by chromatography on alumina. These ethers were then converted into the corresponding dimethoxy derivatives, which were rechromatographed on alumina and then submitted to gas-liquid chromatography (GLC). By these means the presence of several new glyceryl ethers was demonstrated. Besides chimyl, batyl, and selachyl alcohols, compounds with saturated C14, and monounsaturated C16, C20, and C22 chains were found. Small amounts of a glyceryl ether with a C18 chain with two double bonds were also present. By oxidation with chromic acid, the position of the double bond in the hexadecenyl chain was found to be 9: 10; in the eicosenyl and the docosenyl chains the double bond was in position 13: 14. The molecular weight of the dimethoxy derivatives was determined by mass spectrometry. The mass spectrometric fragmentation pattern provided additional proof of the structure of the compounds.