On the analysis of long-chain alkane diols and glycerol ethers in biochemical studies

Abstract

The chromatographic behavior of 1,2-, 1,3-, 1,4-, and 1,12-long-chain alkane diols and 1-O-alkylglycerols and their derivatives has been compared. Thin-layer chromatography on Silica Gel G gives poor separations of the 1,2-, 1,3-, and 1,4-alkane diols, O-alkylglycerols, and some of their isopropylidene derivatives. However, gas–liquid chromatography on 10% EGSS-X (coated on 100–120 mesh Gas-Chrom P) resolves the isopropylidenes of the alkane diols and O-alkylglycerols.We also document the formation of 1,3-alkane diols (after LiAlH4 reduction) from 1-14C-labeled fatty acids incubated with mitochondrial fractions from heart and liver of rats. The labeled 1,3-alkane diol was identified by gas–liquid chromatography of its isopropylidene derivative and by its behavior after periodate oxidation. These results serve to caution investigators in the glycerol ether field against incorrect interpretation of data obtained on the incorporation of labeled fatty acids into alkyl ether bonds of glycerolipids. The methodology described points out a technique for distinguishing several types of alkane diols from O-alkylglycerols.

Keywords

• alkane diols
• O-alkylglycerols
• fatty acids
• glycerol ethers
• LiAlH4 reduction
• mitochondria