Journal of Lipid Research, Vol. 10, 703-709, November 1969
Copyright © 1969 by Lipid Research, Inc.

Mass spectrometric analysis of long-chain esters of diols

W. J. Baumann , J. Seufert , H. W. Hayes , and R. T. Holman

University of Minnesota, The Hormel Institute, Austin, Minnesota 55912

Homologous series of synthetic long-chain monoesters and diesters of 1,2-ethanediol were analyzed by mass spectrometry, and the patterns of fragmentation were studied. Under electron impact saturated ethanediol monoesters yielded prominent ions characteristic of the short-chain diol, such as the rearranged ion formed by 2,3-cleavage (m/e 104) and the ion caused by 3,4-cleavage (m/e 117). Fragments characteristic of the constituent long-chain moieties were the acylium ions [RCO]⁺, [RCO - 1]⁺, and the ions [RC(OH)₂]⁺. The mass spectra of ethanediol diesters exhibited very intense peaks due to the ions formed by loss of the acyloxy group, [M - RCOO]⁺, or one carboxylic acid, [M - RCOOH]⁺. These ions are distinctive for diol diesters. Precise mass measurements by high resolution mass spectrometry verified the composition of the ion fragments.

Spectral studies of some monoesters and diesters of 1,3-propanediol, 1,4-butanediol, 2,3-butanediol, and also of some monounsaturated homologues, demonstrated that mass spectrometry is very suitable for the identification, distinction, and analysis of diol lipids.

Supplementary key words diol lipids • diol monoesters • diol diesters • 1,2-ethanediol • 1,3-propanediol • 1,4-butanediol • 2,3-butanediol

Submitted on May 15, 1969
Accepted on August 5, 1969

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