Journal of Lipid Research, Vol. 10, 370-373, July 1969
Copyright © 1969 by Lipid Research, Inc.

Quantitative analysis and comparison of the physical properties of O-alkyl and S-alkyl monoethers of glycerol

Randall Wood , Claude Piantadosi , and Fred Snyder

Medical Division, Oak Ridge Associated Universities, Oak Ridge, Tennessee 37830, and the School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27515

A homologous series (C₁₀, C₁₂, C₁₄, C₁₆, C₁₈) of synthetic O-alkyl and S-alkyl ethers of glycerol was analyzed by gas-liquid chromatography (GLC) and thin-layer chromatography (TLC), and examined by IR and n.m.r. spectroscopy; the physical properties of the O-alkyl and S-alkyl ethers were compared. Isopropylidene derivatives of the glycerol ethers and thioethers were quantitatively analyzed by GLC on polar and nonpolar liquid phases. On a medium polar liquid phase (ethylene glycol succinate), mixtures of the O-alkyl and S-alkyl ethers were completely resolved. Isopropylidene derivatives of glycerol ethers and of thioethers could be separated as classes (though not into individual homologues) by TLC. O-hexadecyl and S-hexadecyl ethers of glycerol are easily distinguished by IR and n.m.r. spectroscopy.

Supplementary key words glycerol 1-ethers • 1-thioethers • isopropylidene derivatives • gas-liquid chromatography with sulfur filter • thin-layer chromatography • IR spectroscopy • n.m.r. spectroscopy

Submitted on December 19, 1968
Accepted on March 7, 1969

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