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Glyceride isomerizations in lipid chemistry
Author(s) -
Serdarevich B.
Publication year - 1967
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02666775
Subject(s) - isomerization , chemistry , glyceride , glycerol , hydrolysis , column chromatography , nuclear magnetic resonance spectroscopy , organic chemistry , monoglyceride , chromatography , catalysis , fatty acid
Isomerization of isopropylidene glycerol ketals and benzylidene glycerol acetals was studied, and isoraerization equilibria were established. Reaction of benzaldehyde with glycerol gave four benzylidene glycerol isomers, which were separated by column chromatography and characterized by NMR spectroscopy and other methods. Isomerization of 1‐ and 2‐monoglycerides and of 1,2‐ and 1,3‐diglycerides, and their separation by column chromatography, are described. Mechanisms of isomerization in mono‐ and diglycerides and factors which affect them are discussed. Isomerization of 1‐ and 2‐glycerophosphates and of cyclic glycerophosphates by acid and base was also studied. Hydrolysis products of L‐3‐glycerylphosphorylcholine and 2‐glycerylphosphorylcholine were separated by column chromatography and characterized by periodic acid oxidation, optical rotation, and NMR spectroscopy. No isomerization of unhydrolyzed L‐3‐glycerylphosphorylcholine and 2‐glycerylphosphorylcholine was observed. Evidence indicated that acid‐catalyzed hydrolyses of phosphoglycerides are under thermodynamic control whereas most base‐catalyzed hydrolyses are under kinetic control.