Czech J. Food Sci., 2002, 20(5):161-170 | DOI: 10.17221/3527-CJFS

Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates

J. Velíšek, M. Doležal, C. Crews, T. Dvořák
Department of Food Chemistry and Analysis - Institute of Chemical Technology, Prague; Central Science Laboratory, Sand Hutton, York, Great Britain

Protein hydrolysates produced by hydrochloric acid hydrolysis were analysed for 3-chloropropane-1,2-diol and its enantiomers. It was found that (R)-3-chloropropane-1,2-diol and (S)-3-chloropropane-1,2-diol were present in the hydrolysates in equimolar concentrations. Model experiments with glycerol, triolein and soy lecithin heated with hydrochloric acid in solution showed that these materials were precursors of 3-chloropropane-1,2-diol and 2-chloropropane-1,3-diol and, as expected, yielded racemic 3-chloropropane-1,2-diol. Yields of 3-chloropropane-1,2-diols decreased in the order triolein > lecithin > glycerol. The mechanisms of 3-chloropropane-1,2-diol enantiomers formation during the production of protein hydrolysates are presented and discussed as well as the reaction pathways of their decomposition in alkaline media via the corresponding intermediates, (R)- and (S)-glycidol, respectively. Both epoxides are hydrolysed to glycerol and form a variety of products with hydrolysate constituents.

Keywords: chloropropanediols; chloropropanols; 3-chloropropane-1,2-diol; 2-chloropropane-1,3-diol; glycidol; MCPD; enantiomers; protein hydrolysates

Published: October 31, 2002  Show citation

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Velíšek J, Doležal M, Crews C, Dvořák T. Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates. Czech J. Food Sci. 2002;20(5):161-170. doi: 10.17221/3527-CJFS.
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