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Mechanism of formation of chloropropanols present in protein hydrolysates
Author(s) -
Collier P. D.,
Cromie D. D. O.,
Davies A. P.
Publication year - 1991
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/bf02662173
Subject(s) - chemistry , regioselectivity , steric effects , hydrolysate , hydrochloric acid , phosphorylcholine , chloride , nucleophile , nucleophilic substitution , triolein , medicinal chemistry , thin layer chromatography , organic chemistry , chromatography , hydrolysis , catalysis , biochemistry , enzyme , lipase
Chloropropanols are formed in protein hydrolysates by the reaction of hydrochloric acid with residual lipids associated with the proteinaceous materials used in their production. The products formed from glycerol, triolein, 1,2‐diacyl‐ sn ‐glycero‐3‐phosphorylcholine and soya meal have been analyzed by thin‐layer and gas chromatography. The yields and isomer ratios of the chloropropandiols and dichloropropanols formed are interpreted in terms of reaction mechanisms for their formation, which involve preferential nucleophilic substitution by the chloride anion at positions activated by neighboring ester groups. These provide anchimeric assistance and govern regioselectivity through steric and electronic effects.