Mechanism of formation of chloropropanols present in protein hydrolysates

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 b...

Full description

Saved in:
Bibliographic Details
Published inJournal of the American Oil Chemists' Society Vol. 68; no. 10; pp. 785 - 790
Main Authors Collier, P.D. (Unilever Research Laboratory, Sharnbrook, Bedford, U.K.), Cromie, D.D.O, Davies, A.P
Format Journal Article
LanguageEnglish
Published Berlin/Heidelberg Springer‐Verlag 01.10.1991
Subjects
ACIDE CHLORHYDRIQUE
ACIDO CLORHIDRICO
ALCOHOLES
ALCOHOLS
ALCOOL
Chloropropanols
FOSFOLIPIDOS
GLICEROL
glycerides
GLYCEROL
HIDROLISIS
HYDROCHLORIC ACID
HYDROLYSAT DE PROTEINES
HYDROLYSE
HYDROLYSIS
HYDROLYZED PROTEINS
LIPIDE
LIPIDOS
LIPIDS
nucleophilic substitution
PHOSPHATIDE
PHOSPHOLIPIDS
protein hydrolysates
PROTEINAS HIDROLIZADAS
SOYBEAN MEAL
SOYBEAN OILMEAL
TORTAS DE SOJA
TOURTEAU DE SOJA
TRIOLEIN
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:9160039
Q05
ISSN:0003-021X
1558-9331
DOI:10.1007/BF02662173