Journal of the American Oil Chemists Society

, Volume 68, Issue 10, pp 785–790

Mechanism of formation of chloropropanols present in protein hydrolysates


  • P. D. Collier
    • Unilever Research Laboratory
  • D. D. O. Cromie
    • Unilever Research Laboratory
  • A. P. Davies
    • Unilever Research Laboratory

DOI: 10.1007/BF02662173

Cite this article as:
Collier, P.D., Cromie, D.D.O. & Davies, A.P. J Am Oil Chem Soc (1991) 68: 785. doi:10.1007/BF02662173


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.

Key Words

Chloropropanolsglyceridesglycerolhydrochloric acidnucleophilic substitutionphospholipidsprotein hydrolysates.

Copyright information

© American Oil Chemists' Society 1990