Chiral resolution of 3-monochloro-1,2-propanediol optical isomers in edible oils: From ester hydrolysis to enantiomeric analysis.

Abstract

3-monochloro-1,2-propanediol (3-MCPD) is a food-borne contaminant formed during the refining of oils and fats. It can occur in a free form or esterified with fatty acids, and it exists as two enantiomers with distinct biological activities: (S)-3-MCPD exhibits antifertility effects in males, while (R)-3-MCPD is nephrotoxic. In this study, we developed and validated a gas chromatography-mass spectrometry (GC-MS) method for the chiral resolution of 3-MCPD enantiomers after hydrolysis of esterified forms. To our knowledge, this is the first time that chiral resolution has been applied to oil and fat samples, demonstrating the presence of enantiomers in a 1:1 ratio in these matrices. Statistical comparisons with the standard indirect method showed a strong correlation between the two approaches. Since the two enantiomers display distinct toxicity profiles, the proposed method offers complementary insights to the standard approach, enhancing the toxicological evaluation of 3-MCPD.