Formation of 3-monochloro-1,2-propanediol (3-MCPD) di- and monoesters from tristearoylglycerol (TSG) and the potential catalytic effect of Fe²⁺ and Fe³⁺.

doi:10.1021/jf5061216

Paper

Formation of 3-monochloro-1,2-propanediol (3-MCPD) di- and monoesters from tristearoylglycerol (TSG) and the potential catalytic effect of Fe²⁺ and Fe³⁺.

Published Feb 9, 2015 · Zhongfei Zhang, Boyan Gao, Xiaowei Zhang

Journal of agricultural and food chemistry

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48

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1

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Abstract

This study investigated whether and how triacylglycerol (TAG) may serve as a precursor for 3-monochloro-1,2-propanediol (3-MCPD) fatty acid ester formation using tristearoylglycerol (TSG). TSG was reacted with inorganic chloride compounds including NaCl, KCl, FeCl2, CuCl2, ZnCl2, FeCl3 and dry HCl, or organic chlorine compound lindane at different temperatures. Only FeCl2 and FeCl3 were able to form 3-MCPD esters from TSG. Further electron spin resonance (ESR) determination of TSG, Fe2(SO4)3 and 5,5-dimethylpyrroline-N-oxide (DMPO) reactions revealed potential of Fe ion in promoting free radical generations under the experimental conditions. To further confirm the effect of Fe ion, chelating agent (EDTA-2Na) was added to the model reactions. The results showed for the first time that EDTA-2Na was able to reduce the generation of 3-MCPD esters. In addition, FT-IR examination indicated a possible involvement of a carbonyl group during the reaction. Taking all the observations together, the possible mechanisms, involving the formation of either a cyclic acyloxonium or a glycidol ester radical intermediate, were proposed for generating 3-MCPD fatty acid di- and mono- esters from TAG under a high temperature and low moisture condition, as well as the coformation of glycidol esters. The results from this study may be useful for reducing the level of 3-MCPD esters and related toxicants in the refined edible oils and food products.

Study Snapshot

Triacylglycerol can serve as a precursor for 3-MCPD esters formation, potentially reducing toxicants in refined edible oils and food products.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Formation of 3-monochloro-1,2-propanediol (3-MCPD) di- and monoesters from tristearoylglycerol (TSG) and the potential catalytic effect of Fe²⁺ and Fe³⁺.

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References

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Citations

Formation of multiple-membered heterocycles in monochloropropanediol esters using diacylglycerol and glutamic or aminoadipic acids.

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Toxic contaminants formed during vegetable oil and fat processing pose significant health risks to consumers, and effective control and regulatory strategies are crucial for ensuring food safety.

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3-MCPD is a common food contaminant found in edible oil, soy sauce, and infant formula, with higher concentrations in these products compared to infant formula.

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Jenis dan Konsentrasi Tanah Pengelantang untuk Menurunkan Prekursor Senyawa 3-MCPDE dan GE pada Pemucatan CPO

Using BE-4 at 2.5% concentration in the bleaching stage effectively reduces 3-MCPDE precursors and glycidyl ester in bleached palm oil, improving oil quality.