Czech J. Food Sci., 2003, 21(5):153-161 | DOI: 10.17221/3493-CJFS
3-Chloropropane-1,2-diol in models simulating processed foods: Precursors and agents causing its decomposition
- 1 Department of Food Chemistry and Analysis, Institute of Chemical Technology, Prague, Czech Republic
- 2 Central Science Laboratory, Sand Hutton, York, Great Britain
Formation of 3-chloropropane-1,2-diol (3-MCPD) was studied in model mixtures consisting of sodium chloride and either glycerol or various lipids (phospholipids, monoacylglycerols, diacylglycerols, triacylglycerols) derived mainly from palmitic and oleic acids. The average amount of 3-MCPD formed from these precursors after 30 min of heating at 200°C was from 9.7 (lecithin), to 5.1 (diacylglycerols), 4.7 (glycerol), 3.1 (triacylglycerols), and 2.9 (monoacylglycerols) µmol/mol, respectively. The formation of 3-MCPD from glycerol (one of the major precursors) was also studied in the presence of glutathione, cysteine, disodium carbonate and sodium bicarbonate, i.e. compounds having the potential to decompose 3-MCPD or to prevent its formation. The compound the most active in preventing the formation of 3-MCPD was sodium bicarbonate followed by disodium carbonate, cysteine and glutathione. The addition of glutathione lowered the level of 3-MCPD produced from glycerol and NaCl to approximately 80%, of cysteine to 42%, of disodium carbonate to 14%, and of sodium bicarbonate to as little as 8% in comparison to samples with no additive.
Keywords: chloropropanediols; 3-chloropropane-1,2-diol; 3-monochloropropane-1,2-diol; 3-MCPD; acylglycerols; phospholipids; glycerol; glutathione; cysteine; carbonates
Published: October 31, 2003 Show citation
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References
- B H.-D., G W. (1999): Food Chemistry. 2nd Ed., Springer, Berlin.
- C P., V J., D M. (2003): Formation of 3-chloropropane-1,2-diol in systems simulating processed food. Eur. Food Res. Technol. (in press).
- C D.V., B R.K. (1968): A method for synthesis of α-monoricinolein. J. Am. Oil Chem. Soc., 45: 581-582.
Go to original source...
- CODEX (2001): Position paper on chloropropanols for the thirty-third session of the Codex Committee on Food Additives and Contaminants. Joint FAO/WHO Food Standards Programme.
- C P.D., C D.D.O., D A.P. (1991): Mechanism of formation of chloropropanols present in protein hydrolysates. J. Am. Oil Chem. Soc., 68: 785-790.
Go to original source...
- C C., B P., D A. (2001): Effect of domestic cooking on the levels of 3-monochloropeopane-1,2-diol in food. Food Addit. Contam., 18: 271-280.
Go to original source...
Go to PubMed...
- C C., H P., B P., H D., M R., M W. (2002): Survey of 3-monochloropropane-1,2-diol (3-MCPD) in selected food groups, 1999-2000. Food Addit. Contam., 19: 22-27.
Go to original source...
Go to PubMed...
- D J., V J., K V., J G., Š Z. (1980): Glycerol chlorohydrins and their esters as products of the hydrolysis of tripalmitin, tristearin and triolein with hydrochloric acid. Z. Lebensm. Unters. For., 171: 14-17.
Go to original source...
- D J., V J., K V., J G. (1982): New chlorine containing organic compounds in protein hydrolysates. In: B W., C E P.B., P W. (eds): Recent Developments in Food Analysis. Proc. EuroFood Chem I, Vienna, Austria: 17-20 Febr., 1981. Weinheim, Deerfield Beach, Florida: 322-325.
- D R B.M., C J.N.M., R J.R., S H.C.P., V B B.L.M., V N.P.E. (1996): Identification and quantitative determination of 3-chloro-2-hydroxypropylmercapuric acid and alphachlorohydrin in urine of rats treated with epichlorohydrin. J. Chromatogr. B, Biomed. Appl., 685: 241-250.
Go to original source...
Go to PubMed...
- EC Scientific Commi ee for Food (1995): Opinion on 3-Monochloropropane-1,2-diol (3-MCPD) (expressed on 16 December 1994), Annex 4 to document III/5488/94, CS/CNTM/OTH/2 Final. food ingredients from UK food producers and ingredient suppliers. Food Addit. Contam., 19: 15-21.
- M N.W. (1985): Traditional and novel approaches to the analysis of plant phospholipids. In: S F.B., L R.G. (eds): Lecithins. Am. Oil Chem. Soc., USA.
- P W.J., T W.G., S G.H.D. (1991): Determination of 3-chloropropane1,2-diol in liquid hydrolysed vegetable proteins by capillary gas chromatography with flame ionization detection. J. Chromatogr., 555: 311-314.
Go to original source...
- V J. (2002): Chemie potravin 1. Ossis, Tábor.
- V J., D J., H J., K V., J G., M B. (1978): Chlorohydrins in protein hydrolysates. Z. Lebensm. Unters. Forsch., 167: 241-244.
Go to original source...
Go to PubMed...
- V J., D J., K V., B J., T A., H J., J G. (1979): Formation of volatile chlorohydrins from glycerol (triacetin, tributyrin) and hydrochloric acid. Z. Lebensm.-Wiss. u. -Technol., 12: 234-236.
- V J., D J., Š Z., S Z. (1982): Glycerol chlorohydrins and their estersreaction products of lipids with hydrochloric acid. Sci. Papers Prague Inst. Chem. Technol., E53: 55-65.
- V J., D T., D J., K V., V I. (1991): 3-Chloro-1,2-propanediol derived amino acids in protein hydrolysates. J. Food Sci., 56: 139-142.
Go to original source...
- V J., D M., C C., D T. (2002): Optical isomers of chloropropanols: Mechanisms of their formation and decomposition in protein hydrolysates. Czech J. Food Sci., 20: 161-170. Recevied for publication October 8, 2003
Go to original source...
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