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Presence of 3-Monochloropropane-1,2-Diol 3-MCPD and their Esters in Foods, Mechanisms of their Occurence and Detection Methods

Year 2013, Volume: 11 Issue: 2, 102 - 109, 01.06.2013

Abstract

The 3-monochloropropane-1,2-diol 3-MCPD which has a carcinogenic potential, is named as a contaminant originated food or synthesized during food processing. It has been firstly determined in acid-hydrolyzed plant proteins soy sauce, vegetable proteins . In recent years, detection of 3-Mcpd esters in different foods has prompted further interest in these compounds. 3-Mcpd and its esters can be formed in fat containing foods during thermal processes as a result of reactions between glycerol or acylglycerides with hydrochloric acid. Most of the 3-Mcpd compounds found in foods are present as fatty acyl esters. The most important precursors of chloropropanols are known as tryglycerides, phospholipids and glycerol respectively. The formation of 3-Mcpd esters is a characteristic of the variety of processed foods. In recent studies, amounts of these compounds found very high in thermal processed foods. So, maximum daily intake of these compounds were limited to 2 µg/kg body weight by the European Food Safety Authority EFSA

References

  • [1] Hamlet, C.G., Sadd, P.A., Crews, C., Velisek, J., Baxter, D.E., 2002. Occurrence of 3-chloropropane-1, 2-diol (3-MCPD) and related compounds in foods: a review. Food Addit. Contam. 19(7):619–631.
  • [2] Seefelder, W., Varga, N., Studer, A., Williamson, G., Scanlan, F.P., Stadler, R.H., 2008. esters of 3- chloro-1,2-propanediol (3-MCPD) in vegetable oils: Significance in the formation of 3-MCPD. Food Addit Contam. 25(4): 391-400.
  • [3] Baer, I., de la Calle, B., Taylor, P., 2010. 3-MCPD in food other than soy sauce or hydrolyzed vegetable protein (HVP). Anal. Bioanal. Chem. 396:443-456.
  • [4] Anon. 2012. Survey of 3-MCPD in foods. Joint Food Safety and Standards Group.
  • [5] Zelinkova, Z., Svejkovska, B., Velisek, J., Dolezal, M., 2006. Fatty acid esters of 3-chloropropane-1,2- diol in edible oils. Food Addit. Contam. 23:1290– 1298.
  • [6] Weißhaar, R., 2011. Fatty acid esters of 3-MCPD: Overview of occurrence and exposure estimates. Eur. J. Lipid Sci. Technol. 113:304–308.
  • [7] Larsen, J.C., 2009. Esters in Food Products. ILSI Europe Report Series. Summary Report of a Workshop held in February 2009 in Brussels, Belgium.
  • [8] Anonymous, 2009. 3-MCPD Esters in Foods (from www.aocs.org).
  • [9] Haines, T.D., Adlaf, K.J., Pierceall , R.M., Lee, I., Venkitasubramanian, P., Collison, M.W., 2011. Direct determination of MCPD fatty acid esters and glycidyl fatty acid esters in vegetable oils by LC– TOFMS. J Am Oil Chem Soc 88:1–14.
  • [10] Pudel, F.Benecke, P., Fehling, P., Freudenstein, A., Matthaus, B., Schwaf, A., 2011. On the necessity of edible oil refining and possible sources of 3-MCPD and glycidyl esters. Eur. J. Lipid Sci. Technol. 113: 368–373.
  • [11] Watkins, C., 2009. Chloroesters in foods: An emerging issue Inform Magazine of the AOCS, No. 4.
  • [12] Razak, R.A.A., Kuntom, A., Siew, W.L., Ibrahim, N.A., Ramli, M.R., Hussein, R., Nesaretnam, K., 2012. Detection and monitoring of 3- monochloropropane-1,2-diol (3-MCPD) esters in cooking oils. Food Cont. 25: 355-360.
  • [13] Franke, K., Strijowski, U., Fleck, G., Pudel, F., 2009. Influence of chemical refining process and oil type on bound 3-chloro-1,2-propanediol contents in palm oil and rapeseed oil. LWT 42: 1751-1754.
  • [14] Breitling-Utzmann, C.M., Kobler, H., Harbolzheimer, D., Maier, A., 2003. 3-MCPD: occurence in bread crust and various food groups as well as formation in toast. Dtsch Lebensm Rundsch 99(7): 280-285.
  • [15] Breitling-Utzmann, C.M., Hrenn, H., Haase, N.U., Unbehend, G.M., 2005. Influence of dough ingredients on 3-chloropropane-1,2-diol (3-MCPD) formation in toast. Food Addit. Contam. 22(2): 97- 103.
  • [16] Hamlet, C.G., Sadd, P.A., 2004. Effects of yeast stress and organic acids on chloropropanols formation in cereal products. Czech J. Food Sci. 22:255-258.
  • [17] Hamlet, C.G., Sadd, P.A., Gray, D.A., 2004. Generation of monochloropropanediols (MCPDs) in model dough systems. 2. Unleavened doughs. J. Agr. Food Chem. 52(7): 2067-2072.
  • [18] Divinova, V., Dolezal, M., Velisek, J., 2007. Free and bound 3-chloropropane-1,2-diol in coffee surrogates and malts. Czech J. Food Sci. 25(1): 39- 47.
  • [19] Zelinkova, Z., Dolezal, M., Velisek, J., 2009. 3- Chloropropane- 1,2-diol fatty acid esters in potato products. Czech J. Food Sci .27: 421–424.
  • [20] Dolezal, M., Chaloupska, M., Divinova, V., Svejkovska, B., Velisek, J., 2005. Occurrence of 3- chloropropane-1,2-diol and its esters in coffee. Eur. Food Res. Tech. 221(3-4): 221-225.
  • [21] Crews, C., Brereton, P., Davies, A., 2001. The effects of domestic cooking on the levels of 3- monochloropropanediol in foods. Food Addit. Contam. 18(4): 271-280.
  • [22] FAO/WHO, 2007. Discussion paper on chloropropanols derived from the manufacture of acid-HVP and the heat processing of food. In: Proc 1st Session of Codex Committee on Contaminants in Foods, Beijing, China, 16-20 April 2007.
  • [23] Kuntzer, J., Weibhaar, R., 2006. The smoking process: a potent source of 3-chloropropane-1,2- diol (3-MCPD) in meat products. Dtsch Lebensm Rundsch 102(9): 397-400.
  • [24] FAO/WHO, 2006. Discussion paper on acid HVP containing products and other products containing chloropropanols. In: Proc Session 38 of Codex Committee on Food Additives and Contaminants, The Hague, The Netherlads, 24-28 Apr 2006.
  • [25] Reece, 2005. The origin and formation of 3-MCPD in foods and food ingredients (final project report). Food Standards Agency, London.
  • [26] Velisek, J., Davidek, J., Hajslova, J., Kubelka, V., Janicek, G., Mankova, B., 1978 . Chlorohydrins in protein hydrolysates. Z Lebensm Unters Forsch 167(4): 241–244.
  • [27] Davidek, J., Velisek, J., Kubelka, V., Janicek, G., Simicova, Z., 1980. Glycerol chlorohydrins and their esters as products of the hydrolysis of tripalmitin, tristearin and triolein with hydrochloric acid. Z Lebensm Unters Forsch 171(1): 14–17.
  • [28] Lynch, B.S., Bryant, D.W., Hook, G.J., Nestmann, E.R., Munro, I.C., 1998. Carcinogenicity of monochloro-1,2-propanediol (α-chlorohydrin, 3- MCPD). Int. J. Toxicol. 17(1): 47–76.
  • [29] Kim, K., Song, C., Park, Y., Koh, S., Kim, J., Kim, S., Kim, Y., Kim, S.U., Jung, H., 2004. 3- Monochloropropane-1,2-diol Does Not Cause Neurotoxicity in Vitro or Neurobehavioral Deficits in Rats. Neuro.Toxicol. 25(3): 377-385.
  • [30] Hahn, H., Eder, E., Deininger, C., 1991. Genotoxicity of 1,3-dichloro-2-propanol in the SOS chromotests and in the Ames tests. Elucidation of the genotoxic mechanism. Chem. Biol. Interactions 80: 73-88.
  • [31] Anon. 2006. Committee on the Carcinogenicity of chemicals in food, consumer products and the environment.
  • [32] Nyman, P.J., Diachenko, G.W., Perfetti, G.A., 2003. Determination of 1,3-dichloropropanol in soy and related sauces by using gaschromatography/mass spectrometry. Food Addit. Contam. 20(10): 903– 908.
  • [33] Schlatter, J., Baars, A.J., Dinovi, M., Lawrie, S., Lorentzen, R., 2002. Safety evaluation of certain food additives and contaminants: 3-chloro-1, 2- propanediol. WHO Food Addit. Ser. 48: 1–30.
  • [34] Wenzl, T., Lachenmeier, D.W., Gokmen, V., 2007. Analysis of heatinduced contaminants (acrylamide, chloropropanols and furan) in carbohydrate-rich food. Anal. Bioanal. Chem. 389(1): 119–137.
  • [35] Divinova, V., Svejkovska, B., Dolezal, M., Velisek, J., 2004. Determination of free and bound 3- chloropropane-1,2-diol by gas chromatography with mass spectrometric detection using deuterated 3- chloropropane-1,2-diol as internal standard. Czech J. Food Sci. 22(5): 182–189.
  • [36] Weißhaar, R., 2008. Determination of total 3- chloropropane-1,2- diol (3-MCPD) in edible oils by cleavage of MCPD esters with sodium methoxide. Eur. J. Lipid Sci. Technol. 110(2): 183–186.

Gıdalarda 3-Monokloropropan-1,2-Diol 3-MCPD ve Esterlerinin Varlığı, Oluşum Mekanizmaları ve Tespit Yöntemleri

Year 2013, Volume: 11 Issue: 2, 102 - 109, 01.06.2013

Abstract

Potansiyel karsinojen olan 3-monokloropropan-1,2-diol 3-MCPD bileşiği gıda veya gıda işlem kaynaklı kontaminant olarak adlandırılmaktadır. İlk olarak, asitle hidrolize olmuş bitkisel proteinlerde soya sosu, sebze proteinleri tespit edilmiştir. Daha sonraki yıllarda farklı gıdalarda da 3-MCPD ve esterlerinin varlığının tespit edilmesiyle bu bileşiklere olan ilgi artmaya başlamıştır. 3-MCPD ve esterleri ısıl işlem esnasında, yağ içeren gıdalarda gliserol veya açilgliserollerin hidroklorik asit ile reaksiyonu sonucu oluşmaktadır. Birçok gıdada varlığı tespit edilen 3-MCPD, gıdalarda yağ açil esterleri şeklinde bulunur. Kloropropanollerin en önemli çıkış maddeleri sırasıyla trigliseritler, fosfolipitler ve gliserol olarak gösterilmiştir. 3-MCPD esterlerinin oluşumu işlenmiş gıdaların çeşitliliğinin bir karakteristiğidir. Yapılan çalışmalarda, özellikle yüksek ısısal işlem görmüş gıdalardaki miktarları oldukça fazla bulunmuştur. Avrupa Komisyonu tarafından günlük alınması gereken kabul edilebilir maksimum miktar ise vücut ağırlığı başına 2 µg/kg olarak belirlenmiştir

References

  • [1] Hamlet, C.G., Sadd, P.A., Crews, C., Velisek, J., Baxter, D.E., 2002. Occurrence of 3-chloropropane-1, 2-diol (3-MCPD) and related compounds in foods: a review. Food Addit. Contam. 19(7):619–631.
  • [2] Seefelder, W., Varga, N., Studer, A., Williamson, G., Scanlan, F.P., Stadler, R.H., 2008. esters of 3- chloro-1,2-propanediol (3-MCPD) in vegetable oils: Significance in the formation of 3-MCPD. Food Addit Contam. 25(4): 391-400.
  • [3] Baer, I., de la Calle, B., Taylor, P., 2010. 3-MCPD in food other than soy sauce or hydrolyzed vegetable protein (HVP). Anal. Bioanal. Chem. 396:443-456.
  • [4] Anon. 2012. Survey of 3-MCPD in foods. Joint Food Safety and Standards Group.
  • [5] Zelinkova, Z., Svejkovska, B., Velisek, J., Dolezal, M., 2006. Fatty acid esters of 3-chloropropane-1,2- diol in edible oils. Food Addit. Contam. 23:1290– 1298.
  • [6] Weißhaar, R., 2011. Fatty acid esters of 3-MCPD: Overview of occurrence and exposure estimates. Eur. J. Lipid Sci. Technol. 113:304–308.
  • [7] Larsen, J.C., 2009. Esters in Food Products. ILSI Europe Report Series. Summary Report of a Workshop held in February 2009 in Brussels, Belgium.
  • [8] Anonymous, 2009. 3-MCPD Esters in Foods (from www.aocs.org).
  • [9] Haines, T.D., Adlaf, K.J., Pierceall , R.M., Lee, I., Venkitasubramanian, P., Collison, M.W., 2011. Direct determination of MCPD fatty acid esters and glycidyl fatty acid esters in vegetable oils by LC– TOFMS. J Am Oil Chem Soc 88:1–14.
  • [10] Pudel, F.Benecke, P., Fehling, P., Freudenstein, A., Matthaus, B., Schwaf, A., 2011. On the necessity of edible oil refining and possible sources of 3-MCPD and glycidyl esters. Eur. J. Lipid Sci. Technol. 113: 368–373.
  • [11] Watkins, C., 2009. Chloroesters in foods: An emerging issue Inform Magazine of the AOCS, No. 4.
  • [12] Razak, R.A.A., Kuntom, A., Siew, W.L., Ibrahim, N.A., Ramli, M.R., Hussein, R., Nesaretnam, K., 2012. Detection and monitoring of 3- monochloropropane-1,2-diol (3-MCPD) esters in cooking oils. Food Cont. 25: 355-360.
  • [13] Franke, K., Strijowski, U., Fleck, G., Pudel, F., 2009. Influence of chemical refining process and oil type on bound 3-chloro-1,2-propanediol contents in palm oil and rapeseed oil. LWT 42: 1751-1754.
  • [14] Breitling-Utzmann, C.M., Kobler, H., Harbolzheimer, D., Maier, A., 2003. 3-MCPD: occurence in bread crust and various food groups as well as formation in toast. Dtsch Lebensm Rundsch 99(7): 280-285.
  • [15] Breitling-Utzmann, C.M., Hrenn, H., Haase, N.U., Unbehend, G.M., 2005. Influence of dough ingredients on 3-chloropropane-1,2-diol (3-MCPD) formation in toast. Food Addit. Contam. 22(2): 97- 103.
  • [16] Hamlet, C.G., Sadd, P.A., 2004. Effects of yeast stress and organic acids on chloropropanols formation in cereal products. Czech J. Food Sci. 22:255-258.
  • [17] Hamlet, C.G., Sadd, P.A., Gray, D.A., 2004. Generation of monochloropropanediols (MCPDs) in model dough systems. 2. Unleavened doughs. J. Agr. Food Chem. 52(7): 2067-2072.
  • [18] Divinova, V., Dolezal, M., Velisek, J., 2007. Free and bound 3-chloropropane-1,2-diol in coffee surrogates and malts. Czech J. Food Sci. 25(1): 39- 47.
  • [19] Zelinkova, Z., Dolezal, M., Velisek, J., 2009. 3- Chloropropane- 1,2-diol fatty acid esters in potato products. Czech J. Food Sci .27: 421–424.
  • [20] Dolezal, M., Chaloupska, M., Divinova, V., Svejkovska, B., Velisek, J., 2005. Occurrence of 3- chloropropane-1,2-diol and its esters in coffee. Eur. Food Res. Tech. 221(3-4): 221-225.
  • [21] Crews, C., Brereton, P., Davies, A., 2001. The effects of domestic cooking on the levels of 3- monochloropropanediol in foods. Food Addit. Contam. 18(4): 271-280.
  • [22] FAO/WHO, 2007. Discussion paper on chloropropanols derived from the manufacture of acid-HVP and the heat processing of food. In: Proc 1st Session of Codex Committee on Contaminants in Foods, Beijing, China, 16-20 April 2007.
  • [23] Kuntzer, J., Weibhaar, R., 2006. The smoking process: a potent source of 3-chloropropane-1,2- diol (3-MCPD) in meat products. Dtsch Lebensm Rundsch 102(9): 397-400.
  • [24] FAO/WHO, 2006. Discussion paper on acid HVP containing products and other products containing chloropropanols. In: Proc Session 38 of Codex Committee on Food Additives and Contaminants, The Hague, The Netherlads, 24-28 Apr 2006.
  • [25] Reece, 2005. The origin and formation of 3-MCPD in foods and food ingredients (final project report). Food Standards Agency, London.
  • [26] Velisek, J., Davidek, J., Hajslova, J., Kubelka, V., Janicek, G., Mankova, B., 1978 . Chlorohydrins in protein hydrolysates. Z Lebensm Unters Forsch 167(4): 241–244.
  • [27] Davidek, J., Velisek, J., Kubelka, V., Janicek, G., Simicova, Z., 1980. Glycerol chlorohydrins and their esters as products of the hydrolysis of tripalmitin, tristearin and triolein with hydrochloric acid. Z Lebensm Unters Forsch 171(1): 14–17.
  • [28] Lynch, B.S., Bryant, D.W., Hook, G.J., Nestmann, E.R., Munro, I.C., 1998. Carcinogenicity of monochloro-1,2-propanediol (α-chlorohydrin, 3- MCPD). Int. J. Toxicol. 17(1): 47–76.
  • [29] Kim, K., Song, C., Park, Y., Koh, S., Kim, J., Kim, S., Kim, Y., Kim, S.U., Jung, H., 2004. 3- Monochloropropane-1,2-diol Does Not Cause Neurotoxicity in Vitro or Neurobehavioral Deficits in Rats. Neuro.Toxicol. 25(3): 377-385.
  • [30] Hahn, H., Eder, E., Deininger, C., 1991. Genotoxicity of 1,3-dichloro-2-propanol in the SOS chromotests and in the Ames tests. Elucidation of the genotoxic mechanism. Chem. Biol. Interactions 80: 73-88.
  • [31] Anon. 2006. Committee on the Carcinogenicity of chemicals in food, consumer products and the environment.
  • [32] Nyman, P.J., Diachenko, G.W., Perfetti, G.A., 2003. Determination of 1,3-dichloropropanol in soy and related sauces by using gaschromatography/mass spectrometry. Food Addit. Contam. 20(10): 903– 908.
  • [33] Schlatter, J., Baars, A.J., Dinovi, M., Lawrie, S., Lorentzen, R., 2002. Safety evaluation of certain food additives and contaminants: 3-chloro-1, 2- propanediol. WHO Food Addit. Ser. 48: 1–30.
  • [34] Wenzl, T., Lachenmeier, D.W., Gokmen, V., 2007. Analysis of heatinduced contaminants (acrylamide, chloropropanols and furan) in carbohydrate-rich food. Anal. Bioanal. Chem. 389(1): 119–137.
  • [35] Divinova, V., Svejkovska, B., Dolezal, M., Velisek, J., 2004. Determination of free and bound 3- chloropropane-1,2-diol by gas chromatography with mass spectrometric detection using deuterated 3- chloropropane-1,2-diol as internal standard. Czech J. Food Sci. 22(5): 182–189.
  • [36] Weißhaar, R., 2008. Determination of total 3- chloropropane-1,2- diol (3-MCPD) in edible oils by cleavage of MCPD esters with sodium methoxide. Eur. J. Lipid Sci. Technol. 110(2): 183–186.
There are 36 citations in total.

Details

Primary Language Turkish
Journal Section Research Article
Authors

Pelin Günç Ergönül This is me

Tuba Göldeli This is me

Publication Date June 1, 2013
Published in Issue Year 2013 Volume: 11 Issue: 2

Cite

APA Günç Ergönül, P., & Göldeli, T. (2013). Gıdalarda 3-Monokloropropan-1,2-Diol 3-MCPD ve Esterlerinin Varlığı, Oluşum Mekanizmaları ve Tespit Yöntemleri. Akademik Gıda, 11(2), 102-109.
AMA Günç Ergönül P, Göldeli T. Gıdalarda 3-Monokloropropan-1,2-Diol 3-MCPD ve Esterlerinin Varlığı, Oluşum Mekanizmaları ve Tespit Yöntemleri. Akademik Gıda. June 2013;11(2):102-109.
Chicago Günç Ergönül, Pelin, and Tuba Göldeli. “Gıdalarda 3-Monokloropropan-1,2-Diol 3-MCPD Ve Esterlerinin Varlığı, Oluşum Mekanizmaları Ve Tespit Yöntemleri”. Akademik Gıda 11, no. 2 (June 2013): 102-9.
EndNote Günç Ergönül P, Göldeli T (June 1, 2013) Gıdalarda 3-Monokloropropan-1,2-Diol 3-MCPD ve Esterlerinin Varlığı, Oluşum Mekanizmaları ve Tespit Yöntemleri. Akademik Gıda 11 2 102–109.
IEEE P. Günç Ergönül and T. Göldeli, “Gıdalarda 3-Monokloropropan-1,2-Diol 3-MCPD ve Esterlerinin Varlığı, Oluşum Mekanizmaları ve Tespit Yöntemleri”, Akademik Gıda, vol. 11, no. 2, pp. 102–109, 2013.
ISNAD Günç Ergönül, Pelin - Göldeli, Tuba. “Gıdalarda 3-Monokloropropan-1,2-Diol 3-MCPD Ve Esterlerinin Varlığı, Oluşum Mekanizmaları Ve Tespit Yöntemleri”. Akademik Gıda 11/2 (June 2013), 102-109.
JAMA Günç Ergönül P, Göldeli T. Gıdalarda 3-Monokloropropan-1,2-Diol 3-MCPD ve Esterlerinin Varlığı, Oluşum Mekanizmaları ve Tespit Yöntemleri. Akademik Gıda. 2013;11:102–109.
MLA Günç Ergönül, Pelin and Tuba Göldeli. “Gıdalarda 3-Monokloropropan-1,2-Diol 3-MCPD Ve Esterlerinin Varlığı, Oluşum Mekanizmaları Ve Tespit Yöntemleri”. Akademik Gıda, vol. 11, no. 2, 2013, pp. 102-9.
Vancouver Günç Ergönül P, Göldeli T. Gıdalarda 3-Monokloropropan-1,2-Diol 3-MCPD ve Esterlerinin Varlığı, Oluşum Mekanizmaları ve Tespit Yöntemleri. Akademik Gıda. 2013;11(2):102-9.

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