Formation and Determination of Monochloropropanediol Esters in Foods

Yıl 2018, Cilt: 16 Sayı: 2, 210 - 217, 05.08.2018

Semra Turan , Rukiye Solak Şule Keskin

https://doi.org/10.24323/akademik-gida.449866

Cited By: 1

Öz

MCPD (monochloropropanediol) esters are some of the
heat treatment contaminants found in refined oils and oily foods. In
particular, they occur due to the processing of products containing oil and
salt at high temperatures. Dietary MCPD esters are hydrolyzed as triglycerides
in gastrointestinal tract, and free MCPD is released. Since free MCPD is
carcinogenic, it is important to determine the amounts of MCPD esters in
heat-treated foods. In this review, information on the formation, toxicity, identification
and reduction of 3‑MCPD esters and similar compounds are provided.

Anahtar Kelimeler

3-MCPD, 2-MCPD, Glycidol, Deodorisation, Heat treatment

Gıdalarda Monokloropropandiol Esterlerinin Oluşumu ve Belirlenmesi

Öz

MCPD (monokloropropandiol) esterleri rafine yağlarda ve
yağlı gıdalarda varlığı saptanan ısıl işlem kontaminantlarından biridir. Özellikle
yağ ve tuz içeren ürünlerin yüksek sıcaklıklarda işlem görmesi sonucu
oluşmaktadırlar. Diyetle alınan MCPD esterleri gastrointestinal sistemde
trigliseritler gibi hidrolize uğrayarak serbest MCPD açığa çıkmaktadır. Serbest
MCPD’nin kanserojen olduğu bilindiğinden ısıl işlem görmüş gıdalarda MCPD
esterlerinin miktarlarının belirlenmesi önem taşımaktadır. Bu derlemede 3-MCPD
esterleri ve benzer bileşiklerin oluşumu, toksisitesi, belirlenmesi ve
miktarının azaltılmasına yönelik bilgiler verilmeye çalışılmıştır.

Anahtar Kelimeler

3-MCPD, 2-MCPD, Glisidol, Deodorizasyon, Isıl işlem

Kaynakça

• [1] Gökmen, V. (2011). Gıdalarda ısıl işlem bulaşanları. Bilim ve Teknik, 66-67.
• [2] Velisek, J., Davídek, J., Kubelka, V., Bartosova, J., Tuekova, A., Hajslova, J., Janieek, G. (1979). Formation of volatile chlorohydrins from glycerol (triacetin, tributyrin) and hydrochloric acid. Z. Lebens. Wissen Technol, 12, 234-236.
• [3] Davidek, J., Velisek, J., Kubelka, V., Janieek, G., Simicova, Z. (1980). Glycerol chlorohydrins and their esters as products of the hydrolysis of tripalmitin, tristearin and triolein with hydrochloric acid. Zeitschrift für Lebensmittel-Untersuchung und –Forschung, 171, 14-17.
• [4] Zelinkova, Z., Svejkovska, B., Velisek, J., Dolezal, M. (2006). Fatty acid esters of chloropropane-1,2-diol in edible oils. Food Additives and Contaminants, 23, 1290-1298.
• [5] Crews, C., Chiodini, A., Granvogl, M., Hamlet, C., Hrncirik, K., Kuhlmann, J., Lampen, A., Scholz, G., Weisshaar, R., Wenzl, T., Jasti, P.R., Seefelder, W. (2013). Analytical approaches for MCPD esters and glycidyl esters in food and biological samples: a review and future perspectives. Food and Additives and Contaminants: Part A, 30(1), 11-45.
• [6] Ermacora, A., Hrncirik, K. (2014). Influence of composition on the formation of fatty acid esters of 2-chloropropane-1,3-diol (2-MCPD) and 3-chloropropane-1,2-diol (3-MCPD) under conditions simulating oil refining. Food Chemistry, 161, 383-389.
• [7] Seefelder, W., Scholz, G., Schilter, B. (2011). Structural diversity of dietary fatty esters of chloropropanols and related substances. European Journal of Lipid Science and Technology, 113, 319-322.
• [8] Andres, S., Appel, K.E., Lampen, A. (2013). Toxicology, occurrence and risk characterisation of the chloropropanols in food: 2-Monochloro-1,3-propanediol, 1,3-dichloro-2-propanol and 2,3-dichloro-1-propanol. Food and Chemical Toxicology, 58, 467-478.
• [9] Jędrkiewicz, R., Kupska, M., Głowacz, A., Gromadzka, J., Namieśnik, J. (2016). 3-MCPD: A worldwide problem of food chemistry. Critical Reviews in Food Science and Nutrition, 56, 2268-2277.
• [10] Wong, Y.H., Muhamad, H., Abas, F., Lai, O.M., Nyame, K.L., Tan, C.P. (2017). Effects of temperature and NaCl on the formation of 3-MCPD esters and glycidyl esters in refined, bleached and deodorized palmolein during deep-fat frying of potato chips. Food Chemistry, 219, 126–130.
• [11] Arisseto, A.P., Marcolino, P.F.C., Augusti, A.C., Scaranelo, G.R., Berbari, S.A.G., Miguel, A.M.R.O., Morgano, M.A., Vicente, E. (2017). Contamination of fried foods by 3-monochloropropane-1,2-diol fatty acid esters during frying. Journal of the American Oil Chemists' Society, 94, 449-455.
• [12] European Food Safety Authority. (2013). Scientific report of EFSA. Analysis. Analysis of occurrence of 3-monochloropropane-1,2-diol (3-MCPD) in food in Europe in the years 2009-2011 and preliminary exposure assessment. European Food Safety Authority Journal, 11(9), 3381, 45 pp.
• [13] Hori, K., Koriyama, N., Omori, H., Kuriyama, M., Arishima, T., Tsumura, K. (2012). Simultaneous determination of 3-MCPD fatty acid esters and glycidol fatty acid esters in edible oils using liquid chromatography time-of-flight mass spectrometry. LWT - Food Science and Technology, 48, 204-208.
• [14] Karabulut, M., Yemişçioğlu, F. (2012). Rafine bitkisel yağlarda 3-MCPD, Gıda Yem ve Analiz’35, T.C. Gıda Tarım Hayvancılık Bakanlığı İzmir Gıda Laboratuvar Müdürlüğü 8-10.
• [15] Schilter, B., Scholz, G., Seefelder, W. (2011). Fatty acid esters of chloropropanols and related compounds in food: Toxicological aspects. European Journal of Lipid Science and Technology, 113, 309-313.
• [16] Wong, K.O., Cheong, Y.H., Seah, H.L. (2006). 3-Monochloropropane-1,2-diol (3-MCPD) in soy and oyster sauces: Occurrence and dietary intake assessment. Food Control, 17, 408-413.
• [17] Fu, W.S., Zhao, Y., Zhang, G., Zhang, L., Li, J.G., Tang, C.D., Miao, H., Ma, J.B., Zhang, Q., Wu, Y.N. (2007). Occurrence of chloropropanols in soy sauce and other foods in China between 2002 and 2004. Food Additives and Contaminants, 24(8), 812-819.
• [18] Mogol B.A., Pye, C., Anderson, W., Crews, C., Gökmen, V. (2014). Formation of monochloropropane-1,2-diol and its esters in biscuits during baking. Journal of Agricultural and Food Chemistry, 62, 7297-7301.
• [19] Chung, S.W.C., Kwong, K.P., Yau, J.C.W., Wong, A.M.C., Xiao, Y. (2008). Chloropropanols levels in foodstuffs marketed in Hong Kong. Journal of Food Composition and Analysis, 21, 569-573.
• [20] 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 Control, 25, 355-360.
• [21] 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 - Food Science and Technology, 42, 1751-1754.
• [22] Arisseto,A.P., Marcolino, P.F.C., Vicente, E. (2015). 3-Monochloropropane-1,2-diol fatty acid esters in commercial deep-fat fried foods. Food Additives and Contaminants: Part A, 32(9), 1431-1435.
• [23] Kuhlmann, J. (2011). Determination of bound 2,3-epoxy-1-propanol (glycidol) and bound monochloropropanediol (MCPD) in refined oils. European Journal of Lipid Science and Technology, 113, 335-344.
• [24] Jędrkiewicz, R., Głowacz, A., Gromadzka, J., Kloskowski, A., Namieśnik, J. (2016). Indirect determination of MCPD fatty acid esters in lipid fractions of commercially available ınfant formulas for the assessment of infants’ health risk. Food Analytical Methods, 9(12), 3460-3469.
• [25] Weibhaar, R. (2008). 3-MCPD-esters in edible fats and oils – a new and worldwide problem. European Journal of Lipid Science and Technology, 110, 671-672.
• [26] Weibhaar, R. (2011). Fatty acid esters of 3-MCPD: Overview of occurrence and exposure estimates. European Journal of Lipid Science and Technology, 113, 304-308.
• [27] Hammouda, I.B., Zribi, A., Mansour, A.B., Matthäus, B., Bouaziz, M. (2017). Effect of deep-frying on 3-MCPD esters and glycidyl esters contents and quality control of refined olive pomace oil blended with refined palm oil. European Food Research and Technology, 243(7), 1219–1227.
• [28] Jędrkiewicz, R., Głowacz, A., Gromadzka, J., Namieśnik, J. (2016). Determination of 3-MCPD and 2-MCPD esters in edible oils, fish oils and lipid fractions of margarines available on Polish market. Food Control, 59, 487-492.
• [29] Matthäus, B., Pudel, F., Fehling, P., Vosmann, K., Freudenstein, A. (2011). Strategies for the reduction of 3-MCPD esters and related compounds in vegetable oils. European Journal of Lipid Science and Technology, 113, 380-386.
• [30] Matthäus, B. (2012). Organic or not organic- that is the question: How the knowledge about the origin of chlorinated compounds can help to reduce formation of 3-MCPD esters. European Journal of Lipid Science and Technology, 114, 1333-1334.
• [31] Crews, C., Brereton, P., Davies, A. (2001). The effects of domestic cooking on the levels of 3-monochloropropanediol in foods. Food Additives and Contaminants, 18, 271- 280.
• [32] Wong, Y.H., Lai, O.M., Abas, F., Nyam, K.L., Nehdi, I.A. Muhamad, H., Tan, C.P. (2017). Factors impacting the formation of 3-MCPD esters and glycidyl esters during deep fat frying of chicken breast meat. Journal of the American Oil Chemists' Society, 94, 759-765.
• [33] Önal, B., Özdikicierler, O., Yemişçioğlu, F. (2016). Türkiye piyasasında satışa sunulan patates cipslerinde 3-MCPD esterleri ve glisidil esterleri miktarları. Akademik Gıda, 17(3), 267-274.
• [34] Strijowski, U., Heinz, V., Franke, K. (2011). Removal of 3-MCPD esters and related substances after refining by adsorbent material. European Journal of Lipid Science and Technology, 113, 387-392.
• [35] Ramli, M.R., Siew, W.L., Ibrahim, N.A., Hussein, R., Kuntom, A., Razak, R.A.A., Nesaretnam, K. (2011). Effects of degumming and bleaching on 3-MCPD esters formation during physical refining. Journal of the American Oil Chemists' Society, 88, 1839-1844.
• [36] Zulkurnain, M., Lai, O.M., Latip, R.A., Nehdi, I.A., Ling, T.C., Tan, C.P. (2012). The effects of physical refining on the formation of 3-monochloropropane-1,2-diol esters in relation to palm oil minor components. Food Chemistry, 135, 799-805.
• [37] Bornscheuer, U.T., Hesseler, M. (2010). Enzymatic removal of 3-monochloro-1,2-propanediol (3-MCPD) and its esters from oils. European Journal of Lipid Science and Technology, 112, 552-556.