Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması

Kübra EMEKTAR, (Ankara Üniversitesi, Mühendislik Fakültesi, Gıda Mühendisliği Bölümü, Ankara, Türkiye)
Meryem NUR KANTEKİN ERDOĞAN, (Ankara Üniversitesi, Mühendislik Fakültesi, Gıda Mühendisliği Bölümü, Ankara, Türkiye)
Aziz TEKİN (Ankara Üniversitesi, Mühendislik Fakültesi, Gıda Mühendisliği Bölümü, Ankara, Türkiye)
Akademik Gıda
27 4
Yıl: 2020 Cilt: 18 Sayı: 1 Sayfa Aralığı: 96 - 104 Metin Dili: Türkçe DOI: 10.24323/akademik-gida.730218 İndeks Tarihi: 10-11-2020

Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması

Öz:
3-Monokloropropan-1,2-diol (3-MCPD) ve glisidol, serbest veya esterleşmiş formlarda bulunabilen ısıl işlem kaynaklıgıda bulaşanlarıdır. Uluslararası Kanser Araştırma Ajansı (IARC) 3-MCPD’yi Grup 2B (insanlar için olası karsinojen)glisidolü ise Grup 2A (insanlar için muhtemel karsinojen) olarak sınıflandırmıştır. Toksisitesinden dolayı serbest 3-MCPD için maksimum tolere edilebilir günlük alım (TDI) miktarı JECFA tarafından 2 µg/kg vücut ağırlığı olarakbelirlenmiştir. Ayrıca Avrupa Komisyonu’nun 2018 yılında yaptığı son düzenleme ile bitkisel yağlarda glisidil esterlerilimit değeri 1 mg/kg olarak belirlenmiştir. Mono ve digliseritler ile klor iyonu gibi prekürsörlerin rafine bitkisel yağlarda3-MCPD ve glisidil ester bulaşanlarının oluşumundan sorumlu olduğu bildirilmiştir. Bunun yanında bitkisel yağlarınrafinasyonu sırasında uygulanan sıcaklık ve sürenin de bu bulaşanların oluşumunu önemli ölçüde etkilediği tespitedilmiştir. Bu derlemede, ilgili güncel literatür ışığında bitkisel yağlarda 3-MCPD ve glisidil esterleri oluşumuna sebepolan faktörler ve bu bulaşanların azaltılmasında kullanılan yöntemler incelenmiştir.
Anahtar Kelime:

3-Monochloropropane-1,2-diol (3-MCPD) and Glycidyl Esters Formed in Vegetable Oils

Öz:
3-Monochloropropane-1,2-diol (3-MCPD) and glycidol, which can exist in both free or bound forms, are process contaminants that can form during heat processes. The International Agency for Research on Cancer (IARC) classified free 3-MCPD and glycidol under Group 2B (possible carcinogenic to humans) and Group 2A (probably carcinogenic to humans), respectively. Due to its toxicity JECFA recommended a maximum tolerable daily intake (TDI) of 2 µg/kg body weight for free 3-MCPD. Furthermore, the maximum level of glycidyl esters in refined vegetable oil was determined as 1 mg/kg in the regulation of European Commission in 2018. Precursors such as monodiglycerides and chlorine are responsible for the formation of 3-MCPD and glycidol. Additionally, it has been found that the formation of these contaminants can be significantly influenced by temperature and time applied during the refining processes of vegetable oils. In this review, factors affecting 3-MCPD and glycidyl ester formation and the mitigation strategies of these contaminants are discussed.
Anahtar Kelime:

Belge Türü: Makale Makale Türü: Derleme Erişim Türü: Erişime Açık
  • [1] Freudenstein, A., Weking, J., Matthäus, B. (2013). Influence of precursors on the formation of 3‐ MCPD and glycidyl esters in a model oil under simulated deodorization conditions. European Journal of Lipid Science and Technology, 115(3), 286-294.
  • [2] Li, C., Li, L., Jia, H., Wang, Y., Shen, M., Nie, S., Xie, M. (2016). Formation and reduction of 3- monochloropropane-1, 2-diol esters in peanut oil during physical refining. Food Chemistry, 199, 605- 611.
  • [3] EFSA (2013). Analysis of occurrence of 3‐ monochloropropane‐1, 2‐diol (3‐MCPD) in food in Europe in the years 2009‐2011 and preliminary exposure assessment. EFSA Journal, 11(9), 3381.
  • [4] Svejkovska, B., Novotny, O., Divinova, V., Reblova, Z., Dolezal, M. (2004). Esters of 3-chloropropane1, 2-diol in foodstuffs. Czech Journal of Food Sciences, 22(5), 190-196.
  • [5] Velíšek, J., Davidek, J., Hajšlová, J., Kubelka, V., Janíček, G., Mánková, B. (1978). Chlorohydrins in protein hydrolysates Chlorhydrinein. Zeitschrift für Lebensmittel-Untersuchung und Forschung, 167(4), 241-244.
  • [6] Davidek, J., Velíšek, J., Kubelka, V., Janíček, G., Šimicová, 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(1), 14-17.
  • [7] CVUA (2007). 3-MCPD Ester in raffinierten speisefetten und ölen – ein neu erkanntes weltweits problem. Available from: http://www.cvuas.de/pub/beitrag.asp?ID=717&subi d=1 (Accessed:09.12.2018).
  • [8] Zelinková, Z., Novotný, O., Schůrek, J., Velíšek, J., Hajšlová, J., Doležal, M. (2008). Occurrence of 3- MCPD fatty acid esters in human breast milk. Food Additives and Contaminants, 25(6), 669-676.
  • [9] EFSA (2016). Risks for human health related to the presence of 3‐and 2‐monochloropropanediol (MCPD), and their fatty acid esters, and glycidyl fatty acid esters in food. EFSA Journal, 14(5), 04426.
  • [10] IARC (2013). Some chemicals present in industrial and consumer products, food and drinking-water. IARC monographs on the evaluation of carcinogenic risks to humans, Vol. 101, pp. 349- 374.
  • [11] IARC (2000). Some industrial chemicals, IARC monographs on the evaluation of carcinogenic risk of chemicals to humans, Vol. 77, pp. 469–487.
  • [12] EU Directive (2018). Commission Regulation (EC) No 2018/290 of 26 February 2018 Amending Regulation (EC) No 1881/2006 as regards maximum levels of glycidyl fatty acid esters in vegetable oils and fats, infant formula, follow-on formula and foods for special medical purposes intended for infants and young children. Official Journal the European Union, L 55:27-29.
  • [13] TGK (2011). Türk Gıda Kodeksi Bulaşanlar Yönetmeliği, Resmi Gazete sayı: 28157 (3. Mükerrer).
  • [14] EFSA (2018). Update of the risk assessment on 3- monochloropropanediol and its fatty acid esters. EFSA Journal, 16(1), 5083.
  • [15] Li, H., Chen, D., Miao, H., Zhao, Y., Shen, J., Wu, Y. (2015). Direct determination of fatty acid esters of 3-chloro-1, 2-propanediol in edible vegetable oils by isotope dilution-ultra high performance liquid chromatography-triple quadrupole mass spectrometry. Journal of Chromatography A, 1410, 99-109.
  • [16] Bakhiya, N., Abraham, K., Gürtler, R., Appel, K.E., Lampen, A. (2011). Toxicological assessment of 3‐ chloropropane‐1, 2‐diol and glycidol fatty acid esters in food. Molecular Nutrition & Food Research, 55(4), 509-521.
  • [17] Buhrke, T., Weißhaar, R., Lampen, A. (2011). Absorption and metabolism of the food contaminant 3-chloro-1, 2-propanediol (3-MCPD) and its fatty acid esters by human intestinal Caco-2 cells. Archives of Toxicology, 85(10), 1201-1208.
  • [18] 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(3), 380-386.
  • [19] 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(3), 309-313.
  • [20] BfR (2007). Infant formula and follow-up formula may contain harmful 3-MCPD fatty acid esters. BfR Opinion No: 047/2007.
  • [21] Bansal, G., Zhou, W., Barlow, P.J., Lo, H.L., Neo, F.L. (2010). Performance of palm olein in repeated deep frying and controlled heating processes. Food Chemistry, 121(2), 338-347.
  • [22] Hamlet, C.G., Asuncion, L., Velíšek, J., Doležal, M., Zelinková, Z., Crews, C. (2011). Formation and occurrence of esters of 3‐chloropropane‐1, 2‐diol (3‐CPD) in foods: What we know and what we assume. European Journal of Lipid Science and Technology, 113(3), 279-303.
  • [23] Šmidrkal, J., Tesařová, M., Hrádková, I., Berčíková, M., Adamčíková, A., Filip, V. (2016). Mechanism of formation of 3-chloropropan-1, 2-diol (3-MCPD) esters under conditions of the vegetable oil refining. Food Chemistry, 211, 124-129.
  • [24] 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(10), 1751-1754.
  • [25] Zelinková, Z., Svejkovská, B., Velíšek, J., Doležal, M. (2006). Fatty acid esters of 3-chloropropane-1, 2-diol in edible oils. Food Additives and Contaminants, 23(12), 1290-1298.
  • [26] Chung, H.Y., Chung, S.W., Chan, B.T.P., Ho, Y.Y., Xiao, Y. (2013). Dietary exposure of Hong Kong adults to fatty acid esters of 3-monochloropropane1, 2-diol. Food Additives & Contaminants: Part A, 30(9), 1508-1512.
  • [27] Karabulut, M., Yemişçioğlu, F. (2012). Rafine bitkisel yağlarda 3-MCPD. Analiz’35, Gıda Tarım Hayvancılık Bakanlığı, İzmir Gıda Laboratuvar Müdürlüğü, 14(8)-10.
  • [28] Svejkovska, B., Dolezal, M., Velíšek, J. (2006). Formation and decomposition of 3-chloropropane1, 2-diol esters in models simulating processed foods. Czech Journal of Food Sciences, 24(4), 172.
  • [29] 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 Additives and Contaminants, 25(4), 391-400.
  • [30] Kayahan, M. (2005). Yemeklik Yağ Rafinasyon Teknolojisi. TMMOB Gıda Mühendisleri Odası, Ankara, Türkiye.
  • [31] Hrncirik, K., van Duijn, G. (2011). An initial study on the formation of 3‐MCPD esters during oil refining. European Journal of Lipid Science and Technology, 113(3), 374-379.
  • [32] Rahn, A.K.K., Yaylayan, V.A. (2011). What do we know about the molecular mechanism of 3‐MCPD ester formation? European Journal of Lipid science and Technology, 113(3), 323-329.
  • [33] Shahidi, F., Zhong, Y. (2005). Lipid Oxidation: Measurement Methods. In: Bailey's Industrial Oil and Fat Products, Edited by F. Shahidi, John Wiley & Sons Inc., Hoboken, NJ, 2005, pp. 357-385.
  • [34] ILSI (2009). 3-MCPD esters in food products, Summary report of a workshop held in Brussels, Belgium. Available from: http://ilsi.eu/wpcontent/uploads/sites/3/2016/06/Fin al-version-3-MCPD-esters.pdf (Accessed: 20.10.2018).
  • [35] Shimizu, M., Vosmann, K., Matthäus, B. (2012). Generation of 3‐monochloro‐1, 2‐propanediol and related materials from tri‐, di‐, and monoolein at deodorization temperature. European Journal of Lipid Science and Technology, 114(11), 1268- 1273.
  • [36] Craft, B.D., Nagy, K., Seefelder, W., Dubois, M., Destaillats, F. (2012b). Glycidyl esters in refined palm (Elaeis guineensis) oil and related fractions. Part II: practical recommendations for effective mitigation. Food Chemistry, 132(1), 73-79.
  • [37] Weißhaar, R. (2008). 3‐MCPD‐esters in edible fats and oils–a new and worldwide problem. European Journal of Lipid Science and Technology, 110(8), 671-672.
  • [48] Frenkel, M. (1974). Surface acidity of montmorillonites. Clays Clay Miner, 22(5-6), 435- 441.
  • [49] Hew, K.S., Asis, A.J., Tan, T.B., Yusoff, M.M., Lai, O.M., Nehdi, I.A.,Tan, C.P. (2020). Revising degumming and bleaching processes of palm oil refining for the mitigation of 3-monochloropropane1, 2-diol esters (3-MCPDE) and glycidyl esters (GE) contents in refined palm oil. Food Chemistry, 307, 125545.
  • [40] 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(3), 335-344.
  • [41] Codex Alimentarius Commission Committee on Food Additives and Contaminants (2018). Proposed draft code of practice for the reduction of 3-monochloropropane-1,2-diol esters (3-MCPDE) and glycidyl esters (GE) in refined oils and products made with refined oils, especially infant formula. Joint FAO/WHO Food Standards Programme, 12-16 March 2018, Utrecht, The Netherlands. Available from: http://www.fao.org/fao-whocodexalimentarius/resources/circularletters/en/?y=2018 (Accessed: 15.11.2018).
  • [42] Nagy, K., Sandoz, L., Craft, B.D., Destaillats, F. (2011). Mass-defect filtering of isotope signatures to reveal the source of chlorinated palm oil contaminants. Food Additives & Contaminants: Part A, 28(11), 1492-1500.
  • [43] Matthäus, B., Pudel, F. (2013). Mitigation of 3‐ MCPD and glycidyl esters within the production chain of vegetable oils especially palm oil. Lipid Technology, 25(7), 151-155.
  • [44] FEDIOL (2015). MCPD esters and glycidyl esters: Review of mitigation measures. http://www.fediol.be/ (Accessed: 10.10 2018).
  • [45] Craft, B.D., Nagy, K., Sandoz, L., Destaillats, F. (2012a). Factors impacting the formation of monochloropropanediol (MCPD) fatty acid diesters during palm (Elaeis guineensis) oil production. Food Additives & Contaminants: Part A, 29(3), 354- 361.
  • [46] Nagy, K., Redeuil, K., Lahrichi, S., Nicolas, M. (2019). Removal of organochlorines from vegetable oils and its benefits in preventing formation of monochloropropanediol diesters. Food Additives & Contaminants: Part A, 36(5), 712-721.
  • [47] Ramli, M.R., Siew, W.L., Ibrahim, N.A., Hussein, R., Kuntom, A., Abd Razak, R.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(11), 1839-1844.
  • [48] Frenkel, M. (1974). Surface acidity of montmorillonites. Clays Clay Miner, 22(5-6), 435- 441.
  • [49] Hew, K.S., Asis, A.J., Tan, T.B., Yusoff, M.M., Lai, O.M., Nehdi, I.A.,Tan, C.P. (2020). Revising degumming and bleaching processes of palm oil refining for the mitigation of 3-monochloropropane1, 2-diol esters (3-MCPDE) and glycidyl esters (GE) contents in refined palm oil. Food Chemistry, 307, 125545.
  • [50] Destaillats, F., Craft, B.D., Dubois, M., Nagy, K. (2012). Glycidyl esters in refined palm (Elaeis guineensis) oil and related fractions. Part I: Formation mechanism. Food Chemistry, 131(4), 1391-1398.
  • [51] Homma, R., Shimizu, M., Moriwaki, J., Kase, M. (2011). Oil or fat composition, PCT Int. Appl. No. (2011) PCT/JP2010/072478, Pub. No.: WO/2011/074575.
  • [52] Özdikicierler, O., Yemişçioğlu, F., Gümüşkesen, A.S. (2016). Effects of process parameters on 3- MCPD and glycidyl ester formation during steam distillation of olive oil and olive pomace oil. European Food Research and Technology, 242(5), 805-813.
  • [53] Pudel, F., Benecke, P., Vosmann, K., Matthäus, B. (2016). 3‐MCPD‐and glycidyl esters can be mitigated in vegetable oils by use of short path distillation. European Journal of Lipid Science and Technology, 118(3), 396-405.
  • [54] Vogel, A.I., Tatchell, A.R., Furnis, B.S., Hannaford, A.J., Smith, P.W.G. (1996). Vogel's Textbook of Practical Organic Chemistry (5th Edition). [55] Patent (2015). Mitigation of 2-MCPD, 3-MCPD, esters therof and glycidyl esters in vegetable oil, No: US20160227809 A1.
  • [56] 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(5), 552-556.
  • [57] 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(3), 387-392.
  • [58] Matthäus, B., Vosmann, K., Weitkamp, P., Grundmann, D., Kersting, H.J. (2016). Degradation of glycidyl esters in RBD palm oil as a function of storage conditions. European Journal of Lipid Science and Technology, 118(3), 418-424.
  • [59] Li, C., Jia, H., Shen, M., Wang, Y., Nie, S., Chen, Y., Zhou, Y., Wang, Y., Xie, M. (2015). Antioxidants inhibit formation of 3-monochloropropane-1, 2-diol esters in model reactions. Journal of Agricultural and Food Chemistry, 63(44), 9850-9854.
APA Emektar K, KANTEKIN ERDOGAN M, Tekin A (2020). Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması. , 96 - 104. 10.24323/akademik-gida.730218
Chicago Emektar Kübra,KANTEKIN ERDOGAN MERYEM NUR,Tekin Aziz Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması. (2020): 96 - 104. 10.24323/akademik-gida.730218
MLA Emektar Kübra,KANTEKIN ERDOGAN MERYEM NUR,Tekin Aziz Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması. , 2020, ss.96 - 104. 10.24323/akademik-gida.730218
AMA Emektar K,KANTEKIN ERDOGAN M,Tekin A Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması. . 2020; 96 - 104. 10.24323/akademik-gida.730218
Vancouver Emektar K,KANTEKIN ERDOGAN M,Tekin A Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması. . 2020; 96 - 104. 10.24323/akademik-gida.730218
IEEE Emektar K,KANTEKIN ERDOGAN M,Tekin A "Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması." , ss.96 - 104, 2020. 10.24323/akademik-gida.730218
ISNAD Emektar, Kübra vd. "Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması". (2020), 96-104. https://doi.org/10.24323/akademik-gida.730218
APA Emektar K, KANTEKIN ERDOGAN M, Tekin A (2020). Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması. Akademik Gıda, 18(1), 96 - 104. 10.24323/akademik-gida.730218
Chicago Emektar Kübra,KANTEKIN ERDOGAN MERYEM NUR,Tekin Aziz Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması. Akademik Gıda 18, no.1 (2020): 96 - 104. 10.24323/akademik-gida.730218
MLA Emektar Kübra,KANTEKIN ERDOGAN MERYEM NUR,Tekin Aziz Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması. Akademik Gıda, vol.18, no.1, 2020, ss.96 - 104. 10.24323/akademik-gida.730218
AMA Emektar K,KANTEKIN ERDOGAN M,Tekin A Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması. Akademik Gıda. 2020; 18(1): 96 - 104. 10.24323/akademik-gida.730218
Vancouver Emektar K,KANTEKIN ERDOGAN M,Tekin A Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması. Akademik Gıda. 2020; 18(1): 96 - 104. 10.24323/akademik-gida.730218
IEEE Emektar K,KANTEKIN ERDOGAN M,Tekin A "Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması." Akademik Gıda, 18, ss.96 - 104, 2020. 10.24323/akademik-gida.730218
ISNAD Emektar, Kübra vd. "Bitkisel Yağlarda 3-Monokloropropan-1,2-diol (3-MCPD) ve Glisidil Esterleri Oluşumu ve Azaltılması". Akademik Gıda 18/1 (2020), 96-104. https://doi.org/10.24323/akademik-gida.730218
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