MCPD fatty acid esters in vegetable oils: formation, analysis and toxicology
Document Type : Review article
Authors
1 Research Center for Environmental Determinants of Health, Kermanshah University of Medical Sciences, Kermanshah, Iran
2 Student Research Committee, Department of Food Science and Technology, National Nutrition and Food Technology Research Institute, Faculty of Nutrition Science and Food Technology, Shahid Beheshti University of Medical Sciences, Tehran, Iran
3 Faculty of Food Industries and Agriculture, Standard Research Institute-ISIRI, Karaj, Iran
4 Department of Food Science and Technology, Faculty of Agriculture, University of Tabriz, Tabriz, Iran
Abstract
3-monochoropropane-1, 2-diol (3-MCPD) and 2-monochloropropane-1,3-diol (2-MCPD) and glycidol esters (GE) have been known as food contaminants. These compounds are formed during high-temperature process of different food products such as coffee, edible oils, infant formula, potato based products, bakery products, malt, cooked meats, soy sauces and pickles. In vegetable oils, these compounds are formed during refining, particularly during deodorization step. The studies on MCPD content and their formation routes in vegetable oil are a new area of research. Carcinogenic characteristics of these ingredients are a general concern. Thermal processing such as deodorization and deep-frying can trigger the formation of unpleasant substance such as trans fatty acids cyclic fatty acid esters, or acylglycerol polymers. Refining of edible oils, although eliminates contaminants from the oil, but it leads to the formation of unwanted compounds such as glycidol, glycidol esters, MCPD and MCPD esters. This review gives valuable information of present knowledge on analytical aspect, formation mechanisms of 3-MCPD and GE in vegetable oils and their health implications such as toxicity, carcinogenicity and mutagenicity.
Keywords
(CONTAM), E. P. on C. in the F. C. (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), e04426.
(EFSA), E. F. S. A. (2008). Statement of the scientific panel on contaminants in the food chain (contam) on a request from the European commission related to 3‐MCPD esters. EFSA Journal, 6(3), 1048.
Ansari, R., Kazi, T. G., Jamali, M. K., Arain, M. B., Sherazi, S. T., Jalbani, N., & Afridi, H. I. (2008). Improved extraction method for the determination of iron, copper, and nickel in new varieties of sunflower oil by atomic absorption spectroscopy. Journal of AOAC International, 91(2), 400–407.
Ansari, R., Kazi, T. G., Jamali, M. K., Arain, M. B., Wagan, M. D., Jalbani, N., … Shah, A. Q. (2009). Variation in accumulation of heavy metals in different verities of sunflower seed oil with the aid of multivariate technique. Food Chemistry, 115(1), 318–323.
Arisseto, A. P., Marcolino, P. F. C., Augusti, A. C., Scaranelo, G. R., Berbari, S. A. G., Miguel, 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(3), 449–455.
Azadmard‐Damirchi, S., & Dutta, P. C. (2008). Stability of minor lipid components with emphasis on phytosterols during chemical interesterification of a blend of refined olive oil and palm stearin. Journal of the American Oil Chemists’ Society, 85(1), 13–21.
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.
Barocelli, E., Corradi, A., Mutti, A., & Petronini, P. G. (2011). Comparison between 3‐MCPD and its palmitic esters in a 90‐day toxicological study. EFSA Supporting Publications, 8(9), 187E.
Beekman, J. K., Granvogl, M., & MacMahon, S. (2019). Analysis and occurrence of MCPD and glycidyl esters in infant formulas and other complex food matrices. In Food-Borne Toxicants: Formation, Analysis, and Toxicology (pp. 67–90). ACS Publications.
Beekman, J., Grassi, K., MacMahon, S., Kuhlmann, J., Becalski, A., Jaudzems, G., & Robert, F. (2018). Current research at the US Food and Drug Administration related to the analysis of MCPD and glycidyl esters in refined oils and processed foods. Abstracts of Papers of The American Chemical Society, 256. Amer Chemical SOC 1155 16TH ST, NW, Washington, DC 20036 USA.
Beljaars, P. R., & Houwen-Claassen, A. A. (1994). Determination of polymerized triglycerides in frying fats and oils by gel permeation chromatography: interlaboratory study. Journal of AOAC International, 77(3), 667–671.
Bockish, M. (1996). Nahrunghfette und-öle, Handbuch der Lebensmitteltechnologie. Eugen Ulmer GmgH & Co.
Breitling-Utzmann, C. M., Köbler, H., Herbolzheimer, D., & Maier, A. (2003). 3-MCPD: Occurrence in bread crust and various food groups as well as formation in toast. Deutsche Lebensmittel-Rundschau.
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.
Cabras, P., Caboni, P., Cabras, M., Angioni, A., & Russo, M. (2002). Rotenone residues on olives and in olive oil. Journal of Agricultural and Food Chemistry, 50(9), 2576–2580.
Cerbulis, J., Parks, O. W., Liu, R. H., Piotrowski, E. G., & Farrell Jr, H. M. (1984). Occurrence of diesters of 3-chloro-1, 2-propanediol in the neutral lipid fraction of goats’ milk. Journal of Agricultural and Food Chemistry, 32(3), 474–476.
Cheng, W., Liu, G., Wang, X., & Han, L. (2017). Adsorption removal of glycidyl esters from palm oil and oil model solution by using acid-washed oil palm wood-based activated carbon: kinetic and mechanism study. Journal of Agricultural and Food Chemistry, 65(44), 9753–9762.
Cho, W.-S., Han, B. S., Lee, H., Kim, C., Nam, K. T., Park, K., … Jeong, J. (2008). Subchronic toxicity study of 3-monochloropropane-1, 2-diol administered by drinking water to B6C3F1 mice. Food and Chemical Toxicology, 46(5), 1666–1673.
Chon, S.-H., Zhou, Y. X., Dixon, J. L., & Storch, J. (2007). Intestinal monoacylglycerol metabolism developmental and nutritional regulation of monoacylglycerol lipase and monoacylglycerol acyltransferase. Journal of Biological Chemistry, 282(46), 33346–33357.
Chung, H. Y., Chung, S. W. C., Chan, B. T. P., Ho, Y. Y., & Xiao, Y. (2013). Dietary exposure of Hong Kong adults to fatty acid esters of 3-monochloropropane-1, 2-diol. Food Additives & Contaminants: Part A, 30(9), 1508–1512.
Cindric, I. J., Zeiner, M., & Steffan, I. (2007). Trace elemental characterization of edible oils by ICP–AES and GFAAS. Microchemical Journal, 85(1), 136–139.
Craft, B. D., & Nagy, K. (2012). Mitigation of MCPD‐ester and glycidyl‐ester levels during the production of refined palm oil. Lipid Technology, 24(7), 155–157.
Crews, C., Hough, P., Brereton, P., Harvey, D., Macarthur, R., & Matthews, W. (2002). Survey of 3-monochloropropane-1, 2-diol (3-MCPD) in selected food groups, 1999-2000. Food Additives & Contaminants, 19(1), 22–27.
Damirchi, S. A., Savage, G. P., & Dutta, P. C. (2005). Sterol fractions in hazelnut and virgin olive oils and 4, 4′-dimethylsterols as possible markers for detection of adulteration of virgin olive oil. Journal of the American Oil Chemists’ Society, 82(10), 717–725.
Destaillats, F., & Angers, P. (2005). On the mechanisms of cyclic and bicyclic fatty acid monomer formation in heated edible oils. European Journal of Lipid Science and Technology, 107(10), 767–772.
Dolezal, M., & Velisek, J. (2002). Optical isomers of chloropropanols: Mechanisms of their formation and decomposition in foods. Polish Journal of Food And Nutrition Sciences, 11(SPEC; ISS 2), 86–91.
Dolezal, M., Chaloupska, M., Divinova, V., Svejkovska, B., & Velisek, J. (2005). Occurrence of 3-chloropropane-1, 2-diol and its esters in coffee. European Food Research and Technology, 221(3–4), 221–225.
Dubois, M., Empl, A.-M., Jaudzems, G., Basle, Q., & Konings, E. (2019). Determination of 2-and 3-MCPD as well as 2-and 3-MCPD esters and glycidyl esters (GE) in infant and adult/pediatric nutritional formula by gas chromatography coupled to mass spectrometry method, First Action 2018.03. Journal of AOAC International, 102(3), 903–914.
Dubois, M., Tarres, A., Goldmann, T., Empl, A. M., Donaubauer, A., & Seefelder, W. (2012). Comparison of indirect and direct quantification of esters of monochloropropanediol in vegetable oil. Journal of Chromatography A, 1236, 189–201.
Edem, D. O. (1999). Comparative biochemical and hematological studies on rats fed various levels of palm oil-containing diets. Nigeria: PhD Thesis, University of Calabar.
Ermacora, A., & Hrncirik, K. (2013). A novel method for simultaneous monitoring of 2‐MCPD, 3‐MCPD and glycidyl esters in oils and fats. Journal of the American Oil Chemists’ Society, 90(1), 1–8.
Escobar, J., Lorán, S., Gimenez, I., Ferruz, E., Herrera, M., Herrera, A., & Arino, A. (2013). Occurrence and exposure assessment of Fusarium mycotoxins in maize germ, refined corn oil and margarine. Food and Chemical Toxicology, 62, 514–520.
Foundation, B. N. (1995). Iron: Nutritional and Physiological Significance: the Report of the British Nutrition Foundation’s Task Force. Springer-Science+ Business Media, BV.
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.
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.
für Risikobewertung, B. (2007). Sauglingsanfangs-und Folgenahrung kann gesundheitlich bedenkliche 3-MCPD-Fettsäureester enthalten. Stellungnahme.
Gibon, V., De Greyt, W., & Kellens, M. (2007). Palm oil refining. European Journal of Lipid Science and Technology, 109(4), 315–335.
Hamlet, C. G., Jayaratne, S. M., & Matthews, W. (2002). 3-Monochloropropane-1, 2-diol (3-MCPD) in food ingredients from UK food producers and ingredient suppliers. Food Additives & Contaminants, 19(1), 15–21.
Hamlet, C. G., & Sadd, P. A. (2004). Chloropropanols and their esters in cereal products. Czech Journal of Food Sciences, 22(I), 259.
Hamlet, C. G., Sadd, P. A., Crews, C., Velíšek, J., & Baxter, D. E. (2002). Occurrence of 3-chloro-propane-1, 2-diol (3-MCPD) and related compounds in foods: a review. Food Additives & Contaminants, 19(7), 619–631.
Hamlet, C. G., Asuncion, L., Velíšek, J., Dolezal, M., Zelinkova, 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.
Henderson, J., & Osborne, D. J. (2000). The oil palm in all our lives: how this came about. Endeavour, 24(2), 63–68.
Henderson, L. M., Bosworth, H. J., Ransome, S. J., Banks, S. J., Brabbs, C. E., & Tinner, A. J. (1987). An assessment of the mutagenic potential of 1, 3-dichloro-2-propanol, 3-chloro-1, 2-proanediol and a cocktail of chloropropanols using the mouse lymohoma TK locuc assay. Unpublished Report No ULR, 130.
Hu, Z., Cheng, P., Guo, M., Zhang, W., & Qi, Y. (2013). A novel approach of periodate oxidation coupled with HPLC-FLD for the quantitative determination of 3-chloro-1, 2-propanediol in water and vegetable oil. Journal of Agricultural and Food Chemistry, 61(27), 6614–6621.
Huang, M., Jiang, G., He, B., Liu, J., Zhou, Q., Fu, W., & Wu, Y. (2005). Determination of 3-chloropropane-1, 2-diol in liquid hydrolyzed vegetable proteins and soy sauce by solid-phase microextraction and gas chromatography/mass spectrometry. Analytical Sciences, 21(11), 1343–1347.
Humans, I. W. G. on the E. of C. R. to. (2013). Some chemicals present in industrial and consumer products, food and drinking-water. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, 101, 9.
Irwin, R. D., Eustis, S. L., Stefanski, S., & Haseman, J. K. (1996). Carcinogenicity of glycidol in F344 rats and B6C3F1 mice. Journal of Applied Toxicology, 16(3), 201–209.
JECFA. (2016). Joint FAO/WHO expert committee on food additives Eighty-third meeting. In: JECFA/83/SC.
Jędrkiewicz, R., Głowacz, A., Gromadzka, J., & Namiesnik, 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.
Jędrkiewicz, R., Głowacz-Rozynska, A., Gromadzka, J., Konieczka, P., & Namiesnik, J. (2017). Novel fast analytical method for indirect determination of MCPD fatty acid esters in edible oils and fats based on simultaneous extraction and derivatization. Analytical and Bioanalytical Chemistry, 409(17), 4267–4278.
Jeong, J., Han, B. S., Cho, W.-S., Choi, M., Ha, C.-S., Lee, B.-S., … Kim, C.-Y. (2010). Carcinogenicity study of 3-monochloropropane-1, 2-diol (3-MCPD) administered by drinking water to B6C3F1 mice showed no carcinogenic potential. Archives of Toxicology, 84(9), 719–729.
Jones, A. R., Milton, D. H., & Murcott, C. (1978). The oxidative metabolism of α-chlorohydrin in the male rat and the formation of spermatocoeles. Xenobiotica, 8(9), 573–582.
Juranovic, I., Breinhoelder, P., & Steffan, I. (2003). Determination of trace elements in pumpkin seed oils and pumpkin seeds by ICP-AES. Journal of Analytical Atomic Spectrometry, 18(1), 54–58.
Kamikata, K., Vicente, E., Arisseto-Bragotto, A. P., de Oliveira Miguel, A. M. R., Milani, R. F., & Tfouni, S. A. V. (2019). Occurrence of 3-MCPD, 2-MCPD and glycidyl esters in extra virgin olive oils, olive oils and oil blends and correlation with identity and quality parameters. Food Control, 95, 135–141.
King, B., & Sibley, I. (1984). Authenticity of edible vegetable oils and fats. Part II. Palm oil and palm oil fractions. Leatherhead Fd RA Res. Rep, (462).
Kuntzer, J., & Weisshaar, R. (2006). The smoking process-: A potent source of 3-chloropropane-1, 2-diol (3-MCPD) in meat products. Deutsche Lebensmittel-Rundschau, 102(9), 397–400.
Kwack, S. J., Kim, S. S., Choi, Y. W., Rhee, G. S., Lee, R. Da, Seok, J. H., … Choi, K. S. (2004). Mechanism of antifertility in male rats treated with 3-monochloro-1, 2-propanediol (3-MCPD). Journal of Toxicology and Environmental Health, Part A, 67(23–24), 2001–2004.
Kyselka, J., Matejkova, K., Smidrkal, J., Bercikova, M., Pesek, E., Belkova, B., … Filip, V. (2018). Elimination of 3-MCPD fatty acid esters and glycidyl esters during palm oil hydrogenation and wet fractionation. European Food Research and Technology, 244(11), 1887–1895.
Larsen, J. C. (2009). 3-MCPD esters in food products. Summary Report of a Workshop held in February 2009 in Brussels, Belgium. 3-MCPD Esters in Food Products. Summary Report of a Workshop Held in February 2009 in Brussels, Belgium. ILSI Europe.
Lass, A., Zimmermann, R., Oberer, M., & Zechner, R. (2011). Lipolysis–a highly regulated multi-enzyme complex mediates the catabolism of cellular fat stores. Progress in Lipid Research, 50(1), 14–27.
Lee, M.-R., Chiu, T.-C., & Dou, J. (2007). Determination of 1, 3-dichloro-2-propanol and 3-chloro-1, 2-propandiol in soy sauce by headspace derivatization solid-phase microextraction combined with gas chromatography–mass spectrometry. Analytica Chimica Acta, 591(2), 167–172.
León, N., Yusà, V., Pardo, O., & Pastor, A. (2008). Determination of 3-MCPD by GC-MS/MS with PTV-LV injector used for a survey of Spanish foodstuffs. Talanta, 75(3), 824–831.
Li, C., Zhou, Y., Zhu, J., Wang, S., Nie, S., & Xie, M. (2016). Formation of 3-chloropropane-1, 2-diol esters in model systems simulating thermal processing of edible oil. LWT-Food Science and Technology, 69, 586–592.
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.
Liu, M., Gao, B.-Y., Qin, F., Wu, P.-P., Shi, H.-M., Luo, W., … Yu, L.-L. L. (2012). Acute oral toxicity of 3-MCPD mono-and di-palmitic esters in Swiss mice and their cytotoxicity in NRK-52E rat kidney cells. Food and Chemical Toxicology, 50(10), 3785–3791.
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). International Journal of Toxicology, 17(1), 47–76.
MacMahon, S., Begley, T. H., & Diachenko, G. W. (2013). Occurrence of 3-MCPD and glycidyl esters in edible oils in the United States. Food Additives & Contaminants: Part A, 30(12), 2081–2092.
Majerus, P., Graf, N., & Kramer, M. (2009). Rapid determination of zearalenone in edible oils by HPLC with fluorescence detection. Mycotoxin Research, 25(3), 117.
Manorama, R., & Rukmini, C. (1991). Nutritional evaluation of crude palm oil in rats. The American Journal of Clinical Nutrition, 53(4), 1031S–1033S.
Masukawa, Y., Shiro, H., Nakamura, S., Kondo, N., Jin, N., Suzuki, N., … Kudo, N. (2010). A new analytical method for the quantification of glycidol fatty acid esters in edible oils. Journal of Oleo Science, 59(2), 81–88.
May, C. (1991). In vitro sister chromatid exchange assay in mammalian cells. Unpublished Report, 91(4).
Meeting, J. F. E. C. on F. A., & Organization, W. H. (2016). Evaluation of certain food additives and contaminants: eightieth report of the Joint FAO/WHO Expert Committee on Food Additives (Vol. 80). World Health Organization.
Meierhans, D. C., Bruehlmann, S., Meili, J., & Taeschler, C. (1998). Sensitive method for the determination of 3-chloropropane-1, 2-diol and 2-chloropropane-1, 3-diol by capillary gas chromatography with mass spectrometric detection. Journal of Chromatography A, 802(2), 325–333.
Morris, I. D., & Williams, L. M. (1980). Some preliminary observations of the nephrotoxicity of the male antifertility drug (±) α‐chlorohydrin. Journal of Pharmacy and Pharmacology, 32(1), 35–38.
Ozcagli, E., Alpertunga, B., Fenga, C., Berktas, M., Tsitsimpikou, C., Wilks, M. F., & Tsatsakis, Α. M. (2016). Effects of 3-monochloropropane-1, 2-diol (3-MCPD) and its metabolites on DNA damage and repair under in vitro conditions. Food and Chemical Toxicology, 89, 1–7.
Pope, J. L., McPherson, J. C., & Tidwell, H. C. (1966). A study of a monoglyceride-hydrolyzing enzyme of intestinal mucosa. Journal of Biological Chemistry, 241(10), 2306–2310.
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. European Journal of Lipid Science and Technology, 113(3), 368–373.
Racamonde, I., González, P., Lorenzo, R. A., & Carro, A. M. (2011). Determination of chloropropanols in foods by one-step extraction and derivatization using pressurized liquid extraction and gas chromatography–mass spectrometry. Journal of Chromatography A, 1218(39), 6878–6883.
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.
Ramli, M. I., Zakaria, Z., Sahid, I., Ai, T. Y., & Muhamad, H. (2012). Determination of Herbicide diuron levels in palm oil matrices using HPLC-UV. Sains Malaysiana, 41(11), 1451–1459.
Renaud, S. C., Ruf, J. C., & Petithory, D. (1995). The positional distribution of fatty acids in palm oil and lard influences their biologic effects in rats. The Journal of Nutrition, 125(2), 229–237.
Rétho, C., & Blanchard, F. (2005). Determination of 3-chloropropane-1, 2-diol as its 1, 3-dioxolane derivative at the μg kg− 1 level: application to a wide range of foods. Food Additives and Contaminants, 22(12), 1189–1197.
RJones, A. (1983). Antifertility actions of a-chlorohydrin in the male. Australian Journal of Biological Sciences, 36(4), 333–350.
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.
Schlatter, J., Baars, A. J., DiNovi, M., Lawrie, S., & Lorentzen, R. (2002). 3-Chloro-1, 2-propanediol. WHO Food Additives Series, 401–432.
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.
Shi, L.-K., Zhang, D.-D., & Liu, Y.-L. (2016). Incidence and survey of polycyclic aromatic hydrocarbons in edible vegetable oils in China. Food Control, 62, 165–170.
Siegel, D., Andrae, K., Proske, M., Kochan, C., Koch, M., Weber, M., & Nehls, I. (2010). Dynamic covalent hydrazine chemistry as a selective extraction and cleanup technique for the quantification of the Fusarium mycotoxin zearalenone in edible oils. Journal of Chromatography A, 1217(15), 2206–2215.
Smidrkal, J., Ilko, V., Filip, V., Dolezal, M., Zelinkova, Z., Kyselka, J., … Velisek, J. (2011). Formation of acylglycerol chloro derivatives in vegetable oils and mitigation strategy. Czech Journal of Food Sciences, 29(4), 448–456.
Smidrkal, J., Tesarova, M., Hradkova, I., Bercikova, M., Adamcikova, 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.
Stadler, R. H. (2015). Monochloropropane-1, 2-diol esters (MCPDEs) and glycidyl esters (GEs): an update. Current Opinion in Food Science, 6, 12–18.
Starski, A., Jedra, M., Gawarska, H., & Postupolski, J. (2013). Assessing exposure to 3-MCPD from bakery products based on monitoring studies undertaken throughout Poland. Roczniki Państwowego Zakładu Higieny, 64(4).
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.
Sunahara, G., Perrin, I., & Marchesini, M. (1993). Carcinogenicity study on 3-monochloropropane-1, 2-diol (3-MCPD) administered in drinking water to Fischer 344 rats. Unpublished Report No. RE-SR93003 Submitted to EFSA by Nestec Ltd, Research & Development, Switzerland.
Svejkovska, B., Dolezal, M., & Velisek, J. (2006). Formation and decomposition of 3-chloropropane-1, 2-diol esters in models simulating processed foods. Czech Journal of Food Sciences, 24(4), 172.
Svejkovska, B., Novotny, O., Divinova, V., Reblova, Z., & Dolezal, M. (2004). Esters of 3-chloropropane-1, 2-diol in foodstuffs. Czech Journal of Food Sciences-UZPI (Czech Republic).
Van Duuren, B. L., Goldschmidt, B. M., Katz, C., Seidman, I., & Paul, J. S. (1974). Carcinogenic activity of alkylating agents. Journal of the National Cancer Institute, 53(3), 695–700.
Velisek, J., Davidek, J., Hajslova, J., Kubelka, V., Janicek, G., & Mankova, B. (1978). Chlorohydrins in protein hydrolysates. Zeitschrift Für Lebensmittel-Untersuchung Und Forschung, 167(4), 241–244.
Wake, H. (2005). Oil refineries: a review of their ecological impacts on the aquatic environment. Estuarine, Coastal and Shelf Science, 62(1–2), 131–140.
Weisburger, E. K., Ulland, B. M., Nam, J., Gart, J. J., & Weisburger, J. H. (1981). Carcinogenicity tests of certain environmental and industrial chemicals. Journal of the National Cancer Institute, 67(1), 75–88.
Weißhaar, R. (2008). Determination of total 3‐chloropropane‐1, 2‐diol (3‐MCPD) in edible oils by cleavage of MCPD esters with sodium methoxide. European Journal of Lipid Science and Technology, 110(2), 183–186.
Weißhaar, R., & Perz, R. (2010). Fatty acid esters of glycidol in refined fats and oils. European Journal of Lipid Science and Technology, 112(2), 158–165.
Wenzl, T., Lachenmeier, D. W., & Gokmen, V. (2007). Analysis of heat-induced contaminants (acrylamide, chloropropanols and furan) in carbohydrate-rich food. Analytical and Bioanalytical Chemistry, 389(1), 119.
Wittmann, R. (1991). Bestimmung von Dichlorpropanolen und Monochlorpropandiolen in Würzen und würzehaltigen Lebensmitteln. Zeitschrift Für Lebensmittel-Untersuchung Und Forschung, 193(3), 224–229.
Wolff, R. L. (1993). Heat-induced geometrical isomerization of α-linolenic acid: Effect of temperature and heating time on the appearance of individual isomers. Journal of the American Oil Chemists’ Society, 70(4), 425–430.
Wong, Y. H., Goh, K. M., Nyam, K. L., Nehdi, I. A., Sbihi, H. M., & Tan, C. P. (2019). Effects of natural and synthetic antioxidants on changes in 3-MCPD esters and glycidyl ester in palm olein during deep-fat frying. Food Control, 96, 488–493.
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(6), 759–765.
Yamazaki, K., Ogiso, M., Isagawa, S., Urushiyama, T., Ukena, T., & Kibune, N. (2013). A new, direct analytical method using LC-MS/MS for fatty acid esters of 3-chloro-1, 2-propanediol (3-MCPD esters) in edible oils. Food Additives & Contaminants: Part A, 30(1), 52–68.
Yan, J., Oey, S. B., van Leeuwen, S. P. J., & van Ruth, S. M. (2018). Discrimination of processing grades of olive oil and other vegetable oils by monochloropropanediol esters and glycidyl esters. Food Chemistry, 248, 93–100.
Zeiger, E., Anderson, B., Haworth, S., Lawlor, T., & Mortelmans, K. (1992). Salmonella mutagenicity tests: V. Results from the testing of 311 chemicals. Environmental and Molecular Mutagenesis, 19(S21), 2–141.
Zelinkova, Z., Novotny, O., Schurek, J., Velisek, J., Hajslova, J., & Dolezal, M. (2008). Occurrence of 3-MCPD fatty acid esters in human breast milk. Food Additives and Contaminants, 25(6), 669–676.
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.
Zelinková, Z., Doležal, M., & Velíšek, J. (2009). Occurrence of 3-chloropropane-1, 2-diol fatty acid esters in infant and baby foods. European Food Research and Technology, 228(4), 571–578.
Zelinkova, Z., Giri, A., & Wenzl, T. (2017). Assessment of critical steps of a GC/MS based indirect analytical method for the determination of fatty acid esters of monochloropropanediols (MCPDEs) and of glycidol (GEs). Food Control, 77, 65–75.
Zhang, Z., Gao, B., Zhang, X., Jiang, Y., Xu, X., & Yu, L. (2015). Formation of 3-monochloro-1, 2-propanediol (3-MCPD) di-and monoesters from tristearoylglycerol (TSG) and the potential catalytic effect of Fe2+ and Fe3+. Journal of Agricultural and Food Chemistry, 63(6), 1839–1848.
Zhao, Q., Lu, Q., Yu, Q.-W., & Feng, Y.-Q. (2013). Dispersive microextraction based on “magnetic water” coupled to gas chromatography/mass spectrometry for the fast determination of organophosphorus pesticides in cold-pressed vegetable oils. Journal of Agricultural and Food Chemistry, 61(22), 5397–5403.
)