Abstract
3-Monochloropropane-1,2-diol (3-MCPD) is one of the most common food contaminants in processed oils which forms mostly during the deodorization step of edible oil refining process. It has been detected in many types of food products such as infant formula, margarine, bread and soy sauce, which could result in kidney and testicular damage. The presence of 3-MCPD contaminant have been occurring for more a decade, which warrants a maximum permissible amount of 2 µg/kg body weight in food products in national and international levels. The purpose of this review is to provide an overview in the past 12 years on its physicochemical properties, occurrence, potential precursors and formation mechanism of 3-MCPD in foodstuffs. The toxicity, its quantification methods and mitigation strategy are also reviewed with an emphasis on the applicability, efficiency and issues encountered during the analysis. This review provides an elucidation regarding 3-MCPDEs and their food safety implications.
Similar content being viewed by others
References
JECFA, Evaluation of certain contaminants in food, in WHO Technical Report Series (Issue 1002) (2017). http://www.ncbi.nlm.nih.gov/pubmed/29144071
Y.H. Wong, K.M. Goh, K.L. Nyam, I.A. Nehdi, H.M. Sbihi, C.P. Tan, 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 (2018). https://doi.org/10.1016/j.foodcont.2018.10.006
EFSA, 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 J. (2016). https://doi.org/10.2903/j.efsa.2016.4426
S. MacMahon, J. Beekman, 3-Chloro-1,2-propanediol (3-MCPD), 2-chloro-1,3-propanediol (2-MCPD) and glycidyl esters in infant formula: a review. Curr. Opin. Food Sci. 30, 67–72 (2019). https://doi.org/10.1016/j.cofs.2019.05.005
M.E. Mossoba, M.S.T. Mapa, M. Araujo, Y. Zhao, B. Flannery, T. Flynn, J. Sprando, P. Wiesenfeld, R.L. Sprando, In vitro toxicological assessment of free 3-MCPD and select 3-MCPD esters on human proximal tubule HK-2 cells. Cell Biol. Toxicol. 36(3), 209–221 (2020). https://doi.org/10.1007/s10565-019-09498-0
F. Nazari, P. Naserzadeh, R. Dizaji, H.K. Manjili, H. Bahrami, M. Soleimani, A. Sharafi, Toxicological assessment of contaminant of foodstuff in three different in vitro models: involvement of oxidative stress and cell death signaling pathway. J. Food Sci. (2020). https://doi.org/10.1111/1750-3841.15471
EFSA, Update of the risk assessment on 3-monochloropropane diol and its fatty acid esters. EFSA J. 16(1), 1–48 (2018). https://doi.org/10.2903/j.efsa.2018.5083
K.M. Goh, Y.H. Wong, C.P. Tan, K.L. Nyam, A summary of 2-, 3-MCPD esters and glycidyl ester occurrence during frying and baking processes: baking and frying process contaminants. Curr. Res. Food Sci. 4, 460–469 (2021). https://doi.org/10.1016/j.crfs.2021.07.002
L. Girard, K. Herath, H. Escobar, R. Reimschuesse, O. Ceric, H. Jayasuriya, Development of UHPLC/Q-TOF analysis method to screen. Molecules 26, 2449 (2021)
V.G. Samaras, A. Giri, Z. Zelinkova, L. Karasek, G. Buttinger, T. Wenzl, Analytical method for the trace determination of esterified 3- and 2-monochloropropanediol and glycidyl fatty acid esters in various food matrices. J. Chromatogr. A 1466(September), 136–147 (2016). https://doi.org/10.1016/j.chroma.2016.08.071
P. Yang, J. Hu, J. Liu, Y. Zhang, B. Gao, T.T.Y. Wang, L. Jiang, M. Granvogl, L.L. Yu, Ninety-day nephrotoxicity evaluation of 3-MCPD 1-monooleate and 1-monostearate exposures in male Sprague Dawley rats using proteomic analysis. J. Agric. Food Chem. 68(9), 2765–2772 (2020). https://doi.org/10.1021/acs.jafc.0c00281
C.G. Hamlet, P.A. Sadd, C. Crews, J. Velíšek, D.E. Baxter, Occurrence of 3-chloro-propane-1,2-diol (3-MCPD) and related compounds in foods: a review. Food Addit. Contam. 19(7), 619–631 (2002). https://doi.org/10.1080/0265203021013239
B.Q. Lee, S.M. Khor, 3-Chloropropane-1,2-diol (3-MCPD) in soy sauce: a review on the formation, reduction, and detection of this potential carcinogen. Compr. Rev. Food Sci. Food Saf. 14(1), 48–66 (2015). https://doi.org/10.1111/1541-4337.12120
F.A. Arris, V.T.S. Thai, W.N. Manan, M.S. Sajab, A revisit to the formation and mitigation of 3-chloropropane-1,2-diol in palm oil production. Foods 9(12), 1–24 (2020). https://doi.org/10.3390/foods9121769
B. Gao, G. Huang, L.L. Yu, Fatty acid esters of 3-monochloropropanediol: a review fatty acid esters of. Annu. Rev. Food Sci. Technol. (2019). https://doi.org/10.1146/annurev-food-032818-121245
B. Gao, Y. Li, G. Huang, L. Yu, Fatty acid esters of 3-monochloropropanediol: a review. Annu. Rev. Food Sci. Technol. 10, 259–284 (2019). https://doi.org/10.1146/annurev-food-032818-121245
J.H. Spungen, S. MacMahon, J. Leigh, B. Flannery, G. Kim, S. Chirtel, D. Smegal, Estimated US infant exposures to 3-MCPD esters and glycidyl esters from consumption of infant formula. Food Addit. Contam. A 35(6), 1085–1092 (2018). https://doi.org/10.1080/19440049.2018.1459051
S.N. Sulin, M.N. Mokhtar, M.A.P. Mohammed, A.S. Baharuddin, Review on palm oil contaminants related to 3-monochloropropane-1, 2-diol (3-MCPD) and glycidyl esters (GE). Food Res. 4, 11–18 (2020). https://doi.org/10.26656/fr.2017.4(S6).051
B. Svejkovská, O. Novotný, V. Divinová, Z. Réblová, M. Doležal, J. Velíšek, Esters of 3-chloropropane-1,2-diol in foodstuffs. Czech J. Food Sci. 22(5), 190–196 (2004). https://doi.org/10.17221/3423-cjfs
S.F. Wong, B.Q. Lee, K.H. Low, H.S. Jenatabadi, C.W.J.B. Wan Mohamed Radzi, S.M. Khor, Estimation of the dietary intake and risk assessment of food carcinogens (3-MCPD and 1,3-DCP) in soy sauces by Monte Carlo simulation. Food Chem. 311(December 2019), 126033 (2020). https://doi.org/10.1016/j.foodchem.2019.126033
H. Xiang, D. Sun-Waterhouse, L. You, C. Cui, W. Wang, Insight into the formation of 3-monochloropropane-1,2-diol in soy sauce in the presence of pancreatin or other exogenous lipases. J. Food Process. Preserv. 43(11), 1–7 (2019). https://doi.org/10.1111/jfpp.14174
Q. Chai, E. Karangwa, E. Duhoranimana, X. Zhang, S. Xia, J. Yu, Tallow beef flavor: effect of processing conditions and ingredients on 3-chloropropane-1, 2-diol esters generation, and sensory characteristics. Eur. J. Lipid Sci. Technol. (2017). https://doi.org/10.1002/ejlt.201700337
K. Kamikata, E. Vicente, A.P. Arisseto-Bragotto, A.M.R. de Oliveira Miguel, R.F. Milani, S.A.V. Tfouni, 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(July 2018), 135–141 (2019). https://doi.org/10.1016/j.foodcont.2018.07.051
J. Kuhlmann, Analysis and occurrence of dichloropropanol fatty acid esters and related process-induced contaminants in edible oils and fats. Eur. J. Lipid Sci. Technol. 118(3), 382–395 (2016). https://doi.org/10.1002/ejlt.201400518
R. Jedrkiewicz, A. Głowacz, J. Gromadzka, J. Namieśnik, 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 (2016). https://doi.org/10.1016/j.foodcont.2015.05.039
A.P. Arisseto, W.C. Silva, G.R. Scaranelo, E. Vicente, 3-MCPD and glycidyl esters in infant formulas from the Brazilian market: occurrence and risk assessment. Food Control 77, 76–81 (2017). https://doi.org/10.1016/j.foodcont.2017.01.028
J. Leigh, S. MacMahon, Occurrence of 3-monochloropropanediol esters and glycidyl esters in commercial infant formulas in the United States. Food Addit. Contam. A 34(3), 356–370 (2017). https://doi.org/10.1080/19440049.2016.1276304
R. Jędrkiewicz, A. Głowacz-Różyńska, J. Gromadzka, A. Kloskowski, J. Namieśnik, Indirect determination of MCPD fatty acid esters in lipid fractions of commercially available infant formulas for the assessment of infants’ health risk. Food Anal. Methods 9(12), 3460–3469 (2016). https://doi.org/10.1007/s12161-016-0531-5
L. Wang, Y. Ying, Z. Hu, T. Wang, X. Shen, P. Wu, Simultaneous determination of 2- and 3-MCPD esters in infant formula milk powder by solid-phase extraction and GC–MS analysis. J. AOAC Int. 99(3), 786–791 (2016). https://doi.org/10.5740/jaoacint.15-0310
U. Ostermeyer, S. Merkle, H. Karl, J. Fritsche, Free and bound MCPD and glycidyl esters in smoked and thermally treated fishery products of the German market. Eur. Food Res. Technol. 247(7), 1757–1769 (2021). https://doi.org/10.1007/s00217-021-03746-6
H. Karl, S. Merkle, J. Kuhlmann, J. Fritsche, Development of analytical methods for the determination of free and ester bound 2-, 3-MCPD, and esterified glycidol in fishery products. Eur. J. Lipid Sci. Technol. 118(3), 406–417 (2016). https://doi.org/10.1002/ejlt.201400573
S. Merkle, H. Karl, J. Fritsche, Development of an analytical method for the determination of 2-and 3-MCPD fatty acid esters in fish and fish products, in 12th Euro Fed Lipid Congress “Oils, Fats and Lipids: From Lipodomics to Industrial Innovation”, vol 11, no 11 (2014), pp. 14–17
H.Y. Chung, S.W.C. Chung, B.T.P. Chan, Y.Y. Ho, Y. Xiao, Dietary exposure of Hong Kong adults to fatty acid esters of 3-monochloropropane-1,2-diol. Food Addit. Contam. A 30(9), 1508–1512 (2013). https://doi.org/10.1080/19440049.2013.809628
A.P. Arisseto, P.F.C. Marcolino, E. Vicente, 3-Monochloropropane-1,2-diol fatty acid esters in commercial deep-fat fried foods. Food Addit. Contam. A 32(9), 1431–1435 (2015). https://doi.org/10.1080/19440049.2015.1071498
P. Calta, J. Velíšek, M. Doležal, S. Hasnip, C. Crews, Z. Réblová, Formation of 3-chloropropane-1,2-diol in systems simulating processed foods. Eur. Food Res. Technol. 218(6), 501–506 (2004). https://doi.org/10.1007/s00217-003-0865-2
W.W. Cheng, G.Q. Liu, L.Q. Wang, Z.S. Liu, Glycidyl fatty acid esters in refined edible oils: a review on formation, occurrence, analysis, and elimination methods. Compr. Rev. Food Sci. Food Saf. 16(2), 263–281 (2017). https://doi.org/10.1111/1541-4337.12251
A.H. Ahmad Tarmizi, A. Kuntom, The occurrence of 3-monochloropropane-1,2-diol esters and glycidyl esters in vegetable oils during frying. Crit. Rev. Food Sci. Nutr. (2021). https://doi.org/10.1080/10408398.2020.1865264
Z. Huang, D. Xie, Z. Cao, Z. Guo, L. Chen, L. Jiang, X. Sui, Z. Wang, The effects of chloride and the antioxidant capacity of fried foods on 3-chloro-1,2-propanediol esters and glycidyl esters during long-term deep-frying. LWT 145(October 2020), 111511 (2021). https://doi.org/10.1016/j.lwt.2021.111511
Y.H. Wong, H. Muhamad, F. Abas, O.M. Lai, K.L. Nyam, C.P. Tan, Effects of temperature and NaCl on the formation of 3-MCPD esters and glycidyl esters in refined, bleached and deodorized palm olein during deep-fat frying of potato chips. Food Chem. 219, 126–130 (2017). https://doi.org/10.1016/j.foodchem.2016.09.130
Y.H. Wong, O.M. Lai, F. Abas, K.L. Nyam, I.A. Nehdi, H. Muhamad, C.P. Tan, Factors impacting the formation of 3-MCPD esters and glycidyl esters during deep fat frying of chicken breast meat. J. Am. Oil Chem. Soc. 94(6), 759–765 (2017). https://doi.org/10.1007/s11746-017-2991-1
A. Stauff, E. Schneider, F. Heckel, 2-MCPD, 3-MCPD and fatty acid esters of 2-MCPD, 3-MCPD and glycidol in fine bakery wares. Eur. Food Res. Technol. 246(10), 1945–1953 (2020). https://doi.org/10.1007/s00217-020-03546-4
A.A. Martin, E.K. Fodjo, G.B.I. Marc, T. Albert, C. Kong, Simple and rapid detection of free 3-monochloropropane-1,2-diol based on cysteine modified silver nanoparticles. Food Chem. 338(August 2020), 127787 (2021). https://doi.org/10.1016/j.foodchem.2020.127787
O. Kalkan, M. Topkafa, H. Kara, Determination of effect of some parameters on formation of 2-monochloropropanediol, 3-monochloropropanediol and glycidyl esters in the frying process with sunflower oil, by using central composite design. J. Food Compos. Anal. (2020). https://doi.org/10.1016/j.jfca.2020.103681
P.D. Collier, D.D.O. Cromie, A.P. Davies, Mechanism of formation of chloropropanols present in protein hydrolysates. J. Am. Oil Chem. Soc. 68(10), 785–790 (1991). https://doi.org/10.1007/BF02662173
B. Svejkovská, M. Doležal, J. Velíšek, Formation and decomposition of 3-chloropropane-1,2-diol esters in models simulating processed foods. Czech J. Food Sci. 24(4), 172–179 (2006). https://doi.org/10.17221/3314-cjfs
Z. Zhang, B. Gao, X. Zhang, Y. Jiang, X. Xu, L. Yu, Formation of 3-monochloro-1,2-propanediol (3-MCPD) di- and monoesters from tristearoylglycerol (TSG) and the potential catalytic effect of Fe2+ and Fe3+. J. Agric. Food Chem. 63(6), 1839–1848 (2015). https://doi.org/10.1021/jf5061216
Y. Zhao, Y. Zhang, Z. Zhang, J. Liu, Y.L. Wang, B. Gao, Y. Niu, X. Sun, L. Yu, Formation of 3-MCPD fatty acid esters from monostearoyl glycerol and the thermal stability of 3-MCPD monoesters. J. Agric. Food Chem. 64(46), 8918–8926 (2016). https://doi.org/10.1021/acs.jafc.6b04048
J. Šmidrkal, M. Tesařová, I. Hrádková, M. Berčíková, A. Adamčíková, V. Filip, Mechanism of formation of 3-chloropropan-1,2-diol (3-MCPD) esters under conditions of the vegetable oil refining. Food Chem. 211, 124–129 (2016). https://doi.org/10.1016/j.foodchem.2016.05.039
P. Vispute, S. Dabhade, Refining of palm oil: a review on palm oil refining process, 3-MCPD esters in refined palm oil, and possible reduction tactics for 3-MCPD esters. Int. J. Agric. Eng. 11(Special), 81–85 (2018). https://doi.org/10.15740/has/ijae/11.sp.issue/81-85
A.Y.K. Chung, Crude palm oil de-chlorination. Palm Oil Eng. Bull. 128(1), 51–57 (2016)
S.H. Tiong, N. Saparin, H.F. Teh, T.L.M. Ng, M.Z. Bin Md Zain, B.K. Neoh, A. Md Noor, C.P. Tan, O.M. Lai, D.R. Appleton, Natural organochlorines as precursors of 3-monochloropropanediol esters in vegetable oils. J. Agric. Food Chem. 66(4), 999–1007 (2018). https://doi.org/10.1021/acs.jafc.7b04995
R.G. Tivanello, M.F. Capristo, F.M. Leme, R.A. Ferrari, K.A. Sampaio, A.P. Arisseto, E. Vicente, Mitigation studies based on the contribution of chlorides and acids to the formation of 3-MCPD, 2-MCPD, and glycidyl esters in palm oil. ACS Food Sci. Technol. 1(7), 1190–1197 (2021). https://doi.org/10.1021/acsfoodscitech.1c00084
S.C. Chew, C.P. Tan, O.M. Lai, K.L. Nyam, Changes in 3-MCPD esters, glycidyl esters, bioactive compounds and oxidation indexes during kenaf seed oil refining. Food Sci. Biotechnol. 27(3), 905–914 (2018). https://doi.org/10.1007/s10068-017-0295-8
Y. Yao, R. Cao, W. Liu, H. Zhou, C. Li, S. Wang, Molecular reaction mechanism for the formation of 3-chloropropanediol esters in oils and fats [research-article]. J. Agric. Food Chem. 67(9), 2700–2708 (2019). https://doi.org/10.1021/acs.jafc.8b06632
S. Wang, G. Liu, W. Cheng, Chloride-mediated co-formation of 3-monochloropropanediol esters and glycidyl esters in both model vegetable oils and chemical model systems. Food Res. Int. 140, 109879 (2020). https://doi.org/10.1016/j.foodres.2020.109879
M.R. Blumhorst, M.W. Collison, Direct determination of glycidyl esters of fatty acids in vegetable oils by LC–MS. J. Am. Oil Chem. Soc. (2011). https://doi.org/10.1007/s11746-011-1873-1
R.I.M. Almoselhy, A review of emerging health risks with 3-MCPD processing contaminant in refined edible oils. J. Microbiol. Biotechnol. (2021). https://doi.org/10.20935/al1360
R.I.M. Almoselhy, M.M. Eid, W.S. Abd El-Baset, A.E.F.A. Aboelhassan, Determination of 3-MCPD in some edible oils using GC-MS/MS. Egypt. J. Chem. 64(3), 1639–1652 (2021). https://doi.org/10.21608/EJCHEM.2021.64084.3373
C. Li, H. Jia, Y. Wang, M. Shen, S. Nie, M. Xie, Determination of 3-monochloropropane-1,2-diol esters in edible oil—method validation and estimation of measurement uncertainty. Food Anal. Methods 9(4), 845–855 (2015). https://doi.org/10.1007/s12161-015-0256-x
World Health Organization, IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, vol. 77 (World Health Organization, Geneva, 2000)
K. Schultrich, F. Frenzel, A. Oberemm, T. Buhrke, A. Braeuning, A. Lampen, Comparative proteomic analysis of 2-MCPD- and 3-MCPD-induced heart toxicity in the rat. Arch. Toxicol. 91(9), 3145–3155 (2017). https://doi.org/10.1007/s00204-016-1927-0
C.L. Chew, N. Saparin, Principal formation and mitigation strategies for 3-MCPDE in palm oil processing. J. Oil Palm Environ. Health 12, 86–95 (2021). https://doi.org/10.5366/jope.2021.06
S. Genualdi, P. Nyman, L. DeJager, Simultaneous analysis of 3-MCPD and 1,3-DCP in Asian style sauces using QuEChERS extraction and gas chromatography-triple quadrupole mass spectrometry. J. Agric. Food Chem. 65(4), 981–985 (2017). https://doi.org/10.1021/acs.jafc.6b05051
N. Bergau, Z. Zhao, K. Abraham, B.H. Monien, Metabolites of 2- and 3-monochloropropanediol (2- and 3-MCPD) in humans: urinary excretion of 2-chlorohydracrylic acid and 3-chlorolactic acid after controlled exposure to a single high dose of fatty acid esters of 2- and 3-MCPD. Mol. Nutr. Food Res. 65(4), 1–27 (2020). https://doi.org/10.1002/mnfr.202000736
German Federal Institute for Risk Assessment, Possible health risks due to high concentrations of 3-MCPD and glycidyl fatty acid esters in certain foods (2020). https://doi.org/10.17590/20200420-134029
K. Schultrich, F. Oez, N. Bergau, T. Buhrke, A. Braeuning, Absorption and metabolism of 3-MCPD in hepatic and renal cell lines. Toxicol. In Vitro 70(October 2020), 105042 (2021). https://doi.org/10.1016/j.tiv.2020.105042
M.E. Mossoba, M.S.T. Mapa, M. Araujo, Y. Zhao, B. Flannery, T. Flynn, J. Sprando, P. Wiesenfeld, R.L. Sprando, Long-term in vitro effects of exposing the human HK-2 proximal tubule cell line to 3-monochloropropane-1,2-diol. J. Toxicol. Sci. 45(1), 45–56 (2020). https://doi.org/10.2131/jts.45.45
J. Lee, H. Lee, S. Lee, H. Seo, K. Lee, Y. Park, 3-MCPD (3-monochloro-1,2-propanediol) inhibit myogenic differentiation in murine skeletal myoblasts. Chem. Biol. Interact. (2020). https://doi.org/10.1016/j.cbi.2020.109311
Ç. Sevim, M. Özkaraca, M. Kara, N. Ulaş, A.S. Mendil, D. Margina, A. Tsatsakis, Apoptosis is induced by sub-acute exposure to 3-MCPD and glycidol on Wistar Albino rat brain cells. Environ. Toxicol. Pharmacol. (2021). https://doi.org/10.1016/j.etap.2021.103735
G. Huang, Y. Wu, M. Liu, X. Sun, W. Lu, B. Gao, T.T.Y. Wang, L. Yu, Potential biomarkers for early detection of 3-MCPD dipalmitate exposure in Sprague-Dawley rats. J. Agric. Food Chem. 68(35), 9594–9602 (2020). https://doi.org/10.1021/acs.jafc.0c03474
Y.I. Mahmoud, F.S. Abo-Zied, S.T. Salem, Effects of subacute 3-monochloropropane-1,2-diol treatment on the kidney of male albino rats. Biotech. Histochem. 94(3), 199–203 (2018). https://doi.org/10.1080/10520295.2018.1543894
G. Huang, J. Xue, X. Sun, J. Wang, L. Yu, Necroptosis in 3-chloro-1, 2-propanediol (3-MCPD)-dipalmitate-induced acute kidney injury in vivo and its repression by miR-223-3p. Toxicology 406–407(May), 33–43 (2018). https://doi.org/10.1016/j.tox.2018.05.015
Y. Zhong, C. Jin, X. Wang, X. Li, J. Han, W. Xue, P. Wu, X. Peng, X. Xia, Protective effects of apigenin against 3-MCPD-induced renal injury in rat. Chem. Biol. Interact. 296, 9–17 (2018). https://doi.org/10.1016/j.cbi.2018.08.005
H. Xing, B. Fang, G. Pang, F. Ren, 3-Monochloropropane-1, 2-diol causes irreversible damage to reproductive ability independent of hormone changes in adult male rats. Food Chem. Toxicol. (2018). https://doi.org/10.1016/j.fct.2018.11.023
M. Liu, J. Liu, Y. Wu, B. Gao, P. Wu, H. Shi, X. Sun, H. Huang, T.T.Y. Wang, L.L. Yu, Preparation of five 3-MCPD fatty acid esters, and the effects of their chemical structures on acute oral toxicity in Swiss mice. J. Sci. Food Agric. 97(3), 841–848 (2016). https://doi.org/10.1002/jsfa.7805
W. Jia, P. Zhuang, Q. Wang, X. Wan, L. Mao, X. Chen, H. Miao, D. Chen, Y. Ren, Y. Zhang, Urinary non-targeted toxicokinetics and metabolic fingerprinting of exposure to 3-monochloropropane-1,2-diol and glycidol from refined edible oils. Food Res. Int. 152(December 2021), 110898 (2022). https://doi.org/10.1016/j.foodres.2021.110898
H. Xing, S. Chen, X. Wang, J. Li, F. Ren, 3-Monochloropropane-1,2-diol causes spermatogenesis failure in male rats via Sertoli cell dysfunction but not testosterone reduction. Toxicol. Lett. 360(January), 1–10 (2022). https://doi.org/10.1016/j.toxlet.2022.01.006
Y. Zhong, D. Sun, Y. Yao, Q. Liu, T. Guo, X. Wang, X. Peng, Autophagy and mitochondrial dynamics contribute to the protective effect of diosgenin against 3-MCPD induced kidney injury. Chem. Biol. Interact. 355(January), 109850 (2022). https://doi.org/10.1016/j.cbi.2022.109850
E. Fröhlich, S. Salar-Behzadi, Toxicological assessment of inhaled nanoparticles: role of in vivo, ex vivo, in vitro, and in silico studies. Int. J. Mol. Sci. 15(3), 4795–4822 (2014). https://doi.org/10.3390/ijms15034795
J.L. Hidalgo-Ruiz, R. Romero-González, J.L. Martínez Vidal, A. Garrido Frenich, Determination of 3-monochloropropanediol esters and glycidyl esters in fatty matrices by ultra-high performance liquid chromatography-tandem mass spectrometry. J. Chromatogr. A (2021). https://doi.org/10.1016/j.chroma.2021.461940
R.A.A. Razak, A. Kuntom, Analytical methods for the determination of 3-MCPD esters in oils/fats. Palm Oil Dev. 57(12), 11–20 (2021)
M. Xu, Z. Jin, Z. Yang, J. Rao, B. Chen, Optimization and validation of in-situ derivatization and headspace solid-phase microextraction for gas chromatography–mass spectrometry analysis of 3-MCPD esters, 2-MCPD esters and glycidyl esters in edible oils via central composite design. Food Chem. 307(May 2019), 125542 (2019). https://doi.org/10.1016/j.foodchem.2019.125542
Z. Zelinkova, A. Giri, T. Wenzl, 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 (2017). https://doi.org/10.1016/j.foodcont.2017.01.024
S. Macmahon, E. Mazzola, T.H. Begley, G.W. Diachenko, Analysis of processing contaminants in edible oils. Part 1. Liquid chromatography-tandem mass spectrometry method for the direct detection of 3-monochloropropanediol monoesters and glycidyl esters. J. Agric. Food Chem. 61(20), 4737–4747 (2013). https://doi.org/10.1021/jf4005803
H. Tsai, J. Hsu, C. Fang, N. Su, Determination of glycidyl esters and 3-MCPD esters in edible oils by sample pretreatment with the combination of lipase hydrolysis and modified QuEChERS for GC–MS analysis determination of glycidyl esters and 3-MCPD esters in edible oils by sample. J. Food Drug Anal. 29(1), 153–167 (2021)
R. Jędrkiewicz, A. Głowacz-Różyńska, J. Gromadzka, P. Konieczka, J. Namieśnik, Novel fast analytical method for indirect determination of MCPD fatty acid esters in edible oils and fats based on simultaneous extraction and derivatization. Anal. Bioanal. Chem. 409(17), 4267–4278 (2017). https://doi.org/10.1007/s00216-017-0381-z
Y. Zhang, X. Yang, S. Wang, Determination of 2-MCPD and 3-MCPD Fatty Acid Esters in Infant Formula Using an Agilent 8890 GC System with an Agilent 5977B GC/MSD (2021). https://www.agilent.com/cs/library/applications/an-mcpd-infant-formula-8890-gc-5994-3233en-agilent.pdf
B.I. Sim, Y.P. Khor, O.M. Lai, C.B. Yeoh, Y. Wang, Y. Liu, I.A. Nehdi, C.P. Tan, Mitigation of 3-MCPD esters and glycidyl esters during the physical refining process of palm oil by micro and macro laboratory scale refining. Food Chem. 328(March), 127147 (2020). https://doi.org/10.1016/j.foodchem.2020.127147
W.C. Hung, G.J. Peng, W.J. Tsai, M.H. Chang, C.D. Liao, S.H. Tseng, Y.M. Kao, D.Y. Wang, H.F. Cheng, Identification of 3-MCPD esters to verify the adulteration of extra virgin olive oil. Food Addit. Contam. B 10(3), 233–239 (2017). https://doi.org/10.1080/19393210.2017.1330292
K. Miyazaki, K. Koyama, An improved enzymatic indirect method for simultaneous determinations of 3-MCPD esters and glycidyl esters in fish oils. J. Oleo Sci. 66(10), 1085–1093 (2017). https://doi.org/10.5650/jos.ess17082
K. Miyazaki, K. Koyama, An improved enzymatic indirect method for simultaneous determinations of 3-MCPD esters and glycidyl esters in fish oils. J. Oleo Sci. 1093(10), 1085–1093 (2017)
Y.T. Yaman, G. Bolat, T.B. Saygin, S. Abaci, Molecularly imprinted label-free sensor platform for impedimetric detection of 3-monochloropropane-1,2˗diol. Sens. Actuators B 328(June 20), 128986 (2021). https://doi.org/10.1016/j.snb.2020.128986
J.A. Custodio-Mendoza, A.M. Carro, M.A. Lage-Yusty, A. Herrero, I.M. Valente, J.A. Rodrigues, R.A. Lorenzo, Occurrence and exposure of 3-monochloropropanediol diesters in edible oils and oil-based foodstuffs from the Spanish market. Food Chem. 270(July 2018), 214–222 (2019). https://doi.org/10.1016/j.foodchem.2018.07.100
J.A. Custodio-Mendoza, R.A. Lorenzo, I.M. Valente, P.J. Almeida, M.A. Lage, J.A. Rodrigues, A.M. Carro, Development of a partitioned liquid–liquid extraction- dispersive solid phase extraction procedure followed by liquid chromatography-tandem mass spectrometry for analysis of 3-monochloropropane-1,2-diol diesters in edible oils. J. Chromatogr. A 1548, 19–26 (2018). https://doi.org/10.1016/j.chroma.2018.03.017
G. Graziani, A. Gaspari, D. Chianese, L. Conte, Direct determination of 3-chloropropanol esters in edible vegetable oils using high resolution mass spectrometry (HRMS-Orbitrap). Food Addit. Contam. A (2017). https://doi.org/10.1080/19440049.2017.1368721
F. Jumaah, R.G. Discovery, R. Jedrkiewicz, J. Gromadzka, Rapid and green separation of mono- and diesters of monochloropropanediols by ultra-high performance supercritical fluid chromatography-mass spectrometry using neat carbon dioxide. J. Agric. Food Chem. (2017). https://doi.org/10.1021/acs.jafc.7b02857
R.D. O’Brien, Fats and Oils Processing: Formulating and Processing for Applications, 3rd edn. (CRC Press, 2009)
A. Ermacora, K. Hrncirik, A novel method for simultaneous monitoring of 2-MCPD, 3-MCPD and glycidyl esters in oils and fats. J. Am. Oil Chem. Soc. 90(1), 1–8 (2013). https://doi.org/10.1007/s11746-012-2132-9
K.S. Hew, Y.P. Khor, T.B. Tan, M.M. Yusoff, O.M. Lai, A.J. Asis, F.A. Alharthi, I.A. Nehdi, C.P. Tan, Mitigation of 3-monochloropropane-1,2-diol esters and glycidyl esters in refined palm oil: a new and optimized approach. LWT 139(November 2020), 110612 (2021). https://doi.org/10.1016/j.lwt.2020.110612
A.P. Arisseto, W.C. Silva, P.F.C. Marcolino, G.R. Scaranelo, S.A.G. Berbari, A.M.R. de Oliveira Miguel, E. Vicente, Influence of potato cultivar, frying oil and sample pre-treatments on the contamination of French fries by 3-monochloropropane-1,2-diol fatty acid esters. Food Res. Int. 124(April), 43–48 (2019). https://doi.org/10.1016/j.foodres.2018.10.070
R. Tivanello, M. Capristo, E. Vicente, R. Ferrari, K. Sampaio, A. Arisseto, Effects of deodorization temperature and time on the formation of 3-MCPD, 2-MCPD, and glycidyl esters and physicochemical changes of palm oil. J. Food Sci. 85(7), 2255–2260 (2020). https://doi.org/10.1111/1750-3841.15304
Y. Yuan, C. Cui, H. Liu, X. Li, Y. Cao, Y. Zhang, H. Yan, Effects of oxidation and hydrolysis of frying oil on MCPD esters formation in Chinese fried dough sticks. LWT 154, 112576 (2022). https://doi.org/10.1016/j.lwt.2021.112576
S. Turan, R. Solak, S. Keskin, Investigation of the formation of free and bound 2- and 3-monochloropropane-1,2-diols during deep frying of leavened dough using response surface methodology. Eur. J. Lipid Sci. Technol. 121(7), 1–11 (2019). https://doi.org/10.1002/ejlt.201800019
M.R. Ramli, A.H.A. Tarmizi, A.N.A. Hammid, R.A.A. Razak, A. Kuntom, S.W. Lin, R. Radzian, Preliminary large scale mitigation of 3-monochloropropane-1, 2-diol (3-MCPD) esters and glycidyl esters in palm oil. J. Oleo Sci. 69(8), 815–824 (2020). https://doi.org/10.5650/jos.ess20021
U. Strijowski, V. Heinz, K. Franke, Removal of 3-MCPD esters and related substances after refining by adsorbent material. Eur. J. Lipid Sci. Technol. 113(3), 387–392 (2011). https://doi.org/10.1002/ejlt.201000323
E. Restiawaty, A. Maulana, N.T. Umi Culsum, C. Aslan, V. Suendo, N. Nishiyama, Y.W. Budhi, The removal of 3-monochloropropane-1,2-diol ester and glycidyl ester from refined-bleached and deodorized palm oil using activated carbon. RSC Adv. 11(27), 16500–16509 (2021). https://doi.org/10.1039/d1ra00704a
T. Şahin, S. Ok, E. Yılmaz, Application of MOFs and natural clays for removal of MCPD and GEs from edible oils. Grasas Aceites (2022). https://doi.org/10.3989/gya.0556211
M. Zulkurnain, O.M. Lai, R.A. Latip, I.A. Nehdi, T.C. Ling, C.P. Tan, The effects of physical refining on the formation of 3-monochloropropane-1, 2-diol esters in relation to palm oil minor components. Food Chem. 135(2), 799–805 (2012). https://doi.org/10.1016/j.foodchem.2012.04.144
C. Bertoli, F. Cauville, A.J.H. Schoonman, A deodorized edible oil or fat with low levels of bound MCPD and process of making by carboxymethyl cellulose and/or resin purification (Patent No. WO/2011/009843) (2011). http://patent/WO2011009843A1/id
S.B. Oey, V. Fogliano, Mitigation strategies for the reduction of 2- and 3-MCPD esters and glycidyl esters in the vegetable oil processing industry. Compr. Rev. Food Sci. Food Saf. (2019). https://doi.org/10.1111/1541-4337.12415
U.T. Bornscheuer, M. Hesseler, Enzymatic removal of 3-monochloro-1,2-propanediol (3-MCPD) and its esters from oils. Eur. J. Lipid Sci. Technol. 112(5), 552–556 (2010). https://doi.org/10.1002/ejlt.200900245
R. Bel-Rhlid, J.P. Talmon, L.B. Fay, M.A. Juillerat, Biodegradation of 3-Chloro-1,2-propanediol with Saccharomyces cerevisiae. J. Agric. Food Chem. 52, 6165–6169 (2004). https://doi.org/10.7868/s0869803118010010
Q. Chai, K. Hayat, E. Karangwa, E. Duhoranimana, X. Zhang, S. Xia, J. Yu, Investigating the optimum conditions for minimized 3-chloropropane-1,2-diol esters content and improved sensory attributes during savory beef flavor preparation. Food Chem. 243(May 2017), 96–102 (2018). https://doi.org/10.1016/j.foodchem.2017.09.113
Acknowledgements
This review was supported by University Malaya (UM) Impact Oriented Interdisciplinary Research Grant [No. IIRG010B-2019].
Funding
This review was supported by Universiti Malaya, RU Geran-Fakulti Program-GPF015a-2023.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Syed Putra, S.S., Basirun, W.J., Elgharbawy, A.A.M. et al. 3-Monochloropropane-1,2-diol (3-MCPD): a review on properties, occurrence, mechanism of formation, toxicity, analytical approach and mitigation strategy. Food Measure 17, 3592–3615 (2023). https://doi.org/10.1007/s11694-023-01883-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11694-023-01883-y