Research Status of 3-Chloropropanol Esters in Food

SUN Jingwen; HU Benlun; QIN Ruike; JIA Caihua; RONG Jianhua; LIU Ru

doi:10.13386/j.issn1002-0306.2020100231

Volume 42 Issue 23

Nov. 2021

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2021 > 42(23): 400-407. > DOI: 10.13386/j.issn1002-0306.2020100231

SUN Jingwen, HU Benlun, QIN Ruike, et al. Research Status of 3-Chloropropanol Esters in Food[J]. Science and Technology of Food Industry, 2021, 42(23): 400−407. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2020100231.

Citation:

PDF (2440 KB)

Research Status of 3-Chloropropanol Esters in Food

SUN Jingwen^1,,
HU Benlun¹,
QIN Ruike¹,
JIA Caihua^{1, 2},
RONG Jianhua^{1, 2},
LIU Ru^{1, 2, ,}

1.
College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, China
2.
National R&D Branch Center for Conventional Freshwater Fish Processing (Wuhan), Wuhan 430070, China)

More Information

Received Date: October 28, 2020
Available Online: September 23, 2021

Graphical Abstract

Abstract

Abstract

The 3-chloropropanol ester in food could be hydrolyzed into free 3-chloropropanol in human bodies and affect human health, which has become one of the food safety issues of general concern in the world. This article mainly summarizes several generation pathways of 3-chloropropanol ester, including chloride ion direct nucleophilic attack pathway, cyclic oxonium ion intermediate pathway and glycidyl ester intermediate pathway, epoxide ring free radical pathway. 3-chloropropanol ester is mainly affected by heating temperature and time, pH value, water content, sodium chloride content and metal ions. Finally, it is proposed that the content of 3-chloropropanol ester in food could be controlled by the two processes of refining vegetable oil and food processing. On the basis of this, the future research direction is prospected on 3-chloropropanol esters in food.
- 3-chloropropanol ester,
- generation pathway,
- influencing factors,
- control measures,
- food

FullText(HTML)

References (64)

References

[1]	GAO B Y, LI Y F, HUANG G R, et al. Fatty acid esters of 3-monochloropropanediol: A review[J]. Annual Review of Food Science and Technology,2019,10:259−284. doi: 10.1146/annurev-food-032818-121245
[2]	DAVIDEK J, VELISEK J, KUBELKA V, et al. Glycerol chlorohydrins and their esters as products of the hydrolysis of tripalmitin, tristearin and triolein with hydrochloric acid[J]. Zeitschrift Für Lebensmitteluntersuchung Und-Forschung,1980,171(1):14−17.
[3]	CERBULIS J, PARKS O W, LIU R H, et al. Occurrence of diesters of 3-chloro-1, 2-propanediol in the neutral lipid fraction of goats’ milk[J]. Journal of Agricultural and Food Chemistry,1984,32(3):474−476. doi: 10.1021/jf00123a013
[4]	ZELINKOVÁ Z, SVEJKOVSKÁ B, VELÍSEK J, et al. Fatty acid esters of 3-chloropropane-1, 2-diol in edible oils[J]. Food Additives and Contaminants,2006,23(12):1290−1298. doi: 10.1080/02652030600887628
[5]	ZWAGERMAN R, OVERMAN P. A novel method for the automatic sample preparation and analysis of 3-MCPD-, 2-MCPD-, and glycidylesters in edible oils and fats[J]. European Journal of Lipid Science and Technology,2016,118:997−1006. doi: 10.1002/ejlt.201500358
[6]	SVEJKOVSKÁ B, NOVOTNY O, DIBINOVA V, et al. Esters of 3-chloropropane-1, 2-diol in food stuffs[J]. Czech Journal of Food Sciences,2004,22(5):190−196.
[7]	JDRKIEWICZ R, GOWACZ A, GROMADZKA J, et al. Determination of 3-MCPD and 2-MCPD esters in edible oils, fish oils and lipid fractions of margarines available on polish market[J]. Food Control,2016,59:487−492. doi: 10.1016/j.foodcont.2015.05.039
[8]	BECALSKI A, FENG S, LAU P Y, et al. A pilot survey of 2- and 3-monochloropropanediol and glycidol fatty acid esters in foods on the Canadian market 2011-2013[J]. Journal of Food Composition and Analysis,2015,44(6):111−114.
[9]	LEIGH J, MACMAHON S. Occurrence of 3-monochloropropanediol esters and glycidyl esters in commercial infant formulas in the United States[J]. Food Additives and Contaminants,2017,34(3):356−370. doi: 10.1080/19440049.2016.1276304
[10]	DOLEŽAL M, CHALOUPSKÁ M, DIVINOVÁ V, et al. Occurrence of 3-chloropropane-1, 2-diol and its esters in coffee[J]. European Food Research and Technology,2005,221(3-4):221−225. doi: 10.1007/s00217-004-1118-8
[11]	SPUNGEN J H, MACACMAHON S, LEIGH J, et al. Estimated US infant exposures to 3-MCPD esters and glycidyl esters from consumption of infant formula[J]. Food Additives and Contaminants,2018,35(6):1085−1092. doi: 10.1080/19440049.2018.1459051
[12]	HAMLET C G, SADD P A, CREWS C, et al. Occurrence of 3-chloro-propane-1, 2-diol(3-MCPD) and related compounds in foods: A review[J]. Food Additives and Contaminants,2002,19(7):619−631. doi: 10.1080/02652030210132391
[13]	张璟琳, 张璐, 贾雪颖. 油炸食品中氯丙醇酯含量分析[J]. 食品与发酵工业,2019,45(14):209−214. [ZHANG J L, ZHANG L, JIA X Y. Determination of boundmono chloropropanediol (MCPDE) in fried foods[J]. Food and Fermentation Industries,2019,45(14):209−214.
[14]	SEEFELDER W, VARGA N, STUDER A, et al. Esters of 3-chloro-1, 2-propanediol (3-MCPD) in vegetable oils: Significance in the formation of 3-MCPD[J]. Food Additives and Contaminants,2008,25(4):391−400. doi: 10.1080/02652030701385241
[15]	ABRAHAM K, APPE K E, BERGER-PREISS E, et al. Relative oral bioavailability of 3-MCPD from 3-MCPD fatty acid esters in rats[J]. Archives of Technology,2013,87(4):649−659.
[16]	黄剑锋, 傅武胜. 氯丙醇的安全毒理学评价概况[J]. 实用预防医学,2002,9(4):427−430. [HUANG J F, FU W S. General situation of safety toxicological evaluation of chloropropanol[J]. Practical Preventive Medicine,2002,9(4):427−430. doi: 10.3969/j.issn.1006-3110.2002.04.091
[17]	IARC. Some chemicals present in industrial and consumer products, food and drinking-water(Vol. 101)[M]. Lyon France: IARC Monographs, 2012: 349–374.
[18]	FAO/WHO. Evaluation of certain contaminants in foods[R]. World Health Organization Food Additive, 2017, 1002: 90–103.
[19]	EFSA PANEL ON CONTAMINANTS IN THE FOOD CHAIN (CONTAM). Update of the risk assessment on 3-monochloropropane diol and its fatty acid esters[R]. EFSA Journal, 2018, 16(1): 5083.
[20]	金青哲, 王兴国. 氯丙醇酯-油脂食品中新的潜在危害因子[J]. 中国粮油学报,2012,26(11):119−123. [JIN Q Z, WANG X G. Chloropropanol esters in edible fats and oils-new potential risk factors[J]. Journal of The Chinese Cereals and Oils Association,2012,26(11):119−123.
[21]	郭娇娇, 宫智勇. 动植物油脂中3-氯-1, 2-丙二醇酯的研究进展[J]. 食品科学,2011,32(23):339−341. [GUO J J, GONG Z Y. Research progress on 3-chloro-1, 2-propanediol in fats and oils[J]. Food Science,2011,32(23):339−341.
[22]	YAYLAYAN V A. Molecular mechanism of 3-MCPD ester formation: Facts and hypothesis[R]. Belgium: ILSI Workshop on 3-MCPD Esters, 2009.
[23]	杨娇, 金青哲. 食用植物油中3-氯丙醇酯的研究进展[J]. 中国油脂,2011,36(9):1−4. [YANG J, JIN Q Z. Research progress on 3-monochloropropane-1, 2-diol esters in edible oils[J]. China Oils and Fats,2011,36(9):1−4.
[24]	RAHN A K K, YAYLAYAN V A. What do we know about the molecular mechanism of 3-MCPD ester formation?[J]. European Journal of Lipid Science and Technology,2011,113(3):323−329. doi: 10.1002/ejlt.201000310
[25]	李利君, 李加辛, 马传国. 食用油中 3-氯丙醇酯的形成机理与消减方法的研究进展[J]. 河南工业大学学报,2019,40(4):123−132. [LI L J, LI J X, MA C G. Research progress on formation mechanism and subtraction methods of 3-chloropropanol esters in edible oils[J]. Journal of Henan University of Technology,2019,40(4):123−132.
[26]	ZHAO Y, ZHANG Y, ZHANG Z, et al. Formation of 3-MCPD fatty acid esters from monostearoyl glycerol and the thermal stability of 3-MCPD[J]. Journal of Agricultural and Food Chemistry,2016,64:8918−8926. doi: 10.1021/acs.jafc.6b04048
[27]	向晓玲, 赵波, 李春松, 等. 食用油中3-氯丙醇酯的研究进展[J]. 中国油脂,2017,42(7):59−64. [XIANG X L, ZHAO B, LI C S, et al. Progress in 3-MCPD esters in edible oils[J]. China Oils and Fats,2017,42(7):59−64. doi: 10.3969/j.issn.1003-7969.2017.07.013
[28]	HAMLET C G, SADD P A, GRAY D A. Generation of monochloropropanediols (MCPDs) in model dough systems 2 unleavened doughs[J]. Journal of Agricultural and Food Chemistry,2004,52(7):2067−2072. doi: 10.1021/jf035078o
[29]	ZHANG X W, GAO B, QIN F, et al. Free radical mediated formation of 3-monochloropropanediol (3-MCPD) fatty acid diesters[J]. Journal of Agricultural and Food Chemistry,2013,61(10):2548−2555. doi: 10.1021/jf305252q
[30]	ZHANG Z F, GAO B Y, ZHANG X W, et al. 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]. Journal of Agricultural and Food Chemistry,2015,63:1839−1848. doi: 10.1021/jf5061216
[31]	SVEJKOVAKÁ B, DOLEŽAL M, VELÍŠEK J. Formation and decomposition of 3-chloropropane-1, 2-diol esters in models simulating processed foods[J]. Czech Journal of Food Sciences,2006,24:172−179.
[32]	ERMACORA A, HRNCIRIK K. Study on the thermal degradation of 3-MCPD esters in model systems simulating deodorization of vegetable oils[J]. Food Chemistry,2014,150:158−163. doi: 10.1016/j.foodchem.2013.10.063
[33]	BAKHIYA N, ABRAHAM K, GŰRTLER R, et al. Toxicological assessment of 3-chloropropane-1, 2-diol and glycidol fatty acid esters in food[J]. Molecular Nutrition and Food Research,2011,55:509−521. doi: 10.1002/mnfr.201000550
[34]	CUSTODIO-MENDOZA J A, CARRO A M, LAGE-YUSTY M A, et al. Occurrence and exposure of 3-monochloropropanediol diesters in edible oils and oil-based foodstuffs from the Spanish market[J]. Food Chemistry,2019,270:214−222. doi: 10.1016/j.foodchem.2018.07.100
[35]	ALBUQUERQUE T G, COSTA H S, SILVA M A, et al. Are chloropropanols and glycidyl fatty acid esters a matter of concern in palm oil?[J]. Trends in Food Science and Technology,2019,1:1−21.
[36]	KARL H, MERKLE S, KUHLMANN J, et al. Development of analytical methods for the determination of free and ester bound 2-, 3-MCPD, and esterified glycidol in fishery products[J]. European Journal of Lipid Science and Technology,2016,118:406−417. doi: 10.1002/ejlt.201400573
[37]	任雪梅, 田洪芸, 程月红. 食品中氯丙醇酯类物质的研究概况[J]. 食品安全导刊,2019,135(6):166−168. [REN X M, TIAN H Y, CHENG Y H. Research overview of chloropropanol esters in food[J]. China Food Safety Magazine,2019,135(6):166−168.
[38]	MERKLE S, OSTERMEYER U, ROHN S, et al. Formation of ester bound 2- and 3-MCPD and esterified glycidol in deep-fried and pickled herring products[J]. European Journal of Lipid Science and Technology,2018,120:1−9.
[39]	FRANKE K, STRIJOWSKI U, FLECK G, et al. Influence of chemical refining process and oil type on bound 3-chloro-1, 2-propanediol contents in palm oil and rapeseed oil[J]. LWT-Food Science and Technology,2009,42:1751−1754. doi: 10.1016/j.lwt.2009.05.021
[40]	ZELINKOVA Z, DOLEZAL M, VELISEK J. 3-chloropropane-1, 2-diol fatty acid esters in potato products[J]. Czech Journal of Food Sciences,2009,27:421−424. doi: 10.17221/1065-CJFS
[41]	RAZAK R A A, KUNTOM A, SIEW W L, et al. Detection and monitoring of 3-monochloropropane-1, 2-diol (3-MCPD) esters in cooking oils[J]. Food Control,2012,25(1):355−360. doi: 10.1016/j.foodcont.2011.10.058
[42]	DINGEL A, MATISSEK R. Esters of 3-monochloropropane-1, 2-diol and glycidol: No formation by deep frying during large-scale production of potato crisps[J]. European Food Research and Technology,2015,241:719−723. doi: 10.1007/s00217-015-2491-1
[43]	ARISSETO A P, MARCOLINO P F C, AUGUGSTI A C, et al. Contamination of fried foods by 3-monochloropropane-1, 2-diol fatty acid esters during frying[J]. Journal of the American Oil Chemists Society,2017,94:449−455. doi: 10.1007/s11746-017-2951-9
[44]	ZELINKOVÁ Z, DOLEŽAL M, VELIŠEK J, et al. 3-chloropropane-1, 2-diol fatty acid esters in potato products[J]. Czech Journal of Food Sciences,2009,27(6):S421−S424.
[45]	崔霞, 丁颢, 邹建宏, 等. 液态乳中氯丙二醇脂肪酸酯的检测与污染水平初步调查[J]. 食品科学,2014,35(12):93−97. [CUI X, DING J, ZOU J H, et al. Determination and occurrence of fatty acid esters of chloropropanediols in milk[J]. Food Science,2014,35(12):93−97. doi: 10.7506/spkx1002-6630-201412018
[46]	ARISSETO A P, MARCOLINO P F C, VICENTE E. 3-monochloropropane-1, 2-diol fatty acid esters in commercial deep-fat fried foods[J]. Food Additives and Contaminants,2015,10:1−5.
[47]	LI C, ZHOU Y, ZHU J, et al. Formation of 3-chloropropane-1, 2-diol esters in model systems simulating thermal processing of edible oil[J]. LWT-Food Science and Technology,2016,69:586−592. doi: 10.1016/j.lwt.2016.02.012
[48]	WONG Y H, MUHAMAD H, ABAS F, et al. 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[J]. Food Chemistry,2017,219:126−130. doi: 10.1016/j.foodchem.2016.09.130
[49]	ZHOU H R, JIN Q Z, WANG X G, et al. Effects of temperature and water content on the formation of 3-chloropropane-1, 2-diol fatty acid esters in palm oil under conditions simulating deep fat frying[J]. European Food Research and Technology,2014,238:495−501. doi: 10.1007/s00217-013-2126-3
[50]	张渊博. 煎炸过程中单氯丙醇酯及缩水甘油酯的变化规律及其影响因素研究[D]. 无锡: 江南大学, 2018. ZHANG Y B. The study on changes of esters of monochloro propanediol and glycidyl esters and their influencing factors during deep fying[D]. Wuxi: Jiangnan University, 2018.
[51]	FREUDENSTEIN A, WEKING J, MATTHÄUS B. Influence of precursors on the formation of 3-MCPD and glycidyl esters in a model oil under simulated deodorization conditions[J]. European Journal of Lipid Science and Technology,2013,115(3):286−294. doi: 10.1002/ejlt.201200226
[52]	ŠMIDRKAL J, TESAŘOVÁ M, HRÁDKOVÁ I, et al. Mechanism of formation of 3-chloropropan-1, 2-diol (3-MCPD) esters under conditions of the vegetable oil refining[J]. Food Chemistry,2016,211:124−129. doi: 10.1016/j.foodchem.2016.05.039
[53]	CHAI Q Q, HAYAT K, KARANGWA E, et al. Investigating the optimum conditions for minimized 3-chloropropane-1, 2-diol esters content and improved sensory attributes during savory beef flavor preparation[J]. Food Chemistry,2018,243:96−102. doi: 10.1016/j.foodchem.2017.09.113
[54]	CINDRIC I J, ZEINER M, STEFFAN I. Trace elemental characterization of edible oils by ICP-AES and GFAAS[J]. Microchemical Journal,2007,85(1):136−139. doi: 10.1016/j.microc.2006.04.011
[55]	ARISSETO A P, SILVA W C, TIVANELLO R G, et al. Recent advances in toxicity and analytical methods of monochloropropanediols and glycidyl fatty acid esters in foods[J]. Current Opinion in Food Science,2018,24:36−42. doi: 10.1016/j.cofs.2018.10.014
[56]	LI C, JIA H, SHEN M, et al. Antioxidants inhibit formation of 3-monochloropropane-1, 2-diol esters in model reactions[J]. Journal of Agricultural and Food Chemistry,2015,63(44):9850−9854. doi: 10.1021/acs.jafc.5b03503
[57]	MERKLE S, OSTERMEYER U, ROHN S, et al. Mitigation strategies for ester bound 2-/3-MCPD and esterified glycidol in pre-fried breaded and frozen fish products[J]. Food Chemistry,2018,245:196−204. doi: 10.1016/j.foodchem.2017.10.076
[58]	STRIJOWSKI U, HEINZ V, FRANKE K. Removal of 3-MCPD esters and related substances after refining by adsorbent material[J]. European Journal of Lipid Science and Technology,2015,113(3):387−392.
[59]	ZHANG H, JIN P, ZHANG M, et al. Mitigation of 3-monochloro-1, 2-propanediol ester formation by radical scavengers[J]. Journal of Agricultural and Food Chemistry,2016,64(29):5887−5892. doi: 10.1021/acs.jafc.6b02016
[60]	WONG Y H, KOK M G, KAR L N, et al. Effects of natural and synthetic antioxidants on changes in 3-MCPD esters and glycidyl ester in palm olein during deep-fat frying[J]. Food Control,2019,96:488−493. doi: 10.1016/j.foodcont.2018.10.006
[61]	李昌. 油脂中3-氯丙醇酯的暴露评估及其在热加工过程中的形成机理和控制[D]. 南昌: 南昌大学, 2015. LI C. 3-MCPD esters derived from edible oil, their exposure assessment, formation mechanism and control during heat process[D]. Nanchang: Nanchang University, 2015.
[62]	ARISSATO A P, SILVA W C, MARCOLINO P F C, et al. 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[J]. Food Research International,2019,124:43−48. doi: 10.1016/j.foodres.2018.10.070
[63]	MOGOL B A, PYE C, ANDERSON W, et al. Formation of monopropane-1, 2-diol and its esters in biscuits during baking[J]. Journal of Agricultural and Food Chemistry,2014,62:7297−7301. doi: 10.1021/jf502211s
[64]	刘海兰. 油脂煎炸过程3-氯丙醇酯和缩水甘油酯的研究[D]. 郑州: 河南工业大学, 2018. LIU H L. Study on 3-chloropeopanol esters and glycidyl esters during frying process[D]. Zhengzhou: Henan University of Technology, 2018.

[1]	GAO Xiangxin, CHEN Yongfu, Wusigale. Research Progress of Preparation and Application of Probiotic Microencapsulation in Food[J]. Science and Technology of Food Industry, 2023, 44(3): 19-28. DOI: 10.13386/j.issn1002-0306.2022090256
[2]	JIANG Zhe-hui, BAO Yi-hong, JIANG Shi-long. Active Factors and Its Food Status Against Sarcopenia[J]. Science and Technology of Food Industry, 2020, 41(2): 317-323. DOI: 10.13386/j.issn1002-0306.2020.02.051
[3]	ZHAO Jing, SHI Dong-jie, QU Yan-feng, WANG Hong-mei, LI Jing-hai. Research Progress of Potato Whole Meal Food[J]. Science and Technology of Food Industry, 2019, 40(20): 363-367. DOI: 10.13386/j.issn1002-0306.2019.20.058
[4]	LI Jun, DONG Lei, JIANG Fa-tang, XIAO Man. Development of Devices for Measuring the Moisture Contents in Foods[J]. Science and Technology of Food Industry, 2019, 40(8): 297-303. DOI: 10.13386/j.issn1002-0306.2019.08.050
[5]	WANG Ya-nan, WANG Xiao-fei, NIU Lin-lin, LEI Zhuang, ZHANG Hai-tang, WANG Zi-liang. Advance in immunoassay of total aflatoxins in food[J]. Science and Technology of Food Industry, 2017, (13): 344-351. DOI: 10.13386/j.issn1002-0306.2017.13.065
[6]	LIU Yi-jun, LIU Na, ZHANG Yu-meng. Research progress of food authentication technology[J]. Science and Technology of Food Industry, 2016, (22): 374-383. DOI: 10.13386/j.issn1002-0306.2016.22.065
[7]	YIN Yan, ZHANG Wan-gang, ZHOU Guang-hong, XU Xing-lian. Physiological functions of rosemary and its application in food[J]. Science and Technology of Food Industry, 2014, (22): 364-370. DOI: 10.13386/j.issn1002-0306.2014.22.072
[8]	LIU Xiao-yi. Risk control standards analysis on food production and processing[J]. Science and Technology of Food Industry, 2014, (06): 49-51. DOI: 10.13386/j.issn1002-0306.2014.06.015
[9]	NIU Gai-gai, DENG Jian-chao, LI Lai-hao, YANG Xian-qing, QI Bo, CEN Jian-wei. Accelerated Solvent Extraction and its applications in food analysis[J]. Science and Technology of Food Industry, 2014, (01): 375-380. DOI: 10.13386/j.issn1002-0306.2014.01.048
[10]	JIN Hong-guo, LIU Hua-lin, ZHANG Rui, ZHENG Zhi-ming, PENG Zeng-qi, ZHANG Xin-ling, LI Le. Review of analytical methods for the determination of formaldehyde in food[J]. Science and Technology of Food Industry, 2013, (19): 373-377. DOI: 10.13386/j.issn1002-0306.2013.19.058