Resources

New reference topics will be in bold.

Abd Razak, R.A., Kuntom, A., Lin, S.W., Ibrahim, N.A., Ramli, M.R., Hussein, R., and Nesaretnam, K., Detection and monitoring of 3-monochloropropane-1,2-diol (3-MCPD) esters in cooking oils, Food Control 5:355-360 (2011). Web 6 Dec 2011.

Abraham, K., Mielke, H., Lampen, A.,  Hazard characterization of 3-MCPD using benchmark dose modeling: Factors influencing the outcome, European Journal of Lipid Science and Technology 114:1225–1226 (2012). Web 1 Nov 2012.

Abu-El-Haj, S., Bogusz, M.J., Ibrahim, Z., Hassan, H., and Al Tufaila, M., Rapid and Simple Determination of Chloropropanols (3-MCPD and 1,3-DCP) in Food Products using Isotope Dilution GC-MS, Food Control 18:81-90 (2007). Web. 21 Sept 2010.

Bai, L., Sun, M.J., An, J.G., Liu, D.Q., Chen, T.K., and Kord, A.S., Enhancing the Detection Sensitivity of Trace Analysis of Pharmaceutical Genotoxic Impurities by Chemical Derivatization and Coordination Ion Spray-Mass Spectrometry, Journal of Chromatography A 1217:302-306 (2010). Web 7 Feb 2011. 

Becalski, A., Feng, S.-Y., Lau, B.-P., Zhao, T. Glycidyl fatty acid esters in food by LC-MS/MS: method development, Anal Bioanal Chem 2012 Mar 30. Web 11 April 2012.

Blumhorst, M.R., Collison, M.W., Cantrill, R., Shiro, H., Masukawa, Y., Kawai, S., Yasunaga, K., Collaborative Study for the Analysis of Glycidyl Fatty Acid Esters in Edible Oils using LC–MS, Journal of the American Oil Chemists' Society 90:493-500 (2013). Web 14 May 2013. 

Blumhorst, M.R., Venkitasubramanian, P., and Collison, M.W., Direct determination of glycidyl esters of fatty acids in vegetable Oils by LC-MS, Journal of the American Oil Chemists' Society 88:275-1283 (2011). Web 6 Oct 2011.

Bornscheuer, U.T., and Hesseler, M., Enzymatic Removal of 3-Monochloro-1,2-Propanediol (3-MCPD) and its Esters from Oils, European Journal of Lipid Science and Technology 112:552-556 (2010). Web. 21 Sept 2010.

Brereton, P., Kelly, J., Crews, C., Honour, S., Wood, R., Davies, A., Determination of 3-chloro-1,2-propanediol in Foods and Food Ingredients by Gas Chromatography with Mass Spectrometric Detection: Collaborative Study. Journal of AOAC International 84:455-465 (2001). Web. 21 Sept 2010.

Callender, H.L., Forrester, J.S., Ivanova, P., Preininger, A., Milne, S., and Brown, H.A., Quantification of Diacylglycerol Species from Cellular Extracts by Electrospray Ionization Mass Spectrometry Using a Linear Regression Algorithm, Analytical Chemistry 79:263-272 (2007). Web. 21 Sept 2010.

Calta, P., Velíšek, J., Dolezal, M., Hasnip, S., Crews, C., Réblová Z., Formation of 3- Chloropropane-1,2-Diol in Systems Simulating Processed Food, European Food Research and Technology 218:502-506 (2004). Web. 21 Sept 2010.

Cauville, F., and Bertoli, C., A Deodarized Edible Oil or Fat with Low Levels of Bound MCPD and Process of Making Using an Inert Gas, World Intellectual Property Organization, WO/2011/009843 (2011). Web 11 Feb 2011. 

Collier, P.D., Cromie, D.D.O., and Davies, A.P., Mechanism of Formation of Chloropropanols Present in Protein Hydrolysates, Journal of the American Oil Chemists' Society 68:785-790 (1991). Web. 21 Sept 2010.

Craft, B.D., and K. Nagy, Mitigation of MCPD-ester and Glycidyl-ester Levels During the Production of Refined Palm Oil, Lipid Technology 24:155–157, 2012. Web 1 August 2012.

Crews, C., Chiodini, A., Granvogl, M., Hamlet, C., Hrnčiřík, K., Kuhlmann, J., Lampen, A., Scholz, G., Weisshaar, R., Wenzl, T., Jasti, P.R., Seefelder, W., Analytical approaches for MCPD esters and glycidyl esters in food and biological samples: a review and future perspectives, Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 28 Sep 2012. Web 16 October 2012.

Davídek, J., Velíšek, J., Kubelka, V., Janíĉek, G., Ŝimicová, Z., Glycerol Chlorohydrins and Their Esters as Products of the Hydrolysis of Tripalmitin, Tristearin and Triolein with Hydrochloric Acid, Zeitschrift für Lebensmittel-Untersuchung und-Forschung 171:14-17 (1980). Web. 21 Sept 2010.

de Koning, S. Zelinková, Z. Hrncirík, K., Janssen, H., Analysis of 3-MCPD Esters in Edible Oils Using LargeVolume Injection Coupled to Comprehensive GasChromatography – Time-of-Flight Mass Spectrometry, LECO Corporation June 2010. Web 28 February 2013.   

Deutsche Gesellschaft für Fettwissenschaft e.V. DGF Standard Methods CIII 18 (09): Ester-bound 3-chloropropane-1,2-diol (3-MCPD esters) and Glycidol (Glycidyl Esters). Determination in Fats and Oils by GC-MS. Web. 21 Sept 2010.

Divinová, V., Svejkovská, B., Dolezal, M., and Velíšek, J., Determination of Free and Bound 3-Chloropropane-1,2-diol by Gas Chromatography with Mass Spectrometric Detection Using Deuterated 3-Chloropropane-1,2-diol as Internal Standard, Czech Journal of Food Sciences 22:182-189 (2004). Web. 21 Sept 2010.

Dolezal, M., Calta, P., Velíšek, J., Hasnip, S., Study on the formation of 3-Chloropropane-1,2-Diol from Lipids in the Presence of Sodium Chloride, in Euro Food Chem XII Conference on "Strategies for Safe Food: Analytical, Industrial, and Legal Aspects; Challenges in Organisation and Communication," September 24-26, 2003, edited by T. Eklund et al., KVCV, Brugge, Belgium, 251-254 (2003).

Ermacora, A., and Hrncirik, K., 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: 1-8 (2013). Web 6 Feb 2013.

Ermacora, A., and Hrncirik, K., Evaluation of an Improved Indirect Method for the Analysis of 3-MCPD Esters Based on Acid Transesterification, Journal of the American Oil Chemists' Society :1-7 (2011). Web 6 Oct 2011.

Fiebig, H.J., Determination of Ester-bound 3-Chloro-1,2-propanediol and Glycidol in Fats and Oils - A Collaborative Study, European Journal of Lipid Science and Technology 113:393-399 (2011). Web 11 May 2011. 

Freudenstein, A., Weking, J., and Matthäus, B., 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 DOI: 10.1002/ejlt.201200226. Web 28 Nov 2012.

Granvogl, M. and Schieberle, P., Development of a direct quantitation method of glycidyl esters in edible fats and oils via stable isotope dilution analysis (2011). Web 26 Jan 2012. 

Haines, T.D., Adlaf, K.J., Pierceall, R.M., Lee I., Venkitasubramanian, P., and Collison, M.W., Direct Determination of MCPD Fatty Acid Esters and Glycidyl Fatty Acid Esters in Vegetable Oils by LC-TOFMS, Journal of the American Oil Chemists' Society 88:1-14 (2011). Web 11 May 2011. 

Hamlet, C.G. and Sadd, P.A., Chloropropanols and Chloroesters, in Process-Induced Food Toxicants: Occurrence, Formation, Mitigation, and Health Risks, edited by Richard H. Stadler and David R. Lineback, John Wiley & Sons, Inc., pp. 175-214 (2009). Web. 21 Sept 2010.

Hori, K., et al., Fuji Oil announces fast assay for 3-MCPD fatty acid esters by supercritical fluid chromatography/MS, World Congress on Oleo Science 2012. Web 19 October 2012.

Hrncirik, K., and van Duijn, G., An Initial Study on the Formation of 3-MCPD Esters During Oil Refining, European Journal of Lipid Science and Technology 113:374-379 (2011). Web 11 May 2011. 

Hrncirik, K., Zelinkova, Z., and Ermacora, A., Critical Factors of Indirect Determination of 3-Chloropropane-1,2-diol Esters, European Journal of Lipid Science and Technology 113:361-367 (2011). Web 11 May 2011. 

Ilko, V., Zelinková, Z., Doležal, M., Velíšek, J. Formation of 3-MCPD Esters from Acylglycerols in Model Systems, EuroFed Lipids 2012. Web 19 October 2012.

International Conference on Harmonization Expert Working Group. Validation of Analytical Procedures: Text and Methodology, Current Step 4 Version. Web. 21 Sept 2010.

Ismail, B., Reuhs B.L., and Nielsen, S.S., Analysis of Food Contaminants, Residues, and Chemical Constituents of Concern, Food Analysis 3: 317-349 (2010). Web. 21 Sept 2010.

Joffre, F., Griffon, H., Soulet, B., and Lacoste, F., 3-MCPD Esters in Edible Oils: Analytical Aspects, Abstract of the EuroFed Lipid Meeting, Graz, Austria, October 2009 (2009). Web. 21 Sept 2010.

Karasek, L., Wenzl, T., and Ulberth, F., Determination of 3-MCPD esters in edible oil – methods of analysis and comparability of results, European Journal of Lipid Science and Technology (2011). Web 6 Dec 2011. 

Kasaia, N., Suzukib, T., and Idogaki, H., Enzymatic Degradation of Esters of Dichloropropanols: Removal of Chlorinated Glycerides from Processed Foods, LWT-Food Science and Technology 39: 86-90 (2006). Web. 21 Sept 2010.

Kaze, N., Sato, H., Yamamoto, H., and Watanabe, Y., Bidirectional Conversion Between 3-Monochloro-1,2-propanediol and Glycidol in Course of the Procedure of DGF Standard Methods, Journal of the American Oil Chemists' Society:1-9 (2011). Web 11 May 2011.

Kaze, N., Sato, H., Yamamoto, H., and Watanabe, Y., Improvement of accuracy in quantification of 3-monochloropropane-1,2-diol esters by Deutsche Gesellschaft für Fettwissenschaft standard methods C-III 18, European Journal of Lipid Science and Technology 113:168-1171 (2011). Web 6 Oct 2011.

Koning, S. de, Zelinkiova, Z., Hrncirik, K., and Janssen, H.-G., Analysis of 3-MCPD Esters in Edible Oils Using Large Volume Injection Coupled to Comprehensive Gas Chromatography - Time-of-Flight Mass Spectrometry, Chromatography Online 6:17-22 (2010). Web 7 Feb 2011. 

Kraft, R., Brachwitz, H., Etzold, N.G., Langen, P., Zöpfl, H.-J., Halogenolipids. I. Mass Spectrometric Structure Investigation of the Isomeric Halogeno-Propanediols Esterified with Fatty Acids (Deoxyhalogeno-Glycerides), Journal für Praktische Chemie 321:756-768 (1978). Web. 21 Sept 2010.

Kuballa, T., and Ruge, W., Analysis and Detection of 3-Monochloropropane-1,2-diol (3-MCPD) in Food by GC/MS/MS, Varian GC/MS Application Note 73 (2004). Web. 21 Sept 2010.

Kuhlmann, J., Determination of Bound 2,3-Epoxy-1-propanol (Glycidol) and Bound Monochloropropanediol (MCPD) in Refined Oils, European Journal of Lipid Science and Technology 113:335-344 (2011). Web 11 May 2011.

Küsters, M., Bimber, U., Reeser, S., Gallitzendörfer, R., and Gerhartz, M., Simultaneous Determination and Differentiation of Glycidyl Esters and 3-Monochloropropane-1,2-diol (MCPD) Esters in Different Foodstuffs by GC-MS, Journal of Agricultural and Food Chemistry (2011). Web 11 May 2011 

Küsters, M., Bimber, U., Ossenbrüggen, A., Reeser, S., Gallitzendörfer, R., and Gerhartz, M., Rapid and Simple Micromethod for the Simultaneous Determination of 3-MCPD and 3-MCPD Esters in Different Foodstuffs, Journal of Agricultural and Food Chemistry 58:6570-6577. Web. 21 Sept 2010.

Lacoste, F., Joffre, F., Coustille, J., Morin, O., Soulet, B., Brenne, E., and Griffon, H., Détection de Contaminants Dans les Huiles Végétales: Bilan à fin 2009, Oléagineux, Corps Gras, Lipides 17:75-80 (2009). Web. 21 Sept 2010.

Lapit, R.B.A., Krishnan, A.A., Hashim, K.B., Zieverink, M.M.P., and De Ruiter, G.A., Process for Manufacturing Palm Oil Fractions Containing Virtually no 3-monochloropropanediol Fatty Acid Esters, World Intellectual Property Organization, WO/2011/002275 (2011). Web 11 Feb 2011. 

León, N., Yusà, V., Pardo, O., and Pastor, A., Determination of 3-MCPD by GC-MS/MS with PTV-LV Injector Used for a Survey of Spanish Foodstuffs, Talanta 75:824-831 (2008). Web. 21 Sept 2010.

Masukawa, Y., Shiro, H., Kondo, N., and Kudo, N., Generalized Method to Quantify Glycidol Fatty Acid Esters in Edible Oils, Journal of American Oil Chemists' Society 88:15-21 (2010). Web 11 Feb 2011. 

Masukawa, Y., Shiro, H., Nakamura, S., Kondo, N., Jin, N., Suzuki, N., Ooi, N., and Kudo, N., A New Analytical Method for the Quantification of Glycidol Fatty Acid Esters in Edible Oils, Journal of Oleo Science 59:81-88 (2010). Web. 21 Sept 2010.

Matthaus, B., Pudel, F., Fehling, P., Vosmann, K., and Freudenstein, A., Strategies for the Reduction of 3-MCPD Esters and Related Compounds in Vegetable Oils, European Journal of Lipid Science and Technology 113:380-386 (2011). Web 11 May 2011. 

Pudel, F., Benecke, P., Fehling, P., Freudenstein, A., Matthaus, B., and Schwaf, A., On the Necessity of Edible Oil Refining and Possible Sources of 3-MCPD and Glycidyl Esters, European Journal of Lipid Science and Technology 113:368-373 (2011). Web 11 May 2011. 

Racamonde, I., González, P., Lorenzo, R.A., and Carro, A.M., Determination of chloropropanols in foods by one-step extraction and derivatization using pressurized liquid extraction and gas chromatography-mass spectrometry, Journal of Chromatography A 1218:6878-6883 (2011). Web 6 Oct 2011.

Rahn, A.K.K., and Yaylayan, V.A., Monitoring cyclic acyloxonium ion formation in palmitin systems using infrared spectroscopy and isotope labelling technique, European Journal of Lipid Science and Technology 113:330-334 (2011). Web 6 Oct 2011.

Rahn, A.K.K, and Yaylayan, V.A., Thermal Degradation of Sucralose and its Potential in Generating Chloropropanols in the Presence of Glycerol, Food Chemistry 118: 56-61 (2010). Web. 21 Sept 2010.

Ramli, M.R., Siew, W.L., Ibrahim, N.A., Hussein, R., Kuntom, A., Abd. Razak, R.A., and Nesaretnam, K., Effects of Degumming and Bleaching on 3-MCPD Esters Formation During Physical Refining, Journal of the American Oil Chemists' Society :1-6 (2011). Web 6 Oct 2011.

Rahn, A.K.K., and Yaylayan, V.A., What Do We Know About the Molecular Mechanism of 3-MCPD Ester Formation?, European Journal of Lipid Science and Technology 113:323-329 (2011). Web 11 May 2011. 

Reese, P., Report No. FD 04/12, FSA Project No. C03017, 18, 19; The Origin and Formation of 3-MCPD and Formation of 3-MCPD in Food Ingredients (2005). Web. 21 Sept 2010.

Rétho, C., Blanchard, F., 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 22:1189-1197 (2005). Web. 21 Sept 2010.

Robert, M.C., Oberson, J.-M., Stadler, R.H., Model Studies on the Formation of Monochloropropanediols in the Presence of Lipase, Journal of Agricultural Food Chemistry 52:5102-5108 (2004). Web. 21 Sept 2010.

Schurz, K., Method for Reducing the 3-MCPD Content in Refined Vegetable Oils, World Intellectual Property Organization: WO/2010/063450 (2010). Web 7 Feb 2011. 

Shimadzu Corporation, Analysis of 3-MCPD Fatty Acid Diesters in Palm Oil Using a Triple Quadrupole LC/MS/MS [LCMS-8030]. Application News No. C84, First Edition: February 2012, Web 25 April 2012.

Shimizu, M., Kudo, N., Shiro, H., Yasunaga, K., Masukawa, Y., Katsuragi, Y., and Yasumasu, T., A comparison of the indirect and direct quantification of glycidol ester by kinetic analysis, European Journal of Lipid Science and Technology 113:985-991 (2011). Web 6 Oct 2011.

Shimizu, M., N. Kudo, H. Shiro, K. Yasunaga, Y. Masukawa, Y Katsuragi, and T. Yasumasu, Comparison of Indirect and Direct Quantification of Glycidol Fatty Acid Ester in Edible Oils, Journal Oleo Science 59:533-539 (2010). Web. 15 Oct 2010.

Šmidrkal, J., Ilko, V., Filip, V., Doležal, M., Zelinková, Z., Kyselka, J., Hrádková, I., and Velíšek, J., Formation of acylglycerol chloro derivatives in vegetable oils and mitigation strategy, Czech Journal of Food Sciences 29:448-456 (2011). Web 6 Oct 2011.

Stadler, R., Theurillat, V., Studer, A., Scanlan, F., and Seefelder, W., The Formation of 3-Monochloropropane-1,2-diol (3-MCPD) in Food and Potential Measures of Control, in Thermal Processing of Food, edited by Deutsche Forschungsgemeinschaft, Wiley-VCH, Weinheim, Germany, pp. 141-154 (2007). Web. 21 Sept 2010.

Strijowski, U., Heinz, V., and Franke, K., Removal of 3-MCPD Esters and Related Substances After Refining by Adsorbent Material, European Journal of Lipid Science and Technology 113:387-392 (2011). Web 11 May 2011. 

Tesser, R., et al, Kinetics of Glycerol Chlorination with Hydrochloric Acid: A New Route to alpha,gamma-Dichlorohydrin, Industrial and Engineering Chemistry Research 46:6456-6465 (2007). Web. 21 Sept 2010.

Velíšek, J., Chloroproponals, in Process-Induced Food Toxicants: Occurrence, Formation, Mitigation, and Health Risks, edited by Richard H. Stadler and David R. Lineback, John Wiley & Sons, Inc., 2009, pp. 539-562. Web. 21 Sept 2010.

Velíšek, J., Davídek, J., Ŝimicová, Z., Svobodová, Z., Glycerol chlorohydrins and their esters-reaction products of lipids with hydrochloric acid. Scientific Papers of the Prague Institute of Chemical Technology E53:55-65 (1982). 

Velíšek, J., et al, Formation of Volatile Chlorohydrins from Glycerol (Triacetin, Tributyrin) and Hydrochloric Acid, LWT-Food Science and Technology 12:234-236 (1979).

Xing, X., and Cao, Y., Study on Elimination of 3-chloro-1,2-propanediol in Hydrolyzed Vegetable Protein by Capillary Electrophoresis with Electrochemical Detection, Chinese Journal of Chromatography 24: 192-195 (2006). Web. 21 Sept 2010.

Xu, X.-M.., He, H.-L.., Zhu, Y., Feng, L., Ying, Y., Huang, B.-F., Shen, H.-T., Han, J.-L. Ren, Y.-P., Simultaneous Determination of 3-monochloropropane-1,2-diol and Acrylamide in Food by Gas Chromatography-triple Quadrupole Mass Spectrometry with Coupled Column Separation. Analytica Chimica Acta, available online 28 Nov 2012. Web 5 Dec 2012. 

Weißhaar, R., 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 110:183-186 (2008). Web. 21 Sept 2010.

Zulkurnain, M., Lai, O-M., Tan, S. Latip, R., and Tan, C., Optimization of palm oil physical refining process for reduction of 3-MCPD esters formation, J. Agric. Food Chem. DOI: 10.1021/jf4009185 (2013). Web. 13 March 2013.

If you have comments or wish to contribute further information regarding 3-MCPD and glycidyl (glycidol) esters, please contact Richard Cantrill, Director, AOCS Technical Services.