3-monochloro-1,2-propanediol

IARC Monographs on the Evaluation of Carcinogenic Risks to Humans

Volumn 101, Issue , 2012, Pages

[No Author Info available]

Author keywords

[No Author keywords available]

Indexed keywords

3 MONOCHLORO 1,2 PROPANEDIOL; ALPHA CHLOROHYDRIN; PROPANEDIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANCER MODEL; CANCER RISK; CARCINOGENESIS; CARCINOGENICITY; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYTOTOXICITY; ENVIRONMENTAL EXPOSURE; FOOD COMPOSITION; FOOD CONTAMINATION; FOOD CONTROL; GAS CHROMATOGRAPHY; GENOTOXICITY; HUMAN; MOLECULAR WEIGHT; NEPHROTOXICITY; NOMENCLATURE; NONHUMAN; OCCUPATIONAL EXPOSURE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REPRODUCTIVE TOXICITY; REVERTANT; STRUCTURE ACTIVITY RELATION; TOXICOKINETICS; XENOBIOTIC METABOLISM;

EID: 84862268863     PISSN: 10171606     EISSN: None     Source Type: Book Series    
DOI: None     Document Type: Article

References (134)

1. Abu-El-Haj S, Bogusz MJ, Ibrahim Z et al. (2007). Rapid and simple determination of chloropropanols (3-MCPD and 1,3-DCP) in food products using isotope dilution GC-MS. Food Contr, 18: 81-90. doi:10.1016/j. foodcont.2005.08.014
2. Anon (1995). [Bestimmung von 3-Chlor-1,2-Propandiol (3-MCPD) in Speisewürzen (Eiweißhydrolysate). Amtliche Sammlung von Untersuchungsverfahren nach § 35 LMBG. L 52.02-1.] Berlin, Germany: Beuth Verlag.
3. Beilstein (2010). CrossFire Beilstein Database. Frankfurt am Main, Germany: Elsevier Information Systems GmbH
4. Bel-Rhlid R, Talmon JP, Fay LB, Juillerat MA (2004). Biodegradation of 3-chloro-1,2-propanediol with Saccharomyces cerevisiae. J Agric Food Chem, 52: 6165-6169. doi:10.1021/jf048980k PMID:15453682
5. Berger-Preiss E, Gerling S, Apel E et al. (2010). Development and validation of an analytical method for determination of 3-chloropropane-1,2-diol in rat blood and urine by gas chromatography-mass spectrometry in negative chemical ionization mode. Anal Bioanal Chem, 398: 313-318. doi:10.1007/s00216-010-3928-9 PMID:20640896
6. BfR (2007). Infant formula and follow-up formula may contain harmful 3-MCPD fatty acid esters. Berlin, Germany: Bundesinstitut für Risikobewertung.
7. Bodén L, Lundgren M, Stensiö KE, Gorzynski M (1997). Determination of 1,3-dichloro-2-propanol and 3-chloro-1,2-propanediol in papers treated with polyamidoamine-epichlorohydrin wet-strength resins by gas chromatography-mass spectrometry using selective ion monitoring. J Chromatogr A, 788: 195-203. doi:10.1016/S0021-9673(97)00711-5
8. Breitling-Utzmann CM, Hrenn H, Haase NU, Unbehend GM (2005). Influence of dough ingredients on 3-chloropropane-1,2-diol (3-MCPD) formation in toast. Food Addit Contam, 22: 97-103. doi:10.1080/02652030500037936 PMID:15823998
9. Breitling-Utzmann CM, Kobler H, Herbolzheimer D et al. (2003). 3-MCPD-Occurrence in bread crust and various food groups as well as formation in toast.] Deut Lebensm Rundsch, 99: 280-285.
10. Brereton P, Kelly J, Crews C et al. (2001). Determination of 3-chloro-1,2-propanediol in foods and food ingredients by gas chromatography with mass spectrometric detection: collaborative study. J AOAC Int, 84: 455-465. PMID:11324611
11. Brown-Woodman PDC, White IG, Salamon S (1975). Proceedings: effect of α-chlorohydrin on the fertility of rams and on the metabolism of spermatozoa in vitro. J Reprod Fertil, 43: 381 doi:10.1530/jrf.0.0430381 PMID:1127664
12. Bub O, Friedrich L (2005). Cough remedies. In: Ullmann's Encyclopedia of Industrial Chemistry. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA.
13. Buckle A (2005). Rodenticides. In: Ullmann's Encyclopedia of Industrial Chemistry, Weinheim. Germany: Wiley-VCH Verlag GmbH & Co. KGaA.
14. Buhrke T, Weißhaar R, Lampen A (2010). Bioavailability of 3-monochloro-1,2-propanediol (3-MCPD) and 3-MCPD fatty acid esters.] Naunyn Schmiedebergs Arch Pharmacol, 381: 85
15. Byun JA, Ryu MH, Lee JK (2006). The immunomodulatory effects of 3-monochloro-1,2-propanediol on murine splenocyte and peritoneal macrophage function in vitro. Toxicol In Vitro, 20: 272-278. doi:10.1016/j. tiv.2005.06.042 PMID:16122900
16. Calta P, Velíšek J, Doležal M et al. (2004). Formation of 3-chloropropane-1,2-diol in systems simulating processed foods. Eur Food Res Technol, 218: 501-506. doi:10.1007/s00217-003-0865-2
17. Cao XJ, Song GX, Gao YH et al. (2009). A Novel Derivatization Method Coupled with GC-MS for the Simultaneous Determination of Chloropropanols. Chromatographia, 70: 661-664. doi:10.1365/s10337-009-1203-z
18. Cho WS, Han BS, Lee H et al. (2008). Subchronic toxicity study of 3-monochloropropane-1,2-diol administered by drinking water to B6C3F1 mice. Food Chem Toxicol, 46: 1666-1673. doi:10.1016/j.fct.2007.12.030 PMID:18328611
19. Chung WC, Hui KY, Cheng SC (2002). Sensitive method for the determination of 1,3-dichloropropan-2-ol and 3-chloropropane-1,2-diol in soy sauce by capillary gas chromatography with mass spectrometric detection. J Chromatogr A, 952: 185-192. doi:10.1016/S0021-9673(02)00062-6 PMID:12064530
20. Crabo B & Appelgren LE (1972). Distribution of (14 C)-chlorohydrin in mice and rats. J Reprod Fertil, 30: 161-163. doi:10.1530/jrf.0.0300161 PMID:5035336
21. Crews C, Brereton P, Davies A (2001). The effects of domestic cooking on the levels of 3-monochloropropanediol in foods. Food Addit Contam, 18: 271-280. doi:10.1080/02652030120064 PMID:11339260
22. Crews C, LeBrun G, Brereton PA (2002). Determination of 1,3-dichloropropanol in soy sauces by automated headspace gas chromatography-mass spectrometry. Food Addit Contam, 19: 343-349. doi:10.1080/02652030110098580 PMID:11962691
23. Davídek J, Velíšek J, Kubelka V et al. (1980). Glycerol Chlorohydrins and Their Esters As Products of the Hydrolysis of Tripalmitin, Tristearin and Triolein with Hydrochloric-Acid.] Z Lebensm Unters Forsch, 171: 14-17. doi:10.1007/BF01044410
24. Dayrit FM & Niñonuevo MR (2004). Development of an analytical method for 3-monochloropropane-1,2-diol in soy sauce using 4-heptanone as derivatizing agent. Food Addit Contam, 21: 204-209. doi:10.1080/0265203 0310001656352 PMID:15195467
25. Divinová V, Svejkovská B, Doležal M et al. (2004). 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 J Food Sci, 22: 182-189.
26. Dobbie MS, Porter KE, Jones AR (1988). Is the nephrotoxicity of (R)-3-chlorolactate in the rat caused by 3-chloropyruvate? Xenobiotica, 18: 1389-1399. doi:10.3109/00498258809042262 PMID:3245232
27. Doležal M, Calta P, Velíšek J (2004). Formation and decomposition of 3-chloropropane-1,2-diol in model systems. Czech J Food Sci, 22: 263-266.
28. Doležal M, Chaloupská M, Divinová V et al. (2005). Occurrence of 3-chloropropane-1,2-diol and its esters in coffee. Eur Food Res Technol, 221: 221-225. doi:10.1007/s00217-004-1118-8
29. Edwards EM, Jones AR, Waites GM (1975). The entry of α-chlorohydrin into body fluids of male rats and its effect upon the incorporation of glycerol into lipids. J Reprod Fertil, 43: 225-232. doi:10.1530/jrf.0.0430225 PMID:1127646
30. El Ramy R, Ould Elhkim M, Lezmi S, Poul JM (2007). Evaluation of the genotoxic potential of 3-monochloropropane-1,2-diol (3-MCPD) and its metabolites, glycidol and beta-chlorolactic acid, using the single cell gel/comet assay. Food Chem Toxicol, 45: 41-48. doi:10.1016/j.fct.2006.07.014 PMID:16971032
31. EPA (2006). Pesticide fact sheet. In: Alpha-Chlorohydrin. Washington, DC: United States Environmental Protection Agency.
32. Epstein SS, Arnold E, Andrea J et al. (1972). Detection of chemical mutagens by the dominant lethal assay in the mouse. Toxicol Appl Pharmacol, 23: 288-325. doi:10.1016/0041-008X(72)90192-5 PMID:5074577
33. Ericsson RJ (1982). Alpha-chlorohydrin (Epibloc): A toxicant-sterilant as an alternative in rodent control. Marsh RE, editor. Davis, CA: University of California, pp. 6-9.
34. European Commission (2001). Commission Regulation (EC) No 466/2001 of 8 March 2001 setting maximum levels for certain contaminants in foodstuffs Off J Europ Comm, L77: 1-13.
35. European Standard (2005). EN 14573:2004 Foodstuffs-Determination of 3-monochloropropane-1,2-diol by GC/MS. Berlin, Germany: Beuth Verlag.
36. Frei H & Würgler FE (1997). The vicinal chloroalcohols 1,3-dichloro-2-propanol (DC2P), 3-chloro-1,2-propanediol (3CPD) and 2-chloro-1,3-propanediol (2CPD) are not genotoxic in vivo in the wing spot test of Drosophila melanogaster. Mutat Res, 394: 59-68. PMID:9434844
37. Hamlet CG (1998). Analytical methods for the determination of 3-chloro-1,2-propandiol and 2-chloro-1,3-propandiol in hydrolysed vegetable protein, seasonings and food products using gas chromatography/ion trap tandem mass spectrometry. Food Addit Contam, 15: 451-465. doi:10.1080/02652039809374666 PMID:9764216
38. Hamlet CG (2009). Chloropropanols and their Fatty Acid Esters. In: Bioactive compounds in foods. Gilbert J & Senyuva HZ, editors. Oxford, UK: Blackwell Publishing Ltd., pp. 323-357.
39. Hamlet CG, Jayaratne SM, Matthews W (2002b). 3-Monochloropropane-1,2-diol (3-MCPD) in food ingredients from UK food producers and ingredient suppliers. Food Addit Contam, 19: 15-21. doi:10.1080/02652030110072344 PMID:11817372
40. Hamlet CG & Sadd PA (2002). Kinetics of 3-chloropropane-1,2-diol (3-MCPD) degradation in high temperature model systems. Eur Food Res Technol, 215: 46-50. doi:10.1007/s00217-002-0523-0
41. Hamlet CG & Sadd PA (2004). Chloropropanols and their esters in cereal products. Czech J Food Sci, 22: 259-262.
42. Hamlet CG & Sadd PA (2005). Effects of yeast stress and pH on 3-monochloropropanediol (3-MCPD)-producing reactions in model dough systems. Food Addit Contam, 22: 616-623. doi:10.1080/02652030500150093 PMID:16019837
43. Hamlet CG, Sadd PA (2009). Chloropropanols and chloroesters. In: Process-induced food toxicants: occurrence, formation, mitigation and health risks. Stadler RH & Lineback DR, editors. Hoboken, NJ: Wiley, pp. 175-214.
44. Hamlet CG, Sadd PA, Crews C et al. (2002a). Occurrence of 3-chloro-propane-1,2-diol (3-MCPD) and related compounds in foods: a review. Food Addit Contam, 19: 619-631. doi:10.1080/02652030210132391 PMID:12113657
45. Hamlet CG, Sadd PA, Gray DA (2003). Influence of composition, moisture, pH and temperature on the formation and decay kinetics of monochloropropanediols in wheat flour dough. Eur Food Res Technol, 216: 122-128.
46. Hamlet CG, Sadd PA, Gray DA (2004a). Generation of monochloropropanediols (MCPDs) in model dough systems. 1. Leavened doughs. J Agric Food Chem, 52: 2059-2066. doi:10.1021/jf035077w PMID:15053552
47. Hamlet CG, Sadd PA, Gray DA (2004b). Generation of monochloropropanediols (MCPDs) in model dough systems. 2. Unleavened doughs. J Agric Food Chem, 52: 2067-2072. doi:10.1021/jf035078o PMID:15053553
48. Hamlet CG & Sutton PG (1997). Determination of the chloropropanols, 3-chloro-1,2-propandiol and 2-chloro-1,3-propandiol, in hydrolysed vegetable proteins and seasonings by gas chromatography ion trap tandem mass spectrometry. Rapid Commun Mass Spectrom, 11: 1417-1424. doi:10.1002/(SICI)1097-0231(19970830)11:13<1417::AID-RCM986>3.0.CO;2-S
49. Huang MJ, Jiang GB, He B et al. (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. Anal Sci, 21: 1343-1347. doi:10.2116/analsci.21.1343 PMID:16317903
50. Hwang M, Yoon E, Kim J et al. (2009). Toxicity value for 3-monochloropropane-1,2-diol using a benchmark dose methodology. Regul Toxicol Pharmacol, 53: 102-106. doi:10.1016/j.yrtph.2008.12.005 PMID:19133308
51. IARC (2000). Some industrial chemicals. IARC Monogr Eval Carcinog Risks Hum, 77: 1-529. PMID:11236796
52. IARC (2010). Alcohol consumption and ethyl carbamate. IARC Monogr Eval Carcinog Risks Hum, 96: 1-1428.
53. JECFA (2002). 3-Chloro-1,2-propanediol. Safety evaluation of certain food additives and contaminants. Prepared by the fifty-seventh meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA), GenevaWHO Food Addit Ser, 48.
54. JECFA (2007). 3-Chloro-1,2-propanediol (addendum). Safety evaluation of certain food additives and contaminants. Prepared by the sixty-seventh meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA), GenevaWHO Food Addit Ser, 58: 239-267.
55. Jeong J, Han BS, Cho WS et al. (2010). Carcinogenicity study of 3-monochloropropane-1, 2-diol (3-MCPD) administered by drinking water to B6C3F1 mice showed no carcinogenic potential. Arch Toxicol, 84: 719-729. doi:10.1007/s00204-010-0552-6 PMID:20461361
56. Jira W (2010). 3-Monochloropropane-1,2-diol (3-MCPD) in smoked meat products.] Fleischwirtsch, 90: 115-118.
57. Jones AR (1975). The metabolism of 3-chloro,-3-bromoand 3-iodoprpan-1,2-diol in rats and mice. Xenobiotica, 5: 155-165. doi:10.3109/00498257509056101 PMID:1166663
58. Jones AR & Cooper TG (1999). A re-appraisal of the posttesticular action and toxicity of chlorinated antifertility compounds. Int J Androl, 22: 130-138. doi:10.1046/j.1365-2605.1999.00163.x PMID:10367232
59. Jones AR, Davies P, Edwards K, Jackson H (1969). Antifertility effects and metabolism of alpha and epi-chlorhydrins in the rat. Nature, 224: 83 doi:10.1038/224083a0 PMID:5822916
60. Jones AR, Gadiel P, Murcott C (1979). The renal toxicity of the rodenticide α-chlorohydrin in the rat. Naturwissenschaften, 66: 425 doi:10.1007/BF00368082 PMID:503241
61. Jones AR, Milton DH, Murcott C (1978). The oxidative metabolism of α-chlorohydrin in the male rat and the formation of spermatocoeles. Xenobiotica, 8: 573-582. doi:10.3109/00498257809061257 PMID:695700
62. Jones AR & Murcott C (1976). The oxidative metabolism of α-chlorohydrin and the chemical induction of spermatocoeles. Experientia, 32: 1135-1136. doi:10.1007/BF01927587 PMID:971742
63. Jones AR & Porter LM (1995). Inhibition of glycolysis in boar spermatozoa by α-chlorohydrin phosphate appears to be mediated by phosphatase activity. Reprod Fertil Dev, 7: 1089-1094. doi:10.1071/RD9951089 PMID:8848575
64. Jones P & Jackson H (1976). Antifertility and dominant lethal mutation studies in male rats with dl-alphachlorohydrin and an amino-analogue. Contraception, 13: 639-646. doi:10.1016/0010-7824(76)90019-6 PMID:1261265
65. Karšulínová L, Folprechtová B, Doležal M et al. (2007). Analysis of the lipid fractions of coffee creamers, cream aerosols, and bouillon cubes for their health risk associated constituents. Czech J Food Sci, 25: 257-264.
66. Kaur S & Guraya SS (1981a). Effect of low doses of alpha chlorohydrin on the enzymes of glycolytic and phosphogluconate pathways in the rat testis and epididymis. Int J Androl, 4: 196-207. doi:10.1111/j.1365-2605.1981. tb00703.x PMID:6265379
67. Kaur S & Guraya SS (1981b). Biochemical observations on the protein and nucleic acid metabolism of the rat testis and epididymis after treatment with low doses of alphachlorohydrin. Int J Fertil, 26: 8-13. PMID:6165692
68. Kim K (2008). Differential expression of neuronal and inducible nitric oxide synthase in rat brain after subchronic administration of 3-monochloro-1,2-propanediol. Food Chem Toxicol, 46: 955-960. doi:10.1016/j. fct.2007.10.025 PMID:18063462
69. Kirton KT, Ericsson RJ, Ray JA, Forbes AD (1970). Male antifertility compounds: efficacy of U-5897 in primates (Macacamulatta). J Reprod Fertil, 21: 275-278. doi:10.1530/jrf.0.0210275 PMID:4986219
70. Kissa E (1992). Determination of 3-Chloropropanediol and Related Dioxolanes by Gas-Chromatography. J Chromatogr A, 605: 134-138. doi:10.1016/0021-9673(92)85038-U
71. Kleemann A (2008). Cardiovascular drugs. In: Ullmann's Encyclopedia of Industrial Chemistry. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA.
72. Kluwe WM, Gupta BN, Lamb JC 4th (1983). The comparative effects of 1,2-dibromo-3-chloropropane (DBCP) and its metabolites, 3-chloro-1,2-propaneoxide (epichlorohydrin), 3-chloro-1,2-propanediol (alphachlorohydrin), and oxalic acid, on the urogenital system of male rats. Toxicol Appl Pharmacol, 70: 67-86. doi:10.1016/0041-008X(83)90180-1 PMID:6612740
73. Kuballa T & Ruge W (2003). [Nachweis und Bestimmung von 3-Monochlorpropan-1,2-diol (3-MCPD) mit GC-MS/MS] Lebensmittelchem, 57: 57-58.
74. Kuhlmann J (2010). Determination of bound 2,3-epoxy-1-propanol (glycidol) and bound monochloropropanediol (MCPD) in refined oils Eur J Lipid Sci Technol, n/a.
75. Kuntzer J & Weißhaar R (2006). The smoking process-A potent source of 3-chloropropane-1,2-diol (3-MCPD) in meat products.] Deut Lebensm Rundsch, 102: 397-400.
76. Küsters M, Bimber U, Ossenbrüggen A et al. (2010). Rapid and simple micromethod for the simultaneous determination of 3-MCPD and 3-MCPD esters in different foodstuffs. J Agric Food Chem, 58: 6570-6577. doi:10.1021/jf100416w PMID:20450199
77. Kwack SJ, Kim SS, Choi YW et al. (2004). Mechanism of antifertility in male rats treated with 3-monochloro-1,2-propanediol (3-MCPD). J Toxicol Environ Health A, 67: 2001-2011. doi:10.1080/15287390490514651 PMID:15513898
78. Lee JK, Byun JA, Park SH et al. (2004). Evaluation of the potential immunotoxicity of 3-monochloro-1,2-propanediol in Balb/c mice. I. Effect on antibody forming cell, mitogen-stimulated lymphocyte proliferation, splenic subset, and natural killer cell activity. Toxicology, 204: 1-11. doi:10.1016/j.tox.2004.04.005 PMID:15369844
79. Lee JK, Byun JA, Park SH et al. (2005). Evaluation of the potential immunotoxicity of 3-monochloro-1,2-propanediol in Balb/c mice II. Effect on thymic subset, delayed-type hypersensitivity, mixed-lymphocyte reaction, and peritoneal macrophage activity. Toxicology, 211: 187-196. doi:10.1016/j.tox.2005.03.005 PMID:15925022
80. Lee MR, Chiu TC, Dou JP (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 chromatographymass spectrometry. Anal Chim Acta, 591: 167-172. doi:10.1016/j.aca.2007.03.057 PMID:17481404
81. Lin Y (2000). Radiopaques. In: Kirk-Othmer Encyclopedia of Chemical Technology. Hoboken, NJ: John Wiley & Sons.
82. Liu GYT, Richey WF, Betso JE (2005). Chlorohydrins. In: Ullmann's Encyclopedia of Industrial Chemistry. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA.
83. Lynch BS, Bryant DW, Hook GJ et al. (1998). Carcinogenicity of monochloro-1,2-propanediol (α-chlorohydrin, 3-MCPD). Int J Toxicol, 17: 47-76. doi:10.1080/109158198226756
84. Majeska JB & Matheson DW (1983). Quantitative estimate of mutagenicity of tris-[1,3-dichloro-2-propyl]-phosphate (TCPP) and its possible metabolites in Salmonella. Environ Mutagen, 5: 478
85. Matthew BM & Anastasio C (2000). Determination of halogenated mono-alcohols and diols in water by gas chromatography with electron-capture detection. J Chromatogr A, 866: 65-77. doi:10.1016/S0021-9673(99)01081-X PMID:10681010
86. Meierhans DC, 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. J Chromatogr A, 802: 325-333. doi:10.1016/S0021-9673(97)01188-6
87. Merck Index (2010). The Merck Index-An Encyclopedia of Chemicals, Drugs, and Biologicals (14th Edition-Version 14.6). Whitehouse Station, NJ: Merck & Co., Inc.
88. Muller RE, Booer CD, Slaiding IR et al. (2005). Modeling the formation of heat generated toxins during the processing of malt. Proc Congr Eur Brew Conv, 30th: 167-1-167/12.
89. Nienow AM, Poyer IC, Hua I, Jafvert CT (2009). Hydrolysis and H2O2-assisted UV photolysis of 3-chloro-1,2-propanediol. Chemosphere, 75: 1015-1020. doi:10.1016/j. chemosphere.2009.01.053 PMID:19282021
90. Ohkubo T, Hayashi T, Watanabe E et al. (1995). Mutagenicity of chlorohydrins. [in Japanese]Nippon Suisan Gakkai Shi, 61: 596-601. doi:10.2331/suisan.61.596
91. Painter RB & Howard R (1982). The Hela DNA-synthesis inhibition test as a rapid screen for mutagenic carcinogens. Mutat Res, 92: 427-437. doi:10.1016/0027-5107(82)90241-X PMID:7088012
92. Paz G, Carmon A, Homonnai ZT (1985). Effect of α-chlorohydrin on metabolism and testosterone secretion by rat testicular interstitial cells. Int J Androl, 8: 139-146. doi:10.1111/j.1365-2605.1985.tb00827.x PMID:3860478
93. Pesselman RL & Feit MJ (1988). Determination of residual epichlorohydrin and 3-chloropropanediol in water by gas chromatography with electron-capture detection. J Chromatogr A, 439: 448-452. doi:10.1016/S0021-9673(01)83859-0 PMID:3403653
94. Piasecki A, Ruge A, Marquardt H (1990). Malignant transformation of mouse M2-fibroblasts by glycerol chlorohydrines contained in protein hydrolysates and commercial food. Arzneimittelforschung, 40: 1054-1055. PMID:2080943
95. Plantinga WJ, van Toorn WG, van der Stegen GHD (1991). Determination of 3-Chloropropane-1,2-Diol in Liquid Hydrolyzed Vegetable Proteins by Capillary Gas-Chromatography with Flame Ionization Detection. J Chromatogr A, 555: 311-314. doi:10.1016/S0021-9673(01)87196-X
96. Porter KE & Jones AR (1982). The effect of the isomers of α-cholorohydrin and racemic β-chlorolactate on the rat kidney. Chem Biol Interact, 41: 95-104. doi:10.1016/0009-2797(82)90020-5 PMID:6807557
97. Rahn AKK & Yaylayan VA (2010). What do we know about the molecular mechanism of 3-MCPD ester formation? Eur J Lipid Sci Technol, n/a.
98. Rétho C & Blanchard F (2005). Determination of 3-chloropropane-1,2-diol as its 1,3-dioxolane derivative at the microg kg-1 level: application to a wide range of foods. Food Addit Contam, 22: 1189-1197. doi:10.1080/02652030500197680 PMID:16356881
99. Richey WF (2000). Chlorohydrins. In: Kirk-Othmer Encyclopedia of Chemical Technology. Hoboken, NJ: John Wiley & Sons.
100. Robert MC, Oberson JM, Stadler RH (2004). Model studies on the formation of monochloropropanediols in the presence of lipase. J Agric Food Chem, 52: 5102-5108. doi:10.1021/jf049837u PMID:15291482
101. Robjohns S, Marshall R, Fellows M, Kowalczyk G (2003). In vivo genotoxicity studies with 3-monochloropropan-1,2-diol. Mutagenesis, 18: 401-404. doi:10.1093/mutage/geg017 PMID:12960406
102. Rodman LE & Ross RD (1986). Gas-liquid chromatography of 3-chloropropanediol. J Chromatogr A, 369: 97-103. doi:10.1016/S0021-9673(00)90101-8 PMID:3793835
103. Rossi AM, Migliore L, Lascialfari D et al. (1983). Genotoxicity, metabolism and blood kinetics of epichlorohydrin in mice. Mutat Res, 118: 213-226. doi:10.1016/0165-1218(83)90144-1 PMID:6877269
104. SCF (2001). Opinion of the scientific committee on food on 3-monochloro-propane-1,2-diol (3-MCPD). Brussels, Belgium: European Commission.
105. Schilter B, Scholz G, Seefelder W (2010). Fatty acid esters of chloropropanols and related compounds in food: toxicological aspects Eur J Lipid Sci Technol, n/a.
106. Schlee C, Ruge W, Kuballa T et al. (2011). [3-Monochlor-1,2-propandiol in Lebensmitteln. Aktueller Wissensstand und Untersuchungsergebnisse.]Deut Lebensm Rundsch, In press
107. SciFinder (2010). SciFinder Databases: Registry, Chemcats. American Chemical Society.
108. Seefelder W, Varga N, Studer A et al. (2008). Esters of 3-chloro-1,2-propanediol (3-MCPD) in vegetable oils: significance in the formation of 3-MCPD. Food Addit Contam Part A Chem Anal Control Expo Risk Assess, 25: 391-400. PMID:18348037
109. Silhánková L, Smíd F, Cerná M et al. (1982). Mutagenicity of glycerol chlorohydrines and of their esters with higher fatty acids present in protein hydrolysates. Mutat Res, 103: 77-81. doi:10.1016/0165-7992(82)90090-2 PMID:7035914
110. Spyres G (1993). Determination of 3-Chloropropane-1,2-Diol in Hydrolyzed Vegetable Proteins by Capillary Gas-Chromatography with Electrolytic Conductivity Detection. J Chromatogr A, 638: 71-74. doi:10.1016/0021-9673(93)85009-V
111. Stevenson D & Jones AR (1984). The action of (R)-and (S)-α-chlorohydrin and their metabolites on the metabolism of boar sperm. Int J Androl, 7: 79-86. doi:10.1111/j.1365-2605.1984.tb00762.x PMID:6715067
112. Stolzenberg SJ & Hine CH (1979). Mutagenicity of halogenated and oxygenated three-carbon compounds. J Toxicol Environ Health, 5: 1149-1158. doi:10.1080/15287397909529820 PMID:393836
113. Stolzenberg SJ & Hine CH (1980). Mutagenicity of 2-and 3-carbon halogenated compounds in the Salmonella/mammalian-microsome test. Environ Mutagen, 2: 59-66. doi:10.1002/em.2860020109 PMID:7035158
114. Svejkovská B, Novotný O, Divinová V et al. (2004). Esters of 3-chloropropane-1,2-diol in foodstuffs. Czech J Food Sci, 22: 190-196.
115. van Bergen CA, Collier PD, Cromie DDO et al. (1992). Determination of Chloropropanols in Protein Hydrolysates. J Chromatogr A, 589: 109-119. doi:10.1016/0021-9673(92)80011-I
116. van den Wijngaard AJ, Janssen DB, Witholt B (1989). Degradation of epichlorohydrin and halohydrins by bacterial cultures isolated from freshwater sediment. J Gen Microbiol, 135: 2199-2208.
117. Van Duuren BL, Goldschmidt BM, Katz C et al. (1974). Carcinogenic activity of alkylating agents. J Natl Cancer Inst, 53: 695-700. PMID:4412318
118. Velíšek J (2009). Chloropropanols. In: Process-induced food toxicants: occurrence, formation, mitigation and health risks. Stadler RH & Lineback DR, editors. Hoboken, NJ: Wiley, pp. 539-562.
119. Velíšek J, Calta P, Crews C et al. (2003). 3-Chloropropane-1,2-diol in models simulating processed foods: precursors and agents causing its decomposition. Czech J Food Sci, 21: 153-161.
120. Velíšek J, Davídek J, Hajslová J et al. (1978). Chlorohydrins in protein hydrolysates. Z Lebensm Unters Forsch, 167: 241-244. doi:10.1007/BF01135595 PMID:716635
121. Weisburger EK, Ulland BM, Nam J et al. (1981). Carcinogenicity tests of certain environmental and industrial chemicals. J Natl Cancer Inst, 67: 75-88. PMID:6942197
122. Weißhaar R (2008). Determination of total 3-chloropropane-1,2-diol (3-MCPD) in edible oils by cleavage of MCPD esters with sodium methoxide. Eur J Lipid Sci Technol, 110: 183-186. doi:10.1002/ejlt.200700197
123. Weißhaar R & Perz R (2010). Fatty acid esters of glycidol in refined fats and oils. Eur J Lipid Sci Technol, 112: 158-165. doi:10.1002/ejlt.200900137
124. Wenzl T, Lachenmeier DW, Gökmen V (2007). Analysis of heat-induced contaminants (acrylamide, chloropropanols and furan) in carbohydrate-rich food. Anal Bioanal Chem, 389: 119-137. doi:10.1007/s00216-007-1459-9 PMID:17673989
125. Wittmann R (1991). Bestimmung von Dichlorpropanolen und Monochlorpropandiolen in Würzen und würzehaltigen Lebensmitteln Z Lebensm Unters Forsch, 193: 224-229. doi:10.1007/BF01199970
126. Xing X & Cao Y (2007). Determination of 3-chloro-1,2-propanediol in soy sauces by capillary electrophoresis with electrochemical detection. Food Contr, 18: 167-172. doi:10.1016/j.foodcont.2005.09.006
127. Xu X, Ren Y, Wu P et al. (2006). The simultaneous separation and determination of chloropropanols in soy sauce and other flavoring with gas chromatography-mass spectrometry in negative chemical and electron impact ionization modes. Food Addit Contam, 23: 110-119. doi:10.1080/02652030500391929 PMID:16449052
128. Yale HL, Pribyl EJ, Braker W et al. (1950). Muscle-relaxing compounds similar to 3-(o-toloxy)-1,2-propanediol. I. Aromatic ethers of polyhydroxy alcohols and related compounds. J Am Chem Soc, 72: 3710-3716. doi:10.1021/ja01164a107
129. Yau JCW, Kwong KP, Chung SWC et al. (2008). Dietary exposure to chloropropanols of secondary school students in Hong Kong. Food Addit Contam Part B Surveill, 1: 93-99. doi:10.1080/02652030802488142
130. Zeiger E, Anderson B, Haworth S et al. (1988). Salmonella mutagenicity tests: IV. Results from the testing of 300 chemicals. Environ Mol Mutagen, 11: Suppl 121-157. doi:10.1002/em.2850110602 PMID:3277844
131. Zelinková Z, Doležal M, Velíšek J (2009a). 3-Chloropropane-1,2-diol Fatty Acid Esters in Potato Products. Czech J Food Sci, 27: S421-S424.
132. Zelinková Z, Doležal M, Velíšek J (2009b). Occurrence of 3-chloropropane-1,2-diol fatty acid esters in infant and baby foods. Eur Food Res Technol, 228: 571-578. doi:10.1007/s00217-008-0965-0
133. Zelinková Z, Novotný O, Schůrek J et al. (2008). Occurrence of 3-MCPD fatty acid esters in human breast milk. Food Addit Contam Part A Chem Anal Control Expo Risk Assess, 25: 669-676. PMID:18484295
134. Zelinková Z, Svejkovská B, Velísek J, Dolezal M (2006). Fatty acid esters of 3-chloropropane-1,2-diol in edible oils. Food Addit Contam, 23: 1290-1298. doi:10.1080/02652030600887628 PMID:17118872