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Mutagenicity of 1,3-dichloropropan-2-ol (1,3-DCP) and 2,3-dichloropropan-1-ol (2,3-DCP)
COM statement COM/01/S2 - May 2001

Introduction

1. 1,3-Dichloropropan-2-ol (1,3-DCP) and 2,3-dichloropropan-1-ol (2,3-DCP) are members of a group of chemicals called chloropropanols. This group includes 3-monochloro propane 1,2-diol (3-MCPD), which has recently been considered by both the COM (1) and the COC (2). Like 3-MCPD, 1,3-DCP and 2,3-DCP can be present as contaminants in epichlorohyrin/amine coplymers used as flocculants or coaglulant aids in water treatment. These polyamine flocculants have been available for many years as approved products for use in water treatment and therefore 1,3-DCP and 2,3-DCP may potentially be present in drinking water from their use. 1,3-DCP, like 3-MCPD, can also be present as process contaminant of food where acid-hydrolysed vegetable protein (acid-HVP) has been used as an ingredient, such as soy and similar oriental sauces.

2. 1,3-DCP has not previously been considered by COM but has been considered by COC, originally in 1991 and more recently in 2001. The COC noted that in a carcinogenicity study undertaken by Hercules Inc. (3) 1,3-DCP was administered in the drinking water of 80 male and 80 female Wistar rats for 104 weeks. Statistically significant positive trends were observed for benign and malignant tumours (intermediate and high dose level) in the liver, kidney, tongue/oral cavity and thyroid. The COC's conclusions for 1,3 DCP have been published. (4). 2,3-DCP has not been previously considered by COM, but COC conclusions on this substance are contained in the COC statement. (4)

3. In 1993 the FAO/WHO Expert Committee on Food Additives (JECFA) concluded that, because of its carcinogenicity, 1,3-DCP is an undesirable contaminant in food and that levels should be reduced to as low as technologically achievable. (5) 2,3-DCP has not been considered by JECFA. The Drinking Water Inspectorate (DWI) and the Food Standards Agency (FSA) asked the COM for advice on these two chemicals in view of the recently published statements by the COM and COC on 3-MCPD.

COM evaluation

4. The Committee was aware that 1,3-DCP and 2,3-DCP are closely related compounds and structurally similar to 3-MCPD which had been considered at its previous meeting. Members were informed that, at present, there are no mandatory contaminant levels for these chloropropanols, either in food or drinking water.

1,3-DCP

5. Members agreed that the metabolism of 1,3-DCP was likely to produce the reactive epoxide intermediate that could damage DNA. Members were aware that 1,3-DCP had been found to be mutagenic to Salmonella typhimurium in strains TA 1535 and/or TA 100. ( 6-13) Studies with mammalian cells have produced increased frequencies of sister chromatid exchanges and chromosome aberrations. (14,15) A positive result has been obtained in the mouse lymphoma assay. (16,17) 1,3-DCP was negative in the wing spot test in Drosophila melagonaster (a somatic mutation and recombination test). (18) No in-vivo mammalian studies have been carried out.

2,3-DCP

6. Members were aware that there was very little data on the absorption, distribution, and excretion of 2,3-DCP. Theoretically, 2,3-DCP could be metabolised to produce epichlorohydrin (and subsequently glycidol) and therefore there were structural alerts for genotoxicity and carcinogenicity.

7. The Committee noted 2,3-DCP was mutagenic in Salmonella typhimurium strains TA 100 and TA 1535 in a study with and without metabolic activation (10), and mutagenic in another Ames test. (9). Positive results were also obtained for sister chromatid exchange with Chinese Hamster V79 cells both with and without metabolic activation. (14) Members were aware that in the limited studies conducted, 2,3-DCP was genotoxic in-vitro with and without metabolic activation in bacterial and mammalian cells. No in-vivo studies in mammals have been carried out.

COM Conclusion

8. The committee concluded that it would be prudent to regard 1,3-DCP and 2,3-DCP as potentially genotoxic in-vivo and agreed that both compounds should be tested for genotoxicity in-vivo using the approach set out in the COM guidelines.

References

1. Mutagenicity of 3-Monochloro Propane 1,2-Diol (3-MCPD) COM Statement - October 2000 - (COM/00/S4). http://www.doh.gov.uk/mcpd2.htm

2. Carcinogenicity of 3-Monochloro Propane 1,2-Diol (3-MPCD) COC Statement - December 2000 - COC/00/S5 (Update of COC/99/S5). http://www.doh.gov.uk/mcpd1.htm

3. Hercules Inc. (1986). 104-Week Chronic Toxicity and Oncogenicity Study with 1,3-Dichlor-propanol-2-ol in the Rat. Unpublished Report No. 017820 from Research and Consulting Company AG, ltingen, Switzerland.

4. Carcinogenicity of 1,3-dichloropropan-2-ol (1,3 DCP) and 2,3 -dichloropropan-1-ol (2,3 DCP)
COC Statement - May 2001 - (COC/01/S1) http://www.doh.gov.uk/coc.htm

5. Olsen P. (1993) Chloropropanols In: Toxicological Evaluation of Certain Food Additives and Contaminants, Joint Expert Committee on Food Additives, World Health Organization, Geneva, Switzerland, (41st Meeting) (WHO FOOD ADDITIVES SERIES) No. 32:267- 285.

6. Hahn H. Eder E and Deininger C. (1991). Genotoxicity of 1,3-dichloro-2-propanol in the SOS chromotests and in the Ames tests. Elucidation of the genotoxic mechanism. Chem. Biol. Interactions, 80 ; 73-88.

7. Silhankova L. Smid F, Cerna M, Davidek J, and Velisek J. (1982). Mutagenicity of glycerol chlorohydrins and of their esters with higher faty acids present in protein hydrolysates. Mutation research, 103 ; 77-81.

8 Stolzenberg S.J. & Hine C.H. (1980). Mutagenicity of 2- and 3-Carbon halogenated compounds in the Salmonella/Mammalian-Microsome test. Environmental Mutagenesis, 2 ; 59-66.

9. Zeiger E, Anderson B, Haworth S, Lawlor T, Mortelmans K. (1988) Salmonella mutagenicity tests: IV. Results from the testing of 300 chemicals. Environ Molec Mutagen 1 (S12) ; l - 158.

10 Nakamura A. Tateno N, Kogima s, Kaniwa M-A and Kawamura T (1979). The mutagenicity of halogenated alkanols and their phosphoric acid esters for Salmonella typhimurium. Mutation Research, 66 ; 373-380.

11. Ohkubo T, Hayashi T, Watanabe E, Endo H, Goto S, Mizoguchi T, Mori Y (1995) Mutagenicity of chlorohydrins. Nippon Suisan Gakkaishi 61 ; 596-601 (in Japanese)

12 Gold MD, Blum A and Ames B (1978). Another flame retardant, Tris-(1,3-dichloro-2-propyl)-phosphate, and its expected metabolites are mutagens. Science 200 ; 785-787.

13 Lynn RK, Wong K Garvie-Gould C and Kennish JM. (1981). Disposition of the flame retardant, Tris (1,3-dichloro-2-propyl) phosphate in the rat. Drug metabolism and Disposition, 9 ; 434-451.

14. von der Hude W. Scheutwinkel M, Gramlich U, Fissler B and Basler A (1987). Genotoxicity of three-carbon compounds evaluated in the SCE test In-Vitro. Environmental Mutagenesis, 9 ; 401-410.

15. Putman D. & Morris M. (1990). Sister chromatid exchange and chromosome aberration assay in Chinese hamster ovary cells, 1,3-dichloro-2-propanol. Microbiological Associates, Inc. Laborotory study No. T9250.337 NTP.

16 San R. & Blanchard M. (1990). L5178Y TK+/- mouse lymphoma mutagenesis assay, 1,3-dichloro-2-propanol. Microbiological Associates, Inc. Laboratory study No. T9250.702.

17. Henderson LM, Bosworth HJ, Ransome SJ, Banks SJ, Brabbs CE and Tinner AJ . (1987) An assessment of the mutagenic potential of 1,3 -dichloro-2-propanol, 3 -chloro-1,2-proanediol and a cocktail of chloropropanols using the mouse lymohoma TK locuc assay. Unpublished report No ULR 130 ABC/861423 from Huntingdon Research Centre, Huntingdon, Cambridgeshire England.

18. Frei H. & Wurgler F (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 Mut Res 394 ; 59-68

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