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Mutagenic compounds from chlorination of humic substances

  • Session 5: Halogenation Of Humic Substances
  • Conference paper
  • First Online:
Humic Substances in the Aquatic and Terrestrial Environment

Part of the book series: Lecture Notes in Earth Sciences ((LNEARTH,volume 33))

  • 127 Accesses

Abstract

Chlorination of natural humic substances, as well as of lignin, produces a myriad of non-chlorinated and chlorinated compounds. The identification of an important class of strongly mutagenic compounds is reviewed. The most important Ames mutagen in chlorinated drinking waters of various origin is the compound 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone ("MX"). This compound occurs at neutral pH in the acyclic form, i.e. in the form of Z-2-chloro-3-(dichloromethyl)-4-oxobutenoic acid. Its E-isomer (E-MX) is present in chlorinated drinking waters at a similar concentration, but is less mutagenic in Ames test. Both oxidised and reduced forms of MX and E-MX are also present in chlorinated waters. The present knowledge of the chemistry and toxicology of these mutagens is examined. The formation and possible elimination of the chlorination mutagens is discussed. The need of understanding the mechanisms of formation of these mutagens from humic substances during drinking water chlorination is emphasized.

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References

  1. Kronberg, L. and T. Vartiainen. Mutation Res. 206:177 (1988).

    Google Scholar 

  2. Rook, J.J. Water Treat. Exam. 23:234 (1974).

    Google Scholar 

  3. Simmon, V.F. and R.G. Tardiff. Mutation Res. 38:389 (1976).

    Google Scholar 

  4. Loper, J.C., D.R. Lang, R.S. Schoeny, B.S. Richmond, P.M. Gallagher and C.C. Smith. J. Tox. Environ. Health 4:919 (1978).

    Google Scholar 

  5. Rice, R.G. and M. Gomez-Taylor. Environ. Health Persp. 69:31 (1986).

    Google Scholar 

  6. Uden, P.C. and J.W. Miller. J. Am. Water Works Assoc. 75:524 (1983).

    Google Scholar 

  7. Christman, R.F., D.L. Norwood, D.S. Millington, J.D. Johnson and A.A. Stevens. Environ. Sci. Technol. 17:625 (1983).

    Google Scholar 

  8. E.W.B. de Leer, J.S.S. Damste and L. de Galan. In: Water Chlorination. Chemistry, Environmental Impact and Health Effects Vol. 5, p. 843 (Chelsea, MI: Lewis).

    Google Scholar 

  9. Meier, J.R., H.P. Ringhand, W.E. Coleman, J.W. Munch, R.P. Streicher, W.H. Kaylor and K.M. Schenck. Mutation Res. 157:111 (1985).

    Google Scholar 

  10. Holmbom, B.R., R.H. Voss, R.D. Mortimer and A. Wong. Tappi 64:172 (1981).

    Google Scholar 

  11. Holmbom, B.R., R.H. Voss, R.D. Mortimer and A. Wong. Environ. Sci. Technol. 18:333 (1984).

    Google Scholar 

  12. Kronberg, L., B. Holmbom and L. Tikkanen. Vatten 41:106 (1985).

    Google Scholar 

  13. Kronberg, L., B. Holmbom and L. Tikkanen. In: A. Björseth and G. Angeletti, Eds., Organic Micropollutants in the Aquatic Environment, p. 449 (Dordrecht: D. Deidel, 1985).

    Google Scholar 

  14. Padmapriya, A.A., G. Just and N.G. Lewis. Can. J. Chem. 63:828 (1985).

    Google Scholar 

  15. Hemming, J., B. Holmbom, M. Reunanen and L. Kronberg. Chemosphere 15:549 (1986).

    Google Scholar 

  16. Meier, J.R., R.B. Knohl, W.E. Coleman, H.P. Ringhand, J.W. Munch, W.H. Kaylor, R.P. Streicher and F.C. Kopfler. Mutation Res. 189:363 (1987).

    Google Scholar 

  17. Horth. H., Aqua 38:80 (1989).

    Google Scholar 

  18. Backlund, P., E. Wondergem, K. Voogd and A. de Jong. Sci. Total Environ. 84:273 (1989).

    Google Scholar 

  19. Kronberg, L., B. Holmbom, M. Reunanen and L. Tikkanen. Environ. Sci. Technol. 22:1097 (1988).

    Google Scholar 

  20. Holmbom, B., L. Kronberg and A. Smeds. Chemosphere 18:2237 (1989).

    Google Scholar 

  21. Kronberg, L. and R.F. Christman. Sci. Tot. Environ. 81/82:219 (1989).

    Google Scholar 

  22. Horth, H., M. Fielding, T. Gibson, H.A. James and H. Ross. Report BRD 2+38-M, Water Research Centre, Medmemham, U.K. 1989.

    Google Scholar 

  23. Kronberg, L., B. Holmbom and L. Tikkanen. In: Water Chlorination — Chemistry, Environmental Impact and Health Effects, Vol. 6, pp. 137–146 (Chelsea, MI: Lewis 1990).

    Google Scholar 

  24. Ishiguro, Y., R.T. Lalonde and C.W. Dence. Environ. Toxicol. Chem. 6:935 (1987).

    Google Scholar 

  25. Meier, J.R., R.B. Knohl, B.A. Merrick and C.L. Smallwood. In: Water Chlorination Chemistry, Environmental Impact and Health Effects, Vol. 6, pp. 159–170 (Chelsea, MI: Lewis 1990).

    Google Scholar 

  26. Meier, J.R., A.B. De Angelo, F.B. Daniel, K.M. Schenck, M.F. Skelly and S.L. Huang. Paper presented at the Fifth International Conference on Environmental Mutagens, Cleveland, July 10–15, 1989.

    Google Scholar 

  27. Meier, J.R., W.F. Blazak and R.B. Knohl. Environ. Mutag. 10:411 (1987).

    Google Scholar 

  28. Meier, J.R. Mutation Res. 196:211 (1988).

    Google Scholar 

  29. Backlund, P., E. Wondergem, K. Voogd and A. de Jong. Chemosphere 18:1903 (1989).

    Google Scholar 

  30. Nyman, S. M.Sc. Thesis, Åbo Akademi 1989 (in Swedish).

    Google Scholar 

  31. Vartiainen, T., A. Liimatainen, P. Kauranen and L. Hiisivirta. Chemosphere 17:189 (1988).

    Google Scholar 

  32. Holmbom, B., L. Kronberg, P. Backlund, V-A Långvik, J. Hemming, M. Reunanen, A. Smeds and L. Tikkanen. In: Water Chlorination, Chemistry, Environmental Impact and Health Effects, Vol. 6, pp. 125–135 (Chelsea, MI: Lewis 1990).

    Google Scholar 

  33. Backlund, P., L. Kronberg and L. Tikkanen. Chemosphere 17:1329 (1988).

    Google Scholar 

  34. Cheh, A.M., J. Skochdopole, D. Koski and L. Cole. Science 207:90 (1980).

    Google Scholar 

  35. Wilcox, P. and S. Denny. In: Water Chlorination — Chemistry, Environmental Impact and Health Effects, Vol. 5, pp. 1341-(Chelsea, Lewis).

    Google Scholar 

  36. Croue, J-P and D.A. Reckhow. Environ. Sci. Technol. 23:1412 (1989).

    Google Scholar 

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Authors and Affiliations

  1. Department of Forest Products Chemistry, Åbo Akademi, Finland

    Bjarne Holmbom

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  1. Bjarne Holmbom
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Bert Allard Hans Borén Anders Grimvall

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© 1991 Springer-Verlag

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Holmbom, B. (1991). Mutagenic compounds from chlorination of humic substances. In: Allard, B., Borén, H., Grimvall, A. (eds) Humic Substances in the Aquatic and Terrestrial Environment. Lecture Notes in Earth Sciences, vol 33. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0010495

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  • DOI: https://doi.org/10.1007/BFb0010495

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  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-53702-1

  • Online ISBN: 978-3-540-46985-8

  • eBook Packages: Springer Book Archive

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