Skip to main content

Muconaldehyde, A Potential Toxic Intermediate of Benzene Metabolism

  • Chapter
  • First Online:

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 136))

Abstract

The metabolite of benzene that is responsible for its hematological toxicity is unknown. Benzene is of course the parent aromatic hydrocarbon and mush attention has been focussed on classical pathways of aromatic hydrocarbon metabolism in the search for toxic benzene metabolites. Elegant studies by a number of groups, including work presented at this symposium by Snyder, Irons, and Tunek, have evaluated metabolites such as benzene oxide, catechol, phenol, hydroquinone and their derivatives (See reviews by Snyder et al, 1977; Laskin and Goldstein, 1977). While there are some interesting clues concerning potentially toxic intermediates, and much important information has been obtained, the metabolic pathway and agent(s) responsible for the hematological toxicity of benzene remains unidentified.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Beutler, E., Duron, O., and Kelly, B.M., 1963, Improved Method for the determination of blood glutathione, J. Lab. Clin. Med., 61: 882.

    CAS  Google Scholar 

  • Clarke, B.J., and Housman, D., 1977, Characterization of an erythroid precursor cell of high proliferative capacity in normal human peripheral blood, Proc. Natl. Acad. Sci., U.S.A., 74: 1105.

    CAS  PubMed  Google Scholar 

  • Conroy, P.J., Nodes, J.T., Slater, T.F., and White, G.W., 1977, The inhibitory effects of a 4-hydroxy-pentenal: cysteine adduct against sarcoma 180 cells in mice, Europ. J. Cancer, 13: 55.

    CAS  Google Scholar 

  • Davies, S.G., and Whitham, G.H., 1977, Benzene oxide-oxepin. Oxidation to muconaldehyde, J. Chem. Soc., Perkin Trans 1., 1346.

    Google Scholar 

  • Goldstein, B.D., Rozen, M.G., and Snyder, C.A., Prolonged red cell hemolysis in mice inhaling benzene, 1980, Abstr. of Papers, Soc. of Toxicol., 19th Ann. Meet., A 39.

    Google Scholar 

  • Gottfried, E.L., and Robertson, N.A., 1974, Glycerol lysis time as a screening test for erythrocyte disorders, J. Lab. Clin. Med., 83: 323.

    CAS  PubMed  Google Scholar 

  • Javid, J., Pettis, P.K., Koenig, R.J., and Cerami, A., 1978, Immunologic characterization and quantification of haemoglobin Alc, Brit. J. Haematol., 38: 329.

    CAS  Google Scholar 

  • Karrer, P., Eugster, C.H., and Perl, S., 1949, Muconsäuredialdehyd und octadien-(3,5)-dion-(2,7), Hely. chim. Acta, 32: 1013.

    Article  CAS  Google Scholar 

  • Kossmehl, G., and Bohn, B., 1974, Notiz über eine einfache synthese von mucondialdehyd, Chem. Ber., 107: 710.

    CAS  Google Scholar 

  • Laskin, S., and Goldstein, B.D., 1977, Benzene toxicity: a critical evaluation, J. Toxicol. Environ. Hlth., Supplement 2.

    Google Scholar 

  • Loeff, I., and Stein, G., 1959, Aromatic ring opening in the presence of oxygen in irradiated solutions, Nature, 184: 901.

    Article  Google Scholar 

  • Mukai, F.H., and Goldstein, B.D., 1976, Mutagenicity of malonaldehyde, a decomposition product of peroxidized polyunsaturated fatty acids, Science, 191: 868.

    Article  CAS  Google Scholar 

  • Nakajima, M., Tomida, I., and Takei, S., 1959, Zur chemie des benzyglykols, IV, darstellung von cis-benzyglykol, stereoisomeren mucondialdehyden und kondurit-F, Chem. Ber., 92: 163.

    CAS  Google Scholar 

  • Parke, D.V., and Williams, R.T., 1953, Studies in detoxication 49. The metabolism of benzene containing (14C1) benzene, Biochem. J., 54: 231.

    CAS  Google Scholar 

  • Sammet, D., Lee, E.W., Kocsis, J.J., and Snyder, R., 1979, Partial hepatectomy reduces both metabolism and toxicity of benzene, J. Toxicol. Environ. Health, 5: 785.

    Google Scholar 

  • Snyder, R., Lee, E.W., Kocsis, J.J., and Witmer, C.M., 1977, Bone marrow depressant and leukemogenic actions of benzene, Life Sci., 21: 1709.

    CAS  Google Scholar 

  • Tepperman, A.D., Curtis, J.E., and McCulloch, E.A., 1974, Erythropoietic colonies in cultures of human marrow, Blood, 44: 659.

    CAS  PubMed  Google Scholar 

  • Trippet, S., and Walker, D.M., 1961, The phosphobetaines: preparation and properties, J. Chem. Soc., 1266.

    Google Scholar 

  • Yau, T.M., 1979, Mutagenicity and cytotoxicity of malonaldehyde in mammalian cells, Mech. Ageing Development, 11: 137.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1982 Springer Science+Business Media New York

About this chapter

Cite this chapter

Goldstein, B.D., Witz, G., Javid, J., Amoruso, M.A., Rossman, T., Wolder, B. (1982). Muconaldehyde, A Potential Toxic Intermediate of Benzene Metabolism. In: Snyder, R., et al. Biological Reactive Intermediates—II. Advances in Experimental Medicine and Biology, vol 136. Springer, New York, NY. https://doi.org/10.1007/978-1-4757-0674-1_20

Download citation

  • DOI: https://doi.org/10.1007/978-1-4757-0674-1_20

  • Published:

  • Publisher Name: Springer, New York, NY

  • Print ISBN: 978-1-4757-0676-5

  • Online ISBN: 978-1-4757-0674-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics