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Chemical Compound Review

Muconaldehyde     (2E,4E)-hexa-2,4-dienedial

Synonyms: CCRIS 3786, LS-74895, LS-74896, LMFA06000011, AKOS006273631, ...
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Disease relevance of Muconic aldehyde

  • The results are discussed in terms of the toxicity of muconaldehyde at tissues distal from the liver, where it is believed to be formed from the metabolism of benzene [1].

High impact information on Muconic aldehyde


Chemical compound and disease context of Muconic aldehyde


Biological context of Muconic aldehyde


Anatomical context of Muconic aldehyde


Associations of Muconic aldehyde with other chemical compounds


Gene context of Muconic aldehyde

  • Metabolism by contaminating ADH of muconaldehyde formed during microsomal incubation of benzene could be involved in the formation of CHO-M-OH and COOH-M-OH [15].
  • Our laboratory recently identified trans,trans-muconaldehyde (MUC), a six-carbon diene dialdehyde, as a hematotoxic microsomal metabolite of benzene (Latriano et al., Proc Natl Acad Sci USA 83: 8356-8360, 1986) [17].
  • Muconaldehyde-reacted BSA exhibits a decrease in amino groups as measured by the fluorescamine assay [18].
  • Other fractions were found to contain muconaldehyde reductase activity independent of Adh1, and one enzyme was identified as the NADPH-dependent aldehyde reductase AKR1A4 [19].

Analytical, diagnostic and therapeutic context of Muconic aldehyde

  • Separation of muconaldehyde, both with and without trapping with TBA, from other benzene metabolites in the incubation mixture was accomplished by HPLC [2].
  • Gel filtration chromatography on Sephadex G-200 of muconaldehyde-reacted BSA shows elution of a high-molecular-weight fraction and a second fraction which elutes at the elution volume of monomeric unreacted BSA [18].


  1. Reaction of (E,E)-muconaldehyde and its aldehydic metabolites, (E,E)-6-oxohexadienoic acid and (E,E)-6-hydroxyhexa-2,4-dienal, with glutathione. Kline, S.A., Xiang, Q., Goldstein, B.D., Witz, G. Chem. Res. Toxicol. (1993) [Pubmed]
  2. Formation of muconaldehyde, an open-ring metabolite of benzene, in mouse liver microsomes: an additional pathway for toxic metabolites. Latriano, L., Goldstein, B.D., Witz, G. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  3. Increased gene expression in human promyeloid leukemia cells exposed to trans,trans-muconaldehyde, a hematotoxic benzene metabolite. Ho, T.Y., Witz, G. Carcinogenesis (1997) [Pubmed]
  4. DNA-protein crosslink and DNA strand break formation in HL-60 cells treated with trans,trans-muconaldehyde, hydroquinone and their mixtures. Amin, R.P., Witz, G. International journal of toxicology. (2001) [Pubmed]
  5. Studies on the mechanism of benzene toxicity. Snyder, R., Dimitriadis, E., Guy, R., Hu, P., Cooper, K., Bauer, H., Witz, G., Goldstein, B.D. Environ. Health Perspect. (1989) [Pubmed]
  6. Short-term toxicity of trans,trans-muconaldehyde. Witz, G., Rao, G.S., Goldstein, B.D. Toxicol. Appl. Pharmacol. (1985) [Pubmed]
  7. Effect of sorbic acid administration on urinary trans,trans-muconic acid excretion in rats exposed to low levels of benzene. Marrubini, G., Coccini, T., Maestri, L., Manzo, L. Food Chem. Toxicol. (2002) [Pubmed]
  8. Inhibition by reactive aldehydes of superoxide anion radical production in stimulated human neutrophils. Witz, G., Lawrie, N.J., Amoruso, M.A., Goldstein, B.D. Chem. Biol. Interact. (1985) [Pubmed]
  9. Inhibition of microsomal cytochrome c reductase activity by a series of alpha, beta-unsaturated aldehydes. Cooper, K.O., Witmer, C.M., Witz, G. Biochem. Pharmacol. (1987) [Pubmed]
  10. DNA-protein cross-link levels in bone marrow cells of mice treated with benzene or trans,trans-muconaldehyde. Schoenfeld, H.A., Witz, G. J. Toxicol. Environ. Health Part A (1999) [Pubmed]
  11. Pathways of trans,trans-muconaldehyde metabolism in mouse liver cytosol: reversibility of monoreductive metabolism and formation of end products. Zhang, Z., Kline, S.A., Kirley, T.A., Goldstein, B.D., Witz, G. Arch. Toxicol. (1993) [Pubmed]
  12. Benzene metabolites block gap junction intercellular communication. Role in hematotoxicity and leukemia? Rivedal, E., Witz, G. Chem. Biol. Interact. (2005) [Pubmed]
  13. Effect of dimethyl sulfoxide on the genotoxicity and metabolism of benzene in vivo. Anwar, W.A., Au, W.W., Legator, M.S., Sadagopa Ramanujam, V.M. Carcinogenesis (1989) [Pubmed]
  14. Chromatographic and spectrophotometric characterization of adducts formed during the reaction of trans,trans-muconaldehyde with 14C-deoxyguanosine 5'-phosphate. Latriano, L., Witz, G., Goldstein, B.D., Jeffrey, A.M. Environ. Health Perspect. (1989) [Pubmed]
  15. Iron-stimulated ring-opening of benzene in a mouse liver microsomal system. Mechanistic studies and formation of a new metabolite. Zhang, Z., Goldstein, B.D., Witz, G. Biochem. Pharmacol. (1995) [Pubmed]
  16. High-performance liquid chromatography analysis of the thiobarbituric acid adducts of malonaldehyde and trans,trans-muconaldehyde. Yu, L.W., Latriano, L., Duncan, S., Hartwick, R.A., Witz, G. Anal. Biochem. (1986) [Pubmed]
  17. Comparative metabolism of benzene and trans,trans-muconaldehyde to trans,trans-muconic acid in DBA/2N and C57BL/6 mice. Witz, G., Maniara, W., Mylavarapu, V., Goldstein, B.D. Biochem. Pharmacol. (1990) [Pubmed]
  18. Interaction of trans,trans-muconaldehyde with bovine serum albumin. Udupi, V., Goldstein, B.D., Witz, G. Arch. Biochem. Biophys. (1994) [Pubmed]
  19. Metabolism of trans, trans-muconaldehyde, a cytotoxic metabolite of benzene, in mouse liver by alcohol dehydrogenase Adh1 and aldehyde reductase AKR1A4. Short, D.M., Lyon, R., Watson, D.G., Barski, O.A., McGarvie, G., Ellis, E.M. Toxicol. Appl. Pharmacol. (2006) [Pubmed]
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