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Chemical Compound Review

MOLI001868     benzaldehyde

Synonyms: AC1L9PIG
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Disease relevance of MOLI001868


Psychiatry related information on MOLI001868


High impact information on MOLI001868


Chemical compound and disease context of MOLI001868


Biological context of MOLI001868


Anatomical context of MOLI001868

  • The rate of benzaldehyde formation by forestomach microsomes was not detectable in tissue from rats on either diet [19].
  • The effects of benzaldehyde, which has been found in figs as a carcinostatic element, were studied on the uptake of nucleosides, 2-deoxy-D-glucose, and amino acids into simian virus 40-transformed rat fibroblast cells (SV40-transformed cells) and into the parent normal cells (normal cells) [20].
  • UGT1A10 compared with UGT1A7, -1A8, and -1A3 generally exhibited high activity toward acidic nonsteroidal anti-inflammatory drugs and natural benzaldehyde derivatives, while UGT1A3 metabolized most efficiently aromatic transcinnamic acids known to be generated from flavonoid glycosides by microflora in the lower gastrointestinal tract [21].
  • ALDH-3, judged to be so because it is a polymorphic enzyme (pI values ca. 6.0) present in the cytosol that is heat labile, is insensitive to inhibition by disulfiram (25 microM), much prefers benzaldehyde to acetaldehyde as a substrate and, at concentrations of 4 mM, prefers NADP to NAD as a cofactor [22].
  • PBN also decreased hepatocyte GSH content, probably as the result of its metabolism to benzaldehyde [23].

Associations of MOLI001868 with other chemical compounds


Gene context of MOLI001868

  • This confirms the interpretation of the N-terminal sequence comparisons and also indicates that benzaldehyde dehydrogenase I from Acinetobacter may be related to the other two benzaldehyde dehydrogenases [29].
  • Behavioral assays show that a threefold decrease in DSC1 mRNA is accompanied by a threefold shift in the dose response for avoidance of the repellent odorant, benzaldehyde, toward higher odorant concentrations [30].
  • One isozyme, designated ALDH3, which is very active against benzaldehyde, was found to show variable expression in hybrids made between rat hepatoma cells and human fibroblasts or fetal liver [31].
  • More potent inhibition of human CYP2A6 than mouse CYP2A5 enzyme activities by derivatives of phenylethylamine and benzaldehyde [32].
  • Furthermore, the AOH1 protein has benzaldehyde oxidizing activity with electrophoretic characteristics identical to those of a previously identified aldehyde oxidase isoenzyme (Holmes, R. S. (1979) Biochem. Genet. 17, 517-528) [33].

Analytical, diagnostic and therapeutic context of MOLI001868


  1. Selection of biocatalysts for chemical synthesis. van Sint Fiet, S., van Beilen, J.B., Witholt, B. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  2. Organ specificity in the microsomal activation and toxicity of N-nitrosomethylbenzylamine in various species. Mehta, R., Labuc, G.E., Urbanski, S.J., Archer, M.C. Cancer Res. (1984) [Pubmed]
  3. Differential enhancement of cytotoxicity by combination of the carcinostatic agent benzaldehyde and hyperthermia in simian virus 40-transformed and normal cell lines. Ishida, A., Miwa, N., Mizuno, S. Cancer Res. (1983) [Pubmed]
  4. Purification and characterization of benzaldehyde dehydrogenase I from Acinetobacter calcoaceticus. Chalmers, R.M., Fewson, C.A. Biochem. J. (1989) [Pubmed]
  5. Enhanced benzaldehyde tolerance in Zymomonas mobilis biofilms and the potential of biofilm applications in fine-chemical production. Li, X.Z., Webb, J.S., Kjelleberg, S., Rosche, B. Appl. Environ. Microbiol. (2006) [Pubmed]
  6. Final report on the safety assessment of benzaldehyde. Andersen, A. International journal of toxicology. (2006) [Pubmed]
  7. Hydrogen tunneling in enzyme reactions. Cha, Y., Murray, C.J., Klinman, J.P. Science (1989) [Pubmed]
  8. Cationic drug analysis using matrix-assisted laser desorption/ionization mass spectrometry: application to influx kinetics, multidrug resistance, and intracellular chemical change. Rideout, D., Bustamante, A., Siuzdak, G. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  9. Molecular cloning of an olfactory gene from Drosophila melanogaster. Hasan, G. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  10. Changes in aldehyde dehydrogenase occurring during rat hepatocarcinogenesis induced by ethionine combined with dietary choline deficiency. Evces, S., Lindahl, R. Cancer Res. (1986) [Pubmed]
  11. Identification of hepatocarcinogenesis-associated aldehyde dehydrogenase in normal rat urinary bladder. Lindahl, R. Cancer Res. (1986) [Pubmed]
  12. Anaerobic toluene oxidation to benzyl alcohol and benzaldehyde in a denitrifying Pseudomonas strain. Altenschmidt, U., Fuchs, G. J. Bacteriol. (1992) [Pubmed]
  13. Involvement of manganese in conversion of phenylalanine to benzaldehyde by lactic acid bacteria. Nierop Groot, M.N., de Bont, J.A. Appl. Environ. Microbiol. (1999) [Pubmed]
  14. Characterization of an inducible phenylserine aldolase from Pseudomonas putida 24-1. Misono, H., Maeda, H., Tuda, K., Ueshima, S., Miyazaki, N., Nagata, S. Appl. Environ. Microbiol. (2005) [Pubmed]
  15. Toxicity of benzyl alcohol in adult and neonatal mice. McCloskey, S.E., Gershanik, J.J., Lertora, J.J., White, L., George, W.J. Journal of pharmaceutical sciences. (1986) [Pubmed]
  16. Kinetic behavior of Desulfovibrio gigas aldehyde oxidoreductase encapsulated in reverse micelles. Andrade, S.L., Brondino, C.D., Kamenskaya, E.O., Levashov, A.V., Moura, J.J. Biochem. Biophys. Res. Commun. (2003) [Pubmed]
  17. 4,6-Benzylidene-D-glucose, a benzaldehyde derivative that inhibits protein synthesis but not mitosis of NHIK 3025 cells. Pettersen, E.O., Dornish, J.M., Rønning, O.W. Cancer Res. (1985) [Pubmed]
  18. High-resolution crystal structure of AKR11C1 from Bacillus halodurans: an NADPH-dependent 4-hydroxy-2,3-trans-nonenal reductase. Marquardt, T., Kostrewa, D., Balakrishnan, R., Gasperina, A., Kambach, C., Podjarny, A., Winkler, F.K., Balendiran, G.K., Li, X.D. J. Mol. Biol. (2005) [Pubmed]
  19. Esophageal microsomal metabolism of N-nitrosomethylbenzylamine in the zinc-deficient rat. Barch, D.H., Kuemmerle, S.C., Hollenberg, P.F., Iannaccone, P.M. Cancer Res. (1984) [Pubmed]
  20. Selective inhibition by benzaldehyde of the uptake of nucleosides and sugar into simian virus 40-transformed cells. Watanuki, M., Sakaguchi, K. Cancer Res. (1980) [Pubmed]
  21. Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation. Basu, N.K., Kubota, S., Meselhy, M.R., Ciotti, M., Chowdhury, B., Hartori, M., Owens, I.S. J. Biol. Chem. (2004) [Pubmed]
  22. Identification and characterization of a novel class 3 aldehyde dehydrogenase overexpressed in a human breast adenocarcinoma cell line exhibiting oxazaphosphorine-specific acquired resistance. Sreerama, L., Sladek, N.E. Biochem. Pharmacol. (1993) [Pubmed]
  23. Effect of spin traps in isolated rat hepatocytes and liver microsomes. Albano, E., Cheeseman, K.H., Tomasi, A., Carini, R., Dianzani, M.U., Slater, T.F. Biochem. Pharmacol. (1986) [Pubmed]
  24. A specific affinity reagent to distinguish aldehyde dehydrogenases and oxidases. Enzymes catalyzing aldehyde oxidation in an adult moth. Tasayco, M.L., Prestwich, G.D. J. Biol. Chem. (1990) [Pubmed]
  25. Factors affecting the production of L-phenylacetylcarbinol by yeast: a case study. Oliver, A.L., Anderson, B.N., Roddick, F.A. Adv. Microb. Physiol. (1999) [Pubmed]
  26. Investigation of the microheterogeneity and aglycone specificity-conferring residues of black cherry prunasin hydrolases. Zhou, J., Hartmann, S., Shepherd, B.K., Poulton, J.E. Plant Physiol. (2002) [Pubmed]
  27. Variation of transition-state structure as a function of the nucleotide in reactions catalyzed by dehydrogenases. 1. Liver alcohol dehydrogenase with benzyl alcohol and yeast aldehyde dehydrogenase with benzaldehyde. Scharschmidt, M., Fisher, M.A., Cleland, W.W. Biochemistry (1984) [Pubmed]
  28. Mechanism of aldehyde oxidation catalyzed by horse liver alcohol dehydrogenase. Olson, L.P., Luo, J., Almarsson, O., Bruice, T.C. Biochemistry (1996) [Pubmed]
  29. Comparison of benzyl alcohol dehydrogenases and benzaldehyde dehydrogenases from the benzyl alcohol and mandelate pathways in Acinetobacter calcoaceticus and from the TOL-plasmid-encoded toluene pathway in Pseudomonas putida. N-terminal amino acid sequences, amino acid compositions and immunological cross-reactions. Chalmers, R.M., Keen, J.N., Fewson, C.A. Biochem. J. (1991) [Pubmed]
  30. The DSC1 channel, encoded by the smi60E locus, contributes to odor-guided behavior in Drosophila melanogaster. Kulkarni, N.H., Yamamoto, A.H., Robinson, K.O., Mackay, T.F., Anholt, R.R. Genetics (2002) [Pubmed]
  31. Biochemical genetic analysis of human and rodent aldehyde dehydrogenase (ALDH). Hopkinson, D.A., Santisteban, I., Povey, S., Smith, M. Alcohol (1985) [Pubmed]
  32. More potent inhibition of human CYP2A6 than mouse CYP2A5 enzyme activities by derivatives of phenylethylamine and benzaldehyde. Rahnasto, M., Raunio, H., Poso, A., Juvonen, R.O. Xenobiotica (2003) [Pubmed]
  33. Cloning of the cDNAs coding for two novel molybdo-flavoproteins showing high similarity with aldehyde oxidase and xanthine oxidoreductase. Terao, M., Kurosaki, M., Saltini, G., Demontis, S., Marini, M., Salmona, M., Garattini, E. J. Biol. Chem. (2000) [Pubmed]
  34. Michaelis-Menten analysis of bovine plasma amine oxidase by capillary electrophoresis using electrophoretically mediated microanalysis in a partially filled capillary. Van Dyck, S., Van Schepdael, A., Hoogmartens, J. Electrophoresis (2001) [Pubmed]
  35. Natural glycosides containing allopyranose from the passion fruit plant and circular dichroism of benzaldehyde cyanohydrin glycosides. Christensen, J., Jaroszewski, J.W. Org. Lett. (2001) [Pubmed]
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