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Chemical Compound Review

Katechol     benzene-1,2-diol

Synonyms: catechol, Oxyphenate, benzenediol, Benzcatechin, Pyrokatechin, ...
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Disease relevance of CATECHIN


High impact information on CATECHIN

  • Catechol (CAS: 120-80-9), given in drinking water to rats, was the most effective of 5 phenols in enhancing [3H]thymidine incorporation [( 3H]dThd-l) into esophageal DNA [6].
  • Coadministration of 1,2-dihydroxybenzene (catechol) with (+)-[3H]BaP-7,8-diol decreased the formation of (-)-anti-[3H]BPDE and also decreased lipid peroxidation, as measured by the extent of formation of thiobarbituric acid-reactive material in mouse epidermis [7].
  • Here we describe a sensitive radiochemical assay for dihydrodiol dehydrogenase in which the oxidation of benzenedihydrodiol to pyrocatechol is coupled to O-methylation catalyzed by catechol-O-methyltransferase (EC [8].
  • (+/-)-[3H]Epinephrine binds to beta-receptors in calf cerebellar and rat lung membranes in the presence of 1.0 mM pyrocatechol and 1.0 microM phentolamine, with dissociation constants at 4 degrees C of 11 nM and 24 nM, respectively [9].
  • Red clover (Trifolium pratense) leaves contain high levels of polyphenol oxidase (PPO) activity and o-diphenol substrates [10].

Biological context of CATECHIN


Anatomical context of CATECHIN

  • In addition to causing an increase in the pepsinogen-isozyme-1-altered pyloric glands (PAPG), which are considered to be putative preneoplastic precursor lesions in the rat glandular stomach, CC treatment was associated with submucosal growth of pyloric mucosal cells tending to decreased pepsinogen isoenzyme 1 binding [2].
  • Rat hepatocytes released benzene-1,2-dihydrodiol, hydroquinone (HQ), catechol (CT), phenol (PH), trans-trans-muconic acid, and a number of phase II metabolites such as PH sulfate and PH glucuronide [15].
  • Flavin-containing monooxygenase-1 (FMO1) purified to homogeneity from pig liver microsomes catalyzes NADPH- and oxygen-dependent oxidation of salicylaldehyde to pyrocatechol and formate [16].
  • Administration of CA or HR to the arthritic animals was found to have a prophylactic action by stabilizing liver lysosomes and reducing the free lysosomal enzyme activities in serum, liver, kidney and spleen [17].
  • The effects of pyrocatechol and its monosubstituents on the hemolysis of bovine erythrocytes induced by the hydrophilic free radical initiator, 2,2'-azobis(2-amidinopropane)dihydrochloride (AAPH), were investigated [18].

Associations of CATECHIN with other chemical compounds


Gene context of CATECHIN

  • These results contrast with the almost complete inhibition of autoxidation (NADH oxidation) of ortho-hydroquinone during reduction of aminochrome catalyzed by DT-diaphorase in the presence of both superoxide dismutase and catalase [23].
  • Thus, this enzyme shows tyrosine hydroxylase activity and it catalyzes the oxidation of a wide variety of o-diphenol as well as o-methoxy-activated phenols [24].
  • In addition, primers and probes detecting aromatic dioxygenase genes were derived from P. putida ATCC 17484 (ndoB), P. putida F1 (todC1), P. putida ATCC 33015 (xylE and cat23), and P. pseudoalcaligenes KF707 (bphA) [25].
  • The method is based on the COMT-mediated O-methylation of 4-(naphtho [1,2-d] thiazol-2-yl) pyrocatechol, the product of which was determined fluorometrically [26].
  • At pH 7.4, where the oxidative polymerization of catechols proceeds spontaneously, pyrocatechol produced no effect on the toxin binding function of AcChR, whereas comparable concentrations of TMC led to inactivation of half of all available sites [27].

Analytical, diagnostic and therapeutic context of CATECHIN

  • All PAH degraders were examined for the presence of an initial PAH dioxygenase and C230, which catalyse key steps of PAH degradation, by PCR amplification of gene fragments and subsequent hybridization [28].
  • At pH 5.5 and -0.1 V, the calibration graphs of GE based biosensors were hyperbolic if pyrocatechol was used [29].
  • The serum concentration and urinary excretion of these metabolites were also compared after the oral administration of different GSP monomers (gallic acid, CT, and EC), normal GSP, and the high molecular weight components of GSP (GSPH) [30].
  • The sequence analysis of two purified dioxygenases (CatA and PcaGH) indicated that CatA is closely associated with the CatA of Acinetobacter radiresistance, but PcaGH is only moderately associated with the PcaGH of Acinetobacter sp. ADP1 [31].


  1. Double-head haptens. Synthesis of and experimentally induced contact sensitivity to substances containing two unrelated haptens, pyrocatechol and alpha-methylene-gamma-butyrolactone, in the same molecule. Marchand, B., Benezra, C. J. Med. Chem. (1982) [Pubmed]
  2. Early proliferative responses of forestomach and glandular stomach of rats treated with five different phenolic antioxidants. Shibata, M.A., Yamada, M., Hirose, M., Asakawa, E., Tatematsu, M., Ito, N. Carcinogenesis (1990) [Pubmed]
  3. Antimalarial activities and subacute toxicity of RC-12, a 4-amino-substituted pyrocatechol. Schmidt, L.H., Rossan, R.N., Fradkin, R., Sullivan, R., Schulemann, W., Kratz, L. Antimicrob. Agents Chemother. (1985) [Pubmed]
  4. Purification and characterization of catechol 1,2-dioxygenase from Rhodococcus rhodochrous NCIMB 13259 and cloning and sequencing of its catA gene. Strachan, P.D., Freer, A.A., Fewson, C.A. Biochem. J. (1998) [Pubmed]
  5. The chlorobenzoate dioxygenase genes of Burkholderia sp. strain NK8 involved in the catabolism of chlorobenzoates. Francisco, P., Ogawa, N., Suzuki, K., Miyashita, K. Microbiology (Reading, Engl.) (2001) [Pubmed]
  6. Test of catechol, tannic acid, Bidens pilosa, croton oil, and phorbol for cocarcinogenesis of esophageal tumors induced in rats by methyl-n-amylnitrosamine. Mirvish, S.S., Salmasi, S., Lawson, T.A., Pour, P., Sutherland, D. J. Natl. Cancer Inst. (1985) [Pubmed]
  7. Oxidation and DNA binding of (+)-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene in mouse epidermis in vivo and effects of coadministration of catechol. Melikian, A.A., Bagheri, K., Hoffmann, D. Cancer Res. (1990) [Pubmed]
  8. Radiochemical detection of dihydrodiol dehydrogenase: distribution of the enzyme in male Sprague-Dawley rat tissues and its sensitivity to inhibition by indomethacin and 6-medroxyprogesterone acetate. Ivins, J.K., Penning, T.M. Cancer Res. (1987) [Pubmed]
  9. (+/-)-[3H]Epinephrine and (-)[3H]dihydroalprenolol binding to beta1- and beta2-noradrenergic receptors in brain, heart, and lung membranes. U'Prichard, D.C., Bylund, D.B., Snyder, S.H. J. Biol. Chem. (1978) [Pubmed]
  10. Cloning and characterization of red clover polyphenol oxidase cDNAs and expression of active protein in Escherichia coli and transgenic alfalfa. Sullivan, M.L., Hatfield, R.D., Thoma, S.L., Samac, D.A. Plant Physiol. (2004) [Pubmed]
  11. Activation of the mitogen-activated protein kinase (ERK(1/2)) signaling pathway by cyclic AMP potentiates the neuroprotective effect of the neurotransmitter noradrenaline on dopaminergic neurons. Troadec, J.D., Marien, M., Mourlevat, S., Debeir, T., Ruberg, M., Colpaert, F., Michel, P.P. Mol. Pharmacol. (2002) [Pubmed]
  12. The evaluation of genotoxic activities of disinfectants and their metabolites by umu test. Sakagami, Y., Yamazaki, H., Ogasawara, N., Yokoyama, H., Ose, Y., Sato, T. Mutat. Res. (1988) [Pubmed]
  13. Mushroom tyrosinase: catalase activity, inhibition, and suicide inactivation. García-Molina, F., Hiner, A.N., Fenoll, L.G., Rodríguez-Lopez, J.N., García-Ruiz, P.A., García-Cánovas, F., Tudela, J. J. Agric. Food Chem. (2005) [Pubmed]
  14. Kinetics of the reversible tight-binding inhibition of pig liver catechol-O-methyltransferase by [2-(3,4-dihydroxy-2- nitrophenyl)vinyl]phenyl ketone. Pérez, R.A., Fernández-Alvarez, E., Nieto, O., Piedrafita, F.J. J. Enzym. Inhib. (1994) [Pubmed]
  15. Phase II metabolism of benzene. Schrenk, D., Orzechowski, A., Schwarz, L.R., Snyder, R., Burchell, B., Ingelman-Sundberg, M., Bock, K.W. Environ. Health Perspect. (1996) [Pubmed]
  16. Oxidation of aldehydes catalyzed by pig liver flavin-containing monooxygenase. Chen, G.P., Poulsen, L.L., Ziegler, D.M. Drug Metab. Dispos. (1995) [Pubmed]
  17. Effect of bioflavonoids on lysosomal acid hydrolases and lysosomal stability in adjuvant-induced arthritis. Rao, C.N., Rao, V.H., Verbruggen, L., Orloff, S. Scand. J. Rheumatol. (1980) [Pubmed]
  18. Inhibitory effects of catechol derivatives on hydrophilic free radical initiator-induced hemolysis and their interaction with hemoglobin. Kitagawa, S., Sugiyama, Y., Sakuma, T. Chem. Pharm. Bull. (1996) [Pubmed]
  19. Comparison of alternative chromogens for renal immunohistochemistry. Sheibani, K., Tubbs, R.R., Gephardt, G.N., McMahon, J.T., Valenzuela, R. Hum. Pathol. (1981) [Pubmed]
  20. Migration behavior and separation of benzenediamines, aminophenols and benzenediols by capillary zone electrophoresis. Lin, C.E., Chen, Y.T. Journal of chromatography. A. (2000) [Pubmed]
  21. Reversible sodium dodecyl sulfate activation of latent peach polyphenol oxidase by cyclodextrins. Laveda, F., Núñez-Delicado, E., García-Carmona, F., Sánchez-Ferrer, A. Arch. Biochem. Biophys. (2000) [Pubmed]
  22. Micellar electrokinetic chromatography at low pH with polyelectrolyte-coated capillaries. Pranaityte, B., Padarauskas, A. Journal of chromatography. A. (2004) [Pubmed]
  23. Superoxide dismutase and catalase enhance autoxidation during one-electron reduction of aminochrome by NADPH-cytochrome P-450 reductase. Baez, S., Linderson, Y., Segura-Aguilar, J. Biochem. Mol. Med. (1995) [Pubmed]
  24. Location and catalytic characteristics of a multipotent bacterial polyphenol oxidase. Fernández, E., Sanchez-Amat, A., Solano, F. Pigment Cell Res. (1999) [Pubmed]
  25. A survey of indigenous microbial hydrocarbon degradation genes in soils from Antarctica and Brazil. Luz, A.P., Pellizari, V.H., Whyte, L.G., Greer, C.W. Can. J. Microbiol. (2004) [Pubmed]
  26. Assessment of catechol-O-methyltransferase activity and its inhibition in erythrocytes of animals and humans. Zürcher, G., Da Prada, M., Dingemanse, J. Biomed. Chromatogr. (1996) [Pubmed]
  27. Affinity-dependent cross-linking to neurotoxin sites of the acetylcholine receptor mediated by catechol oxidation. Nickoloff, B.J., Grimes, M., Wohlfeil, E., Hudson, R.A. Biochemistry (1985) [Pubmed]
  28. Differential detection of key enzymes of polyaromatic-hydrocarbon-degrading bacteria using PCR and gene probes. Meyer, S., Moser, R., Neef, A., Stahl, U., Kämpfer, P. Microbiology (Reading, Engl.) (1999) [Pubmed]
  29. Amperometric biosensors based on recombinant laccases for phenols determination. Kulys, J., Vidziunaite, R. Biosensors & bioelectronics. (2003) [Pubmed]
  30. Metabolism of grape seed polyphenol in the rat. Nakamura, Y., Tonogai, Y. J. Agric. Food Chem. (2003) [Pubmed]
  31. Characterization of beta-Ketoadipate Pathway from Multi-Drug Resistance Bacterium, Acinetobacter baumannii DU202 by Proteomic Approach. Park, S.H., Kim, J.W., Yun, S.H., Leem, S.H., Kahng, H.Y., Kim, S.I. J. Microbiol. (2006) [Pubmed]
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