Summary: Highly toxic compound which can cause skin irritation and sensitization. It is used in manufacture of azo dyes.

Top Publications

  1. Erel O. A new automated colorimetric method for measuring total oxidant status. Clin Biochem. 2005;38:1103-11 pubmed
    ..66 P<0.01). This easy, stable, reliable, sensitive, inexpensive and fully automated method that is described can be used to measure total oxidant status. ..
  2. Makena P, Chung K. Evidence that 4-aminobiphenyl, benzidine, and benzidine congeners produce genotoxicity through reactive oxygen species. Environ Mol Mutagen. 2007;48:404-13 pubmed
    ..4-Ab and Bz also induced lipid peroxidation in the presence of S9 mix as shown using the thiobarbituric acid reactive substances assay. The results of this study indicate that 4-Ab and Bz induce mutations through the induction of ROS. ..
  3. Savitsky A, Nelen M, Yatsmirsky A, Demcheva M, Ponomarev G, Sinikov I. Kinetics of oxidation of o-dianisidine by hydrogen peroxide in the presence of antibody complexes of iron(III) coproporphyrin. Appl Biochem Biotechnol. 1994;47:317-27 pubmed
    ..of iron(III) coproporphyrinI (FeCPI) with antibody D5E3 was studied as an artificial peroxidase, using o-dianisidine as a substrate...
  4. Nowak D. Hydrogen peroxide release from human polymorphonuclear leukocytes measured with horseradish peroxidase and o-dianisidine. Effect of various stimulators and cytochalasin B. Biomed Biochim Acta. 1990;49:353-62 pubmed
    ..The method is based on the horseradish peroxidase-catalysed oxidation of o-dianisidine by H2O2 which results in the formation of a compound exhibiting an increased absorbance at 470 nm...
  5. Kuzu Karsilayan H, Eryilmaz E, Yillar G, Deniz G, Yanikkaya Demirel G. Spectrophotometric determination of leukocytes in blood. J Clin Lab Anal. 2002;16:233-6 pubmed
    The determination of leukocyte concentration in human blood depending on the detection of oxidized o-dianisidine in acidic solution is studied. The oxidation of o-dianisidine was carried out by peroxidase enzymes found in leukocytes...
  6. Reynolds S, Patterson R, Mennear J, Maronpot R, Anderson M. ras gene activation in rat tumors induced by benzidine congeners and derived dyes. Cancer Res. 1990;50:266-72 pubmed
  7. Segade L. Pyrocatechol as a stabilizing agent for o-tolidine and o-dianisidine: a sensitive new method for HRP neurohistochemistry. J Hirnforsch. 1987;28:331-40 pubmed
    ..is described which is based on the use of pyrocatechol to stabilize the oxidation products of o-tolidine and o-dianisidine in citric acid/ammonium acetate buffer of pH 4.85...
  8. Yoshizawa K, Kissling G, Johnson J, Clayton N, Flagler N, Nyska A. Chemical-induced atrial thrombosis in NTP rodent studies. Toxicol Pathol. 2005;33:517-32 pubmed
    ..A download option appears at the bottom of this abstract. In order to access the full article online, you must either have an individual subscription or a member subscription accessed through www.toxpath.org. ..
  9. Marcinkeviciene J, Magliozzo R, Blanchard J. Purification and characterization of the Mycobacterium smegmatis catalase-peroxidase involved in isoniazid activation. J Biol Chem. 1995;270:22290-5 pubmed
    ..The role of mycobacterial catalase-peroxidases in the oxidative activation of the antitubercular prodrug isoniazid is discussed...

More Information


  1. Imren Eryilmaz E, Kuzu Karsilayan H, Ogan A. Spectrophotometric determination of leukocytes in urine. J Clin Lab Anal. 2004;18:251-4 pubmed
    ..St. Louis, MO). Myeloperoxidase-catalyzed oxidation of o-dianisidine was carried out at 37 degrees C, pH 7...
  2. Catalá Icardo M, Garcia Mateo J, Martinez Calatayud J. o-Dianisidine: a new reagent for selective spectrophotometric, flow injection determination of chlorine. Analyst. 2001;126:2087-92 pubmed
    ..The determination of chlorine is performed on the basis of the oxidation by o-dianisidine as a chromogenic reagent to a coloured product which can be monitored at 445 nm...
  3. Suzuki T, Honda Y, Mukasa Y, Kim S. Characterization of peroxidase in buckwheat seed. Phytochemistry. 2006;67:219-24 pubmed
    ..1 kDa (POX I) and 58.1 kDa (POX II) by gel filtration. While POX I and II each oxidized quercetin, o-dianisidine, ascorbic acid and guaiacol, only POX II oxidized ABTS...
  4. Rice P, Houshaymi B, Abu Groun E, Nicholas R, Miles R. Rapid screening of H(2)O(2) production by Mycoplasma mycoides and differentiation of European subsp. mycoides SC (small colony) isolates. Vet Microbiol. 2001;78:343-51 pubmed
    ..In quantitative assays, H(2)O(2) production by washed cell suspensions was detected by the oxidation of o-dianisidine in the presence of peroxidase...
  5. Machuca A, Aoyama H, Duran N. Isolation and partial characterization of an extracellular low-molecular mass component with high phenoloxidase activity from Thermoascus aurantiacus. Biochem Biophys Res Commun. 1999;256:20-6 pubmed
    ..Iron may be the responsible for the ability for catalyze oxidation reactions, such as o-dianisidine oxidation, by the LMMC...
  6. Gordon L, Weiss D, Prachand S, Weitzman S. Scavenging of superoxide anion by phosphorylethanolamine: studies in human neutrophils and in a cell free system. Free Radic Res Commun. 1991;15:65-71 pubmed
    ..Further, utilizing a system based upon the photo-oxidation of O-dianisidine sensitized by riboflavin, we were able to determine that the scavenging effect of PE was not superoxide ..
  7. Wagner H, Pepich B, Hautman D, Munch D. Analysis of 500-ng/l levels of bromate in drinking water by direct-injection suppressed ion chromatography coupled with a single, pneumatically delivered post-column reagent. J Chromatogr A. 1999;850:119-29 pubmed
    ..conducted at the EPA's Technical Support Center laboratory investigating a single post-column reagent, o-dianisidine (ODA), which has been successfully coupled to EPA Method 300.1 to extend the MDL for bromate...
  8. Urbansky E, Brown S. Influence of reagent purity on the ion chromatographic determination of bromate in water using 3,3'-dimethoxybenzidine as a prochromophore for photometric detection. J Environ Monit. 2000;2:571-5 pubmed
    Variable availability of the purified dihydrochloride salt of 3,3'-dimethoxybenzidine (DMB; ortho-dianisidine) led us to investigate the effects of reagent purity on the analytical results obtained when this reagent is used in the ..
  9. Shiozaki M, Kosaka M, Eto Y. Activin A: a commitment factor in erythroid differentiation. Biochem Biophys Res Commun. 1998;242:631-5 pubmed
    ..The action of activin A commits the cell to death or to differentiation, and the presence of erythropoietin enables differentiation through suppression of apoptosis. ..
  10. Yatsimirskaya E, Gavrilova E, Egorov A. Detection system for membrane immunoassay based on the trapping of a highly colored intermediate of the peroxidase reaction. Anal Biochem. 1993;211:274-8 pubmed
    The oxidation of ortho-dianisidine by membrane bound horseradish peroxidase in the presence of sodium dextran sulfate affords a dark-green insoluble product, identified as an unstable meriquinone intermediate previously reported in ..
  11. Arutla S, Arra G, Prabhakar C, Krishna D. Pro- and anti-oxidant effects of some antileprotic drugs in vitro and their influence on super oxide dismutase activity. Arzneimittelforschung. 1998;48:1024-7 pubmed
    ..The drugs were incubated with a superoxide generating system (photochemical reaction between riboflavin and dianisidine). The change in optical density was measured...
  12. Huidobro J, Sánchez M, Muniategui S, Sancho M. Precise method for the measurement of catalase activity in honey. J AOAC Int. 2005;88:800-4 pubmed
    ..the substrate, H202, with the H202 determined spectrophotometrically at 400 nm in an assay system containing o-dianisidine and peroxidase. Trials indicated that the best solvent for the o-dianisidine was 0...
  13. Ricoux R, Dubuc R, Dupont C, Marechal J, Martin A, Sellier M, et al. Hemozymes peroxidase activity of artificial hemoproteins constructed from the Streptomyces lividans xylanase A and iron(III)-carboxy-substituted porphyrins. Bioconjug Chem. 2008;19:899-910 pubmed publisher
    ..activity, as it was able to catalyze the oxidation of typical peroxidase cosubstrates such as guaiacol and o-dianisidine by H2O2...
  14. Hartnett L, Glynn C, Nolan C, Grealy M, Byrnes L. Insulin-like growth factor-2 regulates early neural and cardiovascular system development in zebrafish embryos. Int J Dev Biol. 2010;54:573-83 pubmed publisher
    ..IGF-2 morphant embryos were then examined further using wholemount in situ hybridisation, TUNEL analysis and O-dianisidine staining...
  15. Toker H, Akpınar A, Aydın H, Poyraz O. Influence of smoking on interleukin-1beta level, oxidant status and antioxidant status in gingival crevicular fluid from chronic periodontitis patients before and after periodontal treatment. J Periodontal Res. 2012;47:572-7 pubmed publisher
    ..Periodontal treatment improved the clinical parameters in both smokers and nonsmokers. The results confirm that periodontal therapy has an effect on IL-1? levels in gingival crevicular fluid, but not on TOS and TAS. ..
  16. Artiukhov V, Basharina O, Iskusnykh A. [Effect of temperature on structure and functional properties of horseradish peroxidase]. Ukr Biokhim Zh (1999). 2003;75:45-9 pubmed
    ..The influence of temperature of 60 degrees C and above induces the protein globule unfolding and loosing of peroxidase activity. ..
  17. Erel O. A novel automated method to measure total antioxidant response against potent free radical reactions. Clin Biochem. 2004;37:112-9 pubmed
    ..Ortho-dianisidine (10 mM) and ferrous ammonium sulfate (45 microM) were dissolved in KCl/HCl solution (75 mM, pH 1.8)...
  18. Jasnowska J, Ligaj M, Stupnicka B, Filipiak M. DNA sensor for o-dianisidine. Bioelectrochemistry. 2004;64:85-90 pubmed
    o-Dianisidine (3,3'-dimethoxybenzidine) is applied in the production of some dyes and also used in analytical tests. However, this compound is anticipated to be a human carcinogen...
  19. Teramoto N, Ichinari H, Kawazoe N, Imanishi Y, Ito Y. Peroxidase activity of in vitro-selected 2'-amino RNAs. Biotechnol Bioeng. 2001;75:463-8 pubmed
    ..Each of them had a different substrate specificity. One of the active clones promoted the oxidation of o-dianisidine and beta-nicotinamide adenine dinucleotide reduced form (NADH) with H(2)O(2) 5 and 15 times faster than hemin ..
  20. Kumar R, Maitra A, Patanjali P, Sharma P. Hollow gold nanoparticles encapsulating horseradish peroxidase. Biomaterials. 2005;26:6743-53 pubmed
    ..Small substrate molecules such as o-dianisidine can easily enter through the pores of the nanoshell and can undergo enzymatic oxidation by H2O2...
  21. Shen W, Deng H, Ren Y, Gao Z. A label-free microRNA biosensor based on DNAzyme-catalyzed and microRNA-guided formation of a thin insulating polymer film. Biosens Bioelectron. 2013;44:171-6 pubmed publisher
    ..The accumulative nature of the PDB deposition drastically improves the detectability of the biosensor. A proof-of-concept study is conducted on the detection of miRNAs in total RNA extracted from cultured cells. ..
  22. You Z, Brezzell M, Das S, Espadas Torre M, Hooberman B, Sinsheimer J. ortho-Substituent effects on the in vitro and in vivo genotoxicity of benzidine derivatives. Mutat Res. 1993;319:19-30 pubmed
    ..In contrast to the in vitro results, while all the amines were genotoxic in vivo, only the 3-nitro derivative had a significant increase in toxicity over benzidine. ..
  23. Hou W, Lin Y. Activity staining of pectinesterase on polyacrylamide gels after acidic or sodium dodecyl sulfate electrophoresis. Electrophoresis. 1998;19:692-4 pubmed
    ..bands on polyacrylamide gels after native acidic PAGE or SDS-PAGE were stained with a combination of tetrazotized o-dianisidine and beta-NA. This fast and sensitive method can be used for enzyme purification and characterization.
  24. Pozdnyakova I, Wittung Stafshede P. Non-linear effects of macromolecular crowding on enzymatic activity of multi-copper oxidase. Biochim Biophys Acta. 2010;1804:740-4 pubmed publisher
    ..The observations are compatible with ordering of a non-optimal substrate-binding site and restricted internal dynamics as a result of excluded volume effects making the protein less structurally 'strained'. ..
  25. Scott N, Jennings P, Brown J, Belch J. Gliclazide: a general free radical scavenger. Eur J Pharmacol. 1991;208:175-7 pubmed
    ..The assay which employs o-dianisidine sensitised by riboflavin can be used to distinguish between superoxide scavengers and general scavengers...
  26. Garcia Martin E, Ayuso P, Martinez C, Agundez J. Improved analytical sensitivity reveals the occurrence of gender-related variability in diamine oxidase enzyme activity in healthy individuals. Clin Biochem. 2007;40:1339-41 pubmed
    ..DAO activity was measured by using cadaverine coupled to O-dianisidine oxidation in 50 healthy individuals. The mean activity was 7.59+/-3.67 U/L for women and 2.38+/-0...
  27. Sentchouk V, Grintsevich E. Oxidation of benzidine and its derivatives by thyroid peroxidase. Biochemistry (Mosc). 2004;69:201-7 pubmed
    ..k(cat) and K(m)) of benzidine (BD), 3,3'-dimethylbenzidine (o-tolidine), 3,3'-dimethoxybenzidine (o-dianisidine), and TMB oxidation at 25 degrees C in 0.05 M phosphate-citrate buffer, pH 5...
  28. Egan R, Hagmann W, Gale P. Naphthalenes as inhibitors of myeloperoxidase: direct and indirect mechanisms of inhibition. Agents Actions. 1990;29:266-76 pubmed
    ..By controlling the enzyme, these compounds protect alpha-1-PI from MPO induced damage, and could serve better than antioxidants to define the role of MPO in elastase induced injury. ..
  29. Rogozhin V, Verkhoturov V. Effect of antioxidants (digoxin, quercetin, and ascorbic acid) on catalytic properties of horseradish peroxidase. Biochemistry (Mosc). 1998;63:657-61 pubmed
    Antioxidants (digoxin, quercetin, and ascorbic acid) inhibited the oxidation of o-dianisidine catalyzed by horseradish peroxidase...
  30. de Mendez I, Young K, Bignon J, Lambre C. Biochemical characteristics of alveolar macrophage-specific peroxidase activities in the rat. Arch Biochem Biophys. 1991;289:319-23 pubmed
    ..Using o-dianisidine as a substrate, the Km for H2O2 of the 58- and 74-kDa Po species was 0.4 and 0...
  31. Nowak D, Piasecka G. The main serum protease inhibitors; alpha-1-proteinase inhibitor and alpha-2-macroglobulin inhibit H2O2 release from human polymorphonuclear leukocytes stimulated with phorbol myristate acetate. Arch Immunol Ther Exp (Warsz). 1991;39:51-60 pubmed
    ..It is suggested that inhibition of H2O2 generation from PMNL may be another additional way by which these serum protease inhibitors may protect tissues (especially lungs) from acute injury related to inflammation. ..
  32. Naito S, Tanaka K, Koga H, Kotoh S, Hirohata T, Kumazawa J. Cancer occurrence among dyestuff workers exposed to aromatic amines. A long term follow-up study. Cancer. 1995;76:1445-52 pubmed
    ..Although the occupational exposure to some aromatic amines is recognized to cause bladder carcinoma, the long term effect of such exposure on the risk for disease, including other malignant tumors, remains unknown...
  33. Beyer W, Fridovich I. An ultrasensitive colorimetric assay for manganese. Anal Biochem. 1988;170:512-9 pubmed
    ..It is based upon the catalysis, by Mn(II), of the photochemical oxidation of o-dianisidine, sensitized by riboflavin...
  34. Gray L, Ostby J. The effects of prenatal administration of azo dyes on testicular development in the mouse: a structure activity profile of dyes derived from benzidine, dimethylbenzidine, or dimethoxybenzidine. Fundam Appl Toxicol. 1993;20:177-83 pubmed
    ..When CBE was administered on Days 8-10 of gestation it reduced testis weight after puberty by 30%, while treatment after Day 13 did not affect testicular function.(ABSTRACT TRUNCATED AT 250 WORDS) ..
  35. Peng Y, Gao Z. Amplified detection of microRNA based on ruthenium oxide nanoparticle-initiated deposition of an insulating film. Anal Chem. 2011;83:820-7 pubmed publisher
    ..This impedance-based biosensor offers an attractive alternative for miRNA expression profiling and may enable the development of a portable multiplexing miRNA profiling system...
  36. Brandon E, Oomen A, Rompelberg C, Versantvoort C, van Engelen J, Sips A. Consumer product in vitro digestion model: Bioaccessibility of contaminants and its application in risk assessment. Regul Toxicol Pharmacol. 2006;44:161-71 pubmed
    ..Although relevant in vivo data are scare, we succeeded to preliminary validate the model for one case. This case showed good correlation and never underestimated the bioavailability. However, validation check needs to be continued. ..
  37. Hushpulian D, Poloznikov A, Savitski P, Rozhkova A, Chubar T, Fechina V, et al. Glutamic acid-141: a heme 'bodyguard' in anionic tobacco peroxidase. Biol Chem. 2007;388:373-80 pubmed
    ..e., it 'guards' heme inside the active center; and (2) it constitutes a shield to protect the active center from solvent-derived radicals. ..
  38. Chopra M, Belch J, Smith W. A comparison of the free radical scavenging activity of leukotrienes and prostaglandins. Free Radic Res Commun. 1988;5:95-9 pubmed
    ..of leukotrienes and prostaglandins to free radicals and the superoxide ion generated by the photo oxidation of dianisidine have been assessed in vitro...
  39. Alonso Mateos A, Almendral Parra M, Fuentes Prieto M. Sequential and simultaneous determination of bromate and chlorite (DBPs) by flow techniques: kinetic differentiation. Talanta. 2008;76:892-8 pubmed publisher
    3-3'-Dimethoxybenzidine (o-dianisidine, ODA) is oxidised by Br(2), among other oxidants, generating a compound that absorbs at 450 nm, while the non-oxidised reagent absorbs in the UV region...
  40. Tayefi Nasrabadi H, Moghaddam G, Rajabi Z. Effect of zinc ion on peroxidase activity of serum in cow. Pak J Biol Sci. 2008;11:2589-93 pubmed
    ..The H2O2-mediated oxidation of o-dianisidine was used to assess the peroxidase activity. Results show that after preincubation of serum with 0...
  41. Bridges A, Scott N, Belch J. Probucol, a superoxide free radical scavenger in vitro. Atherosclerosis. 1991;89:263-5 pubmed
    ..This property may be relevant in its use as a lipid lowering drug in the retardation of the atherosclerotic process. ..
  42. Urzua U, Fernando Larrondo L, Lobos S, Larrain J, Vicuna R. Oxidation reactions catalyzed by manganese peroxidase isoenzymes from Ceriporiopsis subvermispora. FEBS Lett. 1995;371:132-6 pubmed
    ..peroxide, these isoenzymes showed different requirements for Mn(II) in the oxidation of vanillylacetone, o-dianisidine, p-anisidine and ABTS, whereas oxidation of guaiacol by any isoenzyme did not take place when this metal was ..
  43. Himata K, Noda M, Ando S, Yamada Y. Measurement of bromate in bread by liquid chromatography with post-column flow reactor detection. J AOAC Int. 2000;83:347-55 pubmed
    ..Detection is based on the post-column reaction of bromate with o-dianisidine to form an oxidation product that is quantitated spectrophotometrically at 450 nm...
  44. Almendral M, Alonso A, Fuentes M. Development of new methodologies for on-line determination of the bromate ion in samples of water subjected to ozonation treatment. J Environ Monit. 2009;11:1381-8 pubmed publisher
    ..the spectrophotometric determination of bromate based on the bromination reaction of 3-3' dimethoxybenzidine, o-dianisidine (ODA)...
  45. MacPherson I, Rosell F, Scofield M, Mauk A, Murphy M. Directed evolution of copper nitrite reductase to a chromogenic reductant. Protein Eng Des Sel. 2010;23:137-45 pubmed publisher
    ..These variants were shuffled and screened, yielding two double variants. An analog of the DAB substrate, o-dianisidine, which is oxidized to a water-soluble product was used for functional characterization...
  46. Chhaya U, Gupte A. Optimization of media components for laccase production by litter dwelling fungal isolate Fusarium incarnatum LD-3. J Basic Microbiol. 2010;50:43-51 pubmed publisher
    ..Ortho-dianisidine, thiamine HCl and CuSO(4) . 5 H(2)O were identified as significant components for laccase production...
  47. Claxton L, Hughes T, Chung K. Using base-specific Salmonella tester strains to characterize the types of mutation induced by benzidine and benzidine congeners after reductive metabolism. Food Chem Toxicol. 2001;39:1253-61 pubmed
    ..DCBz induced only GC->AT transitions. Because DMBz, DMOBz and TB were not mutagenic in this base-substitution mutagen detection system, their mutagenic activity was attributed strictly to frameshift mechanisms. ..
  48. Padiglia A, Medda R, Pazzaglia G, Rescigno A, Cruciani E, Floris G. Fractionation and characterization of two forms of peroxidase from Oryza sativa. Prep Biochem. 1995;25:11-9 pubmed
    ..In this plant we also found two isoperoxidases called perox I and II. Only perox I was purified to homogeneity and its enzymatic, physical and chemical properties have been studied. ..
  49. Sitthisak S, Howieson K, Amezola C, Jayaswal R. Characterization of a multicopper oxidase gene from Staphylococcus aureus. Appl Environ Microbiol. 2005;71:5650-3 pubmed
    ..Disruption of mco showed copper sensitivity and H(2)O(2) resistance, suggesting roles for mco in copper homeostasis and oxidative stress response. Northern blot analysis showed copper-induced mco transcription. ..
  50. Morgan D, Jameson C, Mennear J, Ulland B, Lemen J. Thirteen-week toxicity studies of 3,3'-dimethoxybenzidene and C.I. Direct Blue 15 in the Fischer 344 rat. Toxicology. 1989;59:297-309 pubmed
    ..Mild chronic nephropathy was the principal histological effect in Blue 15-treated rats surviving to study termination. ..
  51. Kuo C, Fridovich I. Stimulation of the activity of horseradish peroxidase by nitrogenous compounds. J Biol Chem. 1988;263:3811-7 pubmed
    A variety of nitrogenous compounds broaden the activity versus pH profile for the peroxidation of dianisidine catalyzed by horseradish peroxidase (HRP), but not by myeloperoxidase, chloroperoxidase, Escherichia coli hydroperoxidase I, ..
  52. Sharma R, Das S, Maitra A. Enzymes in the cavity of hollow silica nanoparticles. J Colloid Interface Sci. 2005;284:358-61 pubmed
    ..05 x 10(5) s(-1)). The result showed that hollow nanoparticles could be prepared using soft chemical methods and sensitive chemicals like active enzyme could be entrapped in the cavities and it retains its activity. ..
  53. Panosian K, Edberg S. Measurement of constitutive L-pyrrolidonyl peptidase activity from Streptococcus and Enterococcus using tetrazotized 0-dianisidine. Antonie Van Leeuwenhoek. 1989;55:269-75 pubmed
    ..A new indicator system employing tetrazotized 0-dianisidine was developed...