2.0 2012-05-31 13:02:27 -0600 2015-09-13 15:15:20 -0600 ECMDB00957 M2MDB000207 Pyrocatechol Pyrocatechol is a member of the chemical class known as Catechols. These are compounds containing a 1,2-benzenediol moeity. Catechol, also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula C6H4(OH)2. It is the ortho isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. About 20 million kg are produced annually, mainly as a precursor to pesticides, flavors, and fragrances. E. coli can use catechols as substrates to grow on using 2,3-dihydroxicinnamic acid 1,2-dioxygenase or mhpB. 1,2-Benzenediol 1,2-Dihydroxybenzene 2-Hydroxyphenol C.I. Oxidation Base 26 Catechol Catechol (phenol) Durafur Developer C Fouramine PCH Fourrine 68 O-Benzenediol O-Dihydroxybenzene O-Dioxybenzene O-Hydroquinone O-Hydroxyphenol O-Phenylenediol Oxyphenate Oxyphenic acid Pelagol Grey C Phthalhydroquinone Phthalic alcohol Pyrocatechin Pyrocatechine Pyrocatechol C6H6O2 110.1106 110.036779436 benzene-1,2-diol catechol 120-80-9 OC1=CC=CC=C1O InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H YCIMNLLNPGFGHC-UHFFFAOYSA-N Solid Outer membrane Inner membrane logp 0.74 ALOGPS logs -0.17 ALOGPS solubility 7.50e+01 g/l ALOGPS melting_point 105 oC logp 1.37 ChemAxon pka_strongest_acidic 9.34 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac benzene-1,2-diol ChemAxon average_mass 110.1106 ChemAxon mono_mass 110.036779436 ChemAxon smiles OC1=CC=CC=C1O ChemAxon formula C6H6O2 ChemAxon inchi InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H ChemAxon inchikey YCIMNLLNPGFGHC-UHFFFAOYSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 30.02 ChemAxon polarizability 10.69 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon gamma-Hexachlorocyclohexane degradation ec00361 Benzoate degradation via hydroxylation ec00362 Biphenyl degradation ec00621 1,4-Dichlorobenzene degradation ec00627 Fluorobenzoate degradation one step conversion of fluoromuconolactone (5-fluoromuconolactone and 4-fluoromuconolactone ) into maleylactate in order to be degraded following the benzoate degradation This pathway is under revision PW000766 ec00364 Metabolic Microbial metabolism in diverse environments ec01120 Naphthalene degradation ec00626 Aminobenzoate Degradation Delete This pathway shows the various process by which various compounds reach Benzoate degradation. The top most reaction catalyzes (3s)-3-hydroxyacyl-Coa from crotonoyl-Coa and Water through 2,3-dehydroadipyl-CoA hydratase. The second reaction catalyzes Benzoic Acid from benzoyl phosphate through a weak acylphosphatase. The third reaction is 1,2,4 Benzenetriol which is catalyzed from 4-nitrocatechol through a predicted 2Fe-2s cluster-containing protein. This is a isomer of 4-nitrophenol which is produced from 4-phenylphosphate or 4-nitrophenylphosphate through a phosphoanhydride phosphorylase or alkaline phosphatase respectively The fourth reaction is the production of pyrocatechol from phenol, aniline or Nitrobenzene through a predicted 2Fe-2S cluster-containing protein. The fifth reaction is the production of (3s)-3 hydroxyacyl CoA from acetyl oa and 3-hydroxy-5-oxohexanoic through Acetate CoA-transferase (3s)-3-hydroxyacyl-Coa, Benzoic Acid, pyrocatechol and 1,2,4 Benzenetriol then go into Benzoate degradation. PW000757 Metabolic Specdb::CMs 685 Specdb::CMs 5712 Specdb::CMs 26744 Specdb::CMs 27576 Specdb::CMs 27984 Specdb::CMs 29904 Specdb::CMs 30494 Specdb::CMs 31771 Specdb::CMs 37864 Specdb::CMs 134814 Specdb::CMs 142548 Specdb::CMs 1082494 Specdb::CMs 1082495 Specdb::CMs 1082496 Specdb::EiMs 791 Specdb::NmrOneD 1622 Specdb::NmrOneD 8062 Specdb::NmrOneD 8063 Specdb::NmrOneD 8064 Specdb::NmrOneD 8065 Specdb::NmrOneD 8066 Specdb::NmrOneD 8067 Specdb::NmrOneD 8068 Specdb::NmrOneD 8069 Specdb::NmrOneD 8070 Specdb::NmrOneD 8071 Specdb::NmrOneD 8072 Specdb::NmrOneD 8073 Specdb::NmrOneD 8074 Specdb::NmrOneD 8075 Specdb::NmrOneD 8076 Specdb::NmrOneD 8077 Specdb::NmrOneD 8078 Specdb::NmrOneD 8079 Specdb::NmrOneD 8080 Specdb::NmrOneD 8081 Specdb::MsMs 1357 Specdb::MsMs 1358 Specdb::MsMs 1359 Specdb::MsMs 4969 Specdb::MsMs 4970 Specdb::MsMs 4971 Specdb::MsMs 4973 Specdb::MsMs 4974 Specdb::MsMs 20390 Specdb::MsMs 20391 Specdb::MsMs 20392 Specdb::MsMs 21941 Specdb::MsMs 21942 Specdb::MsMs 21943 Specdb::MsMs 439130 Specdb::MsMs 439131 Specdb::MsMs 440140 Specdb::MsMs 2236365 Specdb::MsMs 2237039 Specdb::MsMs 2238424 Specdb::MsMs 2239136 Specdb::MsMs 2240126 Specdb::MsMs 2240556 Specdb::MsMs 2241169 Specdb::MsMs 2241561 Specdb::NmrTwoD 1563 HMDB00957 13837760 C15571 18135 CATECHOL CAQ Pyrocatechol Keseler, I. 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(East) (1986), 4 pp. http://hmdb.ca/system/metabolites/msds/000/000/861/original/HMDB00957.pdf?1358895509 predicted 2Fe-2S cluster-containing protein P0ABR7 yeaW http://ecmdb.ca/proteins/P0ABR7.xml Aniline + Oxygen <> Pyrocatechol + Ammonia R07700 Nitrobenzene + Oxygen <> Pyrocatechol + Nitrite R07706 Aniline > Pyrocatechol PW_R002443 Nitrobenzene > Pyrocatechol PW_R002444