Record Information
Version2.0
Creation Date2012-05-31 13:02:27 -0600
Update Date2015-09-13 15:15:20 -0600
Secondary Accession Numbers
  • ECMDB00957
Identification
Name:Pyrocatechol
DescriptionPyrocatechol 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.
Structure
Thumb
Synonyms:
  • 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
Chemical Formula:C6H6O2
Weight:Average: 110.1106
Monoisotopic: 110.036779436
InChI Key:YCIMNLLNPGFGHC-UHFFFAOYSA-N
InChI:InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
CAS number:120-80-9
IUPAC Name:benzene-1,2-diol
Traditional IUPAC Name:catechol
SMILES:OC1=CC=CC=C1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:105 °C
Experimental Properties:
PropertyValueSource
Water Solubility:461.0 mg/ml [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:1.214PhysProp
Predicted Properties
PropertyValueSource
Water Solubility75 g/LALOGPS
logP0.74ALOGPS
logP1.37ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)9.34ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.02 m³·mol⁻¹ChemAxon
Polarizability10.69 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Aminobenzoate DegradationPW000757 ThumbThumb?image type=greyscaleThumb?image type=simple
Fluorobenzoate degradationPW000766 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • 1,4-Dichlorobenzene degradation ec00627
  • Benzoate degradation via hydroxylation ec00362
  • Biphenyl degradation ec00621
  • Fluorobenzoate degradation ec00364
  • Microbial metabolism in diverse environments ec01120
  • Naphthalene degradation ec00626
  • gamma-Hexachlorocyclohexane degradation ec00361
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udr-1950000000-16187bb35dcb40c26e78View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-8900000000-4e15f35dca47661de590View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9600000000-032a40483dec93738075View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-7900000000-83f892852c355a3863e9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9400000000-90885264baa17f65d954View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udr-1950000000-16187bb35dcb40c26e78View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udr-1930000000-24d2e0a8e36245d9e187View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-7900000000-8b112b8af75eb2d08676View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fl9-9730000000-a35befff1c602124f29eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-9400000000-d59dce8c5e56b026f8b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-632cabc9b371835019c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02t9-9200000000-ac902cb99981017de3b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-03di-8900000000-95af3d2738de98d27f26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-03di-9600000000-032a40483dec93738075View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-03di-7900000000-f5cb1c53768e05ca1530View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0900000000-c94dab4d218dbb3bb108View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0a4i-1900000000-edd8ba1e77bbb2f76304View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-c94dab4d218dbb3bb108View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-1900000000-edd8ba1e77bbb2f76304View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0900000000-12053747e62e910151adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-72e952ea8e487994be54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-19b1bae28f3dfde3323aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-9000000000-33b2a7e7a951547dfafaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-6e731d4eaba18fcad18fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1900000000-a7c1a830ea96e82252bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-3772b2cca96bf4a1b05fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9531f3e0c85e67d6c6edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-5886b926a1814092c4b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-66523f3122b954e6400fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-5fd776e479836f7464afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-2c46a1375dbb634ef735View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-986c93875cb12d90fa90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-a301685abb4194689ca3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9500000000-2017b42835ace86f16eeView in MoNA
MSMass Spectrum (Electron Ionization)splash10-03di-9600000000-b8e03f4f3ea89044828eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Cavalieri EL, Rogan EG, Chakravarti D: Initiation of cancer and other diseases by catechol ortho-quinones: a unifying mechanism. Cell Mol Life Sci. 2002 Apr;59(4):665-81. Pubmed: 12022473
  • Goldstein DS, Holmes C, Kaufmann H, Freeman R: Clinical pharmacokinetics of the norepinephrine precursor L-threo-DOPS in primary chronic autonomic failure. Clin Auton Res. 2004 Dec;14(6):363-8. Pubmed: 15666063
  • Goodall M, Diddle AW: Epinephrine and norepinephrine in pregnancy. A comparative study of the adrenal gland and catechol output in different species of animals and man. Am J Obstet Gynecol. 1971 Dec 1;111(7):896-904. Pubmed: 5118028
  • Habecker BA, Willison BD, Shi X, Woodward WR: Chronic depolarization stimulates norepinephrine transporter expression via catecholamines. J Neurochem. 2006 May;97(4):1044-51. Epub 2006 Mar 29. Pubmed: 16573647
  • Irons RD: Quinones as toxic metabolites of benzene. J Toxicol Environ Health. 1985;16(5):673-8. Pubmed: 4093989
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Kiso Y: Antioxidative roles of sesamin, a functional lignan in sesame seed, and it's effect on lipid- and alcohol-metabolism in the liver: a DNA microarray study. Biofactors. 2004;21(1-4):191-6. Pubmed: 15630196
  • Luffer-Atlas D, Vincent SH, Painter SK, Arison BH, Stearns RA, Chiu SH: Orally active inhibitors of human leukocyte elastase. III. Identification and characterization of metabolites of L-694,458 by liquid chromatography-tandem mass spectrometry. Drug Metab Dispos. 1997 Aug;25(8):940-52. Pubmed: 9280402
  • Moretti M, Villarini M, Simonucci S, Fatigoni C, Scassellati-Sforzolini G, Monarca S, Pasquini R, Angelucci M, Strappini M: Effects of co-exposure to extremely low frequency (ELF) magnetic fields and benzene or benzene metabolites determined in vitro by the alkaline comet assay. Toxicol Lett. 2005 Jun 17;157(2):119-28. Pubmed: 15836999
  • Mosca L, Lendaro E, d'Erme M, Marcellini S, Moretti S, Rosei MA: 5-S-Cysteinyl-dopamine effect on the human dopaminergic neuroblastoma cell line SH-SY5Y. Neurochem Int. 2006 Aug;49(3):262-9. Epub 2006 Mar 20. Pubmed: 16549224
  • Munns AJ, De Voss JJ, Hooper WD, Dickinson RG, Gillam EM: Bioactivation of phenytoin by human cytochrome P450: characterization of the mechanism and targets of covalent adduct formation. Chem Res Toxicol. 1997 Sep;10(9):1049-58. Pubmed: 9305589
  • Nguyen SD, Sok DE: Effect of 3,4-dihydroxyphenylalanine on Cu(2+)-induced inactivation of HDL-associated paraoxonasel and oxidation of HDL; inactivation of paraoxonasel activity independent of HDL lipid oxidation. Free Radic Res. 2004 Sep;38(9):969-76. Pubmed: 15621715
  • Olanow CW, Obeso JA: Pulsatile stimulation of dopamine receptors and levodopa-induced motor complications in Parkinson's disease: implications for the early use of COMT inhibitors. Neurology. 2000;55(11 Suppl 4):S72-7; discussion S78-81. Pubmed: 11147513
  • Poupaert J, Carato P, Colacino E, Yous S: 2(3H)-benzoxazolone and bioisosters as "privileged scaffold" in the design of pharmacological probes. Curr Med Chem. 2005;12(7):877-85. Pubmed: 15853716
  • Purba HS, Maggs JL, Orme ML, Back DJ, Park BK: The metabolism of 17 alpha-ethinyloestradiol by human liver microsomes: formation of catechol and chemically reactive metabolites. Br J Clin Pharmacol. 1987 Apr;23(4):447-53. Pubmed: 3555579
  • Relling MV, Nemec J, Schuetz EG, Schuetz JD, Gonzalez FJ, Korzekwa KR: O-demethylation of epipodophyllotoxins is catalyzed by human cytochrome P450 3A4. Mol Pharmacol. 1994 Feb;45(2):352-8. Pubmed: 8114683
  • Rivest J, Barclay CL, Suchowersky O: COMT inhibitors in Parkinson's disease. Can J Neurol Sci. 1999 Aug;26 Suppl 2:S34-8. Pubmed: 10451758
  • Santens P: Sleep attacks in Parkinson's disease induced by Entacapone, a COMT-inhibitor. Fundam Clin Pharmacol. 2003 Feb;17(1):121-3. Pubmed: 12588639
  • Schapira AH, Obeso JA, Olanow CW: The place of COMT inhibitors in the armamentarium of drugs for the treatment of Parkinson's disease. Neurology. 2000;55(11 Suppl 4):S65-8; discussion S69-71. Pubmed: 11147512
  • Swaminath G, Deupi X, Lee TW, Zhu W, Thian FS, Kobilka TS, Kobilka B: Probing the beta2 adrenoceptor binding site with catechol reveals differences in binding and activation by agonists and partial agonists. J Biol Chem. 2005 Jun 10;280(23):22165-71. Epub 2005 Apr 7. Pubmed: 15817484
  • Zand R, Nelson SD, Slattery JT, Thummel KE, Kalhorn TF, Adams SP, Wright JM: Inhibition and induction of cytochrome P4502E1-catalyzed oxidation by isoniazid in humans. Clin Pharmacol Ther. 1993 Aug;54(2):142-9. Pubmed: 8354023
Synthesis Reference:Lauterbach, Manfred; Zimmermann, Volker; Jaeger, Guenter; Radig, Wolfram; Adam, Johannes; Blady, Regina. Extraction and purification of pyrocatechol. Ger. (East) (1986), 4 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID18135
HMDB IDHMDB00957
Pubchem Compound ID289
Kegg IDC15571
ChemSpider ID13837760
WikipediaPyrocatechol
BioCyc IDCATECHOL
EcoCyc IDCATECHOL
Ligand ExpoCAQ

Enzymes

General function:
Not Available
Specific function:
Not Available
Gene Name:
yeaW
Uniprot ID:
P0ABR7
Molecular weight:
Not Available