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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:28 UTC
HMDB IDHMDB0000957
Secondary Accession Numbers
  • HMDB00957
Metabolite Identification
Common NamePyrocatechol
DescriptionPyrocatechol, often known as catechol or benzene-1,2-diol, is a benzenediol, with formula C6H4(OH)2. It was first prepared in 1839 by H. Reinsch by distilling catechin (the juice of Mimosa catechu). This colourless compound occurs naturally, but about 20000 tons are manufactured each year, mainly as precursors to pesticides, flavors, and fragrances. Its sulfonic acid is often present in the urine of many mammals. Small amounts of catechol occur naturally in fruits and vegetables, along with the enzyme polyphenol oxidase. Upon mixing the enzyme with the substrate and exposure to oxygen (as when a potato or apple is cut), the colorless catechol oxidizes to reddish-brown benzoquinone derivatives. The enzyme is inactivated by adding an acid, such as lemon juice, or by refrigeration. Excluding oxygen also prevents the browning reaction. Catechol melts at 28 °C and boils at 250 °C. It is employed in medicine as an expectorant. The dimethyl ether or veratrol is also used in medicine. Many other pyrocatechin derivatives have been suggested for therapeutic application. Pyrocatechol has also been found to be a microbial metabolite in Escherichia, Mycobacterium and Pseudomonas (PMID:19300498 ; PMID:25281236 ).
Structure
Data?1582752167
Synonyms
ValueSource
1,2-BenzenediolChEBI
1,2-DihydroxybenzeneChEBI
2-HydroxyphenolChEBI
alpha-HydroxyphenolChEBI
BrenzcatechinChEBI
O-BenzenediolChEBI
O-HydroxyphenolChEBI
PyrocatechinChEBI
a-HydroxyphenolGenerator
Α-hydroxyphenolGenerator
CatecholHMDB
Durafur developer CHMDB
Fouramine PCHHMDB
Fourrine 68HMDB
O-DihydroxybenzeneHMDB
O-DioxybenzeneHMDB
O-HydroquinoneHMDB
O-PhenylenediolHMDB
OxyphenateHMDB
Oxyphenic acidHMDB
Pelagol grey CHMDB
PhthalhydroquinoneHMDB
Phthalic alcoholHMDB
PyrocatechineHMDB
1,3-DihydroxybenzeneHMDB
Catechol dipotassium saltHMDB
Catechol, 14C-labeled CPDHMDB
Catechol sodium saltHMDB
Benzene-1,2-diolPhytoBank
PyrocatecholPhytoBank
1,2-HydroxybenzenePhytoBank
Chemical FormulaC6H6O2
Average Molecular Weight110.1106
Monoisotopic Molecular Weight110.036779436
IUPAC Namebenzene-1,2-diol
Traditional Namecatechol
CAS Registry Number120-80-9
SMILES
OC1=CC=CC=C1O
InChI Identifier
InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
InChI KeyYCIMNLLNPGFGHC-UHFFFAOYSA-N
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
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point105 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility461 mg/mLNot Available
LogP0.88HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available115.7http://allccs.zhulab.cn/database/detail?ID=AllCCS00002104
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+119.41231661259
DarkChem[M-H]-115.83631661259
AllCCS[M+H]+123.0532859911
AllCCS[M-H]-117.4532859911
DeepCCS[M+H]+123.59730932474
DeepCCS[M-H]-121.64830932474
DeepCCS[M-2H]-157.10930932474
DeepCCS[M+Na]+131.60430932474
AllCCS[M+H]+123.132859911
AllCCS[M+H-H2O]+118.132859911
AllCCS[M+NH4]+127.732859911
AllCCS[M+Na]+129.032859911
AllCCS[M-H]-117.532859911
AllCCS[M+Na-2H]-120.032859911
AllCCS[M+HCOO]-122.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PyrocatecholOC1=CC=CC=C1O2640.3Standard polar33892256
PyrocatecholOC1=CC=CC=C1O1046.3Standard non polar33892256
PyrocatecholOC1=CC=CC=C1O1207.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pyrocatechol,1TMS,isomer #1C[Si](C)(C)OC1=CC=CC=C1O1206.3Semi standard non polar33892256
Pyrocatechol,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC=C1O[Si](C)(C)C1318.1Semi standard non polar33892256
Pyrocatechol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC=C1O1441.4Semi standard non polar33892256
Pyrocatechol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC=C1O[Si](C)(C)C(C)(C)C1785.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Pyrocatechol GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udr-1950000000-16187bb35dcb40c26e782014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyrocatechol EI-B (Non-derivatized)splash10-03di-8900000000-4e15f35dca47661de5902017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyrocatechol EI-B (Non-derivatized)splash10-03di-9600000000-032a40483dec937380752017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyrocatechol EI-B (Non-derivatized)splash10-03di-7900000000-83f892852c355a3863e92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyrocatechol EI-B (Non-derivatized)splash10-03di-9400000000-90885264baa17f65d9542017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyrocatechol GC-EI-TOF (Non-derivatized)splash10-0udr-1950000000-16187bb35dcb40c26e782017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyrocatechol GC-EI-TOF (Non-derivatized)splash10-0udr-1930000000-24d2e0a8e36245d9e1872017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrocatechol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-7900000000-8b112b8af75eb2d086762017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrocatechol GC-MS (2 TMS) - 70eV, Positivesplash10-0fl9-9730000000-a35befff1c602124f29e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrocatechol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrocatechol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrocatechol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrocatechol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrocatechol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-9600000000-b8e03f4f3ea89044828e2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-01ox-9400000000-d59dce8c5e56b026f8b22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-014i-9000000000-632cabc9b371835019c12012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-02t9-9200000000-ac902cb99981017de3b52012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol EI-B (VARIAN MAT-44) , Positive-QTOFsplash10-03di-8900000000-95af3d2738de98d27f262012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol EI-B (Unknown) , Positive-QTOFsplash10-03di-9600000000-032a40483dec937380752012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol EI-B (HITACHI M-80) , Positive-QTOFsplash10-03di-7900000000-f5cb1c53768e05ca15302012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-0a4i-0900000000-c94dab4d218dbb3bb1082012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative-QTOFsplash10-0a4i-1900000000-edd8ba1e77bbb2f763042012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol LC-ESI-QTOF , negative-QTOFsplash10-0a4i-0900000000-c94dab4d218dbb3bb1082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol LC-ESI-QTOF , negative-QTOFsplash10-0a4i-1900000000-edd8ba1e77bbb2f763042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol , negative-QTOFsplash10-0a4i-0900000000-12053747e62e910151ad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol 10V, Negative-QTOFsplash10-0a4i-0900000000-72e952ea8e487994be542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol 10V, Negative-QTOFsplash10-0a4i-0900000000-19b1bae28f3dfde3323a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol 30V, Negative-QTOFsplash10-0006-9000000000-33b2a7e7a951547dfafa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol 10V, Negative-QTOFsplash10-0a4i-0900000000-6e731d4eaba18fcad18f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol 40V, Negative-QTOFsplash10-0a4i-1900000000-a7c1a830ea96e82252bf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol 10V, Negative-QTOFsplash10-0a4i-0900000000-3772b2cca96bf4a1b05f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol 10V, Negative-QTOFsplash10-0a4i-0900000000-9531f3e0c85e67d6c6ed2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrocatechol 20V, Negative-QTOFsplash10-0a4i-1900000000-5886b926a1814092c4b12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol 10V, Positive-QTOFsplash10-03di-0900000000-66523f3122b954e6400f2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol 20V, Positive-QTOFsplash10-03di-1900000000-5fd776e479836f7464af2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol 40V, Positive-QTOFsplash10-0udi-9000000000-2c46a1375dbb634ef7352015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol 10V, Negative-QTOFsplash10-0a4i-0900000000-986c93875cb12d90fa902015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol 20V, Negative-QTOFsplash10-0a4i-0900000000-a301685abb4194689ca32015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol 40V, Negative-QTOFsplash10-0a4i-9500000000-2017b42835ace86f16ee2015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Gland
  • Bone Marrow
  • Brain
  • Intestine
  • Liver
  • Neuron
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.665 +/- 0.093 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified3.027 +/- 2.529 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified3.269 +/- 2.507 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified1.673 +/- 1.103 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.677 +/- 0.177 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.666 +/- 0.17 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.612 +/- 0.101 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.714 +/- 0.201 uMAdult (>18 years old)Male
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected and Quantified8.900 +/- 2.270 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified10.353 +/- 4.995 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified20.434 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified4.06 +/- 1.80 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0-15 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified6.0 +/- 4.3 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified4.7 (2.0-8.5) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 654 details
UrineDetected and Quantified13.9 +/- 5.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.585 +/- 0.224 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Schizophrenia
  1. Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
Associated OMIM IDs
  • 601313 (Autosomal dominant polycystic kidney disease)
  • 181500 (Schizophrenia)
DrugBank IDDB02232
Phenol Explorer Compound ID654
FooDB IDFDB001512
KNApSAcK IDC00002644
Chemspider ID13837760
KEGG Compound IDC15571
BioCyc IDCATECHOL
BiGG IDNot Available
Wikipedia LinkCatechol
METLIN ID282
PubChem Compound289
PDB IDNot Available
ChEBI ID18135
Food Biomarker OntologyNot Available
VMH IDCATECHOL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLauterbach, 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)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
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  13. 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 ]
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Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
Pyrocatechol → Guaiacoldetails
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P50224
Molecular weight:
34195.96
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:
AKR1C3
Uniprot ID:
P42330
Molecular weight:
36866.91
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails
General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular weight:
36788.02
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails
General function:
Involved in oxidoreductase activity
Specific function:
Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:
AKR1C2
Uniprot ID:
P52895
Molecular weight:
15747.91
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Pyrocatechol → 3,4,5-trihydroxy-6-(2-hydroxyphenoxy)oxane-2-carboxylic aciddetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
DHDH
Uniprot ID:
Q9UQ10
Molecular weight:
36381.705
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails
General function:
Involved in O-methyltransferase activity
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones (By similarity). Required for auditory function.
Gene Name:
LRTOMT
Uniprot ID:
Q8WZ04
Molecular weight:
32154.43