catechol (PAMDB110454)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110454
Identification
Name: catechol
Description:A benzenediol comprising of a benzene core carrying two hydroxy substituents ortho to each other.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • pyrocatechol
  • 2-hydroxyphenol
  • pyrocatechin
  • 1,2-dihydroxybenzene
  • 1,2-benzenediol
Chemical Formula: C6H6O2
Average Molecular Weight: 110.11
Monoisotopic Molecular Weight: 110.0367794368
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:C1(C=CC(=C(C=1)O)O)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as catechols. These are compounds containing a 1,2-benzenediol moiety.
Kingdom Organic compounds
Super ClassBenzenoids
Class Phenols
Sub ClassBenzenediols
Direct Parent Catechols
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 Framework Aromatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 105 °C
Experimental Properties:
PropertyValueReference
Melting Point105 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility461.0 mg/mLNot Available
LogP0.88HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility75.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.02 m3·mol-1ChemAxon
Polarizability10.69 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
anthranilate + Oxygen + NADH-P-OR-NOP + Hydrogen ion → catechol + Carbon dioxide + Ammonium + NAD-P-OR-NOP
3,5-cyclohexadiene-1,2-diol-1-carboxylate + NAD+ → catechol + Carbon dioxide + NADH
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udr-1950000000-16187bb35dcb40c26e78View in MoNA
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
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 Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Topal S, Kocaçaliskan I, Arslan O (2006)Herbicidal potential of catechol as an allelochemical. Zeitschrift fur Naturforschung. C, Journal of biosciences 61, Pubmed: 16610220
  • Baldwin RW, Clegg JA, Curran AC, Austin EB, Khan T, Ma Y, Gunn B, Hudecz F, Byers VS, Lepoittevin JP, Price MR (1999)Regulation of the contact sensitivity response to urushiol with anti-urushiol monoclonal antibody ALG 991. Archives of dermatological research 291, Pubmed: 10651166
  • Oikawa S, Hirosawa I, Hirakawa K, Kawanishi S (2001)Site specificity and mechanism of oxidative DNA damage induced by carcinogenic catechol. Carcinogenesis 22, Pubmed: 11470755
  • Andersson MA, Hellman BE (2005)Different roles of Fpg and Endo III on catechol-induced DNA damage in extended-term cultures of human lymphocytes and L5178Y mouse lymphoma cells. Toxicology in vitro : an international journal published in association with BIBRA 19, Pubmed: 15951152
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
CAS120-80-9
ChEBI18135
ChemSpider13837760
DrugBankDB02232
HMDBHMDB00957
KEGGC00090
MetaboLightsMTBLC18135
PubChem289