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1,2-Benzenediol (FDB001512)

Record Information
Version1.0
Creation date2010-04-08 22:05:00 UTC
Update date2019-11-26 02:56:32 UTC
Primary IDFDB001512
Secondary Accession Numbers
  • FDB030715
  • FDB007351
Chemical Information
FooDB Name1,2-Benzenediol
DescriptionPyrocatechol, also known as 1,2-benzenediol or 2-hydroxyphenol, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Pyrocatechol is an extremely weak basic (essentially neutral) compound (based on its pKa). Pyrocatechol exists in all living organisms, ranging from bacteria to humans. Pyrocatechol is found, on average, in the highest concentration within a few different foods, such as arabica coffee, coffee, and cocoa powders and in a lower concentration in beers. Pyrocatechol has also been detected, but not quantified in, several different foods, such as bamboo shoots, mandarin orange (clementine, tangerine), scarlet beans, naranjilla, and asparagus. This could make pyrocatechol a potential biomarker for the consumption of these foods. Pyrocatechol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.
CAS Number120-80-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H6O2
IUPAC namebenzene-1,2-diol
InChI IdentifierInChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
InChI KeyYCIMNLLNPGFGHC-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=CC=C1O
Average Molecular Weight110.1106
Monoisotopic Molecular Weight110.036779436
Classification
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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting Point105 oC
    Boiling PointNot Available
    Experimental Water Solubility461 mg/mL at 25 oCYALKOWSKY,SH & HE,Y (2003)
    Experimental logP0.88HANSCH,C ET AL. (1995)
    Experimental pKa9.45
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-03di-9600000000-b8e03f4f3ea89044828e2014-09-20View Spectrum
    GC-MS1,2-Benzenediol, non-derivatized, GC-MS Spectrumsplash10-0udr-1950000000-16187bb35dcb40c26e78Spectrum
    GC-MS1,2-Benzenediol, non-derivatized, GC-MS Spectrumsplash10-03di-8900000000-4e15f35dca47661de590Spectrum
    GC-MS1,2-Benzenediol, non-derivatized, GC-MS Spectrumsplash10-03di-9600000000-032a40483dec93738075Spectrum
    GC-MS1,2-Benzenediol, non-derivatized, GC-MS Spectrumsplash10-03di-7900000000-83f892852c355a3863e9Spectrum
    GC-MS1,2-Benzenediol, non-derivatized, GC-MS Spectrumsplash10-03di-9400000000-90885264baa17f65d954Spectrum
    GC-MS1,2-Benzenediol, non-derivatized, GC-MS Spectrumsplash10-0udr-1950000000-16187bb35dcb40c26e78Spectrum
    GC-MS1,2-Benzenediol, non-derivatized, GC-MS Spectrumsplash10-0udr-1930000000-24d2e0a8e36245d9e187Spectrum
    Predicted GC-MS1,2-Benzenediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-7900000000-8b112b8af75eb2d08676Spectrum
    Predicted GC-MS1,2-Benzenediol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fl9-9730000000-a35befff1c602124f29eSpectrum
    Predicted GC-MS1,2-Benzenediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS1,2-Benzenediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS1,2-Benzenediol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS1,2-Benzenediol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS1,2-Benzenediol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-9400000000-d59dce8c5e56b026f8b22012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-632cabc9b371835019c12012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02t9-9200000000-ac902cb99981017de3b52012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-03di-8900000000-95af3d2738de98d27f262012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-03di-9600000000-032a40483dec937380752012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-03di-7900000000-f5cb1c53768e05ca15302012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0900000000-c94dab4d218dbb3bb1082012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0a4i-1900000000-edd8ba1e77bbb2f763042012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-c94dab4d218dbb3bb1082017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-1900000000-edd8ba1e77bbb2f763042017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0900000000-12053747e62e910151ad2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-72e952ea8e487994be542021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-19b1bae28f3dfde3323a2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-9000000000-33b2a7e7a951547dfafa2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-6e731d4eaba18fcad18f2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1900000000-a7c1a830ea96e82252bf2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-3772b2cca96bf4a1b05f2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9531f3e0c85e67d6c6ed2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-5886b926a1814092c4b12021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-66523f3122b954e6400f2015-05-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-5fd776e479836f7464af2015-05-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-2c46a1375dbb634ef7352015-05-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-986c93875cb12d90fa902015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-a301685abb4194689ca32015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9500000000-2017b42835ace86f16ee2015-05-27View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider ID13837760
    ChEMBL IDCHEMBL280998
    KEGG Compound IDC15571
    Pubchem Compound ID289
    Pubchem Substance IDNot Available
    ChEBI ID18135
    Phenol-Explorer ID654
    DrugBank IDDB02232
    HMDB IDHMDB00957
    CRC / DFC (Dictionary of Food Compounds) IDHJX14-Z:HJX14-Z
    EAFUS IDNot Available
    Dr. Duke IDPYROCATECHOL|(+)-CATECHOL|CATECHOL
    BIGG IDNot Available
    KNApSAcK IDC00002644
    HET IDCAQ
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDPyrocatechol
    Phenol-Explorer Metabolite ID654
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    allelochemicDUKE
    allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
    anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti gonadotropicDUKE
    anti hepatitic62868 Any compound that is able to prevent damage to the liver.DUKE
    anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
    antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
    anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
    anti stomatiticDUKE
    anti thiaminDUKE
    anti thyreotropicDUKE
    antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
    cardiovascular38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
    central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
    convulsantDUKE
    dermatitigenicDUKE
    dye37958 DUKE
    fatalDUKE
    herbicide24527 A substance used to destroy plant pests.DUKE
    insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
    nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
    pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
    quinone-reductase inducerDUKE
    tumor promoter50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
    genotoxic50902 A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.CHEBI
    Enzymes
    NameGene NameUniProt ID
    Sulfotransferase 1A3/1A4SULT1A3P50224
    Trans-1,2-dihydrobenzene-1,2-diol dehydrogenaseDHDHQ9UQ10
    Transmembrane O-methyltransferaseLRTOMTQ8WZ04
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.