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
Synonyms
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
    Physico-Chemical Properties - Experimental
    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
    Processing...
    Biological Effects and Interactions
    Health Effects / Bioactivities
    Enzymes
    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.