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Showing Compound 1,2,3-Benzenetriol (FDB008735)

Record Information
Version1.0
Creation date2010-04-08 22:08:13 UTC
Update date2019-11-26 03:03:03 UTC
Primary IDFDB008735
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,2,3-Benzenetriol
Description1,2,3-trihydroxybenzene, also known as pyrogallic acid or 1,2,3-benzenetriol, is a member of the class of compounds known as 5-unsubstituted pyrrogallols. 5-unsubstituted pyrrogallols are pyrrogallols that are unsubstituted at th5-position of the benzene ring. 1,2,3-trihydroxybenzene is soluble (in water) and a very weakly acidic compound (based on its pKa). 1,2,3-trihydroxybenzene can be found in arabica coffee, beer, cocoa powder, and coffee, which makes 1,2,3-trihydroxybenzene a potential biomarker for the consumption of these food products. 1,2,3-trihydroxybenzene can be found primarily in blood, feces, and urine. 1,2,3-trihydroxybenzene is an organic compound with the formula C6H3(OH)3. It is a white water-soluble solid although samples are typically brownish because of its sensitivity toward oxygen. It is one of three isomeric benzenetriols .
CAS Number87-66-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
1,2,3-BenzenetriolChEBI
Benzene-1,2,3-triolChEBI
Pyrogallic acidChEBI
PyrogallolKegg
PyrogallateGenerator
Acid, pyrogallicMeSH
1,2,3-Benzenetriol (acd/name 4.0)HMDB
1,2,3-Trihydroxy-benzeneHMDB
1,2,3-TrihydroxybenzenHMDB
2,3-DihydroxyphenolHMDB
C.I. oxidation base 32HMDB
Fouramine base apHMDB
Fouramine brown apHMDB
Fourrine 85HMDB
Fourrine PGHMDB
PhenolHMDB
PiralHMDB
PyroHMDB
1,2,3-TrihydroxybenzeneHMDB
Pyrogallol, 8CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility51.8 g/LALOGPS
logP0.34ALOGPS
logP1.06ChemAxon
logS-0.39ALOGPS
pKa (Strongest Acidic)8.94ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32 m³·mol⁻¹ChemAxon
Polarizability11.57 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H6O3
IUPAC namebenzene-1,2,3-triol
InChI IdentifierInChI=1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H
InChI KeyWQGWDDDVZFFDIG-UHFFFAOYSA-N
Isomeric SMILES[H]OC1=CC=CC(O[H])=C1O[H]
Average Molecular Weight126.11
Monoisotopic Molecular Weight126.031694058
Classification
Description Belongs to the class of organic compounds known as 5-unsubstituted pyrrogallols. These are pyrrogallols that are unsubstituted at th5-position of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenetriols and derivatives
Direct Parent5-unsubstituted pyrrogallols
Alternative Parents
Substituents
  • 5-unsubstituted pyrrogallol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

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 stateNot Available
    Physical DescriptionNot Available
    Mass CompositionC 57.14%; H 4.80%; O 38.06%DFC
    Melting PointNot Available
    Boiling PointBp12 171.5°DFC
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV Data275 () (MeOH) (Berdy)DFC
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    GC-MS1,2,3-Benzenetriol, 3 TMS, GC-MS Spectrumsplash10-000l-3792000000-204d58c54b6096995794Spectrum
    GC-MS1,2,3-Benzenetriol, non-derivatized, GC-MS Spectrumsplash10-000l-0293000000-317381c3955975af27a6Spectrum
    GC-MS1,2,3-Benzenetriol, non-derivatized, GC-MS Spectrumsplash10-000l-1792000000-9b688a43f00234e626d1Spectrum
    GC-MS1,2,3-Benzenetriol, non-derivatized, GC-MS Spectrumsplash10-000l-3792000000-204d58c54b6096995794Spectrum
    GC-MS1,2,3-Benzenetriol, non-derivatized, GC-MS Spectrumsplash10-000l-2792000000-8c51cf40229b594f969bSpectrum
    Predicted GC-MS1,2,3-Benzenetriol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-8900000000-86a07f617d9e8a040199Spectrum
    Predicted GC-MS1,2,3-Benzenetriol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fu-7394000000-523c320e6717d1157daeSpectrum
    Predicted GC-MS1,2,3-Benzenetriol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-3900000000-aeb92cf5a0c6ea14fff22021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9000000000-7699321c8f67f04102232021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-ea01e7e29e972e1d72462021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2900000000-e697ce0798ac1b834e4c2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000000-44dd7b530071c9df93f62021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-bb91257afdfff20901ae2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-102c-9100000000-c0e14c51a15ee2e09b242021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-912d8a287d687cb0d66c2016-08-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-e3d143390169f9266a862016-08-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-8d1d0e03dd45599fc9c02016-08-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-ea97e3db0a8790646d2e2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-b3160bcc0b389cf211d92016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016v-9300000000-bc0f8f26aacd70e402fe2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-2900000000-4e851cb501d3e45affc92021-09-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-3358a867a0e9fb9492b92021-09-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-9000000000-b92ddc7dd0d4d7cf80812021-09-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-5fac22aad109814b92dd2021-09-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-9200000000-8a4799a05e6d74dbb2cd2021-09-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-1afa6f5c853d02418a3a2021-09-25View Spectrum
    NMRNot Available
    ChemSpider IDNot Available
    ChEMBL IDNot Available
    KEGG Compound IDNot Available
    Pubchem Compound IDNot Available
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID655
    DrugBank IDNot Available
    HMDB IDNot Available
    CRC / DFC (Dictionary of Food Compounds) IDDTZ32-N:DTZ32-N
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID655
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— 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.