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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-04-03 14:10:30 UTC
Update Date2017-10-23 19:06:12 UTC
HMDB IDHMDB0013674
Secondary Accession Numbers
  • HMDB13674
Metabolite Identification
Common Name1,2,3-Trihydroxybenzene
DescriptionPyrogallol or benzene-1,2,3-triol is a benzenetriol. It is a white crystalline powder and a powerful reducing agent. It was first prepared by Scheele 1786 by heating gallic acid. An alternate preparation is heating para-chlorophenoldisulphonic acid with potassium hydroxide.
Structure
Thumb
Synonyms
ValueSource
1,2,3-BenzenetriolChEBI
Benzene-1,2,3-triolChEBI
Pyrogallic acidChEBI
PyrogallateGenerator
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
PyrogallolHMDB
Chemical FormulaC6H6O3
Average Molecular Weight126.11
Monoisotopic Molecular Weight126.031694058
IUPAC Namebenzene-1,2,3-triol
Traditional Namepyrogallol
CAS Registry Number87-66-1
SMILES
OC1=CC=CC(O)=C1O
InChI Identifier
InChI=1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H
InChI KeyWQGWDDDVZFFDIG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrogallols and derivatives. These are compounds containing a 1,2,3-trihydroxybenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentPyrogallols and derivatives
Alternative Parents
Substituents
  • Pyrogallol derivative
  • 1,2-diphenol
  • Polyol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point133 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility507 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-000l-3792000000-204d58c54b6096995794View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000l-0293000000-317381c3955975af27a6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000l-1792000000-9b688a43f00234e626d1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000l-3792000000-204d58c54b6096995794View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000l-2792000000-8c51cf40229b594f969bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-8900000000-86a07f617d9e8a040199View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00fu-7394000000-523c320e6717d1157daeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-912d8a287d687cb0d66cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-e3d143390169f9266a86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-8d1d0e03dd45599fc9c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-ea97e3db0a8790646d2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-b3160bcc0b389cf211d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016v-9300000000-bc0f8f26aacd70e402feView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    UrineDetected and Quantified0.07 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound ID655
    Phenol Explorer Metabolite ID655
    FoodDB IDNot Available
    KNApSAcK IDNot Available
    Chemspider ID13835557
    KEGG Compound IDC01108
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia Link1,2,3-trihydroxybenzene
    METLIN IDNot Available
    PubChem Compound1057
    PDB IDPYG
    ChEBI ID16164
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General ReferencesNot Available

    Enzymes

    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
    1,2,3-Trihydroxybenzene → 6-(2,3-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
    1,2,3-Trihydroxybenzene → 6-(2,6-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails