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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-04-03 14:10:30 UTC
Update Date2020-11-09 23:19:06 UTC
HMDB IDHMDB0013674
Secondary Accession Numbers
  • HMDB13674
Metabolite Identification
Common Name1,2,3-Trihydroxybenzene
Description1,2,3-Trihydroxybenzene, also known as pyrogallic acid or 1,2,3-benzenetriol, 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. 1,2,3-Trihydroxybenzene is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a white, water-soluble solid although samples are typically brownish because of its sensitivity toward oxygen. Outside of the human body, 1,2,3-trihydroxybenzene is found, on average, in the highest concentration in a few different foods, such as coffee, arabica coffee, and cocoa powders and in a lower concentration in beers. 1,2,3-trihydroxybenzene has also been detected, but not quantified in, . This could make 1,2,3-trihydroxybenzene a potential biomarker for the consumption of these foods. This formulation resolved the consistency issues, and Hutchings found that an interaction between the greenish stain given to film by pyro developers and the color sensitivity of modern variable-contrast photographic papers gave the effect of an extreme compensating developer. An alternate preparation involves treating para-chlorophenoldisulphonic acid with potassium hydroxide, a variant on the time-honored route to phenols from sulfonic acids. It can be used for small and large negative formats.
Structure
Data?1582753141
Synonyms
ValueSource
1,2,3-BenzenetriolChEBI
Benzene-1,2,3-triolChEBI
Pyrogallic acidChEBI
PyrogallolKegg
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
Acid, pyrogallicMeSH
Chemical FormulaC6H6O3
Average Molecular Weight126.11
Monoisotopic Molecular Weight126.031694058
IUPAC Namebenzene-1,2,3-triol
Traditional Namepyrogallol
CAS Registry Number87-66-1
SMILES
[H]OC1=CC=CC(O[H])=C1O[H]
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
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:

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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-000l-3792000000-204d58c54b6096995794Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000l-0293000000-317381c3955975af27a6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000l-1792000000-9b688a43f00234e626d1Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000l-3792000000-204d58c54b6096995794Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000l-2792000000-8c51cf40229b594f969bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-8900000000-86a07f617d9e8a040199Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00fu-7394000000-523c320e6717d1157daeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-912d8a287d687cb0d66cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-e3d143390169f9266a86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-8d1d0e03dd45599fc9c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-ea97e3db0a8790646d2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-b3160bcc0b389cf211d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016v-9300000000-bc0f8f26aacd70e402feSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
UrineDetected and Quantified0.07 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID655
FooDB IDFDB008735
KNApSAcK IDC00002670
Chemspider ID13835557
KEGG Compound IDC01108
BioCyc IDPYROGALLOL
BiGG IDNot Available
Wikipedia LinkPyrogallol
METLIN IDNot Available
PubChem Compound1057
PDB IDNot Available
ChEBI ID16164
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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