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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:37 UTC
HMDB IDHMDB00397
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Pyrocatechuic acid
Description2-Pyrocatechuic acid is a normal human benzoic acid metabolite found in plasma (PMID 16351159 ), and is normally found with increased levels after consumption of many nutrients and drugs, i.e.: cranberry juice (PMID 14733499 ), aspirin ingestion. (PMID 3342084 ) It has been found associated with idiopathic oro-facial pain due to stress (oxidative stress might enhance the production of free radicals); it has been suggested that OH radicals are responsible for the production of many systemic and local tissue injury diseases which may initially manifest as pain syndrome, and 2-Pyrocatechuic acid is a biological marker for the detection and quantification of OH radicals, and patients had significantly increased circulating levels of 2-Pyrocatechuic acid after aspirin ingestion than control subjects. (PMID 7748148 ).
Structure
Thumb
Synonyms
ValueSource
2,3-Dihydroxybenzoic acidKegg
2,3-DihydroxybenzoateGenerator
2-PyrocatechuateGenerator
3-HydroxysalicylateHMDB
3-Hydroxysalicylic acidHMDB
CatecholcarboxylateHMDB
Catecholcarboxylic acidHMDB
DHBAHMDB
DOBKHMDB
O-PyrocatechuateHMDB
O-Pyrocatechuic acidHMDB
PyrocatechuateHMDB
Pyrocatechuic acidHMDB
Chemical FormulaC7H6O4
Average Molecular Weight154.1201
Monoisotopic Molecular Weight154.02660868
IUPAC Name2,3-dihydroxybenzoic acid
Traditional Name2,3-dihydroxy-benzoic acid
CAS Registry Number303-38-8
SMILES
OC(=O)C1=CC=CC(O)=C1O
InChI Identifier
InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)
InChI KeyInChIKey=GLDQAMYCGOIJDV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentSalicylic acids
Alternative Parents
Substituents
  • Salicylic acid
  • Benzoic acid
  • 1,2-diphenol
  • Benzoyl
  • Phenol
  • Vinylogous acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.20HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility6.88 mg/mLALOGPS
logP1.42ALOGPS
logP1.67ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.56ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m3·mol-1ChemAxon
Polarizability13.7 Å3ChemAxon
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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0a4i-0924000000-1ed6156dbe82344d29afView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4u-3922000000-0b326da278c57df03c1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-0900000000-9d9306f70123d5d263efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-4900000000-702a14e999a2e830a9d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-7900000000-a88a9646fb3070aef98dView in MoNA
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 430
  • Not Applicable
details
BloodDetected and Quantified0.129 +/- 0.034 uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.11 +/- 0.08 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.11 +/- 0.031 uMAdult (>18 years old)BothIdiopathic oro-facial pain details
UrineDetected and Quantified0.14 +/- 0.05 umol/mmol creatinineAdult (>18 years old)BothIdiopathic oro-facial pain details
Associated Disorders and Diseases
Disease References
Idiopathic oro-facial pain
  1. Aghabeigi B, Haque M, Wasil M, Hodges SJ, Henderson B, Harris M: The role of oxygen free radicals in idiopathic facial pain. Br J Oral Maxillofac Surg. 1997 Jun;35(3):161-5. [9212290 ]
Associated OMIM IDsNone
DrugBank IDDB01672
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID430
Phenol Explorer Metabolite ID430
FoodDB IDFDB012200
KNApSAcK IDC00002669
Chemspider ID18
KEGG Compound IDC00196
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00397
Metagene LinkHMDB00397
METLIN ID5386
PubChem Compound19
PDB IDDBH
ChEBI ID18026
References
Synthesis ReferenceMega, Izumi; Ozawa, Shuji. Manufacture of 2,3-dihydroxybenzoic acid. Jpn. Kokai Tokkyo Koho (2001), 3 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. A J, Trygg J, Gullberg J, Johansson AI, Jonsson P, Antti H, Marklund SL, Moritz T: Extraction and GC/MS analysis of the human blood plasma metabolome. Anal Chem. 2005 Dec 15;77(24):8086-94. [16351159 ]
  2. Grootveld M, Halliwell B: Aromatic hydroxylation as a potential measure of hydroxyl-radical formation in vivo. Identification of hydroxylated derivatives of salicylate in human body fluids. Biochem J. 1986 Jul 15;237(2):499-504. [3026319 ]
  3. Kaur H, Edmonds SE, Blake DR, Halliwell B: Hydroxyl radical generation by rheumatoid blood and knee joint synovial fluid. Ann Rheum Dis. 1996 Dec;55(12):915-20. [9014586 ]
  4. Schulz JB, Dehmer T, Schols L, Mende H, Hardt C, Vorgerd M, Burk K, Matson W, Dichgans J, Beal MF, Bogdanov MB: Oxidative stress in patients with Friedreich ataxia. Neurology. 2000 Dec 12;55(11):1719-21. [11113228 ]
  5. Grootveld M, Halliwell B: 2,3-Dihydroxybenzoic acid is a product of human aspirin metabolism. Biochem Pharmacol. 1988 Jan 15;37(2):271-80. [3342084 ]
  6. Zhang K, Zuo Y: GC-MS determination of flavonoids and phenolic and benzoic acids in human plasma after consumption of cranberry juice. J Agric Food Chem. 2004 Jan 28;52(2):222-7. [14733499 ]
  7. Haque MF, Aghabeighi B, Wasil M, Hodges S, Harris M: Oxygen free radicals in idiopathic facial pain. Bangladesh Med Res Counc Bull. 1994 Dec;20(3):104-16. [7748148 ]