Record Information
Version1.0
Creation date2010-04-08 22:10:02 UTC
Update date2019-11-26 03:06:23 UTC
Primary IDFDB012200
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2,3-Dihydroxybenzoic acid
DescriptionOccurs in Gentiana lutea (yellow gentian) 2-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)
CAS Number303-38-8
Structure
Thumb
Synonyms
SynonymSource
2,3 DHBChEBI
2,3-DIHYDROXY-benzoIC ACIDChEBI
3-Hydroxysalicylic acidChEBI
Catechol-3-carboxylic acidChEBI
DOBKChEBI
O-Pyrocatechuic acidChEBI
Pyrocatechuic acidChEBI
2,3-Dihydroxybenzoic acidKegg
2,3-DIHYDROXY-benzoateGenerator
3-HydroxysalicylateGenerator
Catechol-3-carboxylateGenerator
O-PyrocatechuateGenerator
PyrocatechuateGenerator
2,3-DihydroxybenzoateGenerator
2-PyrocatechuateGenerator
CatecholcarboxylateHMDB
Catecholcarboxylic acidHMDB
DHBAHMDB
2,3-Dihydroxy benzoic acidMeSH, HMDB
2-Pyrocatechuic acid, sodium saltMeSH, HMDB
Ferri-2,3-dihydroxybenzoic acidMeSH, HMDB
1,2-Dihydroxybenzene-3-carboxylic acidPhytoBank
2-Pyrocatechuic acidbiospider
2,3-Dihydroxy-benzoic acidbiospider
o-Pyrocatechuatebiospider
o-Pyrocatechuic aciddb_source
Pyrocatechuic acid, 8CIdb_source
Resorcylic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility6.88 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m³·mol⁻¹ChemAxon
Polarizability13.71 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H6O4
IUPAC name2,3-dihydroxybenzoic acid
InChI IdentifierInChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)
InChI KeyGLDQAMYCGOIJDV-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=C(O)C(O)=CC=C1
Average Molecular Weight154.121
Monoisotopic Molecular Weight154.026608673
Classification
Description 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
  • Benzoyl
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 54.55%; H 3.92%; O 41.52%DFC
Melting PointMp 204° (anhyd.)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP1.20HANSCH,C ET AL. (1995)
Experimental pKapKa 2.91DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data326 () (NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS2,3-Dihydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-0924000000-1ed6156dbe82344d29afSpectrum
GC-MS2,3-Dihydroxybenzoic acid, 3 TMS, GC-MS Spectrumsplash10-0a4u-3922000000-0b326da278c57df03c1aSpectrum
GC-MS2,3-Dihydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-0924000000-1ed6156dbe82344d29afSpectrum
GC-MS2,3-Dihydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0a4u-3922000000-0b326da278c57df03c1aSpectrum
GC-MS2,3-Dihydroxybenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0a4l-0922000000-beddd6836f31d4813a14Spectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zg0-4900000000-44419ba3a3e768caaeeeSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-008a-5192000000-86efa4079dcb0a7d6174Spectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,3-Dihydroxybenzoic acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-0900000000-9d9306f70123d5d263efSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-4900000000-702a14e999a2e830a9d5Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-7900000000-a88a9646fb3070aef98dSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0900000000-9bbc26971da28557772eSpectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0pb9-0900000000-7f5ec409ec11ea326d42Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0900000000-ba9640b66d655cdb3295Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0201-0900000000-40f4ec4c2b33e147f78bSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-c5444a948b6dfffe4059Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-6000163ae935d019ab25Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0pb9-0900000000-b9e3e795548fcdc52ee4Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-9aef155a0507c9c6d986Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0900000000-5d283030559c5931b824Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-68a4f0df325353ecd082Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0900000000-1b11ae0f71a80e056a93Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9200000000-f64ac01c6efb684a4f55Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-cb45151fcc0e74008de3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-df3ca8c192f0fcf2b620Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9700000000-e3faafae5f2aad580cddSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-f9afef76ab6c6ac97e51Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-5900000000-0ca2af142a25251b2a85Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9100000000-18f4a8eefdb99c1dd8ffSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-31cc76875b7e828b57e3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-2b91af5de3160a31b13dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-9100000000-1810b7542f18d07d2e10Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID18
ChEMBL IDCHEMBL1432
KEGG Compound IDC00196
Pubchem Compound ID19
Pubchem Substance IDNot Available
ChEBI ID18026
Phenol-Explorer ID430
DrugBank IDDB01672
HMDB IDHMDB00397
CRC / DFC (Dictionary of Food Compounds) IDHFB57-G:HFB57-G
EAFUS IDNot Available
Dr. Duke IDPYROCATECHUIC-ACID
BIGG IDNot Available
KNApSAcK IDC00002669
HET IDDBH
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID2,3-Dihydroxybenzoic_acid
Phenol-Explorer Metabolite ID430
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
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.