Back to Compounds

Showing Compound 2,3-Dihydroxybenzoic acid (FDB012200)

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
MOLSDFPDBSMILESInChI
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
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-0900000000-9d9306f70123d5d263ef2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-4900000000-702a14e999a2e830a9d52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-7900000000-a88a9646fb3070aef98d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0900000000-9bbc26971da28557772e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0pb9-0900000000-7f5ec409ec11ea326d422017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0900000000-ba9640b66d655cdb32952017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0201-0900000000-40f4ec4c2b33e147f78b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-c5444a948b6dfffe40592021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-6000163ae935d019ab252021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0pb9-0900000000-b9e3e795548fcdc52ee42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-9aef155a0507c9c6d9862021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0900000000-5d283030559c5931b8242021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-68a4f0df325353ecd0822017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0900000000-1b11ae0f71a80e056a932017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9200000000-f64ac01c6efb684a4f552017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-cb45151fcc0e74008de32017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-df3ca8c192f0fcf2b6202017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9700000000-e3faafae5f2aad580cdd2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-f9afef76ab6c6ac97e512021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-5900000000-0ca2af142a25251b2a852021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9100000000-18f4a8eefdb99c1dd8ff2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-31cc76875b7e828b57e32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-2b91af5de3160a31b13d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-9100000000-1810b7542f18d07d2e102021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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.