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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-04-03 14:10:30 UTC
Update Date2020-11-09 23:19:07 UTC
HMDB IDHMDB0013676
Secondary Accession Numbers
  • HMDB13676
Metabolite Identification
Common Name2,6-Dihydroxybenzoic acid
Description2,6-Dihydroxybenzoic acid, also known as 6-hydroxysalicylic acid or gamma-resorcylic acid, belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. 2,6-Dihydroxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2,6-Dihydroxybenzoic acid is found, on average, in the highest concentration within beers and olives. This could make 2,6-dihydroxybenzoic acid a potential biomarker for the consumption of these foods. 2,6-dihydroxybenzoic acid is a secondary metabolite of salicylic acid which has been hydrolyzed by liver enzymes during phase I metabolism.
Structure
Data?1582753142
Synonyms
ValueSource
6-Hydroxysalicylic acidChEBI
gamma-Resorcylic acidChEBI
6-HydroxysalicylateGenerator
g-ResorcylateGenerator
g-Resorcylic acidGenerator
gamma-ResorcylateGenerator
Γ-resorcylateGenerator
Γ-resorcylic acidGenerator
2,6-DihydroxybenzoateGenerator
2,6-Dihydroxy-benzoic acidHMDB
2,6-Dihydroxybenzoic acid (acd/name 4.0)HMDB
2,6-Resorcylic acidHMDB
2-CarboxyresorcinolHMDB
BenzoateHMDB
Benzoic acidHMDB
Chemical FormulaC7H6O4
Average Molecular Weight154.121
Monoisotopic Molecular Weight154.026608673
IUPAC Name2,6-dihydroxybenzoic acid
Traditional Name2,6-dihydroxybenzoic acid
CAS Registry Number303-07-1
SMILES
OC(=O)C1=C(O)C=CC=C1O
InChI Identifier
InChI=1S/C7H6O4/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3,8-9H,(H,10,11)
InChI KeyAKEUNCKRJATALU-UHFFFAOYSA-N
Chemical Taxonomy
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
  • Resorcinol
  • 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
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point165 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.56 mg/mLNot Available
LogP2.20Not Available
Predicted Properties
PropertyValueSource
Water Solubility7.49 g/LALOGPS
logP1.28ALOGPS
logP2.32ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m³·mol⁻¹ChemAxon
Polarizability13.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w2i-4900000000-e371483679ffb975b0b7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-05gi-5092000000-75920741b3da9d472393Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0900000000-d899ed75ac04fcbce213Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-61b442ba35921bf15903Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-9700000000-af21042a1145ed08d24fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0900000000-b2d93bd5c6cc2201063cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-b40aa1f15c5c8ca99961Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-d0ea5ade866525499246Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.014 +/- 0.008 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.011 +/- 0.003 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.022 +/- 0.008 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.026 +/- 0.007 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.012 +/- 0.005 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.005 +/- 0.002 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.01 +/- 0.003 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.009 +/- 0.002 uMAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.09 +/- 0.057 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID437
FooDB IDFDB000845
KNApSAcK IDNot Available
Chemspider ID8974
KEGG Compound IDNot Available
BioCyc IDCPD-8816
BiGG IDNot Available
Wikipedia Link2,6-Dihydroxybenzoic_acid
METLIN IDNot Available
PubChem Compound9338
PDB IDGRE
ChEBI ID68465
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]