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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-08-17 21:44:28 UTC
HMDB IDHMDB00152
Secondary Accession NumbersNone
Metabolite Identification
Common NameGentisic acid
DescriptionGentisic acid is a dihydroxybenzoic acid. It is a crystalline powder that forms monoclinic prism in water solution. Gentisic acid is an active metabolite of salicylic acid degradation. There is an increasing amount of evidence indicating that gentisic acid has a broad spectrum of biological activity, such as anti-inflammatory, antirheumatic and antioxidant properties. Gentisic acid is also a byproduct of tyrosine and benzoate metabolism.
Structure
Thumb
Synonyms
ValueSource
2,5-DihydroxybenzoateChEBI
5-Hydroxysalicylic acidChEBI
GentisateChEBI
Gentisic acidChEBI
Hydroquinonecarboxylic acidChEBI
5-HydroxysalicylateGenerator
HydroquinonecarboxylateGenerator
2,5-DioxybenzoateHMDB
2,5-Dioxybenzoic acidHMDB
3,6-DihydroxybenzoateHMDB
3,6-Dihydroxybenzoic acidHMDB
5-Hydroxy-salicylateHMDB
5-Hydroxy-salicylic acidHMDB
CarboxyhydroquinoneHMDB
DihydroxybenzoicacidHMDB
GensigenHMDB
GensigonHMDB
GentisinateHMDB
Gentisinic acidHMDB
Chemical FormulaC7H6O4
Average Molecular Weight154.1201
Monoisotopic Molecular Weight154.02660868
IUPAC Name2,5-dihydroxybenzoic acid
Traditional Name2,5-dihydroxybenzoic acid
CAS Registry Number490-79-9
SMILES
OC(=O)C1=CC(O)=CC=C1O
InChI Identifier
InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
InChI KeyInChIKey=WXTMDXOMEHJXQO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. These are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Dihydroxybenzoic acid
  • Salicylic acid
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Benzoic acid
  • Hydroquinone
  • 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 locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point199.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.0 mg/mL at 5 °CNot Available
LogP1.74SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility12.3 mg/mLALOGPS
logP1.23ALOGPS
logP1.67ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.53ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m3·mol-1ChemAxon
Polarizability13.78 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-0849000000-d6f7b541cabdb5e20dd6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4i-3955000000-215d684d2fae395f2e76View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-0900000000-816a84a65cefa1b31731View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-1900000000-977e85749e8fa31315c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-1900000000-086d66fbe2d41a2d725cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-e3a62163a69461ab2cffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-0900000000-06431a9cf0c877732fe5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-0900000000-e938fddf26a9bb2cd9e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-0900000000-38ef6d9660431bec9b3bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-0900000000-ac95d834c95477f325a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Positivesplash10-004r-1913000000-eba82100caa3c2664508View in MoNA
LC-MS/MSLC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negativesplash10-0udi-0902000000-6cc114aa94b58c53c123View in MoNA
LC-MS/MSLC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Positivesplash10-0k9i-0930000000-4388abc8fe86bc940e89View in MoNA
LC-MS/MSLC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negativesplash10-0udi-0901000000-077381dba9d80706a097View in MoNA
LC-MS/MSLC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Positivesplash10-0fri-0930000000-4e24b1261f33fba704e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000b-9800000000-35424c6ac43370b30b89View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0900000000-56fe39ec90c2e54662dbView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0f79-7900000000-4ac54ba9a72c8707055dView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.65 +/- 0.19 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified1.0 +/- 0.31 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified1.35 +/- 0.79 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.31 +/- 0.19 uMAdult (>18 years old)BothIdiopathic oro-facial pain details
UrineDetected and Quantified1.48 +/- 0.69 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 IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID416
Phenol Explorer Metabolite ID416
FoodDB IDFDB000844
KNApSAcK IDC00002648
Chemspider ID3350
KEGG Compound IDC00628
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGentisic acid
NuGOwiki LinkHMDB00152
Metagene LinkHMDB00152
METLIN ID618
PubChem Compound3469
PDB IDGTQ
ChEBI ID17189
References
Synthesis Reference Morris, Steward G. Preparation of gentisic acid and its fatty alcohol esters.Journal of the American Chemical Society (1949), 71 2056-7
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ohsako M, Matsumoto Y, Goto S: Transport of aspirin and its metabolites through human erythrocyte membrane. Biol Pharm Bull. 1993 Feb;16(2):154-7. [8364451 ]
  2. Almaas R, Rootwelt T, Oyasaeter S, Saugstad OD: Ascorbic acid enhances hydroxyl radical formation in iron-fortified infant cereals and infant formulas. Eur J Pediatr. 1997 Jun;156(6):488-92. [9208249 ]
  3. Verhaeghe BJ, Lefevere MF, De Leenheer AP: Solid-phase extraction with strong anion-exchange columns for selective isolation and concentration of urinary organic acids. Clin Chem. 1988 Jun;34(6):1077-83. [3378323 ]
  4. Palumbo G, Carlucci G, Mazzeo P, Frieri G, Pimpo MT, Fanini D: Simultaneous determination of 5-aminosalicylic acid, acetyl-5-aminosalicylic acid and 2,5-dihydroxybenzoic acid in endoscopic intestinal biopsy samples in humans by high-performance liquid chromatography with electrochemical detection. J Pharm Biomed Anal. 1995 Dec;14(1-2):175-80. [8833980 ]
  5. 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 ]
  6. Peleg H, Noble AC: Perceptual properties of benzoic acid derivatives. Chem Senses. 1995 Aug;20(4):393-400. [8590024 ]
  7. Buskin JN, Upton RA, Williams RL: Improved liquid-chromatography of aspirin, salicylate, and salicyluric acid in plasma, with a modification for determining aspirin metabolites in urine. Clin Chem. 1982 May;28(5):1200-3. [7074905 ]
  8. Liu JH, Smith PC: Direct analysis of salicylic acid, salicyl acyl glucuronide, salicyluric acid and gentisic acid in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Jan 12;675(1):61-70. [8634769 ]
  9. Coudray C, Talla M, Martin S, Fatome M, Favier A: High-performance liquid chromatography-electrochemical determination of salicylate hydroxylation products as an in vivo marker of oxidative stress. Anal Biochem. 1995 May 1;227(1):101-11. [7668368 ]
  10. Bochner F, Graham GG, Cham BE, Imhoff DM, Haavisto TM: Salicylate metabolite kinetics after several salicylates. Clin Pharmacol Ther. 1981 Aug;30(2):266-75. [7249509 ]
  11. Cham BE, Bochner F, Imhoff DM, Johns D, Rowland M: Simultaneous liquid-chromatographic quantitation of salicylic acid, salicyluric acid, and gentisic acid in urine. Clin Chem. 1980 Jan;26(1):111-4. [7356541 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Reactions
Gentisic acid + Hydrogen peroxide → Gentisate aldehyde + Oxygen + Waterdetails