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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:24:05 UTC
HMDB IDHMDB0000152
Secondary Accession Numbers
  • HMDB00152
Metabolite Identification
Common NameGentisic acid
DescriptionGentisic acid, also known as gentisate or 2,5-dioxybenzoate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. Gentisic acid is also classified as a dihydroxybenzoic acid. It is a derivative of benzoic acid and a minor (1%) product of the metabolic break down of aspirin, which is excreted by the kidneys. Gentisic acid is found in essentially all organisms ranging from bacteria to fungi to plants to animals. Gentisic acid has been associated with a number of useful effects on human health and exhibits anti-inflammatory, antigenotoxic, hepatoprotective, neuroprotective, antimicrobial, and especially antioxidant activities (PMID: 31825145 ). It is widely distributed in plants as a secondary plant product such as Gentiana spp., Citrus spp., Vitis vinifera, Pterocarpus santalinus, Helianthus tuberosus, Hibiscus rosa-sinensis, Olea europaea, and Sesamum indicum and in fruits such as avocados, batoko plum, kiwi fruits, apple, bitter melon, black berries, pears, and some mushrooms (PMID: 31825145 ). Gentisic acid is found in higher concentrations in a number of foods such as tarragons, common thymes, and common sages and in a lower concentration in grape wines, rosemaries, and sweet marjorams. Gentisic acid has also been shown to act as a pathogen-inducible signal for the activation of plant defenses in tomato plants and cucumbers (PMID: 16321412 ; https://doi.org/10.1094/MPMI.1999.12.3.227).
Structure
Data?1582752113
Synonyms
ValueSource
2,5-DihydroxybenzoateChEBI
5-Hydroxysalicylic acidChEBI
GentisateChEBI
Hydroquinonecarboxylic acidChEBI
2,5-Dihydroxybenzoic acidKegg
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
2,5-Dihydroxybenzoic acid, monosodium saltHMDB
Lithium 2,5-dihydroxybenzoateHMDB
Gentisic acidChEBI
Hydroquinone carboxylic acidHMDB
Chemical FormulaC7H6O4
Average Molecular Weight154.121
Monoisotopic Molecular Weight154.026608673
IUPAC Name2,5-dihydroxybenzoic acid
Traditional Name2,5-dihydroxybenzoic acid
CAS Registry Number490-79-9
SMILES
OC(=O)C1=C(O)C=CC(O)=C1
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 KeyWXTMDXOMEHJXQO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives 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
  • Benzoyl
  • Hydroquinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point199.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5 mg/mL at 5 °CNot Available
LogP1.74SANGSTER (1994)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg122.67230932474
[M-H]-Not Available124.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00000286
Predicted Molecular Properties
PropertyValueSource
Water Solubility12.3 g/LALOGPS
logP10(1.23) g/LALOGPS
logP10(1.67) g/LChemAxon
logS10(-1.1) g/LALOGPS
pKa (Strongest Acidic)2.53ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m³·mol⁻¹ChemAxon
Polarizability13.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.48431661259
DarkChem[M-H]-129.18131661259
AllCCS[M+H]+132.58632859911
AllCCS[M-H]-125.70832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Gentisic acidOC(=O)C1=C(O)C=CC(O)=C12929.7Standard polar33892256
Gentisic acidOC(=O)C1=C(O)C=CC(O)=C11547.3Standard non polar33892256
Gentisic acidOC(=O)C1=C(O)C=CC(O)=C11504.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gentisic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1O1724.4Semi standard non polar33892256
Gentisic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(O)C=C1C(=O)O1744.4Semi standard non polar33892256
Gentisic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(O)C(C(=O)O)=C11736.1Semi standard non polar33892256
Gentisic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1O1711.3Semi standard non polar33892256
Gentisic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1O[Si](C)(C)C1765.1Semi standard non polar33892256
Gentisic acid,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(O[Si](C)(C)C)C(C(=O)O)=C11783.2Semi standard non polar33892256
Gentisic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1811.8Semi standard non polar33892256
Gentisic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC=C1O1986.2Semi standard non polar33892256
Gentisic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(O)C=C1C(=O)O1995.7Semi standard non polar33892256
Gentisic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(O)C(C(=O)O)=C11995.8Semi standard non polar33892256
Gentisic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1O2180.3Semi standard non polar33892256
Gentisic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC=C1O[Si](C)(C)C(C)(C)C2248.9Semi standard non polar33892256
Gentisic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C12272.3Semi standard non polar33892256
Gentisic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2451.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Gentisic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0849000000-d6f7b541cabdb5e20dd62014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gentisic acid GC-MS (3 TMS)splash10-0a4i-3955000000-215d684d2fae395f2e762014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gentisic acid EI-B (Non-derivatized)splash10-03di-2009080030-be174b5f8728c96650e72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gentisic acid EI-B (Non-derivatized)splash10-0a4i-0229000000-a4712abe7c7db86a97be2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gentisic acid GC-EI-TOF (Non-derivatized)splash10-0a4i-0849000000-d6f7b541cabdb5e20dd62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gentisic acid GC-MS (Non-derivatized)splash10-0a4i-3955000000-215d684d2fae395f2e762017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gentisic acid GC-EI-TOF (Non-derivatized)splash10-0a4i-1946000000-be25f693c540abb01bde2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-114r-2900000000-c5a4c512f555f4ebce472017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (3 TMS) - 70eV, Positivesplash10-008a-5092000000-1b91af6751ccb58c613c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisic acid GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0f79-7900000000-4ac54ba9a72c8707055d2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-0zfr-0900000000-816a84a65cefa1b317312012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0a4i-1900000000-977e85749e8fa31315c52012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0a4i-1900000000-086d66fbe2d41a2d725c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0udi-0900000000-e3a62163a69461ab2cff2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0a4i-0900000000-06431a9cf0c877732fe52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0a4i-0900000000-e938fddf26a9bb2cd9e32012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0a4i-0900000000-38ef6d9660431bec9b3b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0a4i-0900000000-ac95d834c95477f325a72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Positive-QTOFsplash10-004r-1913000000-eba82100caa3c26645082012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negative-QTOFsplash10-0udi-0902000000-6cc114aa94b58c53c1232012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Positive-QTOFsplash10-0k9i-0930000000-4388abc8fe86bc940e892012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negative-QTOFsplash10-0udi-0901000000-077381dba9d80706a0972012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Positive-QTOFsplash10-0fri-0930000000-4e24b1261f33fba704e22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-000b-9800000000-35424c6ac43370b30b892012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-0a4i-0900000000-56fe39ec90c2e54662db2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid ESI-TOF , Negative-QTOFsplash10-0pdi-0439000000-d097f2b9a5189bc4bb0f2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid ESI-TOF 10V, Negative-QTOFsplash10-0pdi-0439000000-d097f2b9a5189bc4bb0f2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid ESI-TOF , Negative-QTOFsplash10-0pdi-0439000000-d097f2b9a5189bc4bb0f2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gentisic acid ESI-TOF 10V, Negative-QTOFsplash10-0a4i-0900000000-ddf5ec6162fb4b835c3a2017-09-12HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisic acid 10V, Positive-QTOFsplash10-0a4i-0900000000-0fe66ae910e6a6a75fd02017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisic acid 20V, Positive-QTOFsplash10-0a4r-0900000000-92d150f8439f22e9e2bb2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisic acid 40V, Positive-QTOFsplash10-0a7i-9400000000-b1783532af734cb7e8c42017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisic acid 10V, Negative-QTOFsplash10-0zfr-0900000000-64a4c14f26bc9fcf8dfa2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisic acid 20V, Negative-QTOFsplash10-0a4i-0900000000-acfcb8c4421ee8a0c31c2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisic acid 40V, Negative-QTOFsplash10-0a4i-4900000000-dd5469400fff82ccc3582017-06-28Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.35 +/- 0.79 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.31 +/- 0.19 uMAdult (>18 years old)BothIdiopathic oro-facial pain details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
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. [PubMed:9212290 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID416
FooDB IDFDB000844
KNApSAcK IDC00002648
Chemspider ID3350
KEGG Compound IDC00628
BioCyc IDCPD-633
BiGG IDNot Available
Wikipedia LinkGentisic_acid
METLIN ID618
PubChem Compound3469
PDB IDNot Available
ChEBI ID17189
Food Biomarker OntologyNot Available
VMH IDHC00460
MarkerDB IDMDB00000073
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed:3378323 ]
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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
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Gentisic acid → 6-(3-carboxy-4-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Gentisic acid → 6-(2-carboxy-4-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Gentisic acid → 6-(2,5-dihydroxybenzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
Gentisic acid → Gentisuric aciddetails