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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 20:22:29 UTC
NP-MRD IDNP0000017
Secondary Accession NumbersNone
Natural Product 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
Thumb
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 acid
Chemical FormulaC7H6O4
Average Mass154.1210 Da
Monoisotopic Mass154.02661 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, D2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Citrus cultivarsKNApSAcK Database
Citrus limoniaKNApSAcK Database
Citrus spp.KNApSAcK Database
Cymodocea rotundataKNApSAcK Database
Cymodocea serrulataKNApSAcK Database
Eucalyptus grandisKNApSAcK Database
Foeniculum vulgareKNApSAcK Database
Gentiana spp.KNApSAcK Database
Halodule uninervisKNApSAcK Database
Halodule wrightiiKNApSAcK Database
Halophila hawaiianaKNApSAcK Database
Helianthus tuberosusKNApSAcK Database
Leptolaena diospyroideaKNApSAcK Database
Leptolaena paucifloraKNApSAcK Database
Olea europaeaKNApSAcK Database
Phyllospadix scouleriKNApSAcK Database
Phyllospadix serrulatusKNApSAcK Database
Plantago majorKNApSAcK Database
Posidonia oceanicaKNApSAcK Database
Prunus aviumKNApSAcK Database
Pterocarpus santalinusKNApSAcK Database
Raphanus sativusKNApSAcK Database
Rhamnus dispermaKNApSAcK Database
Rhaponticum carthamoidesKNApSAcK Database
Sesamum indicumKNApSAcK Database
Syringodium filiformeKNApSAcK Database
Syringodium isoetifoliumKNApSAcK Database
Taxus baccataKNApSAcK Database
Thalassia hemprichiiKNApSAcK Database
Thalassia testudinumKNApSAcK Database
Thalassodendron ciliatumKNApSAcK Database
Vitis viniferaKNApSAcK Database
Zostera capricorniKNApSAcK Database
Zostera marinaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Penicillium citrinum F5KNApSAcK Database
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point199.5 °CNot Available
Boiling Point406.00 to 407.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility5 mg/mL at 5 °CNot Available
LogP1.74SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility12.3 g/LALOGPS
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 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
External Links
HMDB IDHMDB0000152
DrugBank IDNot Available
Phenol Explorer Compound ID416
FoodDB 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
Good Scents IDrw1165361
References
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 ]
  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. [PubMed: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. [PubMed:3026319 ]
  6. Peleg H, Noble AC: Perceptual properties of benzoic acid derivatives. Chem Senses. 1995 Aug;20(4):393-400. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:7356541 ]
  12. Abedi F, Razavi BM, Hosseinzadeh H: A review on gentisic acid as a plant derived phenolic acid and metabolite of aspirin: Comprehensive pharmacology, toxicology, and some pharmaceutical aspects. Phytother Res. 2020 Apr;34(4):729-741. doi: 10.1002/ptr.6573. Epub 2019 Dec 11. [PubMed:31825145 ]
  13. Fayos J, Belles JM, Lopez-Gresa MP, Primo J, Conejero V: Induction of gentisic acid 5-O-beta-D-xylopyranoside in tomato and cucumber plants infected by different pathogens. Phytochemistry. 2006 Jan;67(2):142-8. doi: 10.1016/j.phytochem.2005.10.014. [PubMed:16321412 ]