GENTISIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H6O4
Molecular Weight	154.1201
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CC(O)=CC=C1O

InChI

InChIKey=WXTMDXOMEHJXQO-UHFFFAOYSA-N

InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)

HIDE SMILES / InChI

Molecular Formula	C7H6O4
Molecular Weight	154.1201
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28594277 | https://www.ncbi.nlm.nih.gov/pubmed/12594007 | https://www.ncbi.nlm.nih.gov/pubmed/13086370

Gentisic acid is an active metabolite of salicylic acid degradation, which possesses a broad spectrum of biological activity, such as anti-inflammatory, antirheumatic and antioxidant properties. The antioxidant activity and radioprotective properties of gentisic acid are exerted by its phenoxyl group. It is also used in cosmetics as a skin-whitening agent for the treatment of skin pigmentary disorders by influencing the synthesis of melanin through inhibition of melanosomal tyrosinase activity Gentisic acid is also a biomarker of Renal Cell Carcinoma.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosinase 41 Target ID: P14679 Gene ID: 7299.0 Gene Symbol: TYR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12594007	Inhibitor 8504
free radical 3 Target ID: free radical Sources: https://www.ncbi.nlm.nih.gov/pubmed/22023109	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Renal cell carcinoma 33 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28594277	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown
Rheumatic polyarthritis 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13086370	Primary		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Determination of hydroxyl radical by capillary zone electrophoresis with amperometric detection.	2003-10-17	14601833
Different antioxidant effects of polyphenols on lipid peroxidation and hydroxyl radicals in the NADPH-, Fe-ascorbate- and Fe-microsomal systems.	2003-10-01	14505792
Phospholipase A2, hydroxyl radicals, and lipid peroxidation in transient cerebral ischemia.	2003-10	14580322
Isolation of free phenolic compounds from arboreal leaves by use of the Florisil/C18 system.	2003-10	12942227
Ascorbic acid: useful as a buffer agent and radiolytic stabilizer for metalloradiopharmaceuticals.	2003-09-18	13129412
Rate and extent of ion-exchange process: the effect of physico-chemical characteristics of salicylate anions.	2003-09-04	12932722
Evaluation of the quantitativeness of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry using an equimolar mixture of uniform poly(ethylene glycol) oligomers.	2003-09	14505322
Co-localization of brain-derived neurotrophic factor (BDNF) and wild-type huntingtin in normal and quinolinic acid-lesioned rat brain.	2003-09	12956709
Therapeutic efficiency of rhenium-188-HEDP in human prostate cancer skeletal metastases.	2003-08-18	12915868
Irradiation effects in MALDI, ablation, ion production, and surface modifications. Part II. 2,5-dihydroxybenzoic acid monocrystals.	2003-08	12892913
Combined effects of electrostatic and pi-pi stacking interactions: selective binding of nucleotides and aromatic carboxylates by platinum(II)-aromatic ligand complexes.	2003-07-21	12866078
Molecular characterization of an inducible gentisate 1,2-dioxygenase gene, xlnE, from Pseudomonas alcaligenes NCIMB 9867.	2003-07-17	12909360
Lithium treatment induces a hypersensitive-like response in tobacco.	2003-07	14520568
Two-laser infrared and ultraviolet matrix-assisted laser desorption/ionization.	2003-07	12898657
Determination of hydroxyl radical by capillary electrophoresis and studies on hydroxyl radical scavenging activities of Chinese herbs.	2003-07	12802570
Antibacterial xanthones from Kielmeyera variabilis mart. (Clusiaceae).	2003-06	12937772
Quinaprilat reduces myocardial infarct size involving nitric oxide production and mitochondrial KATP channel in rabbits.	2003-06	12775974
Defibrillatory action of glibenclamide is independent from ATP-sensitive K+ channels and free radicals.	2003-06	12775970
Photosynthetic responses of corn and soybean to foliar application of salicylates.	2003-05	12806776
Postischemic hypothermia inhibits the generation of hydroxyl radical following transient forebrain ischemia in rats.	2003-05	12803982
Tempol, a novel stable nitroxide, reduces brain damage and free radical production, after acute subdural hematoma in the rat.	2003-04	12866813
Comparison of laser desorption and matrix-assisted laser desorption/ionization for ruthenium and osmium trisbipyridine complexes using Fourier transform mass spectrometry.	2003-04	12686486
Non-steroidal anti-inflammatory drug sodium salicylate, but not diclofenac or celecoxib, protects against 1-methyl-4-phenyl pyridinium-induced dopaminergic neurotoxicity in rats.	2003-03-21	12618347
Fluorinated matrix approach for the characterization of hydrophobic perfluoropolyethers by matrix-assisted laser desorption/ionization time-of-flight MS.	2003-03-15	12659188
Aromatic trap analysis of free radicals production in experimental collagen-induced arthritis in the rat: protective effect of glycosaminoglycans treatment.	2003-03	12688421
Nickel-induced oxidative stress and effect of antioxidants in human lymphocytes.	2003-03	12632251
Effects of phenolic acids on human phenolsulfotransferases in relation to their antioxidant activity.	2003-02-26	12590501
In vitro evaluation of patch formulations for topical delivery of gentisic acid in rats.	2003-02	12594007
Attenuation of methamphetamine induced dopaminergic neurotoxicity by flupirtine: microdialysis study on dopamine release and free radical generation.	2003-02	12589576
Patterned monolayer/polymer films for analysis of dilute or salt-contaminated protein samples by MALDI-MS.	2003-01-15	12553750
Matrix-assisted laser desorption/ionization analysis of lipids and high molecular weight hydrocarbons with lithium 2,5-dihydroxybenzoate matrix.	2003	14515318
Sample preparation effects in matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry of partially depolymerised carboxymethyl cellulose.	2003	12772265
Some aspects of the stability of ion current in a matrix-assisted laser desorption/ionization source.	2003	12717764
Analysis of a bioactive beta-(1 --> 3) polysaccharide (Curdlan) using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2003	12717760
Ionic matrices for matrix-assisted laser desorption/ionization time-of-flight detection of DNA oligomers.	2003	12621617
Sample depletion of the matrix-assisted laser desorption process monitored using radionuclide detection.	2002-12-15	12510739
Internal energy of ions generated by matrix-assisted laser desorption/ionization.	2002-12-15	12510737
Laser desorption/ionization time-of-flight mass spectrometry on sol-gel-derived 2,5-dihydroxybenzoic acid film.	2002-11-15	12463363
[Analysis of aromatic hydrocarbon catabolic genes in strains isolated from soil in Patagonia].	2002-11-06	12415896
Ionization energy reductions in small 2,5-dihydroxybenzoic acid-proline clusters.	2002-11	12447889
Matrix-assisted ultraviolet laser-desorption ionization and electrospray-ionization time-of-flight mass spectrometry of sulfated neocarrabiose oligosaccharides.	2002-09-27	12350325
Solid phase microextraction with matrix assisted laser desorption/ionization introduction to mass spectrometry and ion mobility spectrometry.	2002-09	12375845
Factors governing the solubilization of phosphopeptides retained on ferric NTA IMAC beads and their analysis by MALDI TOFMS.	2002-09	12322952
A quantitative model of ultraviolet matrix-assisted laser desorption/ionization.	2002-08	12203681
Sheng-Mai-San is protective against post-ischemic myocardial dysfunction in rats through its opening of the mitochondrial KATP channels.	2002-08	12197603
Anti-HSV-1 activity of synthetic humic acid-like polymers derived from p-diphenolic starting compounds.	2002-07	12495212
Rapid analysis of intact phospholipids from whole bacterial cells by matrix-assisted laser desorption/ionization mass spectrometry combined with on-probe sample pretreatment.	2002	12271453
Mass spectrometric studies of benzoxazine resorcarenes.	2002	12203236
Small angle neutron scattering measurements of synthetic polymer dispersions in matrix-assisted laser desorption/ionization matrixes.	2002	12125027
[Determination of salicylic acid and its hydroxylated products using high performance liquid chromatography and fluorescence detection].	2001-03	12541674

Patents

Sample Use Guides

In Vivo Use Guide

in rats

Route of Administration: Transdermal

In Vitro Use Guide

Antioxidant activity of gentisic acid has been studied using fast chemical kinetics and two in vitro models, namely the isolated rat liver mitochondria (RLM) and the human erythrocytes. The presence of gentisic acid (GA) during irradiation significantly reduced the levels of gamma radiation induced damages to lipids and proteins in RLM. GA efficiently scavenged hydroxyl radical (k = 1.1 × 10(10) dm(3)mol(-1)s(-1)) to produce reducing adduct radical (~76%) and oxidizing phenoxyl radical (~24%). GA has also scavenged organohaloperoxyl radical (k = 9.3 × 10(7) dm(3) mol(-1)s(-1)).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:54:34 GMT 2025` Edited by `admin` on `Mon Mar 31 17:54:34 GMT 2025`
Record UNII	VP36V95O3T
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

GENTISIC ACID

Official Name

English

2,5-DIHYDROXYBENZOIC ACID

Preferred Name

English

GENTISIC ACID [MI]

Common Name

English

NSC-27224

Code

English

SALICYLIC ACID, 5-HYDROXY-

Common Name

English

GENTISIC ACID [II]

Common Name

English

5-HYDROXYSALICYLIC ACID

Systematic Name

English

MESALAZINE IMPURITY G [EP IMPURITY]

Common Name

English

gentisic acid [INN]

Common Name

English

Gentisic acid [WHO-DD]

Common Name

English

Classification Tree Code System Code

LOINC

79515-3