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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 of GENTISIC ACID

SMILES

OC(=O)C1=C(O)C=CC(O)=C1

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

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P14679
Gene ID: 7299.0
Gene Symbol: TYR
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Evaluation of pyridoindoles, pyridylindoles and pyridylpyridoindoles as matrices for ultraviolet matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
2001
Improvement of in-gel digestion protocol for peptide mass fingerprinting by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
2001
In-source decay characteristics of peptides in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
2001 Apr
Modified cold storage of rat livers with self-made HYD solution.
2001 Feb
Biodegradation of carbaryl by a Micrococcus species.
2001 Jul
A novel pathway of aerobic benzoate catabolism in the bacteria Azoarcus evansii and Bacillus stearothermophilus.
2001 Jul 6
[Determination of salicylic acid and its hydroxylated products using high performance liquid chromatography and fluorescence detection].
2001 Mar
Labelling of Re-ABP with 188Re for bone pain palliation.
2001 Mar
Determination of salicylate, gentisic acid and salicyluric acid in human urine by capillary electrophoresis with laser-induced fluorescence detection.
2001 Mar 5
Studies of pesticides by collision-induced dissociation, postsource-decay, matrix-assisted laser desorption/ionization time of flight mass spectrometry.
2001 May
Measurement of free radical production by in vivo microdialysis during ischemia/reperfusion injury to skeletal muscle.
2001 May 1
Oxidative stress causes nuclear factor-kappaB activation in acute hypovolemic hemorrhagic shock.
2001 May 15
Identification and structural analysis of synthetic oligosaccharides of Shigella sonnei using MALDI-TOF MS.
2001 Sep 7
Rapid analysis of intact phospholipids from whole bacterial cells by matrix-assisted laser desorption/ionization mass spectrometry combined with on-probe sample pretreatment.
2002
Small angle neutron scattering measurements of synthetic polymer dispersions in matrix-assisted laser desorption/ionization matrixes.
2002
Hyphenation of capillary high-performance liquid chromatography with matrix-assisted laser desorption/ionization time-of-flight mass spectrometry for nano-scale screening of single-bead combinatorial libraries.
2002
In-source H/D exchange and ion-molecule reactions using matrix assisted laser desorption/ionization Fourier transform ion cyclotron resonance mass spectrometry with pulsed collision and reaction gases.
2002 Apr
A quantitative model of ultraviolet matrix-assisted laser desorption/ionization.
2002 Aug
Internal energy of ions generated by matrix-assisted laser desorption/ionization.
2002 Dec 15
Anti-HSV-1 activity of synthetic humic acid-like polymers derived from p-diphenolic starting compounds.
2002 Jul
Electrospray mass spectral studies on molybdenum complexes with 2,3- and 2,5-dihydroxybenzoic acid and their degradation products.
2002 Jul
[Analysis of aromatic hydrocarbon catabolic genes in strains isolated from soil in Patagonia].
2002 Jul-Sep
What do matrix-assisted laser desorption/ionization mass spectra reveal about ionization mechanisms?
2002 Jun
Helicobacter pylori-induced oxidative stress and DNA damage in a primary culture of human gastric mucosal cells.
2002 Jun
Measurements of mean initial velocities of analyte and matrix ions in infrared matrix-assisted laser desorption ionization mass spectrometry.
2002 Mar
2,3,4-Trimethyl-5,7-dihydroxy-2,3-dihydrobenzofuran, a novel antioxidant, from Penicillium citrinum F5.
2002 May
Chemiluminescence associated with the oxidative metabolism of salicylic acid in rat liver microsomes.
2002 May 20
Ionization energy reductions in small 2,5-dihydroxybenzoic acid-proline clusters.
2002 Nov
Laser desorption/ionization time-of-flight mass spectrometry on sol-gel-derived 2,5-dihydroxybenzoic acid film.
2002 Nov 15
Solid phase microextraction with matrix assisted laser desorption/ionization introduction to mass spectrometry and ion mobility spectrometry.
2002 Sep
Factors governing the solubilization of phosphopeptides retained on ferric NTA IMAC beads and their analysis by MALDI TOFMS.
2002 Sep
Matrix-assisted ultraviolet laser-desorption ionization and electrospray-ionization time-of-flight mass spectrometry of sulfated neocarrabiose oligosaccharides.
2002 Sep 27
Matrix-assisted laser desorption/ionization analysis of lipids and high molecular weight hydrocarbons with lithium 2,5-dihydroxybenzoate matrix.
2003
Sample preparation effects in matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry of partially depolymerised carboxymethyl cellulose.
2003
Some aspects of the stability of ion current in a matrix-assisted laser desorption/ionization source.
2003
Analysis of a bioactive beta-(1 --> 3) polysaccharide (Curdlan) using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
2003
Irradiation effects in MALDI, ablation, ion production, and surface modifications. Part II. 2,5-dihydroxybenzoic acid monocrystals.
2003 Aug
Attenuation of methamphetamine induced dopaminergic neurotoxicity by flupirtine: microdialysis study on dopamine release and free radical generation.
2003 Feb
Patterned monolayer/polymer films for analysis of dilute or salt-contaminated protein samples by MALDI-MS.
2003 Jan 15
Determination of hydroxyl radical by capillary electrophoresis and studies on hydroxyl radical scavenging activities of Chinese herbs.
2003 Jul
Combined effects of electrostatic and pi-pi stacking interactions: selective binding of nucleotides and aromatic carboxylates by platinum(II)-aromatic ligand complexes.
2003 Jul 21
Antibacterial xanthones from Kielmeyera variabilis mart. (Clusiaceae).
2003 Jun
Aromatic trap analysis of free radicals production in experimental collagen-induced arthritis in the rat: protective effect of glycosaminoglycans treatment.
2003 Mar
Postischemic hypothermia inhibits the generation of hydroxyl radical following transient forebrain ischemia in rats.
2003 May
Isolation of free phenolic compounds from arboreal leaves by use of the Florisil/C18 system.
2003 Oct
Rate and extent of ion-exchange process: the effect of physico-chemical characteristics of salicylate anions.
2003 Sep 4
Patents

Sample Use Guides

in rats
Route of Administration: Transdermal
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 Fri Dec 15 15:20:30 GMT 2023
Edited
by admin
on Fri Dec 15 15:20:30 GMT 2023
Record UNII
VP36V95O3T
Record Status Validated (UNII)
Record Version
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Name Type Language
GENTISIC ACID
II   INN   MI   WHO-DD  
INN  
Official 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
2,5-DIHYDROXYBENZOIC ACID [INCI]
Common Name English
2,5-DIHYDROXYBENZOIC ACID
INCI  
INCI  
Official Name English
Classification Tree Code System Code
LOINC 79515-3
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID4060078
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106782
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
FDA UNII
VP36V95O3T
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
PUBCHEM
3469
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
MERCK INDEX
m5703
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY Merck Index
NSC
27224
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
DRUG CENTRAL
3260
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
WIKIPEDIA
GENTISIC ACID
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
SMS_ID
100000084521
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
INN
756
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
DAILYMED
VP36V95O3T
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
MESH
C010925
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-718-5
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107562
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
CHEBI
58044
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
CONCEPT Industrial Aid
EVMPD
SUB07895MIG
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
NCI_THESAURUS
C76714
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
CAS
490-79-9
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
CHEBI
17189
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY
RXCUI
1368641
Created by admin on Fri Dec 15 15:20:30 GMT 2023 , Edited by admin on Fri Dec 15 15:20:30 GMT 2023
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
MAJOR
URINE
Related Record Type Details
PARENT -> IMPURITY
Correction factors: for the calculation of contents, multiply the peak areas by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY