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Details

Stereochemistry ACHIRAL
Molecular Formula C7H6O4
Molecular Weight 154.1204
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GENTISIC ACID

SMILES

c1cc(c(cc1O)C(=O)O)O

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 154.1204
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)
Target ID: free radical
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Ionization mechanism of oligonucleotides in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
2001
Limits for the detection of (poly-)phosphoinositides by matrix-assisted laser desorption and ionization time-of-flight mass spectrometry (MALDI-TOF MS).
2001 Apr
Comparison of the radical trapping ability of PBN, S-PPBN and NXY-059.
2001 Apr
Mice with a partial deficiency of manganese superoxide dismutase show increased vulnerability to the mitochondrial toxins malonate, 3-nitropropionic acid, and MPTP.
2001 Jan
Biodegradation of carbaryl by a Micrococcus species.
2001 Jul
Comparison of two independent aromatic hydroxylation assays in combination with intracerebral microdialysis to determine hydroxyl free radicals.
2001 Jul 15
A novel pathway of aerobic benzoate catabolism in the bacteria Azoarcus evansii and Bacillus stearothermophilus.
2001 Jul 6
(90)Y and (177)Lu labeling of a DOTA-conjugated vitronectin receptor antagonist useful for tumor therapy.
2001 Jul-Aug
The mechanism of gentisic acid-induced relaxation of the guinea pig isolated trachea: the role of potassium channels and vasoactive intestinal peptide receptors.
2001 Mar
Labelling of Re-ABP with 188Re for bone pain palliation.
2001 Mar
Localization of analyte molecules in MALDI preparations by confocal laser scanning microscopy.
2001 Mar 1
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
Characterization of Rhodococcus opacus R7, a strain able to degrade naphthalene and o-xylene isolated from a polycyclic aromatic hydrocarbon-contaminated soil.
2001 Sep
Mass spectrometric studies of benzoxazine resorcarenes.
2002
Sheng-Mai-San is protective against post-ischemic myocardial dysfunction in rats through its opening of the mitochondrial KATP channels.
2002 Aug
Sample depletion of the matrix-assisted laser desorption process monitored using radionuclide detection.
2002 Dec 15
2,3,4-Trimethyl-5,7-dihydroxy-2,3-dihydrobenzofuran, a novel antioxidant, from Penicillium citrinum F5.
2002 May
Factors governing the solubilization of phosphopeptides retained on ferric NTA IMAC beads and their analysis by MALDI TOFMS.
2002 Sep
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
Tempol, a novel stable nitroxide, reduces brain damage and free radical production, after acute subdural hematoma in the rat.
2003 Apr
Irradiation effects in MALDI, ablation, ion production, and surface modifications. Part II. 2,5-dihydroxybenzoic acid monocrystals.
2003 Aug
In vitro evaluation of patch formulations for topical delivery of gentisic acid in rats.
2003 Feb
Patterned monolayer/polymer films for analysis of dilute or salt-contaminated protein samples by MALDI-MS.
2003 Jan 15
Lithium treatment induces a hypersensitive-like response in tobacco.
2003 Jul
Two-laser infrared and ultraviolet matrix-assisted laser desorption/ionization.
2003 Jul
Determination of hydroxyl radical by capillary electrophoresis and studies on hydroxyl radical scavenging activities of Chinese herbs.
2003 Jul
Molecular characterization of an inducible gentisate 1,2-dioxygenase gene, xlnE, from Pseudomonas alcaligenes NCIMB 9867.
2003 Jul 17
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
Quinaprilat reduces myocardial infarct size involving nitric oxide production and mitochondrial KATP channel in rabbits.
2003 Jun
Defibrillatory action of glibenclamide is independent from ATP-sensitive K+ channels and free radicals.
2003 Jun
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 Mar 21
Photosynthetic responses of corn and soybean to foliar application of salicylates.
2003 May
Phospholipase A2, hydroxyl radicals, and lipid peroxidation in transient cerebral ischemia.
2003 Oct
Different antioxidant effects of polyphenols on lipid peroxidation and hydroxyl radicals in the NADPH-, Fe-ascorbate- and Fe-microsomal systems.
2003 Oct 1
Determination of hydroxyl radical by capillary zone electrophoresis with amperometric detection.
2003 Oct 17
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 Sep
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 Sat Jun 26 00:28:38 UTC 2021
Edited
by admin
on Sat Jun 26 00:28:38 UTC 2021
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
GENTISIC ACID [WHO-DD]
Common Name English
SALICYLIC ACID, 5-HYDROXY-
Common Name English
GENTISIC ACID [II]
Common Name English
5-HYDROXYSALICYLIC ACID
Systematic Name English
GENTISIC ACID [INN]
Common Name English
MESALAZINE IMPURITY G [EP]
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 Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
Code System Code Type Description
EPA CompTox
490-79-9
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
PRIMARY
ChEMBL
CHEMBL2106782
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
PRIMARY
FDA UNII
VP36V95O3T
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
PRIMARY
PUBCHEM
3469
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
PRIMARY
MERCK INDEX
M5703
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
3260
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
PRIMARY
WIKIPEDIA
GENTISIC ACID
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
PRIMARY
INN
756
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
PRIMARY
MESH
C010925
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-718-5
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
PRIMARY
ChEMBL
CHEMBL2107562
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
CONCEPT Industrial Aid
EVMPD
SUB07895MIG
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
PRIMARY
NCI_THESAURUS
C76714
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
PRIMARY
CAS
490-79-9
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
PRIMARY
RXCUI
1368641
Created by admin on Sat Jun 26 00:28:38 UTC 2021 , Edited by admin on Sat Jun 26 00:28:38 UTC 2021
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