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=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

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 8297
free radical 3 Target ID: free radical Sources: https://www.ncbi.nlm.nih.gov/pubmed/22023109	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Renal cell carcinoma 31 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 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Evaluation of pyridoindoles, pyridylindoles and pyridylpyridoindoles as matrices for ultraviolet matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2001	11746903
Two-photon ionization thresholds of matrix-assisted laser desorption/ionization matrix clusters.	2001	11507754
Improvement of in-gel digestion protocol for peptide mass fingerprinting by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2001	11507753
Comparison of the radical trapping ability of PBN, S-PPBN and NXY-059.	2001 Apr	11328677
Mice with a partial deficiency of manganese superoxide dismutase show increased vulnerability to the mitochondrial toxins malonate, 3-nitropropionic acid, and MPTP.	2001 Jan	11161607
Biodegradation of carbaryl by a Micrococcus species.	2001 Jul	11375667
Stability of phenolic compounds during extraction with superheated solvents.	2001 Jul 6	11471800
A novel pathway of aerobic benzoate catabolism in the bacteria Azoarcus evansii and Bacillus stearothermophilus.	2001 Jul 6	11306574
[Determination of salicylic acid and its hydroxylated products using high performance liquid chromatography and fluorescence detection].	2001 Mar	12541674
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	11262590
Localization of analyte molecules in MALDI preparations by confocal laser scanning microscopy.	2001 Mar 1	11289411
Oxidative stress causes nuclear factor-kappaB activation in acute hypovolemic hemorrhagic shock.	2001 May 15	11369495
Ionization and fragmentation of neutral and acidic glycosphingolipids with a Q-TOF mass spectrometer fitted with a MALDI ion source.	2001 Nov	11720398
Matrix-assisted laser desorption/ionization collision-induced dissociation of linear single oligomers of nylon-6.	2001 Oct	11747103
Identification of amino acid residues essential for catalytic activity of gentisate 1,2-dioxygenase from Pseudomonas alcaligenes NCIB 9867.	2001 Oct 16	11682193
Characterization of Rhodococcus opacus R7, a strain able to degrade naphthalene and o-xylene isolated from a polycyclic aromatic hydrocarbon-contaminated soil.	2001 Sep	11605984
Identification and structural analysis of synthetic oligosaccharides of Shigella sonnei using MALDI-TOF MS.	2001 Sep 7	11527533
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	11951968
Sheng-Mai-San is protective against post-ischemic myocardial dysfunction in rats through its opening of the mitochondrial KATP channels.	2002 Aug	12197603
Anti-HSV-1 activity of synthetic humic acid-like polymers derived from p-diphenolic starting compounds.	2002 Jul	12495212
What do matrix-assisted laser desorption/ionization mass spectra reveal about ionization mechanisms?	2002 Jun	12112747
Helicobacter pylori-induced oxidative stress and DNA damage in a primary culture of human gastric mucosal cells.	2002 Jun	12064819
Nickel-induced plasma lipid peroxidation and effect of antioxidants in human blood: involvement hydroxyl radical formation and depletion of alpha-tocopherol.	2002 Jun 28	12079610
2,3,4-Trimethyl-5,7-dihydroxy-2,3-dihydrobenzofuran, a novel antioxidant, from Penicillium citrinum F5.	2002 May	12027755
Chemiluminescence associated with the oxidative metabolism of salicylic acid in rat liver microsomes.	2002 May 20	12076519
Ionization energy reductions in small 2,5-dihydroxybenzoic acid-proline clusters.	2002 Nov	12447889
Laser desorption/ionization time-of-flight mass spectrometry on sol-gel-derived 2,5-dihydroxybenzoic acid film.	2002 Nov 15	12463363
Sample preparation effects in matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry of partially depolymerised carboxymethyl cellulose.	2003	12772265
Comparison of laser desorption and matrix-assisted laser desorption/ionization for ruthenium and osmium trisbipyridine complexes using Fourier transform mass spectrometry.	2003 Apr	12686486
In vitro evaluation of patch formulations for topical delivery of gentisic acid in rats.	2003 Feb	12594007
Attenuation of methamphetamine induced dopaminergic neurotoxicity by flupirtine: microdialysis study on dopamine release and free radical generation.	2003 Feb	12589576
Effects of phenolic acids on human phenolsulfotransferases in relation to their antioxidant activity.	2003 Feb 26	12590501
Patterned monolayer/polymer films for analysis of dilute or salt-contaminated protein samples by MALDI-MS.	2003 Jan 15	12553750
Lithium treatment induces a hypersensitive-like response in tobacco.	2003 Jul	14520568
Quinaprilat reduces myocardial infarct size involving nitric oxide production and mitochondrial KATP channel in rabbits.	2003 Jun	12775974
Defibrillatory action of glibenclamide is independent from ATP-sensitive K+ channels and free radicals.	2003 Jun	12775970
Aromatic trap analysis of free radicals production in experimental collagen-induced arthritis in the rat: protective effect of glycosaminoglycans treatment.	2003 Mar	12688421
Isolation of free phenolic compounds from arboreal leaves by use of the Florisil/C18 system.	2003 Oct	12942227

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 `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

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

Official Name

English

Classification Tree Code System Code

LOINC

79515-3