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

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
Effect of impurities on the matrix-assisted laser desorption/ionization mass spectra of insulin.	2001	11746906
Evaluation of pyridoindoles, pyridylindoles and pyridylpyridoindoles as matrices for ultraviolet matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2001	11746903
Improvement of in-gel digestion protocol for peptide mass fingerprinting by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2001	11507753
Ionization mechanism of oligonucleotides in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2001	11135425
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
Stability of phenolic compounds during extraction with superheated solvents.	2001 Jul 6	11471800
The mechanism of matrix to analyte proton transfer in clusters of 2,5-dihydroxybenzoic acid and the tripeptide VPL.	2001 Jun	11401163
Studies of pesticides by collision-induced dissociation, postsource-decay, matrix-assisted laser desorption/ionization time of flight mass spectrometry.	2001 May	11349957
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
A quantitative model of ultraviolet matrix-assisted laser desorption/ionization.	2002 Aug	12203681
Catabolic enzyme levels in bacteria grown on binary and ternary substrate mixtures in continuous culture.	2002 Jul 20	12115435
[Analysis of aromatic hydrocarbon catabolic genes in strains isolated from soil in Patagonia].	2002 Jul-Sep	12415896
Measurements of mean initial velocities of analyte and matrix ions in infrared matrix-assisted laser desorption ionization mass spectrometry.	2002 Mar	11908801
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
Solid phase microextraction with matrix assisted laser desorption/ionization introduction to mass spectrometry and ion mobility spectrometry.	2002 Sep	12375845
Sample preparation effects in matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry of partially depolymerised carboxymethyl cellulose.	2003	12772265
Analysis of a bioactive beta-(1 --> 3) polysaccharide (Curdlan) using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2003	12717760
Comparison of laser desorption and matrix-assisted laser desorption/ionization for ruthenium and osmium trisbipyridine complexes using Fourier transform mass spectrometry.	2003 Apr	12686486
Effects of phenolic acids on human phenolsulfotransferases in relation to their antioxidant activity.	2003 Feb 26	12590501
Lithium treatment induces a hypersensitive-like response in tobacco.	2003 Jul	14520568
Determination of hydroxyl radical by capillary electrophoresis and studies on hydroxyl radical scavenging activities of Chinese herbs.	2003 Jul	12802570
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
Phospholipase A2, hydroxyl radicals, and lipid peroxidation in transient cerebral ischemia.	2003 Oct	14580322
Different antioxidant effects of polyphenols on lipid peroxidation and hydroxyl radicals in the NADPH-, Fe-ascorbate- and Fe-microsomal systems.	2003 Oct 1	14505792
Determination of hydroxyl radical by capillary zone electrophoresis with amperometric detection.	2003 Oct 17	14601833
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	14505322

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)).

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