GENTISIC ACID

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 Search

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

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 7728
Target ID: free radical Sources: https://www.ncbi.nlm.nih.gov/pubmed/22023109	Binding Agent 996

Conditions

Condition	Modality	Targets	Highest Phase	Product
Renal cell carcinoma 27 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 492	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ionization mechanism of oligonucleotides in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2001	11135425
Limits for the detection of (poly-)phosphoinositides by matrix-assisted laser desorption and ionization time-of-flight mass spectrometry (MALDI-TOF MS).	2001 Apr	11369324
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
Comparison of two independent aromatic hydroxylation assays in combination with intracerebral microdialysis to determine hydroxyl free radicals.	2001 Jul 15	11459618
A novel pathway of aerobic benzoate catabolism in the bacteria Azoarcus evansii and Bacillus stearothermophilus.	2001 Jul 6	11306574
(90)Y and (177)Lu labeling of a DOTA-conjugated vitronectin receptor antagonist useful for tumor therapy.	2001 Jul-Aug	11459461
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
Labelling of Re-ABP with 188Re for bone pain palliation.	2001 Mar	11214878
Localization of analyte molecules in MALDI preparations by confocal laser scanning microscopy.	2001 Mar 1	11289411
Determination of salicylate, gentisic acid and salicyluric acid in human urine by capillary electrophoresis with laser-induced fluorescence detection.	2001 Mar 5	11254191
Studies of pesticides by collision-induced dissociation, postsource-decay, matrix-assisted laser desorption/ionization time of flight mass spectrometry.	2001 May	11349957
Measurement of free radical production by in vivo microdialysis during ischemia/reperfusion injury to skeletal muscle.	2001 May 1	11316577
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
Mass spectrometric studies of benzoxazine resorcarenes.	2002	12203236
Sheng-Mai-San is protective against post-ischemic myocardial dysfunction in rats through its opening of the mitochondrial KATP channels.	2002 Aug	12197603
Sample depletion of the matrix-assisted laser desorption process monitored using radionuclide detection.	2002 Dec 15	12510739
2,3,4-Trimethyl-5,7-dihydroxy-2,3-dihydrobenzofuran, a novel antioxidant, from Penicillium citrinum F5.	2002 May	12027755
Factors governing the solubilization of phosphopeptides retained on ferric NTA IMAC beads and their analysis by MALDI TOFMS.	2002 Sep	12322952
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
Tempol, a novel stable nitroxide, reduces brain damage and free radical production, after acute subdural hematoma in the rat.	2003 Apr	12866813
Irradiation effects in MALDI, ablation, ion production, and surface modifications. Part II. 2,5-dihydroxybenzoic acid monocrystals.	2003 Aug	12892913
In vitro evaluation of patch formulations for topical delivery of gentisic acid in rats.	2003 Feb	12594007
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
Two-laser infrared and ultraviolet matrix-assisted laser desorption/ionization.	2003 Jul	12898657
Determination of hydroxyl radical by capillary electrophoresis and studies on hydroxyl radical scavenging activities of Chinese herbs.	2003 Jul	12802570
Molecular characterization of an inducible gentisate 1,2-dioxygenase gene, xlnE, from Pseudomonas alcaligenes NCIMB 9867.	2003 Jul 17	12909360
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	12866078
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
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	12618347
Photosynthetic responses of corn and soybean to foliar application of salicylates.	2003 May	12806776
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
Rate and extent of ion-exchange process: the effect of physico-chemical characteristics of salicylate anions.	2003 Sep 4	12932722

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 `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

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

Official Name

English

Classification Tree Code System Code

LOINC

79515-3