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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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	Inhibitor 8,297
free radical 3	Binding Agent 1,064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Renal cell carcinoma 31	Diagnostic		Natural Metabolite	Unknown
Rheumatic polyarthritis 3	Primary		Not Provided 504	Unknown

PubMed

Show entries

Title	Date	PubMed
Two-photon ionization thresholds of matrix-assisted laser desorption/ionization matrix clusters.	2001	11507754
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
A novel pathway of aerobic benzoate catabolism in the bacteria Azoarcus evansii and Bacillus stearothermophilus.	2001 Jul 6	11306574
Silver cluster interferences in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry of nonpolar polymers.	2001 Jun	11401164
The mechanism of matrix to analyte proton transfer in clusters of 2,5-dihydroxybenzoic acid and the tripeptide VPL.	2001 Jun	11401163

Showing 1 to 5 of 22 entries

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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)).