4-Methylcatechol

4-Methylcatechol is an intermediate in the degradation of some alkylbenzenes and an orally active suicide inhibitor of catechol 2,3-dioxygenase (C23O) . 4-Methylcatechol induces apoptosis in melanoma cells through oxidative stress, but some studies have also shown that 4-Methylcatechol is carcinogenic. In addition, 4-Methylcatechol has antiplatelet and blood pressure-lowering activities. 4-Methylcatechol can also inhibit protein oxidation in beef but does not disulfide formation[1][2][3][4][5][6].

Product Specifications

CAS Number

[452-86-8]

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Apoptosis; Endogenous Metabolite; Reactive Oxygen Species (ROS)

Type

Natural Products

Related Pathways

Apoptosis; Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB

Applications

Metabolism-protein/nucleotide metabolism

Field of Research

Cancer; Inflammation/Immunology; Cardiovascular Disease

Assay Protocol

https://www.medchemexpress.com/4-Methylbenzene-1,2-diol.html

Purity

99.52

Solubility

DMSO : 100 mg/mL (ultrasonic) |H2O : ≥ 100 mg/mL

Smiles

OC1=CC=C(C)C=C1O

Molecular Formula

C7H8O2

Molecular Weight

124.14

Precautions

H302, H315, H319, H335

References & Citations

[1]Okuta A, et al. Construction of chimeric catechol 2,3-dioxygenase exhibiting improved activity against the suicide inhibitor 4-methylcatechol. Appl Environ Microbiol. 2004 Mar;70 (3) :1804-10.|[2]Jongberg S, et al. 4-methylcatechol inhibits protein oxidation in meat but not disulfide formation. J Agric Food Chem. 2011 Sep 28;59 (18) :10329-35.|[3]Asakawa E, et al. Carcinogenicity of 4-methoxyphenol and 4-methylcatechol in F344 rats. Int J Cancer. 1994 Jan 2;56 (1) :146-52. |[4]Payton F, et al. 4-Methylcatechol-induced oxidative stress induces intrinsic apoptotic pathway in metastatic melanoma cells. Biochem Pharmacol. 2011 May 15;81 (10) :1211-8.|[5]Pourová J, et al. Two flavonoid metabolites, 3,4-dihydroxyphenylacetic acid and 4-methylcatechol, relax arteries ex vivo and decrease blood pressure in vivo. Vascul Pharmacol. 2018 Dec;111:36-43.|[6]Applová L, et al. 4-Methylcatechol, a Flavonoid Metabolite with Potent Antiplatelet Effects. Mol Nutr Food Res. 2019 Aug 7;63 (20) :e1900261.