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4-Methylcatechol

CAT: 0804-HY-W012814-03Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-W012814-03Size:500 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
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].
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.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

4-Methylcatechol

4-methylcatechol is a methylcatechol having a single methyl substituent at the 4-position. It has been isolated from Picea abies. It has a role as an antioxidant, a carcinogenic agent, a hapten, a plant metabolite and a human metabolite.

CAS Number452-86-8
PubChem CID9958
IUPAC Name4-methylbenzene-1,2-diol
Molecular FormulaC7H8O2
Molecular Weight124.14
XLogP1.4
Topological Polar Surface Area40.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Heavy Atom Count9
Formal Charge0
Complexity92
SMILES
CC1=CC(=C(C=C1)O)O
InChI
InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3
InChIKey
ZBCATMYQYDCTIZ-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 4-Methylcatechol
CAS: 452-86-8
CID: 9958
Formula: C7H8O2
MW: 124.14
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight124.14
XLogP31.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass124.052429494
Monoisotopic Mass124.052429494
Topological Polar Surface Area40.5 Ų
Heavy Atom Count9
Formal Charge0
Complexity92.9
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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