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3-O-Methyltolcapone

CAT: 0804-HY-100642-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-100642-01Size:5 mg
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Description
3-O-Methyltolcapone (Ro 40-7591) is a metabolite of Tolcapone. Tolcapone (Ro 40-7592) is a selective, potent and orally active COMT inhibitor with an IC50of 773 nM. Tolcapone can inhibits α-syn and Aβ42 oligomerization and fibrillogenesis. Tolcapone can cause oxidative stress and induce cancer cells apoptosis and ROS production. Tolcapone can be used for the researches of cancer and neurological disease, such as Parkinson disease and neuroblastoma[1][2][3][4][5][6].
CAS Number
134612-80-9
Product Name Alternative
Ro 40-7591
UNSPSC
12352005
Hazard Statement
H315, H319, H335
Target
Amyloid-β; Apoptosis; COMT; Drug Metabolite; Reactive Oxygen Species (ROS)
Type
Reference compound
Related Pathways
Apoptosis; Immunology/Inflammation; Metabolic Enzyme/Protease; Neuronal Signaling; NF-κB
Applications
Neuroscience-Neurodegeneration
Field of Research
Cancer; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/3-o-methyltolcapone.html
Purity
99.95
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C(C1=CC([N+]([O-])=O)=C(O)C(OC)=C1)C2=CC=C(C)C=C2
Molecular Formula
C15H13NO5
Molecular Weight
287.27
Precautions
H315, H319, H335
References & Citations
[1]De Santi C, et al. Catechol-O-methyltransferase: variation in enzyme activity and inhibition by entacapone and tolcapone. Eur J Clin Pharmacol. 1998 May;54 (3) :215-9.|[2]Di Giovanni S, et al. Entacapone and tolcapone, two catechol O-methyltransferase inhibitors, block fibril formation of alpha-synuclein and beta-amyloid and protect against amyloid-induced toxicity. J Biol Chem. 2010 May 14;285 (20) :14941-14954. |[3]Ceravolo R, et al. 18F-dopa PET evidence that tolcapone acts as a central COMT inhibitor in Parkinson's disease. Synapse. 2002 Mar 1;43 (3) :201-7.|[4]Maser T, et al. Tolcapone induces oxidative stress leading to apoptosis and inhibition of tumor growth in Neuroblastoma. Cancer Med. 2017 Jun;6 (6) :1341-1352. |[5]Jorga K, et al. Metabolism and excretion of tolcapone, a novel inhibitor of catechol-O-methyltransferase. Br J Clin Pharmacol. 1999 Oct;48 (4) :513-20.|[6]Poonsiri T, et al. 3-O-Methyltolcapone and Its Lipophilic Analogues Are Potent Inhibitors of Transthyretin Amyloidogenesis with High Permeability and Low Toxicity. Int J Mol Sci. 2023 Dec 29;25 (1) :479.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

3-O-Methyltolcapone

3-O-methyltolcapone is a member of benzophenones.

CAS Number134612-80-9
PubChem CID126117
IUPAC Name(4-hydroxy-3-methoxy-5-nitrophenyl)-(4-methylphenyl)methanone
Molecular FormulaC15H13NO5
Molecular Weight287.27
XLogP3.6
Topological Polar Surface Area92.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Heavy Atom Count21
Formal Charge0
Complexity386
SMILES
CC1=CC=C(C=C1)C(=O)C2=CC(=C(C(=C2)OC)O)[N+](=O)[O-]
InChI
InChI=1S/C15H13NO5/c1-9-3-5-10(6-4-9)14(17)11-7-12(16(19)20)15(18)13(8-11)21-2/h3-8,18H,1-2H3
InChIKey
VCNSNEJUGBEWTA-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 3-O-Methyltolcapone
CAS: 134612-80-9
CID: 126117
Formula: C15H13NO5
MW: 287.27
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight287.27
XLogP33.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass287.07937252
Monoisotopic Mass287.07937252
Topological Polar Surface Area92.4 Ų
Heavy Atom Count21
Formal Charge0
Complexity386
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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