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4-Hydroxycoumarin

CAT: 0804-HY-N6856-02Size: 50 gDry Ice: NoHazardous: No
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CAT#:0804-HY-N6856-02Size:50 g
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Description
4-Hydroxycoumarin is an orally active coumarin derivative, one of the most versatile heterocyclic scaffolds, often used in the synthesis of various organic compounds. 4-Hydroxycoumarin possesses both electrophilic and nucleophilic properties. 4-Hydroxycoumarin is an HIV protease inhibitor and tyrosine kinase inhibitor. 4-Hydroxycoumarin has anti-inflammatory, antibacterial and anti-tumor effects[1][2][3][4].
CAS Number
1076-38-6
UNSPSC
12352005
Hazard Statement
H302
Target
Bacterial; Endogenous Metabolite
Type
Natural Products
Related Pathways
Anti-infection; Metabolic Enzyme/Protease
Applications
COVID-19-anti-virus
Field of Research
Infection; Cancer
Assay Protocol
https://www.medchemexpress.com/4-hydroxycoumarin.html
Purity
99.96
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C1C=C(O)C2=CC=CC=C2O1
Molecular Formula
C9H6O3
Molecular Weight
162.14
Precautions
H302
References & Citations
[1]Mohammadi Ziarani G, et al. The molecular diversity scope of 4-hydroxycoumarin in the synthesis of heterocyclic compounds via multicomponent reactions. Mol Divers. 2019 Jan 29. doi: 10.1007/s11030-019-09918-7.|[2]Velasco-Velázquez MA, et al. 4-Hydroxycoumarin disorganizes the actin cytoskeleton in B16-F10 melanoma cells but not in B82 fibroblasts, decreasing their adhesion to extracellular matrix proteins and motility. Cancer Lett. 2003 Aug 20;198 (2) :179-86.|[3]Salinas-Jazmín N, et al. Antimetastatic, antineoplastic, and toxic effects of 4-hydroxycoumarin in a preclinical mouse melanoma model. Cancer Chemother Pharmacol. 2010 Apr;65 (5) :931-40.|[4]Luchini AC, et al. Intestinal anti-inflammatory activity of coumarin and 4-hydroxycoumarin in the trinitrobenzenesulphonic acid model of rat colitis. Biol Pharm Bull. 2008 Jul;31 (7) :1343-50.
Shipping Conditions
Room Temperature
Storage Conditions
Store at room temperature 3 years
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

4-Hydroxycoumarin

4-hydroxycoumarin is a hydroxycoumarin that is coumarin in which the hydrogen at position 4 is replaced by a hydroxy group. It is a conjugate acid of a 4-hydroxycoumarin(1-).

CAS Number1076-38-6
PubChem CID54682930
IUPAC Name4-hydroxychromen-2-one
Molecular FormulaC9H6O3
Molecular Weight162.14
XLogP1.3
Topological Polar Surface Area46.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Heavy Atom Count12
Formal Charge0
Complexity232
SMILES
C1=CC=C2C(=C1)C(=CC(=O)O2)O
InChI
InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H
InChIKey
VXIXUWQIVKSKSA-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 4-Hydroxycoumarin
CAS: 1076-38-6
CID: 54682930
Formula: C9H6O3
MW: 162.14
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight162.14
XLogP31.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass162.031694049
Monoisotopic Mass162.031694049
Topological Polar Surface Area46.5 Ų
Heavy Atom Count12
Formal Charge0
Complexity232
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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