86-44-2

Basic information

• Product Name: 3-BENZYL-7-HYDROXY-4-METHYL-2H-CHROMEN-2-ONE
• Synonyms: 3-BENZYL-7-HYDROXY-4-METHYL-2H-CHROMEN-2-ONE;3-benzyl-4-methylumbelliferone;3-Benzyl-7-hydroxy-4-methyl-2H-chromen-2-one, 7-Hydroxy-4-methyl-3-(phenylmethyl)-2H-1-benzopyran-2-one;2H-1-Benzopyran-2-one, 7-hydroxy-4-methyl-3-(phenylmethyl)-;2H-Chromen-2-one, 3-benzyl-7-hydroxy-4-methyl-;3-Benzyl-4-methylumbelliferon;7-hydroxy-4-methyl-3-(phenylmethyl)-2-chromenone;7-hydroxy-4-methyl-3-(phenylmethyl)chromen-2-one
• CAS NO: 86-44-2
• Molecular Formula: C₁₇H₁₄O₃
• Molecular Weight: 266.29126
• Mol File: 86-44-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 481.6°C at 760 mmHg
• Flash Point: 208.1°C
• Appearance: /
• Density: 1.269g/cm³
• Vapor Pressure: 6.69E-10mmHg at 25°C
• Refractive Index: 1.639
• CAS DataBase Reference: 3-BENZYL-7-HYDROXY-4-METHYL-2H-CHROMEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BENZYL-7-HYDROXY-4-METHYL-2H-CHROMEN-2-ONE(86-44-2)
• EPA Substance Registry System: 3-BENZYL-7-HYDROXY-4-METHYL-2H-CHROMEN-2-ONE(86-44-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 86-44-2(Hazardous Substances Data)

Usage

Description

3-Benzyl-7-hydroxy-4-methyl-2H-chromen-2-one is a flavonoid compound characterized by a benzene ring attached to a chromenone ring, featuring a hydroxyl group at the 7th position, a methyl group at the 4th position, and a benzyl group attached to the chromenone ring. It is known for its antioxidant, anti-inflammatory, and potential anti-cancer properties.
Used in Pharmaceutical Industry:
3-Benzyl-7-hydroxy-4-methyl-2H-chromen-2-one is used as a pharmaceutical agent for its potential anti-cancer, anti-inflammatory, and antioxidant effects. It is being studied for its ability to modulate various biological pathways and may contribute to the development of new therapeutics for various health conditions.
Used in Natural Health Products:
3-Benzyl-7-hydroxy-4-methyl-2H-chromen-2-one is used as an ingredient in natural health products due to its beneficial properties. Its antioxidant and anti-inflammatory actions may support overall health and wellness, and it could be incorporated into supplements or other health-related products for these purposes.

InChI:InChI=1/C17H14O3/c1-11-14-8-7-13(18)10-16(14)20-17(19)15(11)9-12-5-3-2-4-6-12/h2-8,10,18H,9H2,1H3

Upstream product

• 620-79-1 Ethyl 2-benzylacetoacetate 
• 108-46-3 recorcinol 
• 7446-70-0 aluminium trichloride 
• 98-95-3 nitrobenzene 
• 2150-47-2 methyl 2,4-dihydroxybenzoate 
• 433733-19-8 2-benzyl-buta-2,3-dienoic acid ethyl ester 
• 100-39-0 benzyl bromide 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 393810-34-9 3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl dimethylcarbamate 
• 1428239-08-0 3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl diethylcarbamate 
• 312941-17-6 3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl propionate 
• 1428238-96-3 3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl pentanoate 
• 1428238-95-2 3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl pivalate 
• 1428238-78-1 3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl butyrate 
• 780790-52-5 3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl benzenesulfonate 
• 1428238-97-4 3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl 4-methylbenzenesulfonate 
• 548764-31-4 methyl-phenyl-carbamic acid 3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl ester 
• 548764-73-4 3,4-Dihydro-2H-quinoline-1-carboxylic acid 3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl ester 

Relevant articles and documents

Development of coumarine derivatives as potent anti-filovirus entry inhibitors targeting viral glycoprotein

Filoviruses, including Ebolavirus (EBOV), Marburgvirus (MARV) and Cuevavirus, cause hemorrhagic fevers in humans with up to 90% mortality rates. In the 2014–2016 West Africa Ebola epidemic, there are 15,261 laboratory confirmed cases and 11,325 total deaths. The lack of effective vaccines and medicines for the prevention and treatment of filovirus infection in humans stresses the urgency to develop antiviral therapeutics against filovirus-associated diseases. Our previous study identified a histamine receptor antagonist compound CP19 as an entry inhibitor against both EBOV and MARV. The preliminary structure-activity relationship (SAR) studies of CP19 showed that its piperidine, coumarin and linker were related with its antiviral activities. In this study, we performed detailed SAR studies on these groups with synthesized CP19 derivatives. We discovered that 1) the piperidine group could be optimized with heterocycles, 2) the substitution groups of C3 and C4 of coumarin should be relatively large hydrophobic groups and 3) the linker part should be least substituted. Based on the SAR analysis, we synthesized compound 32 as a potent entry inhibitor of EBOV and MARV (IC50 = 0.5 μM for EBOV and 1.5 μM for MARV). The mutation studies of Ebola glycoprotein and molecular docking studies showed that the coumarin and its substituted groups of compound 32 bind to the pocket of Ebola glycoprotein in a similar way to the published entry inhibitor compound 118a. However, the carboxamide group of compound 32 does not have strong interaction with N61 as compound 118a does. The coumarin skeleton structure and the binding model of compound 32 elucidated by this study could be utilized to guide further design and optimization of entry inhibitors targeting the filovirus glycoproteins.

Agents and methods for treating ischemic and other diseases

This invention relates to compounds that modulate TRPM7 protein activity and use of the same for treatment or prophylaxis of ischemia, cancer, pain or glaucoma.

Synthesis of substituted coumarins via Bronsted acid mediated condensation of allenes with substituted phenols or anisoles

Coumarins were obtained from the condensation of electron-rich arenes with allenes in the presence of TfOH in good yield. Depending on the substituent pattern of allenes employed, the general synthetic method of 4-substituted and 3,4-disubstituted 3-arylc