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

General Description

3-Benzyl-7-hydroxy-4-methyl-2H-chromen-2-one is a chemical compound with a structure consisting of a benzene ring attached to a chromenone ring. It is a member of the flavonoid family of compounds, known for their antioxidant and anti-inflammatory properties. This specific compound has a hydroxyl group at the 7th position and a methyl group at the 4th position of the chromenone ring, as well as a benzyl group attached to the chromenone ring. It has been studied for its potential pharmacological activities, including its anti-cancer, anti-inflammatory, and antioxidant effects. It may have potential applications in the development of pharmaceuticals and natural health products.

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

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Downstream Products

• 2550-26-7 4-Phenyl-2-butanone 
• 89-86-1 4-hydroxysalicylic acid 
• 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