59887-88-6

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 6-Methoxy-
• Synonyms: 4H-1-Benzopyran-4-one, 6-Methoxy-
• CAS NO: 59887-88-6
• Molecular Formula: C₁₀H₈O₃
• Molecular Weight: 176.16872
• Mol File: 59887-88-6.mol
• Article Data: 14

Chemical Properties

• Melting Point: 170 °C
• Boiling Point: 305.9±42.0 °C(Predicted)
• Appearance: /
• Density: 1.248±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 6-Methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 6-Methoxy-(59887-88-6)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 6-Methoxy-(59887-88-6)

Safety Data

• Hazardous Substances Data: 59887-88-6(Hazardous Substances Data)

Usage

General Description

4H-1-Benzopyran-4-one, 6-methoxy- is a chemical compound with the formula C10H8O3 that belongs to the class of benzopyrans. It is commonly known as 6-methoxy coumarin and is found in a variety of plant species. 6-methoxy coumarin is used in the production of perfumes and as a flavoring agent in food products. It is also known for its potential health benefits, including its anti-inflammatory and antioxidant properties. Additionally, it has been studied for its potential in treating certain skin conditions and its ability to inhibit the growth of certain cancer cells.

Upstream product

• 38445-24-8 6-hydroxy-4H-1-benzopyran-4-one 
• 74-88-4 methyl iodide 
• 110450-49-2 1-(2-hydroxy-5-methoxyphenyl)-3,3-dimethoxy-1-propanone 
• 90920-97-1 4-methoxyphenyl propynoate 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 150-76-5 4-methoxy-phenol 
• 110450-42-5 4-methoxyphenyl 3,3-dimethoxypropanoate 
• 123-31-9 hydroquinone 
• 310411-89-3 3-iodo-6-methoxy-4H-1-benzopyran-4-one 
• 124-40-3 dimethyl amine 
• 110450-46-9 1-(2-hydroxy-5-methoxyphenyl)propynone 
• 42059-79-0 6-methoxy-4-oxo-4H-chromene-3-carbaldehyde 

Downstream Products

• 1071596-80-9 4-oxo-4H-chromen-6-yl acetate 
• 84531-15-7 4-(2-Hydroxy-4-methoxy-benzoyl)-1H-pyrrole-2-carboxylic acid ethyl ester 
• 3034-04-6 6-methoxyflavanone 
• 190831-06-2 6-methoxy-2-phenylchroman-4-one 
• 18385-74-5 6-methoxy-chroman-4-ol 
• 102877-54-3 1-(6-hydroxy-3-methoxy-2-nitro-phenyl)-ethanone 
• 18385-84-7 6-methoxy-2H-chromene 

Relevant articles and documents

Synthesis of (±)-3,3′-bis(4-hydroxy-2H-benzopyran): A literature correction

The synthesis of bisbenzopyran-4-ol (1) was performed through the key steps of iodination, nickel(0)-modified Ullmann-type reaction, hydrogen-transfer hydrogenation and diastereoselective reduction. The X-ray diffraction experiment of compound 9 confirmed that the reported structure in the literature was not the real natural product.

The study on structure-activity relationship between chromone derivatives and inhibition of superoxide anion generating from human neutrophils

Over activation of neutrophils has been linked to many inflammatory diseases; one of critical pathologic mechanisms is that generation and exocellular release of superoxide anion from neutrophils results in peripheral tissues damage. Besides, in this study, 2-(3,5-dimethoxyphenoxy)-5,7-dimethoxy-chromen-4-one (4), a 2-phexnoychromone from our compound bank, was demonstrated to have the moderate inhibitory effect on superoxide anion generating. Therefore, serial chromones substituted with phenols or 3-flourothiophenol were designed, synthesized, and examined for suppression of superoxide anion generation. In accordance with the results, the methoxy group at 7 position (R3) of the chromone, as well as a hydrogen bond donor at a meta site of the phenyl ring greatly impacted on the activity. 2-(3-fluorophenyl)sulfanyl-7-methoxy-chromen-4-one (16), a successful example of bioisosteres from a phenol to a thiophenol, exhibited prominent anti-inflammatory effects with the IC50 value against superoxide anion generation of 5.0 ± 1.4 μM.

Direct Enantio- and Diastereoselective Vinylogous Addition of Butenolides to Chromones Catalyzed by Zn-ProPhenol

We report the first enantio- and diastereoselective 1,4-addition of butenolides to chromones. Both α,β- and β,γ-butenolide nucleophiles are compatible with the Zn-ProPhenol catalyst, and preactivation as the siloxyfurans is not required. The scope of electrophiles includes a variety of substituted chromones, as well as a thiochromone and a quinolone, and the resulting vinylogous addition products are generated in good yield (31 to 98%), diastereo- (3:1 to >30:1), and enantioselectivity (90:10 to 99:1 er). These Michael adducts allow rapid access to several natural product analogs, and can be easily transformed into a variety of other interesting scaffolds as well.