6344-21-4

Basic information

• Product Name: 2-(3,4-dimethoxyphenyl)-2,3-dihydro-4H-chromen-4-one
• Synonyms: 4H-1-benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-2,3-dihydro-
• CAS NO: 6344-21-4
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.3065
• Mol File: 6344-21-4.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 439°C at 760 mmHg
• Flash Point: 195.3°C
• Density: 1.204g/cm³
• Vapor Pressure: 6.61E-08mmHg at 25°C
• Refractive Index: 1.574
• CAS DataBase Reference: 2-(3,4-dimethoxyphenyl)-2,3-dihydro-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-dimethoxyphenyl)-2,3-dihydro-4H-chromen-4-one(6344-21-4)
• EPA Substance Registry System: 2-(3,4-dimethoxyphenyl)-2,3-dihydro-4H-chromen-4-one(6344-21-4)

Safety Data

• Hazardous Substances Data: 6344-21-4(Hazardous Substances Data)

Usage

Derivative of flavone

3,4-Dimethoxyflavone

Biological activities

Anti-inflammatory, anti-cancer, and anti-oxidant properties

Therapeutic potential

Studied for its potential therapeutic effects, showing promising results in preclinical and animal studies

Significance for future research

Unique structure and diverse biological activities make it a significant compound for drug development.

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 19152-36-4 (E)-2'-hydroxy-3,4-dimethoxychalcone 
• 86383-39-3 3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)propan-1-one 
• 108-95-2 phenol 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 3055-86-5 3-phenoxypropionitrile 
• 491-38-3 1-benzopyran-4(4H)-one 
• 58113-19-2 2-hydroxy-3',4'-dimethoxychalcone 
• 79140-20-8 2'-hydroxy-3,4-dimethoxychalcone 
• 116194-64-0 2-(3,4-dimethoxyphenyl)chroman-4-ol 
• 105166-58-3 2-Hydroxy-benzoic acid [2-(3,4-dimethoxy-phenyl)-chroman-(4E)-ylidene]-hydrazide 

Downstream Products

• 95561-18-5 N‐{[(4‐methylphenyl)sulfonyl]oxy}‐2‐(3,4‐dimethoxyphenyl)‐2,3‐dihydro‐4H‐chromen‐4‐imine 
• 88214-66-8 4α,3',4'-trimethoxyflavan 
• 88214-60-2 4α-chloro-3',4'-dimethoxyflavan 
• 78113-65-2 (2S,3S)-3-Bromo-2-(3,4-dimethoxy-phenyl)-chroman-4-one 
• 62082-72-8 3',4'-dimethoxyflavan-4β-ol 
• 116215-62-4 10-(3,4-Dimethoxy-phenyl)-10H-4,9-dioxa-2-aza-phenanthrene-1,3-dione 
• 116215-66-8 10-(3,4-Dimethoxy-phenyl)-3,3-dioxo-2,3-dihydro-10H-4,9-dioxa-3λ⁶-thia-2-aza-phenanthren-1-one 
• 4143-62-8 3',4'-dimethoxyflavone 
• 6889-80-1 2-(3,4-dimethoxyphenyl)-3-hydroxy-4H-chromen-4-one 

Relevant articles and documents

Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride

A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

Synthesis and hplc-ecd study of cytostatic condensed o,n-heterocycles obtained from 3-aminoflavanones

Racemic chiral O,N-heterocycles containing 2-arylchroman or 2-aryl-2H-chromene subunit condensed with morpholine, thiazole, or pyrrole moieties at the C-3-C-4 bond were synthesized with various substitution patterns of the aryl group by the cyclization of cis- or trans-3- aminoflavanone analogues. The 3-aminoflavanone precursors were obtained in a Neber rearrangement of oxime tosylates of flavanones, which provided the trans diastereomer as the major product and enabled the isolation of both the cis- and trans-diastereomers. The cis- and transaminoflavanones were utilized to prepare three diastereomers of 5-aryl-chromeno[4,3- b][1,4]oxazines. Antiproliferative activity of the condensed heterocycles and precursors was evaluated against A2780 and WM35 cancer cell lines. For a 3-(N-chloroacetylamino)-flavan-4-ol derivative, showing structural analogy with acyclic acid ceramidase inhibitors, 0.15 μM, 3.50 μM, and 6.06 μM IC50 values were measured against A2780, WM35, and HaCat cell lines, and apoptotic mechanism was confirmed. Low micromolar IC50 values down to 2.14 μM were identified for the thiazole- and pyrrole-condensed 2H-chromene derivatives. Enantiomers of the condensed heterocycles were separated by HPLC using chiral stationary phase, HPLC-ECD spectra were recorded and TDDFT-ECD calculations were performed to determine the absolute configuration and solution conformation. Characteristic ECD transitions of the separated enantiomers were correlated with the absolute configuration and effect of substitution pattern on the HPLC elution order was determined.

Water-mediated phosphorylative cyclodehydrogenation: An efficient preparation of flavones and flavanones

A new synthetic strategy utilizing POCl3-water for the conversion of 2′-hydroxychalcones to flavanones and flavones has been developed. The reagent efficiently promoted one-pot conversion of 2′-hydroxychalcones to flavones through flavanones involving cyclization and oxidative dehydrogenation. By changing the stoichiometery of the reagents, the reaction can be tuned to generate either flavanone or flavone. The developed protocol was found to be applicable for a variety of 2′-hydroxychalcones.