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 
• 86383-39-3 3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)propan-1-one 
• 79140-20-8 2'-hydroxy-3,4-dimethoxychalcone 
• 491-38-3 1-benzopyran-4(4H)-one 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 58113-19-2 2-hydroxy-3',4'-dimethoxychalcone 
• 19152-36-4 (E)-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 
• 108-95-2 phenol 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 3055-86-5 3-phenoxypropionitrile 

Downstream Products

• 95561-18-5 N‐{[(4‐methylphenyl)sulfonyl]oxy}‐2‐(3,4‐dimethoxyphenyl)‐2,3‐dihydro‐4H‐chromen‐4‐imine 
• 6889-80-1 2-(3,4-dimethoxyphenyl)-3-hydroxy-4H-chromen-4-one 
• 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 

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.

Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis

Peptidyl-prolyl cis-trans isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (AF-39) was identified as a novel Pin1 inhibitor. Biochemical tests indicate that AF-39 potently inhibits Pin1 activity with an IC50 values of 1.008 μm, and also displays high selectivity for Pin1 among peptidyl prolyl isomerases. Furthermore, AF-39 significantly suppresses cell proliferation of HCC cells in a dose- and time-dependent manner. Mechanistically, AF-39 regulates the subcellular distribution of XPO5 and increases miRNAs biogenesis in HCC cells. This work provides a promising lead compound for HCC treatment, highlighting the therapeutic potential of miRNA-based therapy against human cancer.