25826-69-1

Basic information

• Product Name: 4',7-dimethoxyflavanone
• Synonyms: 4',7-dimethoxyflavanone
• CAS NO: 25826-69-1
• Molecular Weight: 284.312
• Mol File: 25826-69-1.mol

Chemical Properties

• CAS DataBase Reference: 4',7-dimethoxyflavanone(CAS DataBase Reference)
• NIST Chemistry Reference: 4',7-dimethoxyflavanone(25826-69-1)
• EPA Substance Registry System: 4',7-dimethoxyflavanone(25826-69-1)

Safety Data

• Hazardous Substances Data: 25826-69-1(Hazardous Substances Data)

Upstream product

• 75-11-6 diiodomethane 
• 2198-19-8 2'-hydroxy-4,4'-dimethoxychalcone 
• 2198-19-8 2'-hydroxy-4,4'-dimethoxychalcone 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 150-19-6 O-methylresorcine 
• 5720-07-0 4-methoxyphenylboronic acid 
• 42327-52-6 7-methoxy-chroman-4-one 
• 6279-84-1 β-(m-methoxyphenoxy)propionitrile 
• 3034-08-0 2-(4-methoxyphenyl)-2,3-dihydro-4H-chromen-4-one 
• 108-46-3 recorcinol 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 186581-53-3 diazomethane 

Downstream Products

• 111599-79-2 3-(4-Methoxybenzylidene)-7,4'-dimethoxyflavanone 
• 69097-97-8 7,4'-dihydroxy-dihydroflavone 
• 1157-39-7 7-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one 
• 20979-50-4 4,7-dimethoxyflavone 
• 2198-19-8 2'-hydroxy-4,4'-dimethoxychalcone 
• 96761-52-3 4',7-Dimethoxy-flavanon-oxim-toluol-4-sulfonat 
• 6515-26-0 (+/-)-2,3-trans-7,4'-dimethoxyflavanonol 

Relevant articles and documents

TWO POLYPHENOL GLUCOSIDES AND TANNINS FROM ROSA CYMOSA

Two new polyphenol glucosides, rocymosins A and B, were isolated from Rosa cymosa and characterized as 3-O-(6'-O-galloyl)-β-D-glucopyranosyl-4-hydroxyphenethyl alcohol and 2'-O-β-D-glucopyranosyl-4,4',β-trihydroxy-dihydrochalcone, respectively.Eight known tannins, casuarinin, rugosin D, stenophyllanins A and B, (+)-catechin, procyanidin B-3, procyanidin B-3 3-O-gallate and catechin-(4α->6)-catechin-(4α->6)-epicatechin, were also isolated. Key Word Index - Rosa cymosa; Rosaceae; root; tannin; procyanidin; 3-O-(6'-O-galloyl)-β-D-glucopyranosyl-4-hydroxyphenethyl alcohol; rocymosin A; β-hydroxydihydrochalcone glucoside; rocymosin B.

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.

CuO nanoparticles as an efficient catalyst for the synthesis of flavanones

CuO nanoparticle was found to be an efficient catalyst for the synthesis of flavanones derivatives from the reactions between 2-hydroxyacetophenones and aromatic aldehydes at room temperature. The protocol offers advantages in terms of higher yields, short reaction times, and mild reaction conditions, with reusability of the catalyst. The structures of the synthesized substituted flavanones were confirmed by their Melting point, FT-IR,1 HNMR,13 CNMR and mass spectral analysis.

Impact of mono- and disubstitution on the colorimetric dynamic covalent switching chalcone/flavanone scaffold

The effect of aryl substitution on various aspects of the interconversion of ortho-hydroxychalcones and flavanones has been studied using multiple spectroscopic techniques. Derivatization of the core scaffold predictably alters the midpoint pH of this equilibration process suggesting its viability for application as a functional colorimetric molecular switch.

Mild and efficient one-pot synthesis of diverse flavanone derivatives via an organocatalyzed Mannich-type reaction

A facile ethylenediamine diacetate (EDDA)-catalyzed one-pot synthesis of biologically interesting flavanone derivatives from 2-hydroxyacetophenones, aromatic aldehydes, and aniline via a Mannich-type reaction is described. This synthetic method provides a rapid access to biologically interesting flavanone derivatives. To demonstrate this method, several biologically interesting natural products bearing a flavanone moiety were synthesized as racemates.

An efficient and facile synthesis of flavanones catalyzed by N-methylimidazole

The use of N-methylimidazole as an efficient catalyst for the cyclization of 2'-hydroxychalcones to the corresponding flavanones in DMSO was investigated. The scope of this process was studied and various flavanones were obtained exclusively in good yields. Copyright

A new series of flavones, thioflavones, and flavanones as selective monoamine oxidase-B inhibitors

A new series of synthetic flavones, thioflavones, and flavanones has been synthesized and evaluated as potential inhibitors of monoamine oxidase isoforms (MAO-A and -B). The most active series is the flavanone one with higher selective inhibitory activity against MAO-B. Some of these flavanones (mainly the most effective) have been separated and tested as single enantiomers. In order to investigate the MAOs recognition of the most active and selective compounds, a molecular modeling study has been performed using available Protein Data Bank (PDB) structures as receptor models for docking experiments.

CHEMOTHERAPEUTIC FLAVONOIDS, AND SYNTHESES THEREOF

Substituted flavonoid compounds, and pharmaceutical formulations of flavonoid compounds are described. Also described are processes for preparing flavonid compounds, as are methods for treating cancer in mammals using the described flavonoid compounds or pharmaceutical formulations thereof.

Synthesis and biological evaluation of (±)-abyssinone II and its analogues as aromatase inhibitors for chemoprevention of breast cancer

An efficient and economical synthesis of the naturally occurring aromatase inhibitor abyssinone II was performed. The synthesis features an optimized aromatic prenylation reaction in which an arylcopper intermediate is reacted with prenyl bromide to afford a key intermediate that was converted to a prenylated aromatic aldehyde. Condensation of the aldehyde with an o-hydroxyacetophenone under Claisen-Schmidt conditions afforded a chalcone that was deprotected and cyclized in the presence of sodium acetate in refluxing ethanol to afford (±)-abyssinone II. The synthesis proved to be versatile enough to provide an array of abyssinone II derivatives that were evaluated as aromatase inhibitors. Methylation of the 4′-hydroxyl group of (±)-abyssinone II resulted in a significant increase in aromatase inhibitory activity, and further smaller increases in activity resulted from the methylation of the 7-hydroxyl group and removal of the prenyl side chain. As a result of these structural changes, the most active flavanone of the series was 20 times more potent than (±)-abyssinone II (IC50 40.95 μM).

New synthesis of flavanones catalyzed by L-proline

L-Proline is utilized as an efficient organocatalyst for the synthesis of substituted flavanones and chalcones in good yields. The efficiency of the catalyst was proved with a variety of substrates ranging from electron-deficient to electron-rich aryl aldehydes and 2-hydroxyacetophenones.