1277188-85-8

Basic information

• Product Name: (2R)-5,7-Dimethoxyflavanone
• Synonyms: (2R)-5,7-Dimethoxyflavanone
• CAS NO: 1277188-85-8
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.30654
• Mol File: 1277188-85-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2R)-5,7-Dimethoxyflavanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-5,7-Dimethoxyflavanone(1277188-85-8)
• EPA Substance Registry System: (2R)-5,7-Dimethoxyflavanone(1277188-85-8)

Safety Data

• Hazardous Substances Data: 1277188-85-8(Hazardous Substances Data)

Usage

General Description

(2R)-5,7-Dimethoxyflavanone is a chemical compound belonging to the flavanone class, which is a type of flavonoid. Flavanones are known for their antioxidant properties and are often found in fruits and vegetables. The specific compound (2R)-5,7-Dimethoxyflavanone is characterized by the presence of two methoxy groups (CH3O-) at positions 5 and 7 on the flavanone structure. (2R)-5,7-Dimethoxyflavanone has shown potential biological activities and pharmacological properties, including anti-inflammatory and anti-cancer effects. It has also been studied for its potential to modulate enzymes and proteins involved in various cellular processes. (2R)-5,7-Dimethoxyflavanone is being investigated for its potential use in pharmaceutical and nutraceutical products.

Upstream product

• 500-99-2 3,5-dimethoxyphenol 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 59887-91-1 5,7-dimethoxy-4H-chromen-4-one 
• 98-80-6 phenylboronic acid 

Downstream Products

• 221385-53-1 5-hydroxy-7-methoxyflavonone 

Relevant articles and documents

Asymmetric Synthesis of Sakuranetin-Relevant Flavanones for the Identification of New Chiral Antifungal Leads

Discovery and efficient synthesis of new promising leads have a central role in agrochemical science. Reported herein is the sakuranetin-directed synergistic exploration of an asymmetric synthesis and an antifungal evaluation of chiral flavanones. A new palladium catalytic system with CarOx-type ligands was successfully identified for the highly enantioselective addition of arylboronic acids to chromones. This enabled the facile and programmable construction of a constellation of chiral flavanones (up to 98% yield and 97% ee), in which (R)-pinostrobin was efficiently constructed without laborious protecting/deprotecting operations. Its good performance in asymmetric induction and functional tolerance expanded the chemical space of pharmaceutically important flavanones. The chiral differentiation of flavanones based on antifungal activity and a concise structure-activity relationship model was disclosed and summarized. This synergistic project culminated with acquisition of the naturally unprecedented flavanones with better antifungal potentials than sakuranetin, in which the R-enantiomer of flavanone 54 (EC50 = 0.8 μM) demonstrated better performance than boscalid against Rhizoctonia solani. The novel scaffold and predicted new target compared with the commercial fungicides in the FRAC reinforce the value of further exploration.

Highly enantioselective and efficient synthesis of flavanones including pinostrobin through the rhodium-catalyzed asymmetric 1,4-addition

An efficient synthesis of bioactive chiral flavanones (1) was achieved through the αh-catalyzed asymmetric 1,4-addition of arylboronic acid to chromone. The reaction in toluene proceeded smoothly at room temperature in the presence of 0.5% Rh catalyst with electron-poor chiral diphosphine MeO-F 12-BIPHEP. In this reaction, the 1,2-addition to (S)-1 frequently occurred to yield (2S,4α)-2,4-diaryl-4-chromanol as a byproduct, which could be reduced by changing the reaction solvent to CH2C 12 to deactivate the Rh catalyst (3% required).