5128-54-1

Usage

Preparation

Obtained by alkaline degradation of afromosin (7-hydroxy-6,4′-dimethoxyisoflavone). Afromosin (m.p. 228–229°), was isolated from afromosia elata Harms. Afromosin is the aglycone of wistin (m.p. 209–210°), itself isolated from the bark of wistaria floribunda DC.

Upstream product

• 550-79-8 afromosin 
• 40232-88-0 4-benzyloxy-3-methoxyphenol 
• 104-47-2 p-methoxybenzylnitrile 
• 104-01-8 4-Methoxyphenylacetic acid 
• 6100-60-3 4-methoxybenzene-1,3-diol 

Downstream Products

• 550-79-8 afromosin 
• 109469-77-4 2,4,5,4'-Tetramethoxy-benzil 

Relevant academic research and scientific papers

Aminomethylation of Afromosin, Cladrastin, and Their 2-Methyl Derivatives

Aminomethylation of the natural isoflavones afromosin and cladrastin and their 2-methyl derivatives was studied. Several new Mannich bases of 7-hydroxy-6-methoxyisoflavones were synthesized under Mannich reaction conditions using aminals of secondary amin

A Direct Synthesis of 2-(ω-Carboxyalkyl)isoflavones from ortho-Hydroxylated Deoxybenzoins

As part of a program focused on the development of new antineoplastic agents based on scaffolds found in natural products, we explored the isoflavone family as potential enzyme inhibitors. We required biotin-modified isoflavones to identify potential biological targets, and we selected the C-2 position in isoflavones as an attachment site for an alkyl group bearing a terminal carboxylic acid to which we could attach a biotin derivative. The base-catalyzed condensation of 2,4-dihydroxy-substituted deoxybenzoins with cyclic anhydrides mediated by a combination of triethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene led to an efficient synthesis of the desired 2-(ω-carboxyalkyl)isoflavones with functional groups at C-5, 6 and 7 and with various substituents in the C-3 phenyl group.

Synthesis of various kinds of isoflavones, isoflavanes, and biphenyl- ketones and their 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities

Forty-eight kinds of isoflavones (8), thirty-one isoflavanes (9), and forty-seven biphenyl-ketones (10, 10') were synthesized from eleven kinds of substituted phenols (11) and six phenylacetic acids (12). Among them, seventy-five compounds are new. The radical scavenging activities of these compounds were evaluated using 1,1- diphenyl-2-picrylhydrazyl (DPPH) at pH 6.0. We found that thirty-nine out of forty-three compounds having a catechol moiety on either the A- or the B-ring exhibited a high activity (ED50=12-54 μM) similar to that of catechin. In these cases, the remaining part of their structure seemed to have little effect on their activity. Many 6- or 8-hydroxyisoflavanes (9E-I) and their biphenyl-ketone derivatives (10E-H) also showed a high activity (ED50=50=26-32 μM). This study suggests that natural isoflavones have the possibilities of exhibiting antioxidant activities through the hydroxylation at the C6-, C8-, or C3'-position or the formation of the isoflavanes (9) and/or the biphenyl-ketone derivatives (10') by metabolism or biotransformation.