76472-88-3

Basic information

• Product Name: Morachalcone A
• Synonyms: Morachalcone A;(2E)-1-[2,4-Dihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(2,4-dihydroxyphenyl)-2-propen-1-one
• CAS NO: 76472-88-3
• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.3698
• Mol File: 76472-88-3.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Morachalcone A(CAS DataBase Reference)
• NIST Chemistry Reference: Morachalcone A(76472-88-3)
• EPA Substance Registry System: Morachalcone A(76472-88-3)

Safety Data

• Hazardous Substances Data: 76472-88-3(Hazardous Substances Data)

Usage

General Description

Morachalcone A is a natural compound found in the plant Morus alba L. It belongs to the class of flavonoids and is known for its significant biological activities, including anti-inflammatory, anti-cancer, and anti-diabetic properties. Morachalcone A has also been shown to possess antioxidant effects and has potential as a therapeutic agent for a variety of diseases. Its chemical structure consists of a chalcone backbone with hydroxyl and methoxy groups attached, which contribute to its bioactivity. Research on Morachalcone A continues to uncover its potential as a valuable therapeutic agent for various medical conditions.

Upstream product

• 358-72-5 dimethylallyl diphosphate 
• 25972-30-9 (E)-1-(2,4-dihydroxyphenyl)-3-(2,4-dihydroxyphenyl)-2-propen-1-one 
• 850868-90-5 (2E)-3-[2',4'-bis(methoxymethoxy)phenyl]-1-(2-hydroxy-3-(3-methylbut-2-en-1-yl)-4-{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)prop-2-en-1-one 
• 850868-89-2 (2E)-3-[2',4'-bis(methoxymethoxy)phenyl]-1-(2-[(3-methylbut-2-en-1-yl)oxy]-4-{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)prop-2-en-1-one 
• 850868-87-0 (E)-3-(2,4-Bis-methoxymethoxy-phenyl)-1-[2-hydroxy-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-propenone 
• 850868-88-1 1-(2-hydroxy-4-{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)ethanone 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 13709-06-3 2,4-bis(methoxymethoxy)benzaldehyde 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 

Relevant articles and documents

Molecular Characterization and Phylogenetic Analysis of Two Novel Regio-specific Flavonoid Prenyltransferases from Morus alba and Cudrania tricuspidata

Prenylated flavonoids are attractive specialized metabolites with a wide range of biological activities and are distributed in several plant families. The prenylation catalyzed by prenyltransferases represents a Friedel-Crafts alkylation of the flavonoid skeleton in the biosynthesis of natural prenylated flavonoids and contributes to the structural diversity and biological activities of these compounds. To date, all identified plant flavonoid prenyltransferases (FPTs) have been identified in Leguminosae. In the present study two new FPTs, Morus alba isoliquiritigenin 3′-dimethylallyltransferase (MaIDT) and Cudrania tricuspidata isoliquiritigenin 3′-dimethylallyltransferase (CtIDT), were identified from moraceous plants M. alba and C. tricuspidata, respectively. MaIDT and CtIDT shared low levels of homology with the leguminous FPTs. MaIDT and CtIDT are predicted to be membrane-bound proteins with predicted transit peptides, seven transmembrane regions, and conserved functional domains that are similar to other homogentisate prenyltransferases. Recombinant MaIDT and CtIDT were able to regioselectively introduce dimethylallyl diphosphate into the A ring of three flavonoids with different skeleton types (chalcones, isoflavones, and flavones). Phylogenetic analysis revealed thatMaIDT and CtIDT are distantly related to their homologs in Leguminosae, which suggests that FPTs in Moraceae and Leguminosae might have evolved independently. MaIDT and CtIDT represent the first two non-Leguminosae FPTs to be identified in plants and could thus lead to the identification of additional evolutionarily varied FPTs in other non-Leguminosae plants and could elucidate the biosyntheses of prenylated flavonoids in various plants. Furthermore, MaIDT and CtIDT might be used for regiospecific prenylation of flavonoids to produce bioactive compounds for potential therapeutic applications due to their high efficiency and catalytic promiscuity.

A short synthesis of morachalcone A

Advanced C-prenylated intermediates for three aromatase inhibitors, including morachalcone A, can be synthesized through a Claisen-Schmidt condensation followed by Florisil-catalyzed [1,3]-sigmatropic rearrangement of a prenyl phenyl ether.