1157-39-7

Basic information

• Product Name: 4',7-Dimethoxyisoflavone
• Synonyms: 7,4'-DIMETHOXYISOFLAVONE;4',7-DIMETHOXYISOFLAVONE;4',7-DIMETHOXYISOFLAVONE DIMETHYL ETHER;DAIDZEIN DIMETHYL ETHER;DIMETHOXYISOFLAVONE,4',7-;7-methoxy-3-(4-methoxyphenyl)chromen-4-one;7-methoxy-3-(4-methoxyphenyl)chromone;7-Methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one
• CAS NO: 1157-39-7
• Molecular Formula: C₁₇H₁₄O₄
• Molecular Weight: 282.29
• Product Categories: Iso-Flavones
• Mol File: 1157-39-7.mol
• Article Data: 33

Chemical Properties

• Melting Point: 161-163°C
• Boiling Point: 452.8 °C at 760 mmHg
• Flash Point: 202.2 °C
• Appearance: /
• Density: 1.242g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 265550
• CAS DataBase Reference: 4',7-Dimethoxyisoflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 4',7-Dimethoxyisoflavone(1157-39-7)
• EPA Substance Registry System: 4',7-Dimethoxyisoflavone(1157-39-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 1157-39-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellow crystal, soluble in methanol, ethanol, DMSO and other organic solvents.

Uses

4',7-Dimethoxyisoflavone is a flavonoid compound. It is isolated from the leaves of Albizzia lebbeck, which shows antifungal activity. It has been shown to inhibit the proliferation of cancer cells in vitro. It also inhibits the activity of a-ring hydroxylase and epoxide hydrolase. The optimum concentration for 4',7-dimethoxyisoflavone is 10 μM. This chemical is metabolized by cytochrome P450 enzymes, with bosentan as an inhibitor. Bosentan also inhibits the formation rate of 4',7-dimethoxyisoflavone by hydrogen bonding with this chemical in vitro.

in vitro

4',7-Dimethoxyisoflavone shows antifungal activity against some plant pathogenic fungi tested in vitro, and the sensitivity of different fungi to this chemical varied considerably.

Upstream product

• 39604-64-3 1-(2-hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 109-94-4 formic acid ethyl ester 
• 25369-54-4 1-(2-Hydroxy-4-methoxy-phenyl)-3,3-dimethoxy-2-(4-methoxy-phenyl)-propan-1-one 
• 186581-53-3 diazomethane 
• 485-72-3 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 25826-69-1 4',7-dimethoxyflavanone 
• 68-12-2 N,N-dimethyl-formamide 
• 104-01-8 4-Methoxyphenylacetic acid 
• 2198-19-8 2'-hydroxy-4,4'-dimethoxychalcone 
• 122-51-0 orthoformic acid triethyl ester 
• 486-66-8 daidzein 
• 74-88-4 methyl iodide 
• 206051-18-5 N-methoxy-N-methyl-2,4-dimethoxybenzamide 
• 67804-60-8 1-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanone 

Downstream Products

• 4842-56-2 1-(2-Hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)propan-1-one 
• 87538-73-6 2-amino-5-(4-methoxyphenyl)-6-(2-hydroxy-4-methoxyphenyl)pyrimidine 
• 1179998-12-9 2-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-pyrimido[1,2-a]benzimidazole 
• 1357294-43-9 5-(2-hydroxy-4-methoxyphenyl)-6-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine 
• 1169703-72-3 2-mercapto-4-(2-hydroxy-4-methoxyphenyl)-5-(4-methoxyphenyl)pyrimidine 
• 1380484-10-5 8-carbamoyl-4-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)imidazo[1,5-a]pyrimidine 
• 1427272-59-0 3-cyano-6-(2-hydroxy-4-methoxyphenyl)-5-(4-methoxyphenyl)-pyridine-2(1H)-thione 
• 75187-63-2 8-hydroxydaidzein 
• 117375-28-7 8-bromo-4′,7-dimethoxyisoflavone 
• 1621-61-0 cabreuvin 

Relevant articles and documents

Daidzein as an antioxidant of lipid: Effects of the microenvironment in relation to chemical structure

Isoflavone daidzein (D, pKa1 = 7.47 ± 0.02 and pK a2 = 9.65 ± 0.07) was, through a study of the parent compound and its three methyl anisol derivatives 7-methyldaidzein (7-Me-D, pKa = 9.89 ± 0.05), 4'-methyldaidzein (4'-Me-D, pKa = 7.43 ± 0.03), and 7,4'-dimethyldaidzein (7,4'-diMe-D), found to retard lipid oxidation in liposomal membranes through two mechanisms: (i) radical scavenging for which the 4'-OH was more effective than the 7-OH group in agreement with the oxidation potentials: 0.69 V for 4'-OH and 0.92 V for 7-OH versus Ag/AgCl in acidic solution and 0.44 V for 4'-O- and 0.49 V for 7-O- in alkaline solution and (ii) change in membrane fluidity through incorporation of the isoflavones, in effect hampering radical mobility. The radical scavenging efficiency measured by the rate of the reaction with the ABTS?+ in aqueous solution followed the order D > 7-Me-D > 4'-Me-D > 7,4'-diMe-D, as also found for antioxidant efficiency in liposomes when oxidation was initiated with the water-soluble AAPH radical and monitored as the formation of conjugate dienes. For oxidation initiated by the lipid-soluble AMVN radical, the antioxidant efficiency was ranked as 4'-Me-D > D > 7,4'-diMe-D > 7-Me-D, and change in fluorescence anisotropy of fluorescent probes bound to the membrane surface or inside the lipid bilayer confirmed the effects of isoflavones on the membrane fluidity, especially for 7,4'-diMe-D.

-

-

Synthesis of isoflavones via base catalysed condensation reaction of deoxybenzoin

Base catalysed condensation reaction of o-hydroxyl-α- phenylacetophenones with formyl reagents affords various substituted isoflavones. Many bases were tested in the condensation reaction and DMAP was found to be the most effective catalysis.

-

-

Synthesis of isoflavones from 2′-hydroxychalcones using poly[4-(diacetoxy)iodo]styrene or related hypervalent iodine reagent

Isoflavones are synthesized in an one-pot reaction by treating the hypervalent iodine(III) reagent, [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser's reagent) with 2′-benzoyloxychalcones in MeOH. A combined use of (diacetoxyiodo)benzene (DIB)/p-toluenesulfoni

Stille coupling for the synthesis of isoflavones by a reusable palladium catalyst in water

Isoflavones were synthesized from the reaction of 3-bromochromone derivatives and aryltributylstannanes via Stille coupling catalyzed by a water-soluble and reusable PdCl2(NH3)2/2,2′-cationic bipyridyl system in aqueous solution. For prototype 3-bromochromone, the coupling reaction was performed at 80°C for 24 hr with 2.5 mol% catalyst in water in the presence of tetrabutylammonium fluoride. After the reaction, the aqueous solution could be reused for several runs, indicating that its activity was only slightly decreased. For substituted 3-bromochromones, the addition of NaHCO3 and a higher reaction temperature (120°C) were required to gain satisfactory outcomes. In addition, naturally occurring products, such as daidzein, could be obtained by this protocol via a one-pot reaction.

Synthesis method of 3 ', 4', 7-trihydroxy isoflavone

The invention discloses a synthesis method of 3', 4', 7-trihydroxy isoflavone. The method comprises the steps that 4', 7-dimethoxyisoflavone and bromine are subjected to a mixed reaction in a dichloromethane medium to obtain 3'-bromo-4 ', 7-dimethoxyisoflavone, wherein the molar ratio of 4', 7-dimethoxyisoflavone to bromine is 1: 1.1-1.5, and the reaction temperature is 20-30 DEG C; the 3'-bromo-4', 7-dimethoxyisoflavone reacts with sodium methoxide under the action of cuprous salt to obtain 3', 4', 7-trimethoxyisoflavone; and the 3', 4', 7-trimethoxyisoflavone is demethylated to obtain the 3', 4', 7-trihydroxy isoflavone. Compared with the prior art, the method has the advantages of abundant sources of initial raw materials, mild reaction conditions, high selectivity and high yield, and is suitable for industrial production.