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

• 15236-11-0 4',7-dimethoxyisoflavanone 
• 186581-53-3 diazomethane 
• 485-72-3 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 39604-64-3 1-(2-hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 109-94-4 formic acid ethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 104-01-8 4-Methoxyphenylacetic acid 
• 150-19-6 O-methylresorcine 
• 77-78-1 dimethyl sulfate 
• 122-51-0 orthoformic acid triethyl ester 
• 486-66-8 daidzein 
• 74-88-4 methyl iodide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 73220-42-5 3-iodo-7-methoxy-chromen-4-one 

Downstream Products

• 132184-52-2 4-(2-Hydroxy-4-methoxyphenyl)-5-(4-methoxyphenyl)-2-(4-aminobenzenesulphonylamino)pyrimidine 
• 87538-73-6 2-amino-5-(4-methoxyphenyl)-6-(2-hydroxy-4-methoxyphenyl)pyrimidine 
• 39923-40-5 4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-1-benzopyran-2-one 
• 113434-79-0 4',7-dimethoxyisoflavone epoxide 
• 77200-42-1 5-(2-hydroxy-4-methoxyphenyl)-4-(4-methoxyphenyl)isoxazole 
• 4842-56-2 1-(2-Hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)propan-1-one 
• 113435-00-0 2-hydroxy-α,4,4'-trimethoxydeoxybenzoin 
• 113434-84-7 2-hydroxy-3,4',7-trimethoxyisoflavanone 
• 113434-83-6 3-hydroxy-2,4',7-trimethoxyisoflavanone 
• 113434-86-9 2-acetoxy-3,4',7-trimethoxyisoflavanone 
• 113434-85-8 3-acetoxy-2,4',7-trimethoxyisoflavanone 
• 113434-92-7 4,6-dihydroxy-2-(2'-hydroxy-4'-methoxyphenyl)-3-(4''-methoxyphenyl)-benzofuran 
• 113434-98-3 3-acetoxy-4',7-dimethoxy-2-(3''-methoxyphenoxy)isoflavanone 
• 113434-99-4 2-acetoxy-4',7-dimethoxy-3-(3''-methoxyphenoxy)isoflavanone 

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.

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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.

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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

Enantioselective Synthesis of Isoflavanones and Pterocarpans through a RuII-Catalyzed ATH-DKR of Isoflavones

Noyori-Ikariya RuII complexes promoted the one-pot C=C/C=O bonds reduction of isoflavones using sodium formate as the hydrogen source through Asymmetric Transfer Hydrogenation-Dynamic Kinetic Resolution (ATH-DKR). Due to the neutral conditions employed, isoflavones with different substituents at the 2’-position of B-ring (H, OH, OMe and Br) were successfully reduced. Ten cis-3-phenylchroman-4-ols were selectively obtained (>20 : 1 dr) in good yields (up to 86 %) and excellent enantioselectivities (up to >99 : 1 er). The synthetic applications of these chiral compounds were also demonstrated. Enantioenriched isoflavanones were obtained under mild metal-free oxidation of the cis-3-phenylchroman-4-ols while pterocarpans were synthesized by two strategies: an acid-catalyzed cyclization and a novel approach based on a Pd-catalyzed C?O intramolecular cross-coupling reaction.

Synthetic method of polyhydroxy isoflavone

The invention discloses a synthetic method of polyhydroxy isoflavone. The method comprises the following steps: (1) reacting 4', 7-dimethoxyisoflavone with N-bromosuccinimide, and controlling the molar ratio of 4', 7-dimethoxyisoflavone to N-bromosuccinimide and a reaction temperature to enable one or two hydrogen atoms on a 4', 7-dimethoxyisoflavone carbon ring to be substituted by bromine atomsto generate corresponding bromide; (2), enabling the bromide in the (2) to react with sodium methoxide under the action of cuprous salt to enable bromine atoms on a carbon ring of the bromide to be substituted by methoxy to obtain a methoxylation product; and (3), carrying out a demethylation reaction on the methoxylation product obtained in the (3) under the action of aluminum chloride and dimethyl sulfide to obtain polyhydroxy isoflavone. The method has the advantages of abundant sources of initial raw materials, mild reaction conditions, good selectivity and high yield, and is suitable forindustrial production. The purity of the product is greater than 99.0%, and the product can be used for pharmacological activity research.