491-80-5

Basic information

• Product Name: 5,7-Dihydrox -4'-methoxyisoflavone
• Synonyms: 5,7-dihydroxy-3-(4-methoxyphenyl)-4h-1-benzopyran-4-on;5,7-dihydroxy-3-(4-methoxyphenyl)-4H-1-Benzopyran-4-one;APIGENIN 4-METHYL ETHER;BIOCHANIN A;5,7-DIHYDROXY-4'-METHOXYISOFLAVONE;5,7-DIHYDROXY-4-METHOXYISOFLAVONE;Genistein 4′-methyl ether ;5,7-dihydroxy-3-p-methoxyphenyl-4H-chromen-4-one
• CAS NO: 491-80-5
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26
• EINECS: 207-744-7
• Product Categories: Iso-Flavones;Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 491-80-5.mol
• Article Data: 27

Chemical Properties

• Melting Point: 210-213 °C(lit.)
• Boiling Point: 518.6 °C at 760 mmHg
• Flash Point: 198.2 °C
• Appearance: /Powder
• Density: 1.42 g/cm³
• Vapor Pressure: 2.25E-11mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: 0-6°C
• Solubility: acetone: 10 mg/mL, clear, brown
• PKA: 6.50±0.20(Predicted)
• Water Solubility: Soluble in water (<1 mg/ml at 25°C), chloroform, methanol, DMSO (57 mg/ml at 25°C), and ethanol (9 mg/ml at 25°C).
• BRN: 278107
• CAS DataBase Reference: 5,7-Dihydrox -4'-methoxyisoflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-Dihydrox -4'-methoxyisoflavone(491-80-5)
• EPA Substance Registry System: 5,7-Dihydrox -4'-methoxyisoflavone(491-80-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: DJ3002500
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 491-80-5(Hazardous Substances Data)

Usage

Description

Biochanin A is a natural isoflavone with diverse biological actions, most notably as a phytoestrogen. It can affect hormone levels by inhibiting 5α-reductase and 17β-hydroxysteroid dehydrogenase or altering aromatase (CYP19A1) activity. Also known as 4’-methyl genistein, biochanin A can be metabolized in vivo to genistein , another phytoestrogen with diverse effects. Biochanin A also intersects with signaling through peroxisome proliferator-activated receptors (PPARs), as it activates PPARγ (EC50 = 19 μM) and has also been shown to activate a PPARα promoter. Moreover, it increases the expression of the PPARγ coactivator PGC-1α, promoting mitochondrial biogenesis. Biochanin A also inhibits fatty acid amide hydrolase (IC50 = 2.4 μM) and acts as an agonist of the aryl hydrocarbon receptor (EC50 = 0.25 μM).

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 491-80-5 differently. You can refer to the following data:
1. It has putative benefits in dietary cancer prophylaxis. It has also been found to inhibit fatty acid amide hydrolase and to act as agonist of PPARgamma, nuclear receptor that is current pharmacological target for the treatment of diabetes type 2. It acts as an antineoplastic agent. It is a selective agonist at ER-β estrogen receptors, and may have chemopreventive efficacy against breast cancer. In line with its low activity at ER-α estrogen receptors, it is essentially devoid of uterotrophic activity. Biochanin A is also a ligand for the aryl hydrocarbon receptor (AhR). It reduces arterial resistance and enhances microcirculation perhaps via effects on potassium and/or calcium ion channels. Induction of sulfotransferases for xenobiotic detoxification has been proposed as a mechanism of its cancer preventive effects. It is a nitric oxide synthase inhibitor and apoptosis inducer
2. An isoflavone with anticancer proliferation, differentiation and chemopreventitive properties. Inhibits metabolic activation of benzo[a]pyrene

General Description

Biochanin A (BCA) is synthesized in vitro from phloroglucinol. A series of steps involving Friedel?Crafts reaction results in an intermediate product 1-(2,4,6-trihydroxyphenyl)-2-(4 methoxyphenyl) ethanone, which post cyclization leads to BCA. It is catabolized to isoflavone genistein post ingestion.

Biochem/physiol Actions

Biochanin A is an isoflavone phytoestrogen found in red clover (Trifolium pratense) that is a selective agonist at ER-β estrogen receptors, and may have chemopreventive efficacy against breast cancer. In line with its low activity at ER-α estrogen receptors, it is essentially devoid of uterotrophic activity. Biochanin A is also a ligand for the aryl hydrocarbon receptor (AhR). It reduces arterial resistance and enhances microcirculation perhaps via effects on potassium and/or calcium ion channels. Induction of sulfotransferases for xenobiotic detoxification has been proposed as a mechanism of its cancer preventive effects.

InChI:InChI=1/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3

Upstream product

• 15485-66-2 2,4,6-trihydroxy-4'-methoxydeoxybenzoin 
• 54443-59-3 acetic acid 7-acetoxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yl ester 
• 113029-08-6 2-carbethoxy-5,7-dihydroxy-4'-methoxyisoflavone 
• 5720-07-0 4-methoxyphenylboronic acid 
• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 
• 485-80-3 S-adenosyl-L-methionine 
• 1236208-90-4 3-iodo-5,7-bis(methoxymethoxy)-4H-1-benzopyran-4-one 
• 1236208-89-1 3-(N,N-dimethylamino)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 1005418-09-6 5-hydroxy-7-(methoxymethoxy)-3-(4-methoxyphenyl)-4H-chromen-4-one 
• 487-70-7 2,4,6-trihydroxybenzaldehyde 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 31721-94-5 5,7-dihydroxy-chromen-4-one 

Downstream Products

• 15485-66-2 2,4,6-trihydroxy-4'-methoxydeoxybenzoin 
• 6650-29-9 7-ethoxycarbonylmethoxy-5-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one 
• 1005418-09-6 5-hydroxy-7-(methoxymethoxy)-3-(4-methoxyphenyl)-4H-chromen-4-one 
• 1203579-96-7 4'-methoxy-5,7-dihydroxyisoflavothione 
• 27762-99-8 5,7-dihydroxy-3-(4-methoxyphenyl)-6-(3-methylbut-2-enyl)-4H-chromen-4-one 
• 2284-31-3 3',5,7-trihydroxy-4'-methoxyisoflavone 

Relevant articles and documents

Isoflavonoid glycosides from Dalbergia sissoo

Two isoflavone glycosides, biochanin A 7-O-[β-D-apiofuranosyl-(1 → 5)-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside] and tectorigenin 7-O-[β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside], were isolated from Dalbergia sissoo. Their structures were elucidate

Synthesis method of biochanin A

The invention discloses a synthesis method of biochanin A. The synthesis method comprises the following steps: (1) carrying out condensation reaction on p-methoxyacetophenone and N-bromosuccinimide in the presence of absolute ethyl alcohol to obtain Alpha-bromo-4-methoxyacetophenone; and (2) by taking absolute ethyl alcohol as a reaction solvent, carrying out condensation reaction on 2, 4, 6-trihydroxy benzaldehyde and Alpha-bromo-4-methoxyacetophenone in the presence of a catalyst, evaporating reaction liquid, and separating and purifying a solid product by using column chromatography to obtain the biochanin A. The novel catalyst is adopted for catalysis, the product yield is high, reaction conditions are mild, and raw materials of the catalyst are easy to obtain and low in price. The synthesis method disclosed by the invention is simple in process, low in cost, time-saving, high in yield, low in equipment corrosion degree and suitable for industrial production.

Cytosine N-isoflavone compound as well as preparation method and application thereof

The invention relates to a cytosine N-isoflavone compound as well as a preparation method and application thereof. The compound has a structural formula as shown in the specification, wherein R1 is selected from one of hydroxyl, alkoxy, amido or halo, R2 is selected from one of hydrogen, alkyl or aryl, and R3 is selected from one or a combination of several of hydroxyl, alkoxy, amido or halo. Compared with the prior art, the cytosine N-isoflavone compound has the characteristic that an isoflavone compound serving as a structural unit is spliced to N on the 12th position of cytosine by using acombined synthesis technology, so that a series of cytosine-isoflavone derivatives are synthesized, and a novel active pharmacological action is exerted.