| Identification | More | [Name]
5,7-Dihydrox-4'-methoxyisoflavone | [CAS]
491-80-5 | [Synonyms]
5,7-DIHYDROXY-4'-METHOXYISOFLAVONE
5,7-DIHYDROXY-4-METHOXYISOFLAVONE
APIGENIN 4-METHYL ETHER
BIOCHANIN A
5,7-dihydroxy-3-(4-methoxyphenyl)-4h-1-benzopyran-4-on
5,7-dihydroxy-3-(4-methoxyphenyl)-4H-1-Benzopyran-4-one
Genistein 4′-methyl ether
5,7-dihydroxy-3-p-methoxyphenyl-4H-chromen-4-one
Biochani,Olmelin
5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one
BIOCHANIN A (AHP)
BIOCHANIN
5,7-DIHYDROXY-4''-METHOXYISOFLAVONE, 98% BIOCHANIN A
5,7-Dihydrox-4'-methoxyisoflavone
5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
Biochanin A, (5,7-Dihydroxy-4’-methoxyisoflavone)
Biochanin A，Genistein 4'-methyl ether，5,7-Dihydrox-4'-methoxyisoflavone
3-(4-Methoxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
4'-Methylgenistein | [EINECS(EC#)]
207-744-7 | [Molecular Formula]
C16H12O5 | [MDL Number]
MFCD00006839 | [Molecular Weight]
284.26 | [MOL File]
491-80-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
210-213 °C(lit.)
| [Boiling point ]
340-355 °C(Press: 0.5 Torr) | [density ]
1.420±0.06 g/cm3(Predicted) | [storage temp. ]
0-6°C | [solubility ]
acetone: 10 mg/mL, clear, brown
| [form ]
Powder | [pka]
6.50±0.20(Predicted) | [color ]
Off-White to Beige | [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). | [Usage]
An isoflavone with anticancer proliferation, differentiation and chemopreventitive properties. Inhibits metabolic activation of benzo[a]pyrene | [λmax]
263nm(EtOH)(lit.) | [BRN ]
278107 | [LogP]
3.341 (est) | [CAS DataBase Reference]
491-80-5(CAS DataBase Reference) | [EPA Substance Registry System]
491-80-5(EPA Substance) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
DJ3002500 | [F ]
10 | [TSCA ]
Yes | [HS Code ]
29329990 |
| Hazard Information | Back Directory | [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.1,2 Also known as 4’-methyl genistein, biochanin A can be metabolized in vivo to genistein (Item No. 10005167), another phytoestrogen with diverse effects.3 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.4 Moreover, it increases the expression of the PPARγ coactivator PGC-1α, promoting mitochondrial biogenesis.5 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).6,7 | [Chemical Properties]
Off-White Solid | [Uses]
An isoflavone with anticancer proliferation, differentiation and chemopreventitive properties. Inhibits metabolic activation of benzo[a]pyrene | [Uses]
phytoestrogen | [Definition]
ChEBI: Biochanin A is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at position 5 and a methoxy group at position 4'. A phytoestrogen, it has putative benefits in dietary cancer prophylaxis. It has a role as a phytoestrogen, a plant metabolite, an EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor, a tyrosine kinase inhibitor and an antineoplastic agent. It is a member of 7-hydroxyisoflavones and a member of 4'-methoxyisoflavones. It is a conjugate acid of a biochanin A(1-). | [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. |
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