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491-80-5

491-80-5 Structure

491-80-5 Structure
IdentificationMore
[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 PropertiesBack 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 DataBack 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 InformationBack 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. Also known as 4’-methyl genistein, biochanin A can be metabolized in vivo to genistein (Item No. 10005167), 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]

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.
Spectrum DetailBack Directory
[Spectrum Detail]

5,7-Dihydrox -4'-methoxyisoflavone(491-80-5)MS
5,7-Dihydrox -4'-methoxyisoflavone(491-80-5)1HNMR
5,7-Dihydrox -4'-methoxyisoflavone(491-80-5)IR1
5,7-Dihydrox -4'-methoxyisoflavone(491-80-5)IR2
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

5,7-Dihydroxy-4'-methoxyisoflavone, 98%(491-80-5)
[Sigma Aldrich]

491-80-5(sigmaaldrich)
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