5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

• ChemBase ID: 73001
• Molecular Formular: C16H12O5
• Molecular Mass: 284.26348
• Monoisotopic Mass: 284.06847348
• SMILES: c1(cc(c2c(c1)occ(c2=O)c1ccc(cc1)OC)O)O
• Canonical SMILES: COc1ccc(cc1)c1coc2c(c1=O)c(O)cc(c2)O
• InChI: InChI=1S/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
• InChIKey: WUADCCWRTIWANL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: biochanin; 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
• Synonyms: 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one; 4-Methylgenistein; Biochanin A; 5,7-Dihydroxy-4’-methoxyisoflavone; 5,7-Dihydroxy-4'-methoxyisoflavone; 5,7-Dihydroxy-4′-methoxyisoflavone; Genistein 4′-methyl ether; Biochanin A; Biochanin A; 5,7-DIHYDROXY-4'-METHOXYISOFLAVONE; Genistein 4'-methyl ether; Pratensol; Olmelin; 5,7-二羟基-4'-甲氧基异黄酮

Database IDs

• CAS Number: 491-80-5
• EC Number: 207-744-7
• MDL Number: MFCD00006839
• Beilstein Number: 278107
• PubChem SID: 24893597; 162037921
• PubChem CID: 5280373

CALCULATED PROPERTIES

• Acid pKa: 6.547949
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.1857247
• LogD (pH = 7.4): 2.2726228
• Log P: 3.2227664
• Molar Refractivity: 76.1652 cm^3
• Polarizability: 29.012978 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid; Powder
• Melting Point: 210-213 °C(lit.); 210-213°C; 210-213°C

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... CYP19A1(1588)mouse ... Aldh1a2(19378), Maoa(17161)
• Mechanism of Action: Estrogen

Product Information

• Purity: 98%
• Salt Data: Free Base
• Biological Source: Constit. of clover (Trifolium repens), Dalbergia and Cotoneaster spp. Widely distributed in the Leguminosae (Papilionoideae), also in Cotoneaster pannosa and Cotoneaster serotina (Rosaceae), Virola caducifolia (Myricaceae) and others
• Application(s): Possesses sl. estrogenic activity

DETAILS

MP Biomedicals - 02157745

(Biochanin A)

Selleck Chemicals - S2377

Research Area: Cancer
Biological Activity:
Biochanin A(4-Methylgenistein) is an O-methylated isoflavone. It is a natural organic compound in the class of phytochemicals known as flavonoids. Biochanin A is classified as a phytoestrogen and has putative benefits in dietary cancer prophylaxis. [1]

Sigma Aldrich - D2016

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.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D2016.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - B387250

An isoflavone with anticancer proliferation, differentiation and chemopreventitive properties. Inhibits metabolic activation of benzo[a]pyrene.

REFERENCES

• http://en.wikipedia.org/wiki/Biochanin_A
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