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D2016
Sigma
Biochanin A
| Synonym: | 5,7-Dihydroxy-4′-methoxyisoflavone, Genistein 4′-methyl ether |
| CAS Number: | 491-80-5 |
| Linear Formula: | C16H12O5 |
| Molecular Weight: | 284.26 |
| Beilstein Registry Number: | 278107 |
| EC Number: | 207-744-7 |
| MDL number: | MFCD00006839 |
| PubChem Substance ID: | 24893597 |
Description
| 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. |
Properties
| mp | 210-213 °C(lit.) |
| Gene Information | human ... CYP19A1(1588) |
| mouse ... Aldh1a2(19378), Maoa(17161) |
Safety
| Personal Protective Equipment | Eyeshields, Gloves, Respirators |
| Safety Statements | 22-24/25 |
| WGK Germany | 3 |
References
| Reference | Escande, A., et al., Evaluation of ligand selectivity using reporter cell lines stably expressing estrogen receptor α or β. Biochem. Pharmacol. 71, 1459-1469, (2006) |
| Wang, H.P., et al., Mechanisms underlying biochanin A-induced relaxation of the aorta differ between normotensive and hypertensive rats. Clin. Exp. Pharmacol. Physiol. 33, 802-807, (2006) | |
| Han, E.H., et al., Effect of biochanin A on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells. Arch. Pharm. Res. 29, 570-576, (2006) | |
| Torregrosa, G., et al., Pharmacological profile of phytoestrogens in cerebral vessels: in vitro study with rabbit basilar artery. Eur. J. Pharmacol. 482, 227-234, (2003) | |
| Beilstein | Beil. 18,V,4,595 |
| reference | FT-IR 2 (2), 2509:A / FT-IR 1 (2), 95:D / FT-NMR 1 (2), 920:A / IR-Spectra (3), 906:B / IR-Spectra (2), 792:H / NMR-Reference 2 (2), 98:C / RegBook 1 (2), 1697:G / Sigma FT-IR 1 (2), 476:A / Structure Index 1, 270:B:1 |
