Biochanin A
SIGMA/D2016
Synonym: 4′-Methylgenistein; 5,7-Dihydroxy-4′-methoxyisoflavone; Genistein 4′-methyl ether; Olmelin
CAS Number: 491-80-5
Empirical Formula (Hill Notation): C16H12O5
Molecular Weight: 284.26
EC Number: 207-744-7
MDL Number: MFCD00006839
Linear Formula: C16H12O5
Product Type: Chemical
| form | powder |
| InChI | 1S/C16H12O5/c1-20-11-4-2- |
| InChI key | WUADCCWRTIWANL-UHFFFAOYSA |
| mp | 210-213 °C (lit.) |
| Quality Level | 100  |
| SMILES string | COc1ccc(cc1)C2=COc3cc(O)c |
| Application: | Biochanin A has been used to evaluate its effect on the ergotamine (ERT)-induced contractility in bovine mesenteric vasculature. It may be used to test its anticancer potential in human glioblastoma cell lines. It has been used as a reference standard in high-performance liquid chromatography−tandem mass spectrometry. |
| 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. |
| 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. |
| 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 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| mp | 210-213 °C (lit.) |
| UNSPSC | 41116107 |