D2016

Biochanin A

• Sinônimo(s): 4′-Methylgenistein, 5,7-Dihydroxy-4′-methoxyisoflavone, Genistein 4′-methyl ether, Olmelin
• Fórmula empírica (Notação de Hill): C₁₆H₁₂O₅
• Número CAS: 491-80-5
• Peso molecular: 284.26
• Beilstein: 278107
• Número CE: 207-744-7
• Número MDL: MFCD00006839
• Código UNSPSC: 41116107
• ID de substância PubChem: 24893597
• NACRES: NA.25

Propriedades

• Formulário: powder
• pf: 210-213 °C (lit.)
• cadeia de caracteres SMILES: COc1ccc(cc1)C2=COc3cc(O)cc(O)c3C2=O
• 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
• chave InChI: WUADCCWRTIWANL-UHFFFAOYSA-N
• Informações sobre genes: human ... CYP19A1(1588) ; mouse ... Aldh1a2(19378) , Maoa(17161)

Descrição

Descrição geral

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.[1]

Aplicação

Biochanin A has been used to evaluate its effect on the ergotamine (ERT)-induced contractility in bovine mesenteric vasculature.[2] It may be used to test its anticancer potential in human glioblastoma cell lines.[3] It has been used as a reference standard in high-performance liquid chromatography−tandem mass spectrometry.[4]

Ações bioquímicas/fisiológicas

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.

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.

Informações de segurança

• Código de classe de armazenamento: 11 - Combustible Solids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable
• Equipamento de proteção individual: Eyeshields, Gloves, type N95 (US)