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

• ChemBase编号: 73001
• 分子式: C16H12O5
• 平均质量: 284.26348
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
• IUPAC传统名: biochanin; 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
• 别名: 5,7-二羟基-4'-甲氧基异黄酮; 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

登记号

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

理论计算性质

• Acid pKa: 6.547949
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 3.1857247
• LogD (pH = 7.4): 2.2726228
• Log P: 3.2227664
• 摩尔折射率: 76.1652 cm^3
• 极化性: 29.012978 Å^3
• 极化表面积: 75.99 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: Off-White Solid; Powder
• 熔点: 210-213 °C(lit.); 210-213°C; 210-213°C

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C)
• 德国WGK号: 3
• TSCA收录: 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 相关基因信息: human ... CYP19A1(1588)mouse ... Aldh1a2(19378), Maoa(17161)
• 生物活性机理: Estrogen

产品相关信息

• 纯度: 98%
• 成盐信息: Free Base
• 生物来源: 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
• 应用领域: Possesses sl. estrogenic activity

详细说明

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.

参考文献

• http://en.wikipedia.org/wiki/Biochanin_A
• Chae, Y.H., et al.: Chem. Biol. Interactions, 82, 181 (1992)
• Jing, Y. and Waxman, S.: Anticancer Res., 15(1992)
• 1147 (1995)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 95D, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 920A, (nmr)
• Baker, W. et al., J.C.S., 1953, 1852, (synth)
• Pelter, A. et al., Synthesis, 1976, 326, (synth)
• Diedrich, D.F. et al., J. Chem. Eng. Data, 1977, 22, 448, (pmr)
• Bass, R.J. et al., J.C.S. Perkin 1, 1978, 666, (cmr)
• Ashdown, D.H.J. et al., Synthesis, 1978, 843, (synth)
• Ingham, J.L., Prog. Chem. Org. Nat. Prod., 1983, 43, 1, (rev, occur)
• Elgamal, M.H.A. et al., J. Prakt. Chem., 1986, 328, 893, (ms)
• Murthy, M.S.R. et al., Magn. Reson. Chem., 1986, 24, 225, (cmr)
• Sekizaki, H. et al., Chem. Pharm. Bull., 1988, 36, 4876, (synth)
• Aparecida dos Santos, S. et al., J. Braz. Chem. Soc., 1995, 6, 349, (pmr, cmr)
• Balasubramanian, S. et al., Synth. Commun., 2000, 30, 469-484, (synth, pmr)