5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one

• ChemBase编号: 72924
• 分子式: C15H10O5
• 平均质量: 270.2369
• 单一同位素质量: 270.05282342
• SMILES: c1(c(c(c2c(c1)oc(cc2=O)c1ccccc1)O)O)O
• Canonical SMILES: Oc1cc2oc(cc(=O)c2c(c1O)O)c1ccccc1
• InChI: InChI=1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H
• InChIKey: FXNFHKRTJBSTCS-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one
• IUPAC传统名: baicalein; 5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one
• 别名: 5,6,7-三羟基黄酮; 三羟黄酮; 5,6,7-三羟基黄酮; Baicalein; 5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one; 5,6,7-Trihydroxyflavone; 5,6,7-Trihydroxyflavone; Baicalein; Baicalein; Noroxylin

登记号

• CAS号: 491-67-8
• MDL号: MFCD00017459
• Beilstein号: 272683
• 默克索引号: 14942
• PubChem SID: 24870246; 162037844; 24847315
• PubChem CID: 5281605
• CHEBI ID: 2979
• CHEMBL: 8260
• Chemspider ID: 4444924
• 美国药典/FDA物质标识码: 49QAH60606
• 维基百科标题: Baicalein

理论计算性质

• 里宾斯基五规则: true
• Acid pKa: 6.755033
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 2.6833563
• LogD (pH = 7.4): 1.9496312
• Log P: 2.7066891
• 摩尔折射率: 72.9139 cm^3
• 极化性: 27.111025 Å^3
• 极化表面积: 86.99 Å^2
• 可自由旋转的化学键: 1

分子性质

理化性质

• 外观: Yellow powder
• 熔点: 256-271 °C(lit.); 268-270°C

安全信息

• 保存条件: -20°C
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36; 26-37
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: mouse ... Hexa(15211)rat ... Alox15(81639), Alox5(25290)
• 生物活性机理: ICAM 1 antagonist

产品相关信息

• 纯度: ≥98.0% (UV); 97%; 98%; 98.0
• 成盐信息: Free Base
• 生物来源: Isol. from Scutellaria spp. and other plants
• 应用领域: Shows anti-HIV activity
• Empirical Formula (Hill Notation): C15H10O5

详细说明

Selleck Chemicals - S2268

Research Area: Infection
Biological Activity:
Baicalein is a CYP2C9 and prolyl endopeptidase inhibitor. It is a flavone, a type of flavonoid, originally isolated from the roots of Scutellaria baicalensis. It is also reported in Oroxylum indicum or Indian trumpetflower. It is the aglycone of baicalin.The flavonoid has been shown to inhibit certain types of lipoxygenases and act as an anti-inflammatory agent. [1]References on Baicalein[1] http://en.wikipedia.org/wiki/Baicalein, ,

Sigma Aldrich - 465119

Biochem/physiol Actions
尼泊尔和中日天然药物中的类黄酮组分。1,2三羟黄酮（黄芩的主要黄酮），可抑制花生四烯酸代谢的 12-脂氧合酶 (12-LOX) 途径，从而抑制癌细胞增殖并诱导癌细胞凋亡。
包装
100, 500 mg in glass bottle

Sigma Aldrich - 11712

Other Notes
反转录酶和 12-脂氧合酶的特异性抑制剂1,2

参考文献

• http://en.wikipedia.org/wiki/Baicalein
• Kutney, J.P. et al., Phytochemistry, 1971, 10, 3298, (isol)
• Mezey-Vandor, G. et al., Chem. Ber., 1980, 113, 1945, (synth)
• Takahashi, H. et al., Bull. Chem. Soc. Jpn., 1987, 60, 2261, (isol)
• Stierle, D.B. et al., Phytochemistry, 1988, 27, 517, (isol, cmr)
• The Flavonoids: Advances in Research since 1980, (Ed. Harborne, J.B.), Chapman and Hall, London, 1988
• Ng, A.S. et al., J. Nat. Prod., 1990, 53, 747, (synth)
• Koh, L.L. et al., Acta Cryst. C, 1993, 49, 105, (cryst struct, derivs)
• Parmar, S.V. et al., Indian J. Chem., Sect. B, 1993, 32, 244, (synth, bibl)
• Liu, Q. et al., Phytochemistry, 1993, 32, 925; 34, 167, (derivs)
• Zhou, L. et al., CA, 1999, 130, 107543j, (Baicalein, activity)
• Rossi, M. et al., J. Nat. Prod., 2001, 64, 26-31, (uv, cryst struct)