Baicalein 黄芩素

CAS 491-67-8 MFCD00017459

化学结构图

491-67-8
SMILES: O=c1cc(-c2ccccc2)oc2cc(O)c(O)c(O)c12

化学属性

Mol. FormulaC15H10O5
Mol. Weight270.24
Melting Point256-271°C
TSCANo
Density1.548
Appearance 黄色粉末，熔点264-265℃，溶于乙醇、甲醇、乙醚、丙酮、醋酸乙酯和热冰醋酸，微溶于氯仿和硝基苯，几乎不溶于水。溶于稀氢氧化钠呈绿棕色，溶于浓硫酸呈黄色并有绿色荧光。
SolubilitySoluble in alcohol, methanol, ether, acetone, ethyl acetate, hot glacial acetic acid, dilute sodium hydroxide, and DMSO (50 mM). Insoluble in water
Stability对光和热敏感
Boiling Point650.2°C at 760 mmHg

别名和识别编码

Chemical NameBaicalein
Synonym 6 Baicalein {} {} {} {SNA} 三羟黄酮 貝加因 黃芩素 黄芩素 黄芩黄素 黄芪素
MDL NumberMFCD00017459
PubChem Substance ID5281605
Beilstein Registry Number272683
CAS Number491-67-8
Reaxys-RN272683
Merck Number942
Chemical Name Translation黄芩素
InChIInChI=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
LabNetwork Molecule IDLN00194973
Canonical SMILESO=C1C=C(C2=CC=CC=C2)OC3=CC(O)=C(O)C(O)=C13
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分类

  • {SA} B, Bioactive Small Molecules, Building Blocks, C15 to C38, Cancer Research, Carbonyl Compounds, Cell Biology, Chemical Synthesis, Chemopreventive Agents, Flavonoids, Flavonols, and Flavanols,
  • {SNA} Building Blocks,
  • B, Bioactive Small Molecules, Building Blocks, C15 to C38, Cancer Research, Carbonyl Compounds, Cell Biology, Chemical Synthesis, Chemopreventive Agents, Flavonoids, Flavonols, and Flavanols, Ketones, Nutrition Research, Organic Building Blocks, Phytochemicals by Chemical Classification, Phytoestrogens
  • {SNA} Building Bloc

产品应用

  • An inhibitor of Ca2+ uptake, 5-LO, and 12-LO

相关文献及参考

  • [2]. Patwardhan RS, et al. Baicalein exhibits anti-inflammatory effects via inhibition of NF-κB transactivation. Biochem Pharmacol. 2016 May 15;108:75-89.
  • [3]. Ma X, et al. Baicalein suppresses metastasis of breast cancer cells by inhibiting EMT via downregulation of SATB1 and Wnt/β-catenin pathway.
  • [4]. Kong EK, et al. A novel anti-fibrotic agent, baicalein, for the treatment of myocardial fibrosis in spontaneously hypertensiverats. Eur J Pharmacol. 2011 May 11;658(2-3):175-81.
  • Drug Des Devel Ther. 2016 Apr 18;10:1419-41.
  • Drug Des Devel Ther. 2016 Apr 18;10:1419-41.
  • Merck 14 ,942
  • Merck: 14,942
  • Merck: 14,942 Beilstein:18(5)4,569
  • [1]. Shieh DE,et al. Antioxidant and free radical scavenging effects of baicalein, baicalin and wogonin. Anticancer Res. 2000 Sep-Oct
  • [1]. Shieh DE,et al. Antioxidant and free radical scavenging effects of baicalein, baicalin and wogonin. Anticancer Res. 2000 Sep-Oct;20(5A):2861-5.

安全信息

WGK Germany3
GHS Symbol
Precautionary statements
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
Hazard Codes Xi
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Signal word
RTECSDJ3100898
Storage condition 0-10 0-10°C 2-8°C 2-8°C, protect from light 储存温度2-8℃
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S37 Wear suitable gloves 戴适当手套；
  • S36 Wear suitable protective clothing 穿戴适当的防护服；
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性

其他信息

  • Alfa Aesar:5,6,7-三羟基黄酮,97% 5,6,7-Trihydroxyflavone, 97%(491-67-8)
  • Baicalein is a cell-permeable flavone, originally isolated from the roots of Scutellaria baicalensis, that inhibits cellular Ca2+ uptake, calcium mobilization, and adjuvant-induced arthritis. Baicalein has been shown to inhibit platelet 5-LO (5-lipoxygenase) (IC50=9.5 mM) and 12-LO (12-lipoxygenases) (IC50=0.12 mM) and reverse transcriptase. Baicalein reduces leukotriene biosynthesis and inhibits the release of lysosomal enzymes. Baicalein is a potent anti-inflammatory and anti-tumor agent, and it blocks PREP (prolyl oligopeptidase). Baicalein induces the S-phase arrest and apoptosis in proliferation of human lung squamous carcinoma CH27 cells. The declining expression of cdk1, cdk2, cyclin D2 and cyclin A by Baicalein resulted in the G1 and G2 cell cycle arrest in C6 rat glioma cells. Baicalein has anti-thrombotic, antiproliferative and anti-mitogenic effects. Baicalein inhibits protein tyrosine kinase in leukemia (CEM) cells and PMA-stimulated PKC (protein kinase C). Baicalein is an inhibitor of 15-LO and CYP2C9.
  • MOL 文件:491-67-8.mol
  • 溶于乙醇、甲醇、乙醚、丙酮、醋酸乙酯、热冰醋酸，微溶于氯仿和硝基苯，几乎不溶于水，溶于稀氢氧化钠呈绿棕色，浓硫酸中呈黄色并显绿色荧光。
  • Hazard Note:Irritant
  • 黄芩素价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2010/05/25 L14185 5,6,7-三羟基黄酮, 97% 5,6,7-Trihydroxyflavone, 97% 500mg 1198元 2010/05/25 L14185 5,6,7-三羟基黄酮, 97% 5,6,7-Trihydroxyflavone, 97% 100mg 357元
  • 用途一:具有抗炎、抗变态反应、利尿、利胆、降胆固醇、抗血栓形成、缓解哮喘等作用。也为哺乳动物肝脏涎酶的特异性抑制剂，具有调节某些疾病的作用。工业上以其为原料制取黄芩苷原磷酸酯用于过敏、喘息性肺炎，也作收敛剂、止血药。
  • Sigma Aldrich:491-67-8(sigmaaldrich)

系列性分类

  1. Life Science 生命科学
  2. Cancer Research
  3. Chemopreventive Agents - Cancer Research
  4. Phytoestrogens - Chemopreventive Agents
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Bioactive Small Molecules - Cell Biology
  4. B - Bioactive Small Molecules
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Ketones - Carbonyl Compounds
  6. C15 to C38 - Ketones
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Enzymes, Inhibitors, and Substrates - Biochemicals and Reagents
  4. Enzyme Inhibitors - Enzymes, Inhibitors, and Substrates
  5. Enzyme Inhibitors by Type - Enzyme Inhibitors
  6. Other - Enzyme Inhibitors by Type
  1. Functional Group 官能团索引
  2. 1,2-diphenol
  1. Medical Research Areas
  2. Metabolism
  3. Xanthine Oxidase  (黄嘌呤氧化酶)

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