4-羟基查耳酮
| 中文名称 | 4-羟基查耳酮 |
|---|---|
| 中文同义词 | 4-羟基查耳酮;4-羟苯基苯丙烯酮;1-(4-羟基苯基)-3-苯基丙-2-烯-1-酮;4'-羟基查耳酮;4′-羟基查耳酮,10 MM DMSO 溶液;4′-羟基查耳酮 4'-Hydroxychalcone;4'-Hydroxychalcone 4'-羟基查耳酮,S4937;4'-Hydroxychalcone 4'-羟基查耳酮，S4937 |
| 英文名称 | 4'-Hydroxychalcone |
| 英文同义词 | 2-Benzal-4'-hydroxyacetophenone 2-Benzylidene-4'-hydroxyacetophenone;1-(4-Hydroxyphenyl)-3-phenyl-2-propen-1-one;1-(p-Hydroxyphenyl)-3-phenyl-2-propene-1-one;4'-Hydroxychalcone,97%;4'-Hydroxychalcone 98%;HYDROXYCHALCONE, 4-(RG);4'-Hydroxychalcone98%;HYDROXYCHALCONE, 4'- |
| CAS号 | 2657-25-2 |
| 分子式 | C15H12O2 |
| 分子量 | 224.25 |
| EINECS号 | |
| 相关类别 | 苯酚;植物提取物;中药对照品;Chalcones;Biochemistry;Flavonoids |
| Mol文件 | 2657-25-2.mol |
| 结构式 |  |
4-羟基查耳酮 性质
| 熔点 | 174-178 °C |
|---|---|
| 沸点 | 419.6±45.0 °C(Predicted) |
| 密度 | 1.191±0.06 g/cm3(Predicted) |
| 储存条件 | Inert atmosphere,Room Temperature |
| 溶解度 | DMF：30mg/mL； DMSO：30mg/mL；乙醇：30mg/mL；乙醇:PBS (pH 7.2) (1:4): 0.2 mg/mL |
| 形态 | 粉末晶体 |
| 酸度系数(pKa) | 7.72±0.15(Predicted) |
| 颜色 | 浅橙色至黄色至绿色 |
| BRN | 2049150 |
| InChI | InChI=1S/C15H12O2/c16-14-9-7-13(8-10-14)15(17)11-6-12-4-2-1-3-5-12/h1-11,16H |
| InChIKey | UAHGNXFYLAJDIN-IZZDOVSWSA-N |
| SMILES | C(C1=CC=C(O)C=C1)(=O)C=CC1=CC=CC=C1 |
| LogP | 3.650 (est) |
| CAS 数据库 | 2657-25-2(CAS DataBase Reference) |
| Target | Value |
|
NF-κB
() |
4'-Hydroxychalcone (20-40 μM ; 2 hours) inhibits TNFα-induced (20 ng/mL; 6 hours) NF-kB pathway activation in a dose-dependent manner.
4'-Hydroxychalcone (0.1-25 μM ; 8 hours) inhibits proteasome activity in a dose-dependent manner but has no effect on IKK activity.
4'-Hydroxychalcone inhibits TNFα-dependent degradation of IkBα and subsequently prevents p50/p65 nuclear translocation leading to 4'-Hydroxychalcone-inhibited expression of NF-kB target genes.
4'-Hydroxychalcone affects cancer cell viability but has no significant effect on non-transformed cell viability.
Cell Viability Assay
| Cell Line: | K562 cells, Jurkat cells, U937 cells, PBMCs |
| Concentration: | 5 μM, 10 μM, 20 μM, 24 μM, 28 μM, 32 μM, 40 μM, 60 μM |
| Incubation Time: | 24 hours |
| Result: | Affected cancer cell viability but has no significant effect on non-transformed cell viability. |
Western Blot Analysis
| Cell Line: | Jurkat cells |
| Concentration: | 60 μM (followed by TNFα 20 ng/mL ) |
| Incubation Time: | 2 hours |
| Result: | Inhibited TNFα -dependent degradation of IkBα and prevents p50/p65 nuclear translocation. |
4'-Hydroxychalcone has hepatoprotective activity against Acetaminophen induced hepatotoxicity in mice.
| Animal Model: | Male albino mice(5-30 g) |
| Dosage: | 25 mg/kg, 50 mg/kg, 100 mg/kg |
| Administration: | Oral administration, 12h intervals, 4 doses |
| Result: | Significantly reduced the mortality rate induced by Acetaminophen (1 g/kg). |
100-52-7
99-93-4
2657-25-2
向反应瓶中加入对羟基苯乙酮（1 mmol）和苯甲醛（表2中2 mmol；表3中1 mmol），以及Mo10V2/SiO2催化剂（负载量为40 wt%，其中Mo10V2占19-32.5 wt%，ICP分析结果显示Mo含量略低于制备时的化学计量预期，具体为0.06 g，即0.010 mol/mol Mo10V2相对于底物酮）。将混合物在50℃下搅拌反应适当时间。反应进程通过薄层色谱（TLC）监控，使用正己烷/乙酸乙酯（10:4，v/v）作为洗脱剂。反应完成后，向反应混合物中加入乙醚（2×10 mL），过滤分离催化剂。催化剂经洗涤干燥后可重复使用。滤液经减压浓缩除去溶剂后，通过柱色谱分离得到纯的1-(4-羟基苯基)-3-苯基丙-2-烯-1-酮。
参考文献：
[1] Journal of the American Chemical Society, 2018, vol. 140, # 3, p. 1011 - 1018
[2] Monatshefte fur Chemie, 2013, vol. 144, # 3, p. 361 - 367
[3] Journal of the Chilean Chemical Society, 2013, vol. 58, # 3, p. 1926 - 1929
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 8, p. 682 - 687
[5] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 4, p. 578 - 587
安全信息
| 危险品标志 | Xi |
|---|---|
| 危险类别码 | 36/37/38 |
| 安全说明 | 37/39-26-37 |
| 海关编码 | 29145090 |