返回ChemicalBook首页>CAS数据库列表>2657-25-2

2657-25-2

中文名称 4-羟基查耳酮
英文名称 4'-HYDROXYCHALCONE
CAS 2657-25-2
分子式 C15H12O2
MDL 编号 MFCD00016484
分子量 224.25
MOL 文件 2657-25-2.mol
更新日期 2025/07/28 09:46:19
2657-25-2 结构式 2657-25-2 结构式

基本信息

中文别名
4-羟基查耳酮
英文别名
2-BENZAL-4'-HYDROXYACETOPHENONE
2-BENZYLIDENE-4'-HYDROXYACETOPHENONE
4'-HYDROXYCHALCONE
BENZYLIDENE-(4-HYDROXYACETOPHENONE)
BENZYLIDENE-4'-HYDROXYACETOPHENONE
HYDROXYCHALCONE, 4'-
4'-Hydroxychalcone,97%
4'-Hydroxychalcone 98%
HYDROXYCHALCONE, 4-(RG)
4'-Hydroxychalcone98%
1-(4-Hydroxyphenyl)-3-phenyl-2-propen-1-one
1-(p-Hydroxyphenyl)-3-phenyl-2-propene-1-one
所属类别
生物化工:提取物

物理化学性质

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: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS (pH 7.2) (1:4): 0.2 mg/ml
酸度系数(pKa)7.72±0.15(Predicted)
形态粉末晶体
颜色浅橙色至黄色至绿色
BRN2049150
InChIInChI=1S/C15H12O2/c16-14-9-7-13(8-10-14)15(17)11-6-12-4-2-1-3-5-12/h1-11,16H
InChIKeyUAHGNXFYLAJDIN-IZZDOVSWSA-N
SMILESC(C1=CC=C(O)C=C1)(=O)C=CC1=CC=CC=C1
LogP3.650 (est)

安全数据

危险性符号(GHS)GHS hazard pictograms
GHS07
警示词警告
危险性描述H315-H319-H335
危险品标志Xi
危险类别码R36/37/38
安全说明S37/39-S26
海关编码29145090

制备方法

方法1
苯甲醛

100-52-7

对羟基苯乙酮

99-93-4

4-羟基查耳酮

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

常见问题列表

生物活性
4'-Hydroxychalcone (P-Cinnamoylphenol),存在于草药、香料和茶叶中,是一种刺甘草查尔酮。它具有多种生物活性,能够抑制TNF-α诱导的NF-κB通路激活、并激活BMP信号通路。
靶点
TargetValue
NF-κB
()
体外研究

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.
体内研究

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).
"2657-25-2" 相关产品信息
961-29-5 548-83-4 959-23-9 2657-25-2 38183-03-8 520-27-4 520-36-5 6665-86-7 24292-52-2 480-16-0 153-18-4 529-44-2 117-39-5 480-40-0 42224-53-3 1214-47-7 644-78-0 20426-12-4