CasImg
1,8-二羟基蒽醌
产品纠错
CAS号:117-10-2 | 英文名称:1,8-Dihydroxyanthraquinone
分子式 C14H8O4
分子量 240
EINECS号 204-173-5
MDL MFCD00001211
Smiles C1(O)=C2C(C(=O)C3=C(C2=O)C(O)=CC=C3)=CC=C1
InChIKey QBPFLULOKWLNNW-UHFFFAOYSA-N
乙二醇化学百科
基本信息
中文名称 1,8-二羟基蒽醌
英文名称 1,8-Dihydroxyanthraquinone
CAS号 117-10-2
分子式 C14H8O4
分子量 240.21
EINECS号 204-173-5
物化性质
熔点 191-193 °C (lit.)
沸点 342.92°C (rough estimate)
密度 1.3032 (rough estimate)
折射率 1.5430 (estimate)
闪点 >200°C
LogP 4.570 (est)
溶解度 溶于热乙酸中呈现微浑浊
形态 粉末
酸度系数(pKa) 6.27±0.20(Predicted)
颜色 橙棕色或棕色
水溶解性 insoluble
Merck 14,2815
BRN 2054727
(IARC)致癌物分类 2B (Vol. 50) 1990
安全信息
危险品标志 Xn
危险类别码 40
安全说明 36/37-36-22
危险品运输编号 2811
WGK Germany 1
RTECS号 CB6650000
TSCA Yes
海关编码 29146990
危险等级 IRRITANT
毒害物质数据 117-10-2(Hazardous Substances Data)
毒性 LD50 orally in mice: <7 g/kg (Case)
生产及用途
Danthron (Chrysazin, Antrapurol) 通过激活 AMPK 来调节葡萄糖和脂质代谢。Danthron是从传统中药大黄中提取的天然产物。Danthron曾经是一种泻药,现在被用作合成润滑剂中的抗氧化剂,实验抗肿瘤剂的合成,杀真菌剂和制造染料的中间体。

AMPK

Danthron (0.1, 1, and 10 μM) dose-dependently promotes the phosphorylation of AMPK and acetyl-CoA carboxylase (ACC) in both HepG2 and C2C12 cells. Meanwhile, Danthron treatment significantly reduces the lipid synthesis related sterol regulatory element-binding protein 1c (SREBP1c) and fatty acid synthetase (FAS) gene expressions, and the total cholesterol (TC) and triglyceride (TG) levels. In addition, Danthron treatment efficiently increases glucose consumption. Danthron effectively reduces intracellular lipid contents and enhances glucose consumption in vitro via activation of AMPK signaling pathway. 10 μM Danthron/24 h is safe for HepG2 cells. With 80% confluence, HepG2 cells are incubated with Danthron (0.1-10 μM) in FBS-Free media for 8 h. Subsequently, cells are harvested for Western blot assay. Danthron increases the p-AMPK protein in a dose-dependent manner, and no changes in t-AMPK protein are observed. Danthron inhibits 9-cis retinoic acid (9cRA)-induced retinoic X receptor α (RXRα) transactivation by IC 50 at 0.11 μM. To further clarify the stoichimetric ratio of Danthron binding to RXRα-ligand-binding domain (LBD), isothermal titration calorimetry (ITC) experiment is performed. The K D value of Danthron binds to RXRα-LBD by ITC experiment is determined at 7.5 μM.

Danthron functions as an insulin sensitizer in vivo. Danthron improves insulin sensitivity in diet-induced obese (DIO) mice. The insulin tolerance test result shows that Danthron (5 mg/kg) treated diet-induced obesity mice exhibit lower glucose levels after insulin challenge, compared with the control vehicle-treated group.

化学性质 
橙色针状结晶,溶于甲醇、乙醇、乙酸乙酯、乙醚、三氯甲烷,几乎不溶于水,来源于雷公藤,丹参。
用途 
检定铍。染料中间体。
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