9-顺式维甲酸

概述制备生物活性体外研究体内研究 9-顺式维甲酸试剂级价格

9-顺式维甲酸

CAS号:5300-03-8
英文名:9-CIS-RETINOIC ACID
中文名:9-顺式维甲酸
CBNumber:CB2386395
分子式:C20H28O2
分子量:300.44
MOL File:5300-03-8.mol

9-顺式维甲酸化学性质

熔点 :189-191°C
沸点 :462.8±14.0 °C(Predicted)
密度 :1.011±0.06 g/cm3(Predicted)
RTECS号 :VH6450000
储存条件 :-20°C
溶解度 :Acetonitrile (Very Slightly), Chloroform (Slightly), DMSO (Slightly), Ethanol (
酸度系数(pKa) :4.73±0.33(Predicted)
形态 :Light yellow to orange crystalline powder.
颜色 :Pale Yellow to Yellow
水溶解性 :Soluble in chloroform (50 mg/ml), DMSO (~25 mg/ml), ethanol (25 mg/ml), and acetone (25 mg/ml). Insoluble in water.
敏感性 :Moisture & Light Sensitive
稳定性 :Store Dry in Freezer at -20°C for up to 1 year; in Solution at -20°C for up to 3 Months.
CAS 数据库 :5300-03-8(CAS DataBase Reference)

安全信息

危险品标志 :T
危险类别码 :61-36/37/38
安全说明 :53-26-36/37/39-45
WGK Germany :3
海关编码 :29162090
毒害物质数据 :5300-03-8(Hazardous Substances Data)

9-顺式维甲酸性质、用途与生产工艺

概述
异维A酸EP杂质D是异维A酸合成过程中产生产生的杂质，又名阿利维甲酸，是治疗皮肤病领域的重要药物，是全反式维甲酸(式II，化学名：3，7-二甲基-9-(2，6，6-三甲基环己烯-1-基)-2E，4E，6E，8E-全反式壬四烯酸)的9-顺异构体。
制备
异维A酸EP杂质D（式I化合物）的制备：在氮气保护下，往反应瓶中加入乙醇2L、全反式维甲酸100g，搅拌，然后升温至50～55℃，加入PdCl289mg。反应1.5h后，经HPLC检测产物纯度为21％。反应液缓慢降温至0～5℃，保温180分钟，抽滤；滤液加入另一干净反应瓶中，继续降温至-10～-6℃，保温20分钟，抽滤，得到产物异维A酸EP杂质D 12.1g，总收率12.1％，HPLC纯度99.60％。以全反式维甲酸为原料，采用钯化合物催化，在普通的工业级有机溶剂中可得到阿利维甲酸。方法操作简便，成本低，条件可控，便于工业生产；经过后处理步骤后，可得到纯度99％以上的阿利维甲酸，产物收率达到12％以上，具有较高的应用价值。
生物活性 9-cis-Retinoic acid (ALRT1057)，维生素 A 的衍生物，是一种有效的 RAR/RXR 激动剂。9-cis-Retinoic acid 可诱导细胞凋亡 (apoptosis)，调节细胞周期并具有抗癌，抗炎和神经保护活性。

体外研究

9-cis-Retinoic acid (1-10 μM; 0-5 days; CA 9-22 and NA cells) treatment significantly decreases proliferation in a dose-dependent manner in CA 9-22 and NA cells.
9-cis-Retinoic acid (1 μM; 24 hours) treatment significantly increases PPARγ functional activity by >200% in CA 9-22 and NA aerodigestive cells.
9-cis-Retinoic acid treatment results in the formation of a nuclear PPARγ-RXRα heterodimer supershift complex in CA 9-22 cells.
9-cis-Retinoic acid inhibits proliferation and induces apoptosis in cutaneous T-cell lymphoma (CTCL) in a dose-dependent and time-dependent manner. 9-cis-Retinoic acid also induces G0/G1 cell cycle arrest by downregulation of cyclin D1. 9-cis-Retinoic acid significantly decreases phosphorylation of JAK1, STAT3, and STAT5 and downregulated Bcl-xL and cyclin D1.

Cell Proliferation Assay

Cell Line:	CA 9-22 and NA cells
Concentration:	1 μM, 10 μM
Incubation Time:	0 day, 1 day, 3 days, 5 days
Result:	Significantly decreased proliferation.

体内研究

9-cis-Retinoic acid (1 mg/kg; intravenous injection; daily; for 10 days; male C57BL/6J mice) treatment significantly decreases the serum ALT and AST level, alleviates hepatic necrosis of the bile duct ligation (BDL)-mice.

Animal Model:	Male C57BL/6J mice (6-8 weeks; 19-22 g) treatment with bile duct ligated
Dosage:	1 mg/kg
Administration:	Intravenous injection; daily; for 10 days
Result:	Significantly decreased the serum ALT and AST level, alleviated hepatic necrosis.