棉籽酚
中文名称:
棉籽酚
中文同义词:
醋酸棉籽酚;棉酚, 来源于棉花籽;棉籽酚/棉酚;棉酚溶液标准物质;棉酚溶液, 100PPM;棉酚, 来源于棉花;棉籽酚/棉酚标准品;棉籽酚、棉酚、棉子醇
英文名称:
GOSSYPOL
英文同义词:
GOSSYPOL(P);Gossypol from cotton seeds,2,2′-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene);Thespesin;GOSSYPOL;NSC 624336;NSC 56817;1,1,6,6,7,7-HEXAHYDROXY-3,3-DIMETHYL-5,5-BIS(1-METHYLETHYL)-[2,2-BINAPHTHALENE]-8,8-DICARBOXALDEHYDE;2,2-BIS[8-FORMYL-1,6,7-TRIHYDROXY-5-ISOPROPYL-3-METHYLNAPHTHALENE]
CAS号:
303-45-7
分子式:
C30H30O8
分子量:
518.55
EINECS号:
636-899-7
相关类别:
中草药成分;标准品-对照品;植物提取物;小分子抑制剂，天然产物;合成;对照品;中药对照品;Aromatic Phenols;Antitumour;标准品;原料药;中间体;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;标准品-中药标准品;标准品 -中药标准品;标准品，对照品
Mol文件:
303-45-7.mol
熔点
181-183 C
沸点
522.63°C (rough estimate)
密度
1.1912 (rough estimate)
折射率
1.4900 (estimate)
储存条件
2-8°C
酸度系数(pKa)
7.15±0.50(Predicted)
形态
Off-white to yellow solid.
水溶解性
Soluble in 100%ethanol (25 mg/ml), DMF (25 mg/ml), acetone, DMSO (25 mM), methanol (2 mg/ml), ether, chloroform, sodium carbonate, and dilute aqueous solutions of ammonia . Insoluble in water. Gossypol is a male antifertility agent with antispermatogenic activity and has been shown to contain antitumor, anitviral, and antioxidant properties.
InChIKey
QBKSWRVVCFFDOT-UHFFFAOYSA-N
CAS 数据库
303-45-7
EPA化学物质信息
[2,2-Binaphthalene]-8,8-dicarboxaldehyde, 1,1,6,6,7,7-hexahydroxy-3,3-dimethyl-5,5-bis(1-methylethyl)- (303-45-7)
简介
棉酚（gossypol），又称棉毒素或棉籽醇，是棉属植物体内形成的一种黄色多酚二萘化合物。
生物活性
Gossypol (BL 193) 是一种从棉籽和根中分离出来的口服活性的多酚。Gossypol 是一种 5α-reductase 1 和 3α-hydroxysteroid dehydrogenase 的有效抑制剂，在无细胞试验中，对应的IC50值分别为3.33 μM和0.52 μM。Gossypol 还可抑制BH3肽与Bcl蛋白的结合，对 Bcl-XL 和 Bcl-2 的IC50值分别为0.4 μM和10 μM。Gossypol 在各种癌细胞中可诱导凋亡和细胞的生长抑制。
靶点
Target Value
Bcl-xL
(Cell-free assay) 0.4 μM
3α-hydroxysteroid dehydrogenase
(Cell-free assay) 0.52 μM
5α-reductase 1
(Cell-free assay) 3.33 μM
Bcl-2
(Cell-free assay) 10 μM
Target
Value
Bcl-xL
(Cell-free assay)
0.4 μM
3α-hydroxysteroid dehydrogenase
(Cell-free assay)
0.52 μM
5α-reductase 1
(Cell-free assay)
3.33 μM
Bcl-2
(Cell-free assay)
10 μM
体外研究
Gossypol, a natural product isolated from cottonseeds and roots that has been studied as an anticancer agent. The racemic form of Gossypol [(±)-Gossypol] is tested in several clinical trials and is well tolerated. The racemic form Gossypol ((±)-Gossypol) binds to Bcl-xL protein with a K i of 0.5 to 0.6 μM. (±)-Gossypol also potently binds to Bcl-2 protein with a K i value of 0.2-0.3 mM. The natural racemic Gossypol has two enantiomers, namely the (-)-Gossypol and (+)-Gossypol enantiomers. The racemic form and each of the enantiomers of Gossypol are tested against UM-SCC-6 and UM-SCC-14A in 6-day MTT assays. (-)-Gossypol exhibits greater growth inhibition relative to (±)-Gossypol than (+)-Gossypol in both cell lines tested (P<0.001). An intermediate growth inhibitory effect is observed with (±)-Gossypol but this effect is only observed at the higher dose of Gossypol (10 μM, P<0.0001).
化学性质
棕黄色粉末，可溶于甲醇、乙醇、DMSO等有机溶剂，来源于锦葵植物棉花的根、茎、叶和种子内，棉籽仁中含量最高。
用途
棉酚具有抗肿瘤的作用，同时可用作男性避孕药。
类别
有毒物质
毒性分级
高毒
急性毒性
口服- 大鼠 LD50: 325 毫克/ 公斤; 口服- 小鼠 LD50: 765 毫克/立方米/4小时
可燃性危险特性
可燃, 火场排出辛辣刺激烟雾
储运特性
库房低温, 通风, 干燥; 与食品原料分开存放
灭火剂
水, 二氧化碳, 干粉, 砂土
危险品标志
Xn,Xi
危险类别码
22-40-36/37/38
安全说明
22-36-36/37/39-27-26
WGK Germany
3
RTECS号
DU3100000
海关编码
29124990
