棉酚

棉酚化学性质

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
溶解度 :≥25.95 mg/mL in DMSO; insoluble in H2O; ≥2.1 mg/mL in EtOH
形态 :Off-white to yellow solid.
酸度系数(pKa) :7.15±0.50(Predicted)
颜色 :Light yellow to yellow
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
LogP :5.419 (est)
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)

安全信息

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
毒害物质数据 :303-45-7(Hazardous Substances Data)
毒性 :A secondary plant product produced by some varieties of cotton and found in cottonseed meal and cottonseed oil from those varieties. Affects the male reproductive system and has potential use as a male contraceptive agent. May be irritating to the GI tract. In animal studies large doses caused lung edema and paralysis.

棉酚性质、用途与生产工艺

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

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