棉酚 , 标准物质 Gossypol, reference material CAS#:303-45-7

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棉酚 , 标准物质

产品纠错

CAS号：303-45-7 | 英文名称：Gossypol, reference material

分子式

分子量

EINECS号

MDL

Smiles

InChIKey

乙二醇化学百科

基本信息

中文名称	棉酚
英文名称	GOSSYPOL
CAS号	303-45-7
分子式	C30H30O8
分子量	518.55
EINECS号	636-899-7

物化性质

熔点	181-183 C
沸点	522.63°C (rough estimate)
密度	1.1912 (rough estimate)
折射率	1.4900 (estimate)
LogP	5.419 (est)
溶解度	DMSO 中≥25.95 mg/mL；不溶于水；乙醇中≥2.1 mg/mL
形态	灰白色至黄色固体。
酸度系数(pKa)	7.15±0.50(Predicted)
颜色	浅黄至黄色
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.

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 plantproduct produced by some varieties of cotton and found incottonseed meal and cottonseed oil from those varieties.Affects the male reproductive system and has potential use asa male contraceptive agent. May be irritating to the GI tract.In animal studies large doses caused lung edema and paralysis.

生产及用途

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