303-45-7

中文名称棉籽酚

英文名称 GOSSYPOL

CAS 303-45-7

分子式 C30H30O8

分子量 518.55

MOL 文件 303-45-7.mol

更新日期 2024/06/03 16:58:53

303-45-7 结构式

基本信息物理化学性质安全数据应用领域常见问题列表图谱信息

基本信息

中文别名

棉酚
棉子醇
棉子酚
棉籽酚
醋酸棉籽酚
棉酚溶液标准物质
棉酚, 来源于棉花籽

英文别名

Pogosin
GOSSYPOL
Thespesin
NSC 56817
NSC 624336
GOSSYPOL(P)
Gossypol solution
TIMTEC-BB SBB012338
3’-dimethyl-sopropyl-
GOSSYPOL, COTTON SEEDS

所属类别

原料药：避孕药

物理化学性质

外观性状棕黄色粉末，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。

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

酸度系数(pKa)7.15±0.50(Predicted)

形态灰白色至黄色固体。

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.

InChIKeyQBKSWRVVCFFDOT-UHFFFAOYSA-N

LogP5.419 (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)

安全数据

危险性符号(GHS)

GHS07,GHS08

警示词危险

危险性描述H302-H360F

防范说明P201-P202-P264-P270-P301+P312-P308+P313

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 Germany3

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.

应用领域

用途1

棉酚具有抗肿瘤的作用，同时可用作男性避孕药。

常见问题列表

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).

图谱信息

棉籽酚(303-45-7)核磁图(¹HNMR)