棉酚
| 中文名称 | 棉酚 |
|---|---|
| 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;原料药;中间体;标准品;Aromatic Phenols;Antitumour;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 |
| 结构式 |  |
棉酚 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 | DMSO 中≥25.95 mg/mL；不溶于水；乙醇中≥2.1 mg/mL |
| 酸度系数(pKa) | 7.15±0.50(Predicted) |
| 形态 | 灰白色至黄色固体。 |
| 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. |
| InChI | InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3 |
| InChIKey | QBKSWRVVCFFDOT-UHFFFAOYSA-N |
| SMILES | C1(O)=C2C(C(C(C)C)=C(O)C(O)=C2C=O)=CC(C)=C1C1=C(C)C=C2C(=C1O)C(C=O)=C(O)C(O)=C2C(C)C |
| 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) |
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。
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。| 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 |
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).
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 |
| 存储类别 | 6.1C - 可燃，急性毒性 类别3 毒性化合物或者引起慢性影响的化合物 |
| 危险性类别 | 急性毒性 类别4 经口 生殖毒性 类别1B |
| 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. |
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英文
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