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303-45-7

中文名稱 棉籽酚
英文名稱 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 2024/10/25 16:44:59
303-45-7 結(jié)構(gòu)式 303-45-7 結(jié)構(gòu)式

基本信息

中文別名
棉酚
棉子醇
棉子酚
棉籽酚
醋酸棉籽酚
棉酚溶液標(biāo)準(zhǔn)物質(zhì)
棉酚, 來源于棉花籽
英文別名
Pogosin
GOSSYPOL
Thespesin
NSC 56817
NSC 624336
GOSSYPOL(P)
Gossypol solution
TIMTEC-BB SBB012338
3’-dimethyl-sopropyl-
GOSSYPOL, COTTON SEEDS
所屬類別
原料藥:避孕藥

物理化學(xué)性質(zhì)

外觀性狀棕黃色粉末,可溶于甲醇、乙醇、DMSO等有機(jī)溶劑,來源于錦葵植物棉花的根、莖、葉和種子內(nèi),棉籽仁中含量最高。
熔點(diǎn)181-183 C
沸點(diǎn)522.63°C (rough estimate)
密度1.1912 (rough estimate)
折射率1.4900 (estimate)
儲(chǔ)存條件2-8°C
儲(chǔ)存條件2-8°C
溶解度≥25.95 mg/mL in DMSO; insoluble in H2O; ≥2.1 mg/mL in EtOH
酸度系數(shù)(pKa)7.15±0.50(Predicted)
形態(tài)灰白色至黃色固體。
顏色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.
InChIKeyQBKSWRVVCFFDOT-UHFFFAOYSA-N
LogP5.419 (est)
CAS 數(shù)據(jù)庫303-45-7

安全數(shù)據(jù)

危險(xiǎn)性符號(GHS)GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
警示詞危險(xiǎn)
危險(xiǎn)性描述H302-H360F
危險(xiǎn)品標(biāo)志Xn,Xi
危險(xiǎn)類別碼22-40-36/37/38
WGK Germany3
WGK Germany3
RTECS號DU3100000
海關(guān)編碼29124990
毒害物質(zhì)數(shù)據(jù)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.

應(yīng)用領(lǐng)域

用途1
棉酚具有抗腫瘤的作用,同時(shí)可用作男性避孕藥。

常見問題列表

簡介

棉酚(gossypol),又稱棉毒素或棉籽醇,是棉屬植物體內(nèi)形成的一種黃色多酚二萘化合物。

生物活性
Gossypol (BL 193) 是一種從棉籽和根中分離出來的口服活性的多酚。Gossypol 是一種 5α-reductase 1 和 3α-hydroxysteroid dehydrogenase 的有效抑制劑,在無細(xì)胞試驗(yàn)中,對應(yīng)的IC50值分別為3.33 μM和0.52 μM。Gossypol 還可抑制BH3肽與Bcl蛋白的結(jié)合,對 Bcl-XL 和 Bcl-2 的IC50值分別為0.4 μM和10 μM。Gossypol 在各種癌細(xì)胞中可誘導(dǎo)凋亡和細(xì)胞的生長抑制。
靶點(diǎn)
TargetValue
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
體外研究

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).

圖譜信息

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