303-45-7

• 常用中文名：棉酚
• 常用英文名：Gossypol
• CAS号：303-45-7
• 分子式：C₃₀H₃₀O₈
• 分子量：518.554
• 相关类别： 原料药 激素及调节内分泌功能类药 避孕药
• 发布时间：2018-04-22 08:00:00
• 更新时间：2024-01-02 04:13:21
• Gossypol 是一种从棉籽和根中分离出来的天然产物,分别与 Bcl-xL 蛋白和 Bcl-2 蛋白结合,Ki 值分别为 0.5-0.6 μM 和 0.2-0.3 mM。

名称

• 中文名: 棉酚
• 英文名: gossypol
• 中文别名: 棉子酚
• 英文别名: MFCD00017352; 1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl[2,2'-binaphthalene]-8,8'-dicarboxaldehyde; 1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthalene-8,8'-dicarbaldehyde; 2,2'-BI[8-FORMYL-1,6,7-TRIHYDROXY-5-ISOPROPYL-3-METHYLNAPHTHALENE]; 2,2'-Bis[1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene]; 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-di(propan-2-yl)-2,2'-binaphthalene-8,8'-dicarbaldehyde; Gossypol; gossypol from cotton seeds; (rac)-2,2'-bis(8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene); 2,2'-bis[8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene]; (-)-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-METHYLNAPTHALENE]; 1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-(2,2'-binaphthalene)-8,8'-dicarboxaldehyde; 1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthalen-8,8'-dicarbaldehyd; Thespesin; [2,2'-Binaphthalene]-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-; 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-2,2'-binaphthalene-8,8'-dicarbaldehyde; roduct Name; (+/-)-gossypol; 1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde

物化性质

• 密度: 1.4±0.1 g/cm3
• 沸点: 707.9±55.0 °C at 760 mmHg
• 熔点: 181-183ºC
• 分子式: C₃₀H₃₀O₈
• 分子量: 518.554
• 闪点: 395.9±28.0 °C
• 精确质量: 518.194092
• PSA: 155.52000
• LogP: 6.16
• 外观性状: 棕黄色粉末
• 蒸汽压: 0.0±2.3 mmHg at 25°C
• 折射率: 1.742
• 储存条件:

  聚乙烯塑料袋密封包装。贮存于阴凉干燥处。

• 计算化学:

  1.疏水参数计算参考值（XlogP）:6.9

  2.氢键供体数量:6

  3.氢键受体数量:8

  4.可旋转化学键数量:5

  5.互变异构体数量:996

  6.拓扑分子极性表面积156

  7.重原子数量:38

  8.表面电荷:0

  9.复杂度:780

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1. 性状：棉酚为淡黄至黄色板状或针状结晶，无臭，无味。

  2. 密度（g/mL, 25 ℃ ）：未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：棉酚的羟醛式(石油醚中结晶)熔点为214℃；内醚式(氯仿中结晶)熔点为199℃；羰式(乙醚中结晶)熔点为184℃。

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC,12mmHg）：未确定

  7. 折射率(n20/D)：未确定

  8. 闪点（ºF）：未确定

  9. 比旋光度（º）：未确定

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（mmHg,25ºC）：未确定

  12. 饱和蒸气压（kPa,83-85ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：不溶于水，微溶于乙醇，可溶于氯仿、乙醚、丙酮、乙酸乙酯、二氯乙烷、四氯化碳和吡啶等有机溶剂。较难溶于环己烷、苯和石油醚

生物活性

• 描述: Gossypol 是一种从棉籽和根中分离出来的天然产物,分别与 Bcl-xL 蛋白和 Bcl-2 蛋白结合,Ki 值分别为 0.5-0.6 μM 和 0.2-0.3 mM。
• 相关类别:
  信号通路 >> 细胞凋亡 >> Bcl-2家族
  研究领域 >> 癌症
  天然产物 >> 酚类
• 靶点:

  Bcl-xL:0.5-0.6 μM (Ki)

  Bcl-2:0.2-0.3 mM (Ki)

• 体外研究: 棉酚,一种从棉籽和根中分离出来的天然产品,已被研究作为抗癌剂。外消旋形式的棉酚[(±)-棉酚]在几个临床试验中进行了测试,并且耐受性良好。外消旋形式Gossypol((±)-Gossypol)与Bcl-xL蛋白结合,Ki为0.5至0.6μM。 (±)-棉酚也有效结合Bcl-2蛋白,Ki值为0.2-0.3mM。天然外消旋棉酚具有两种对映体,即(-)-棉酚和(+)-棉酚对映体。在6天MTT测定中,针对UM-SCC-6和UM-SCC-14A测试外消旋形式和棉酚的每种对映体。 (-)-在所测试的两种细胞系中,棉酚相对于(±)-棉酚表现出比(+)-棉酚更大的生长抑制(P <0.001)。用(±)-Gossypol观察到中间生长抑制作用,但这种作用仅在较高剂量的棉酚(10μM,P <0.0001)[1]时观察到。
• 细胞实验: 两种代表性的UM-SCC细胞系UM-SCC-6和UM-SCC-14A持续暴露于0（载体对照），5或10μM（±） - 棉酚，（ - ） - 棉酚或（+） - 棉酚在6天的MTT细胞存活试验中[1]。
• 参考文献:

  [1]. Oliver CL, et al. In vitro effects of the BH3 mimetic, (-)-Gossypol, on head and neck squamous cell carcinoma cells. Clin Cancer Res. 2004 Nov 15;10(22):7757-63.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : DU3100000 CHEMICAL NAME : (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl- 3,3'-dimethyl- CAS REGISTRY NUMBER : 303-45-7 BEILSTEIN REFERENCE NO. : 1917878 LAST UPDATED : 199803 DATA ITEMS CITED : 18 MOLECULAR FORMULA : C30-H30-O8 MOLECULAR WEIGHT : 518.60 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 2315 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - pig DOSE/DURATION : 550 mg/kg TOXIC EFFECTS : Behavioral - muscle weakness Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 17 mg/kg SEX/DURATION : male 60 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 700 mg/kg SEX/DURATION : male 35 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 1050 mg/kg SEX/DURATION : male 35 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Effects on Newborn - live birth index (measured after birth) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 4500 mg/kg SEX/DURATION : male 90 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 525 mg/kg SEX/DURATION : male 35 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 700 mg/kg SEX/DURATION : male 70 day(s) pre-mating TOXIC EFFECTS : Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females) MUTATION DATA TYPE OF TEST : Mutation test systems - not otherwise specified TEST SYSTEM : Rodent - hamster Ovary DOSE/DURATION : 10 mg/L/48H REFERENCE : ITCSAF In Vitro. (Rockville, MD) V.1-20, 1965-85. For publisher information, see ICDBEO. Volume(issue)/page/year: 19,53,1983

安全

• 符号: GHS08
• 信号词: Warning
• 危害声明: H351
• 警示性声明: P281
• 个人防护装备: Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
• 危害码 (欧洲): Xn
• 风险声明 (欧洲): R22;R40
• 安全声明 (欧洲): S22-S36
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 3.0
• RTECS号: DU3100000

合成路线

40817-07-0 ~77% 303-45-7

文献：Li, Ling; Liu, Yuxiu; Wang, Qingmin European Journal of Organic Chemistry, 2013 , # 35 p. 8014 - 8021

784206-41-3 864131-95-3 ~73% 303-45-7

文献：Meltzer; Bickford; Lambert Journal of Organic Chemistry, 1985 , vol. 50, # 17 p. 3121 - 3124

1665-99-2 ~% 303-45-7

文献：European Journal of Organic Chemistry, , # 35 p. 8014 - 8021

499-75-2 ~% 303-45-7

文献：European Journal of Organic Chemistry, , # 35 p. 8014 - 8021

50399-96-7 ~% 303-45-7

文献：European Journal of Organic Chemistry, , # 35 p. 8014 - 8021

1256723-09-7 ~% 303-45-7

文献：European Journal of Organic Chemistry, , # 35 p. 8014 - 8021

17273-29-9 ~% 303-45-7

文献：Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), , # 9 p. 1359 - 1362

73728-76-4 ~% 303-45-7

文献：Chemistry of Natural Compounds, , vol. 26, # 2 p. 129 - 138 Khimiya Prirodnykh Soedinenii, , # 2 p. 166 - 177

7664-93-9 6952-36-9 ~% 303-45-7

文献：Journal of Biological Chemistry, , vol. 76, p. 233

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40817-07-0 864131-95-3 1665-99-2 499-75-2
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