cis-Zearalenol | 5916-52-9

• 物质功能分类: 分析化学 - 标准品 - 食品和化妆品标准品
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: cis-Zearalenol
• 英文别名: (12Z)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraen-2-one
• CAS: 5916-52-9；36455-71-7；36455-72-8；38055-76-4；71030-11-0
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: FPQFYIAXQDXNOR-CLTKARDFSA-N

物化性质

• 熔点：
  158-161°C
• 沸点：
  599.0±50.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)
• 闪点：
  2℃
• 溶解度：
  乙醇中≤20mg/ml；DMSO 中≤30mg/ml；二甲基甲酰胺中≤30mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S36/37,S61
• 危险类别码：
  R20/21/22,R40,R68/20/21/22,R52/53
• WGK Germany：
  2,3
• 海关编码：
  29322090

制备方法与用途

生物活性

α-Zearalenol 是一种对雌激素受体 (ER) 具有高亲和力的霉菌毒素, α-Zearalenol 是 zearalenone (ZEN) 的衍生物，由于其异种雌激素效应可引起动物的生殖障碍。

体外研究

α-Zearalenol (α-zol) (0.001-10 μM; 24-72 hours) shows the highest RPE (90.5%) at 9.37 µM α-ZOL exposure in MFC-7 cells with an IC ₅₀ of 12.5 μM. α-Zearalenol (α-zol) (0.001-10 μM; 24-72 hours) induces an increase of cell viability on MCF-7 cells mainly after 72 h of treatment whereas it is slightly cytotoxic on MDA-MB231 cells. α-Zearalenol (α-zol) (0.001-10 μM; 24-72 hours) increases MCF7 cell population in the S phase and in the G2/M phase, no visible change in cell cycle phases is observed in MDA-MB231 cells. α-Zearalenol (α-zol) (1-10 μM; 24 hours) reduces the expression of TNF-α, α-ZOL combines with β-ZOL shows an antagonistic effect on inflammation for IL-1β and act synergic for IL-8 at high toxin concentrations.

Cell Proliferation Assay

Cell Line:	MFC-7 cells
Concentration:	6.25 µM-25 µM
Incubation Time:	24 hours
Result:	Observed the highest RPE (90.5%) at 9.37 µM α-ZOL exposure in MFC-7 cells.

Cell Viability Assay

Cell Line:	Breast cancer cell lines: MCF-7 and MDA-MB231
Concentration:	0.001 μM, 0.1 μM and 10 μM
Incubation Time:	24 hours, 48 hours, 72 hours
Result:	Modified the cell growth in two breast cancer cell lines.

Cell Cycle Analysis

Cell Line:	MCF7 cells, MDA-MB231 cells
Concentration:	0.001 μM, 0.1 μM and 10 μM
Incubation Time:	72 hours
Result:	Observed an increase of cells in cell cycle in MCF7 cells.

RT-PCR

Cell Line:	HepG2 cells
Concentration:	1 μM, 5 μM, 10 μM
Incubation Time:	72 hours
Result:	Induced a decrease of the expression of TNF-α, IL-1β and IL-8, that was in most cases statistically significant for the higher doses.

文献信息

• [EN] A PROCESS FOR MANUFACTURING ZERANOL<br/>[FR] PROCÉDÉ DE FABRICATION DE ZÉRANOL
  申请人：INTERVET INT BV

  公开号：WO2010115478A1

  公开（公告）日：2010-10-14

  This invention is directed generally to a process for producing Zeranol that eliminates high pressure and high temperature hydrogenations and provides high selectivity for Zeranol at improved yields.

  这项发明通常涉及一种生产Zeranol的过程，该过程消除了高压和高温氢化反应，并且在高产率下为Zeranol提供了高选择性。
• A PROCESS FOR MANUFACTURING ZERANOL
  申请人：Intervet International B.V.

  公开号：EP2417118A1

  公开（公告）日：2012-02-15