cholest-4α-methyl-7-en-3β-ol acetate | 6702-46-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cholest-4α-methyl-7-en-3β-ol acetate
• 英文别名: lophenyl acetate；Lophenyl-acetat；Lophenolacetat；3β-acetoxy-4α-methyl-5α-cholest-7-ene；3β-Acetoxy-4α-methyl-5α-cholest-7-en；[(3S,4S,5S,9R,10S,13R,14R,17R)-4,10,13-trimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 6702-46-1
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: SQJKDEQVXPFQGL-MTFRKTCUSA-N

物化性质

• 熔点：
  119.0-120.5 °C
• 沸点：
  501.4±49.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cholest-4α-methyl-7-en-3β-ol acetate 在 chromium(VI) oxide 、 盐酸 、 硫酸 、 溶剂黄146 、 铂 作用下， 生成 4α-methyl-5α-cholestan-3-one
  参考文献：
  名称：

  The Neutral Constituents of the Cactus Lophocereus schottii. The Structure of Lophenol--4α-Methyl-Δ⁷-cholesten-3β-ol--A Link in Sterol Biogenesis^1-3

  摘要：

  DOI：

  10.1021/ja01556a031

文献信息

• Synthesis of 4α-Methyl-Δ⁷-steroiäs. The Interrelationship of Cholesterol, Citrostadienol and Lophenol
  作者：Yehuda Mazur、Franz Sondheimer

  DOI：10.1021/ja01556a033

  日期：1958.12
• Synthesis and antitumor activity of cholest-4α-methyl-7-en-3β-ol derivatives
  作者：Lan He、Yumei Liu、Jiangong Shi、Qiang Pei

  DOI：10.1016/j.steroids.2006.01.006

  日期：2006.6

  Cholest-4 alpha-methyl-7-en-3 beta-ol (1) has potent inhibitory activity against pc 12 tumor with 0.5043 ratio (10 mu g/mL). This paper describes a series of structural modification of this compound, which focus on 3 beta-hydroxyl group and 7(8)-double bond. The synthesized derivatives of I were tested for human cancer cell lines including colon cancer (HCT-8), liver cancer (BEL-7402) and nasopharyngeal cancer (KB) cells. The results showed that cholest-4 alpha-methyl-8-en-3 beta,7 alpha-diol 6a inhibits KB cell significantly with IC50 1.32 x 10(-9) mu g/ml. In addition, the cytotoxic properties of this compound against HCT-8 and BEL-7402 are excellent with IC50 1.2 mu g/mL. (c) 2006 Elsevier Inc. All rights reserved.