17-oxo-5-androsten-3β-ol linoleate | 55393-66-3

• 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: 17-oxo-5-androsten-3β-ol linoleate
• 英文别名: 5-androsten-3β-ol-17-one linoleate；DHEA-3-yl octadeca-9,12-dienoate；[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] (9Z,12Z)-octadeca-9,12-dienoate
• CAS: 55393-66-3
• 化学式: C₃₇H₅₈O₃
• 分子量: 550.866
• InChiKey: FYMBGTCWEMSFKV-SDAOKRCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 、 去氢表雄酮 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 potassium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以58%的产率得到17-oxo-5-androsten-3β-ol linoleate
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Dehydroepiandrosterone Derivatives on Es-2, A549, and HepG2 Cells in vitro

  摘要：

  A series of dehydroepiandrosterone derivatives containing an acid ester was synthesized and evaluated for their antitumor activity on ES‐2, A549, and HepG2 cells by the MTT assay. Most compounds showed antitumor activity, while compounds 1c, 2i, and 2o exhibited more potential inhibitory effects compared with dehydroepiandrosterone on ES‐2 cells, A549 cells, and HepG2 cells, respectively.

  DOI：

  10.1111/j.1747-0285.2011.01311.x

文献信息

• Rapid synthesis of long chain fatty acid esters of steroids in ionic liquids with microwave irradiation: Expedient one-pot procedure for estradiol monoesters
  作者：Somdatta Deb、Kristiina Wähälä

  DOI：10.1016/j.steroids.2010.03.005

  日期：2010.10

  We report the rapid synthesis (1min) in high yield of fatty acid ester (FAE) derivatives of several steroids under microwave irradiation in an ionic liquid (IL). An expedient regioselective hydrolysis at C-3 of estradiol diesters is also reported.

  我们报告了在离子液体 (IL) 中微波照射下几种类固醇的脂肪酸酯 (FAE) 衍生物的高产率快速合成 (1 分钟)。还报道了在雌二醇二酯的 C-3 处进行权宜的区域选择性水解。
• Synthesis and Antitumor Activity of Dehydroepiandrosterone Derivatives on Es-2, A549, and HepG2 Cells in vitro
  作者：Xue-Kun Liu、Bai-Jun Ye、Yan Wu、Ji-Xing Nan、Zhen-Hua Lin、Hu-Ri Piao

  DOI：10.1111/j.1747-0285.2011.01311.x

  日期：2012.4

  A series of dehydroepiandrosterone derivatives containing an acid ester was synthesized and evaluated for their antitumor activity on ES‐2, A549, and HepG2 cells by the MTT assay. Most compounds showed antitumor activity, while compounds 1c, 2i, and 2o exhibited more potential inhibitory effects compared with dehydroepiandrosterone on ES‐2 cells, A549 cells, and HepG2 cells, respectively.