3-O-acetyl lithocholic acid | 95672-09-6

• 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: 3-O-acetyl lithocholic acid
• 英文别名: 3α-acetoxy-5α-cholanoic acid-(24)；3α-Acetoxy-5α-cholansaeure-(24)；(4R)-4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-acetyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 95672-09-6
• 化学式: C₂₆H₄₂O₄
• 分子量: 418.617
• InChiKey: FCQRLHQHKFKTQE-XXRCNXDISA-N

物化性质

• 沸点：
  520.6±23.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-O-acetyl lithocholic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Acetic acid (3R,5S,8R,9S,10S,13R,14S,17R)-17-((R)-3-{6-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-hexylcarbamoyl}-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Steroid and lipid conjugates of siRNAs to enhance cellular uptake and gene silencing in liver cells

  摘要：

  Double-stranded short interfering RNAs (siRNAs) mediate post-transcriptional inhibition of gene expression in a variety of biological systems. However, human liver cells show poor uptake of these nucleic acids. In order to improve the delivery of siRNA into these cells without transfection agents, we have synthesized two series of lipophilic siRNAs conjugated with derivatives of cholesterol, lithocholic acid or lauric acid. The lipid moieties were covalently linked to the 5'-ends of the RNAs using phosphoramidite chemistry. The potency of these chemically modified siRNAs to inhibit reporter gene expression was further investigated in vitro with beta-galactosidase expressing liver cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.018
• 作为产物：
  描述：

  5-alpha-胆甾烷-3-alpha-醇乙酸酯 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 3-O-acetyl lithocholic acid
  参考文献：
  名称：

  Kuwada; Joyama, Yakugaku Zasshi, 1935, vol. 55, p. 978,984; dtsch. Ref. S. 183

  摘要：

  DOI：

文献信息

• Space-filling effects in membrane disruption by cationic amphiphiles
  作者：Tomoko Fujiwara、Naohide Hirashima、Seiji Hasegawa、Mamoru Nakanishi、Tomohiko Ohwada

  DOI：10.1016/s0968-0896(00)00326-6

  日期：2001.4

  steroid-polyamine conjugates consisting of a rigid hydrophobic steroid unit, and a flexible hydrophilic polyamine unit connected by a linker. The steroid structure, polyamine chain length, and the presence of a hydrophobic substituent on the steroid, all influenced the activity. Analysis of the time dependence of hemolysis suggested that these structurally related cationic amphiphiles have different mechanisms of

  我们研究了由刚性疏水类固醇单元和通过接头连接的柔性亲水性聚胺单元组成的新型合成类固醇-多胺缀合物对牛红细胞的溶血活性。类固醇的结构，多胺链长和类固醇上疏水取代基的存在均影响活性。对溶血的时间依赖性的分析表明，这些结构相关的阳离子两亲物具有不同的膜扰动机制。