24(S),25-Dihydroxycholesterol | 60103-15-3

• 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: 24(S),25-Dihydroxycholesterol
• 英文别名: 24S,25-Dihydroxycholesterol；(3S,6R)-6-[(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptane-2,3-diol
• CAS: 60103-15-3
• 化学式: C₂₇H₄₆O₃
• 分子量: 418.66
• InChiKey: OFNJCHBCBBSWHW-XVYZBDJZSA-N

物化性质

• 沸点：
  554.4±25.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  24(S),25-Dihydroxycholesterol 生成 (24S)-24,25-dihydroxyvitamin D₃
  参考文献：
  名称：

  Koizumi, Naoyuki; Ishiguro, Masaji; Yasuda, Mitsuhiro, Journal of the Chemical Society. Perkin transactions I, 1983, # 7, p. 1401 - 1410

  摘要：

  DOI：
• 作为产物：
  描述：

  (3beta)-3-(叔-丁基二甲基硅烷基)氧基-胆-5-烯-24-酸甲酯 在 四氧化锇 、 Hydroquinone 1,4-phthalazinediyl diether 、 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 52.0h， 生成 24(S),25-Dihydroxycholesterol
  参考文献：
  名称：

  Stereocontrolled syntheses of 24(S),25-epoxycholesterol and related oxysterols for studies on the activation of LXR receptors

  摘要：

  Efficient syntheses are described of desmosterol (4), the corresponding 24(S),25 epoxide (6) and various analogs of 6 for evaluation as ligands and functional activators of LXR receptors. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02181-9

文献信息

• Oxidation of 7-dehydrocholesterol and desmosterol by human cytochrome P450 46A1
  作者：Sandeep Goyal、Yi Xiao、Ned A. Porter、Libin Xu、F. Peter Guengerich

  DOI：10.1194/jlr.m051508

  日期：2014.9

  cholesterol, 7-dehydrocholesterol has not been found to be a substrate of P450 46A1 and desmosterol has not been previously tested. However, 24-hydroxy-7-dehydrocholesterol was recently identified in brain tissues, which prompted us to reexamine this enzyme and its potential substrates. Here we report that P450 46A1 oxidizes 7-dehydrocholesterol to 24-hydroxy-7-dehydrocholesterol and 25-hydroxy-7-dehydrocholesterol

  细胞色素 P450（P450 或 CYP）46A1 在大脑中表达，其特征是能够将胆固醇氧化为 24S-羟基胆固醇。此外，已知相同的酶可进一步将 24S-羟基胆固醇氧化成 24,25- 和 24,27- 二羟基产物，以及催化 7α-羟基胆固醇和胆固醇的侧链氧化。作为胆固醇生物合成中的前体，尚未发现 7-脱氢胆固醇是 P450 46A1 的底物，并且先前未测试过去甾醇。然而，最近在脑组织中发现了 24-羟基-7-脱氢胆固醇，这促使我们重新审视这种酶及其潜在的底物。在这里，我们报告了 P450 46A1 将 7-脱氢胆固醇氧化为 24-羟基-7-脱氢胆固醇和 25-羟基-7-脱氢胆固醇，经 LC-MS 和 GC-MS 证实。总体，催化形成速率以24-羟基-7-脱氢胆固醇< 24-羟基胆固醇< 25-羟基-7-脱氢胆固醇的顺序增加，比例为1:2.5:5。在去甾醇的情况下，观察到环氧化为 24S,25-环氧胆固醇和
• Treatment for age-related macular degeneration (AMD)
  申请人：——

  公开号：US20030162758A1

  公开（公告）日：2003-08-28

  The present invention addresses the treatment of age-related macular degeneration using regulation of pathogenic mechanisms similar to atherosclerosis. In further specific embodiments, reverse cholesterol transport components, such as transporters and HDL fractions, are utilized as diagnostic and therapeutic targets for age-related macular degeneration. In a specific embodiment, the lipid content of the retinal pigment epithelium, and/or Bruch's membrane is reduced.

  本发明利用与动脉粥样硬化类似的致病机制的调节来治疗老年性黄斑变性。在更具体的实施方案中，反向胆固醇转运成分，如转运体和高密度脂蛋白组分，被用作老年性黄斑变性的诊断和治疗靶标。在一个具体的实施方案中，视网膜色素上皮和/或布鲁氏膜的脂质含量降低。
• Treatments for age-related macular degeneration (AMD)
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20030229062A1

  公开（公告）日：2003-12-11

  The present invention addresses the treatment of age-related macular degeneration using regulation of pathogenic mechanisms similar to atherosclerosis. In further specific embodiments, reverse cholesterol transport components, such as transporters and HDL fractions, are utilized as diagnostic and therapeutic targets for age-related macular degeneration. In a specific embodiment, the lipid content of the retinal pigment epithelium, and/or Bruch's membrane is reduced.

  本发明利用与动脉粥样硬化类似的致病机制的调节来治疗老年性黄斑变性。在更具体的实施方案中，反向胆固醇转运成分，如转运体和高密度脂蛋白组分，被用作老年性黄斑变性的诊断和治疗靶标。在一个具体的实施方案中，视网膜色素上皮和/或布鲁氏膜的脂质含量降低。
• Compositions and methods for modulating HDL cholesterol and triglyceride levels
  申请人：——

  公开号：US20040137423A1

  公开（公告）日：2004-07-15

  The invention provides methods for identifying agents that modulate HDL-levels in animals by evaluating the ability of LXR-modulating agents to increase ABCA1-gene expression in a cell as well as using such agents to treat conditions involving lower than normal HDL-levels, higher than normal triglyceride levels and the like.

  本发明提供了通过评估 LXR 调节药剂增加细胞中 ABCA1 基因表达的能力，以及使用此类药剂治疗高密度脂蛋白水平低于正常、甘油三酯水平高于正常等病症，从而确定调节动物体内高密度脂蛋白水平的药剂的方法。
• 24(R), 25-Dihydroxycholesterol; An Attempt for Side-Chain Stereocontrol Via Iodolactonization
  作者：J. van Der Eycken、L. van Wabeeke、M. Vandewalle

  DOI：10.1002/bscb.19860950410

  日期：——

  AbstractStereocontrolled formation of the side‐chain of 24(R), 25‐dihydroxycholesterol (1) via an iodolactonization process, involving a C‐10 carboxylic function and a 24, 25 double bond, has been studied. Low stereoselectivity was observed.