3β,4β,7α-trihydroxy-5-cholestene | 219131-32-5

• 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: 3β,4β,7α-trihydroxy-5-cholestene
• 英文别名: cholest-5-ene-3β,4β,7α-triol；4β,7α-dihydroxycholesterol；cholestene-(5)-triol-(3β,4β,7α)；(10R)-3c,4c,7t-Trihydroxy-10r,13c-dimethyl-17c-((R)-1,5-dimethyl-hexyl)-(8cH,9tH,14tH)-Δ⁵-tetradecahydro-1H-cyclopenta[a]phenanthren；3β,4β,7α-Trihydroxy-10,13-dimethyl-17β-((R)-1,5-dimethyl-hexyl)-gonen-(5)；Cholesten-(5)-triol-(3β,4β,7α)；4beta,7alpha-Dihydroxycholesterol；(3S,4R,7S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,4,7-triol
• CAS: 219131-32-5
• 化学式: C₂₇H₄₆O₃
• 分子量: 418.66
• InChiKey: NEITZYUKMAAGFE-DNPWHXEXSA-N

物化性质

• 沸点：
  535.1±50.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 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：

  3β,4β,7α-trihydroxy-5-cholestene 在 p-toluenesulfonic acid on sillica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以54%的产率得到4,6-胆固醇二烯-3-酮
  参考文献：
  名称：

  p -TsOH催化二和三羟基类固醇向各种A / B环氧代官能化的一锅转化

  摘要：

  固体支持物介导的p -TsOH催化的温和转化方案已开发出来，以提供各种环A和/或环B的氧官能化类固醇。为了通过一锅法提供涉及生物分子A / B环的有趣异构体，发现只有固体支持物（而不是溶液！）有效。p -TsOH /的SiO 2氧化作用的4β羟基胆固醇，在人体循环的主要氧固醇，成胆甾-4-烯-3-酮的混合物，胆甾-4-烯-3,6-二酮，和5α-胆甾-3，6-二酮是本文研究的起点。对该反应方案进行了详细的优化，并努力获得对有利于固体支持物的机理方面的理解，以及可能涉及的协同催化体系。p -TsOH和SiO 2被认为是关键部分。将该新方法应用于4β，7α-二羟基类固醇，通过氧化/氧化脱水产生了所需的多种酮类固醇，这使该过程推广为一种简便的多-氧-官能化类固醇转化。

  DOI：

  10.1039/c7nj01878a
• 作为产物：
  描述：

  (3R,4R)-17-(1,5-Dimethyl-hexyl)-3,4-dihydroxy-10,13-dimethyl-1,2,3,4,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-7-one 在 aluminum isopropoxide 、 异丙醇 作用下， 生成 3β,4β,7α-trihydroxy-5-cholestene
  参考文献：
  名称：

  ▵⁵-Cholestene-3β,4β,7α-triol and the Inhibition of the Oxidation of Hydroxyl Groups by Vicinal Substituents

  摘要：

  DOI：

  10.1021/ja01167a119

文献信息

• Oxidation with selenium dioxide: the first report of solvent-selective steroidal aromatization, efficient access to 4β,7α-dihydroxy steroids, and syntheses of natural diaromatic ergosterols
  作者：Pranab Ghosh、Jayanta Das、Antara Sarkar、Seik Weng Ng、Edward R.T. Tiekink

  DOI：10.1016/j.tet.2012.05.110

  日期：2012.8

  Selenium dioxide oxidation of cholesterol reveals a solvent-dependent product selectivity and facile one-pot synthesis of three derivatives, including aromatic analogues of naturally occurring ergosterol. Efficient access to 4β,7α-dihydroxy cholesterol is described. Analogous chemistry of β-sitosterol and diosgenin is also reported. The protocol is found effective to synthesize two diaromatic ergosterol

  胆固醇的二氧化硒氧化显示出溶剂依赖性的产物选择性和三种衍生物的轻松一锅合成，其中包括天然麦角固醇的芳香类似物。描述了有效获取4β，7α-二羟基胆固醇的方法。还报道了β-谷甾醇和薯os皂苷元的相似化学。发现该方案对于合成两种二芳族麦角固醇天然产物是有效的。通过X射线晶体学证明了代表性的二芳族胆固醇衍生物和三乙酰化的4β，7α-二羟基胆固醇衍生物的分子结构的简要描述。
• Ultrastructural Localisation of Sialoadhesin (Siglec- 1) on Macrophages in Rodent Lymphoid Tissues
  作者：Inge L. Schadee-Eestermans、Elizabeth C.M. Hoefsmit、Marja Van De Ende、Paul R. Crocker、Timo K. Van Den Berg

  DOI：10.1016/s0171-2985(00)80036-4

  日期：2000.11

  In previous studies it has been demonstrated that sialoadhesin is a macrophage-restricted adhesion receptor for lymphocytes and myeloid cells. It is under normal circumstances expressed by subpopulations of macrophages in lymphoid and haemopoietic tissues. In this study different immunoelectronmicroscopical techniques are used to investigate the ultrastructural localisation of sialoadhesin within the lymph node and spleen of rodents. The results show that sialoadhesin is selectively expressed by a subset of macrophages in peripheral lymphoid tissues. Sialoadhesin was localised predominantly on the plasma membrane and in particular in areas of intimate contact with lymphocytes, thereby visualizing putative local interaction between these cells. Interestingly, sialoadhesin was also detected in intracellular vesicles that were apparently taken up by macrophages. These findings are consistent with the putative role of sialoadhesin in local cell-cell interactions in lymphoid tissues. Surprisingly, sialoadhesin was also found at contact points of macrophages with other macrophages, sinus-lining cells and reticulum cells, suggesting that sialoadhesin also mediates interactions with these cell types.
• Lasalvia, Maria; Musumeci, Domenica; Piccialli, Vincenzo, Journal of Chemical Research, Miniprint, 1998, # 11, p. 2988 - 2995
  作者：Lasalvia, Maria、Musumeci, Domenica、Piccialli, Vincenzo、Sica, Donato

  DOI：——

  日期：——
• Metabolism of 4β-Hydroxycholesterol in Humans
  作者：Karl Bodin、Ulla Andersson、Eva Rystedt、Ewa Ellis、Maria Norlin、Irina Pikuleva、Gösta Eggertsen、Ingemar Björkhem、Ulf Diczfalusy

  DOI：10.1074/jbc.m201712200

  日期：2002.8

  One of the major oxysterols in the human circulation is 4beta-hydroxycholesterol formed from cholesterol by the drug-metabolizing enzyme cytochrome P450 3A4. Deuterium-labeled 4beta-hydroxycholesterol was injected into two healthy volunteers, and the apparent half-life was found to be 64 and 60 h, respectively. We have determined earlier the half-lives for 7alpha-, 27-, and 24-hydroxycholesterol to be similar to0.5, 0.75, and 14 h, respectively. Patients treated with certain antiepileptic drugs have up to 20-fold increased plasma concentrations of 4beta-hydroxycholesterol. The apparent half-life of deuteriumlabeled 4beta-hydroxycholesterol in such a patient was found to be 52 h, suggesting that the high plasma concentration was because of increased synthesis rather than impaired clearance. 4beta-Hydroxycholesterol was converted into acidic products at a much slower rate than 7alpha-hydroxycholesterol in primary human hepatocytes, and 4beta-hydroxycholesterol was 7alpha-hydroxylated at a slower rate than cholesterol by recombinant human CYP7A1. CYP7B1 and CYP39A1 had no activity toward 4beta-hydroxycholesterol. These results suggest that the high plasma concentration of 4beta-hydroxycholesterol is because of its exceptionally slow elimination, probably in part because of the low rate of 7alpha-hydroxylation of the steroid. The findings are discussed in relation to a potential role of 4beta-hydroxycholesterol as a ligand for the nuclear receptor LXR.
• p-TsOH-Catalyzed one-pot transformation of di- and trihydroxy steroids towards diverse A/B-ring oxo-functionalization
  作者：Antara Sarkar、Jayanta Das、Pranab Ghosh

  DOI：10.1039/c7nj01878a

  日期：——

  A solid support-mediated p-TsOH-catalyzed milder transformative protocol was developed to furnish diverse ring-A and/or ring-B oxo-functionalized steroids. To furnish interesting isomers involving the A/B-ring of biomolecules in a one-pot approach, only solid supports (and not solution!) were found to be effective. p-TsOH/SiO2-oxidation of 4β-hydroxycholesterol, the major oxysterol in human circulation

  固体支持物介导的p -TsOH催化的温和转化方案已开发出来，以提供各种环A和/或环B的氧官能化类固醇。为了通过一锅法提供涉及生物分子A / B环的有趣异构体，发现只有固体支持物（而不是溶液！）有效。p -TsOH /的SiO 2氧化作用的4β羟基胆固醇，在人体循环的主要氧固醇，成胆甾-4-烯-3-酮的混合物，胆甾-4-烯-3,6-二酮，和5α-胆甾-3，6-二酮是本文研究的起点。对该反应方案进行了详细的优化，并努力获得对有利于固体支持物的机理方面的理解，以及可能涉及的协同催化体系。p -TsOH和SiO 2被认为是关键部分。将该新方法应用于4β，7α-二羟基类固醇，通过氧化/氧化脱水产生了所需的多种酮类固醇，这使该过程推广为一种简便的多-氧-官能化类固醇转化。