5α-cholest-8-en-3-one | 632-33-7

• 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: 5α-cholest-8-en-3-one
• 英文别名: 5α-Cholest-8-en-3-on；5α-Cholesten-(8)-on-(3)；5alpha-Cholest-8-en-3-one；(5S,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 632-33-7
• 化学式: C₂₇H₄₄O
• 分子量: 384.646
• InChiKey: RZSXSHNNQBIPTL-ZSBATXSLSA-N

物化性质

• 沸点：
  477.8±44.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)
• 熔点：
  124-125 °C

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5α-cholest-8-en-3-one 在 盐酸 、 氯仿 、 aluminum isopropoxide 、 异丙醇 、 甲苯 作用下， 生成 5α（H）-Cholestan-3α醇
  参考文献：
  名称：

  Wieland; Benend, Chemische Berichte, 1942, vol. 75, p. 1708,1714

  摘要：

  DOI：
• 作为产物：
  描述：

  3α-hydroxy-10.13-dimethyl-17β-((R)-1.5-dimethyl-hexyl)-5α-gonene-(8) 在 环己酮 、 aluminum isopropoxide 、 甲苯 作用下， 生成 5α-cholest-8-en-3-one
  参考文献：
  名称：

  Wieland; Benend, Chemische Berichte, 1942, vol. 75, p. 1708,1714

  摘要：

  DOI：

文献信息

• Genetic effects of mercury contamination on aquatic snail populations: Allozyme genotypes and DNA strand breakage
  作者：Michael J. Benton、Michelle L. Malott、Jan Trybula、Deborah M. Dean、Sheldon I. Guttman

  DOI：10.1002/etc.5620210317

  日期：2002.3

  significantly lower in the populations from the most highly contaminated sites. The DNA strand break frequency was significantly correlated to whole-body total mercury concentration in snails from three sites. These data add to the evidence supporting the use of DNA strand breakage as an indicator of chemical contamination and the use of allozyme analysis as a marker of contamination and possible selection

  比较了美国弗吉尼亚州西南部北福克霍尔斯顿河 (NFHR) 上五个汞污染不同地点的 Pleurocera canaliculatum 种群的等位酶数据和 DNA 链断裂频率。四个位点的等位酶基因型频率在来自三个污染最严重的地点的人群和来自两个污染程度较低的地点的人群之间存在显着差异。此外，在污染最严重的地点的人群中，其中三个位点的杂合性显着降低。DNA 链断裂频率与来自三个地点的蜗牛的全身总汞浓度显着相关。这些数据增加了支持使用 DNA 链断裂作为化学污染指标和使用异位酶分析作为污染标志物和可能选择抗污染性的证据。然而，污染物引起的中枢代谢酶遗传变异的变化与抗性选择可能起作用的功能之间的关系仍不清楚，必须考虑抗性选择以外的机制。来自其他生化途径的酶的使用可能适用于其他物种或处于其他化学污染压力下的物种。污染物引起的中枢代谢酶遗传变异的变化与抗性选择可能起作用的功能之间的关系仍不清楚，必须考虑
• The gene mutated in bare patches and striated mice encodes a novel 3β-hydroxysteroid dehydrogenase
  作者：Xiao Yu Liu、Andrew W. Dangel、Richard I. Kelley、Wei Zhao、Paul Denny、Marc Botcherby、Bruce Cattanach、Jo Peters、Patricia R. Hunsicker、Ann-Marie Mallon、Mark A. Strivens、Rachael Bate、Webb Miller、Michael Rhodes、Stephen D.M. Brown、Gail E. Herman

  DOI：10.1038/9700

  日期：1999.6

  X-linked dominant disorders that are exclusively lethal prenatally in hemizygous males have been described in human and mouse1. None of the genes responsible has been isolated in either species. The bare patches (Bpa ) and striated (Str) mouse mutations were originally identified in female offspring of X-irradiated males2,3. Subsequently, additional independent alleles were described. We have previously mapped these X-linked dominant, male-lethal mutations to an overlapping region of 600 kb that is homologous to human Xq28 (ref. 4) and identified several candidate genes in this interval5. Here we report mutations in one of these genes, Nsdhl, encoding an NAD(P)H steroid dehydrogenase-like protein, in two independent Bpa and three independent Str alleles. Quantitative analysis of sterols from tissues of affected Bpa mice support a role for Nsdhl in cholesterol biosynthesis. Our results demonstrate that Bpa and Str are allelic mutations and identify the first mammalian locus associated with an X-linked dominant, male-lethal phenotype. They also expand the spectrum of phenotypes associated with abnormalities of cholesterol metabolism.

  人类和小鼠中都有X连锁显性遗传病，这种病在单倍体雄性中仅在产前致死，1。但在这两种物种中，都没有分离出相关的基因。裸斑（Bpa）和条纹（Str）小鼠突变最初是在X射线照射雄性小鼠的雌性后代中发现的2,3。随后，又发现了其他独立等位基因。我们之前将这些X连锁显性、雄性致死突变定位到与人类Xq28同源的600kb重叠区域（参考文献4），并在此区间内确定了几个候选基因5。在此，我们报告了其中一种基因Nsdhl的突变，该基因编码一种NAD（P）H类固醇脱氢酶样蛋白，在两个独立的Bpa和三个独立的Str等位基因中都有突变。对患病Bpa小鼠组织中的固醇进行定量分析，证实了Nsdhl在胆固醇生物合成中的作用。我们的研究结果表明，Bpa和Str是等位基因突变，并确定了第一个与X连锁显性、雄性致死表型相关的哺乳动物基因座。它们还扩展了与胆固醇代谢异常相关的表型谱。
• 420. Steroids and related compounds. Part XIV. 5β-Methyl-19-norcoprost-9(10)-ene-3β : 6β : -diol
  作者：B. Ellis、V. Petrow

  DOI：10.1039/jr9520002246

  日期：——
• Wieland; Rath; Benend, Justus Liebigs Annalen der Chemie, 1941, vol. 548, p. 19,29
  作者：Wieland、Rath、Benend

  DOI：——

  日期：——
• Synthesis of [3α-3H]cholesta-5,8-dien-3β-ol and tritium-labeled forms of other sterols of potential importance in the Smith-Lemli-Optiz syndrome⋆
  作者：B Ruan

  DOI：10.1016/s0039-128x(99)00079-3

  日期：2000.1

  Five unsaturated sterols relevant to the Smith-Lemli-Opitz syndrome have been prepared in high radiochemical purity with a tritium label at the 3 alpha position. Swern oxidation of cholesta-5,8-dien-3 beta-ol and other unlabeled C-27 sterols afforded the corresponding 3-ketosteroids, and reduction with tritiated NaBH4 gave the desired 3 alpha-H-3 sterols, with double bonds at the Delta(5,8), Delta(5,8(14)), Delta(6,8), Delta(6,8(14)), and Delta(8) positions. High radiochemical purity of the tritiated sterols was demonstrated by normal phase, reversed phase, and silver-ion (Ag+) high-performance liquid chromatography (HPLC). In the course of this work, we developed a medium-pressure variant of Ag+-HPLC for purifying radiolabeled samples, documented significant isotopic fractionation of the 3 alpha-tritiated sterols and their acetates on Ag+-HPLC, and discovered unexpected effects of a Delta(8(14)) bond on the conformation of 3-keto-Delta(5)-steroids. The synthetic and analytical methodologies described herein should provide a sound basis for investigating the origin and metabolism of sterols involved in the Smith-Lemli-Opitz syndrome and in late stages of cholesterol biosynthesis. (C) 2000 Elsevier Science Inc. All rights reserved.