24-methyl-23-dehydrocholesteryl acetate | 72962-54-0

• 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-methyl-23-dehydrocholesteryl acetate
• 英文别名: 24-methylcholesta-5,E-23-dien-3β-yl acetate；ergosta-5,E-23-dien-3β-yl acetate；24-methyl-E-23-dehydrocholesteryl acetate；(E)-ergosta-5,23-dienyl 3β-acetate；[(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R)-5,6-dimethylhept-4-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 72962-54-0
• 化学式: C₃₀H₄₈O₂
• 分子量: 440.71
• InChiKey: FPNGSVYWFLQCOM-VSQVQSJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  24-methylene cholesteryl acetate 在 碘 作用下， 以 苯 为溶剂， 以30.4%的产率得到24-methyl-24-dehydrocholesteryl acetate
  参考文献：
  名称：

  24-Methyl-23-dehydrocholesterol: A new sterol intermediate in C-24 demethylation from the nematodes Panagrellus redivivus and Caenorhabditis elegans?

  摘要：

  Panagrellus redivivus produced 24-methyl-23-dehydrocholesterol as 4.0% of the 4-desmethylsterols when propagated in a medium containing campesterol as the dietary sterol. The re-examination of previous data revealed that Caenorhabditis elegans produced 1.8% 24-methyl-23-dehydrocholesterol when propagated in medium containing campesterol. 24-Methyl-23-dehydrocholesterol was not detected when the nematodes were propagated in medium containing 22-dihydrobrassicasterol or 24-methylenecholesterol. This may be a result of the greater efficiency of dealkylation of the latter two sterols. This is the first report of the natural occurrence of this sterol in a non-photosynthetic organism, and the first report in organisms that dealkylate 24-alkylsterols.

  DOI：

  10.1016/0039-128x(86)90031-0

文献信息

• Preparative Method for the Quantitative Separation of Methylenic Sterols from Unsaturated Sterol Mixtures by Chemoselective Hydroxymercuration-Deoxymercuration
  作者：Laïla El Kihel、Georges Charles

  DOI：10.1055/s-2006-942495

  日期：2006.8

  intermediates were easily purified by flash chromatography on silica gel column and the reactive alkenes were regenerated by deoxymercuration in a biphasic system (ethyl acetate/I M HCl, 2:1 ratio). These conditions leave the ring double bonds of steroids intact. No isomerization of methylene double bonds was observed.

  报道了一种前所未有的选择性和定量方法，允许从不饱和甾醇混合物中分离亚甲基甾醇。我们已将改良布朗条件下的羟基汞化反应扩展到对三十种不饱和甾醇作为各种甾醇混合物的系统研究。在甾醇的亚甲基侧链上实现了高产的定向化学选择性羟基汞化。得到的有机汞中间体很容易通过硅胶柱上的快速色谱法纯化，反应性烯烃通过在双相系统（乙酸乙酯/1M HCl，2:1比例）中脱氧汞再生。这些条件使类固醇的环双键完好无损。没有观察到亚甲基双键的异构化。
• Investigations on the Δ23-, Δ24(28)- and Δ25-Sterols of zea mays
  作者：Neil L.A. Misso、L. John Goad

  DOI：10.1016/0031-9422(84)83081-2

  日期：1984.1

  25 -compound, cyclolaudenol, were recognized. These various Δ 23 - and Δ 25 -sterols may have some importance in alternative biosynthetic routes to the major sterols, particularly the 24β-methylcholest-5-en-3β-ol component of the C 28 -sterols. Radioactivity from both [2- 14 C]MVA and [methyl- 14 C]methionine was incorporated by Z. mays shoots into the sterol mixture. Although 24-methylene and 24-ethylidene

  摘要 用薄层色谱、高效液相色谱、气相色谱/质谱联用技术和 1 H 核磁共振技术分离并表征了玉米笋中的甾醇。总共鉴定了 22 种 4-去甲基甾醇，它们包括痕量的 Δ 23 -、Δ 24 - 和Δ 25 - 甾醇、24-甲基胆甾醇-5、E -23-dien-3β-ol、24-甲基胆甾醇- 5, Z -23-dien-3β-ol, 24-methylcholesta-5,25-dien-3β-ol, 24-ethylcholesta-5,25-dien-3β-ol 和 24-ethylcholesta-5,24-dien- 3β-醇。在 4,4-二甲基甾醇级分中，环木蒿醇和 24-亚甲基环木桐醇是主要的甾醇成分，但也发现了少量的 Δ 23 - 化合物环沙多和 Δ 25 - 化合物环月桂醇。这些不同的 Δ 23 - 和 Δ 25 - 甾醇在主要甾醇的替代生物合成途径中可能具有一定的重要性，特别是 C
• 24-Methyl-23-dehydrocholesterol: A new sterol intermediate in C-24 demethylation from the nematodes Panagrellus redivivus and Caenorhabditis elegans?
  作者：Thomas A. Salt、Ruben Lozano、William R. Lusby、David J. Chitwood、Malcolm J. Thompson

  DOI：10.1016/0039-128x(86)90031-0

  日期：1986.11

  Panagrellus redivivus produced 24-methyl-23-dehydrocholesterol as 4.0% of the 4-desmethylsterols when propagated in a medium containing campesterol as the dietary sterol. The re-examination of previous data revealed that Caenorhabditis elegans produced 1.8% 24-methyl-23-dehydrocholesterol when propagated in medium containing campesterol. 24-Methyl-23-dehydrocholesterol was not detected when the nematodes were propagated in medium containing 22-dihydrobrassicasterol or 24-methylenecholesterol. This may be a result of the greater efficiency of dealkylation of the latter two sterols. This is the first report of the natural occurrence of this sterol in a non-photosynthetic organism, and the first report in organisms that dealkylate 24-alkylsterols.