(24S)-saringosterol | 87859-99-2

• 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: (24S)-saringosterol
• 英文别名: (24R)-saringosterol；(3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4R)-4-hydroxy-4-isopropyl-1-methyl-hex-5-enyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol；(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-hydroxy-5-propan-2-ylhept-6-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 87859-99-2
• 化学式: C₂₉H₄₈O₂
• 分子量: 428.699
• InChiKey: OPGVEUGCNGNPSX-MEBFPAKGSA-N

物化性质

• 沸点：
  533.3±25.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (24S)-saringosterol 在 吡啶 、 三氯氧磷 作用下， 反应 24.0h， 生成
  参考文献：
  名称：

  “Dinoflagellate Sterols” in marine diatoms

  摘要：

  Sterol compositions for three diatom species, recently shown to contain sterols with side chains typically found in dinoflagellates, were determined by HPLC and (1)H NMR spectroscopic analyses. The centric diatom Triceratium dubium (= Biddulphia sp., CCMP 147) contained the highest percentage of 23-methylated sterols (37.2% (24R)-23-methylergosta-5,22-dienol), whereas the pennate diatom Delphineis sp. (CCMP 1095) contained the cyclopropyl sterol gorgosterol, as well as the 27-norsterol occelasterol. The sterol composition of Ditylum brightwellii (CCMP 358) was the most complex, containing Delta(0)- and Delta(7)-sterols, in addition to the predominant Delta(5)-sterols. A pair of previously unknown sterols, stigmasta-5,24,28-trienol and stigmasta-24,28-dienol, were detected in D. brightwellii and their structures were determined by NMR spectroscopic analysis and by synthesis of the former sterol from saringosterol. Also detected in D. brightwellii was the previously unknown 23-methylcholesta-7,22-dienol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2011.05.002
• 作为产物：
  描述：

  (3beta,5beta,6alpha)-3,6-二羟基胆烷-24-酸 在 4-二甲氨基吡啶 、 硫酸 、 异丙基氯化镁 、 potassium acetate 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 57.0h， 生成 (24S)-saringosterol 、 (24S)-saringosterol
  参考文献：
  名称：

  一种马尾藻甾醇的合成方法

  摘要：

  本发明公开了一种马尾藻甾醇的合成方法，以猪去氧胆酸为原料进行酯化生成猪去氧胆酸酯或直接以猪去氧胆酸酯为原料，经磺酰化反应生成3，6‑二磺酰基猪去氧胆酸酯，再经亲核取代‑消除反应生成3β‑羟基胆‑5‑烯‑24‑酸酯，随后与N,O‑二甲基羟胺反应制备weinreb酰胺，再经两步格林尼亚反应，最终得到马尾藻甾醇。本发明的合成方法反应条件温和，反应时间较短，起始原料猪去氧胆酸和反应试剂价格低廉，最终产率较高，适用于马尾藻甾醇的大规模制备。

  公开号：

  CN113861258A

文献信息

• Synthesis of (24R)- and (24S)-5,28-stigmastadien-3.beta.-ol and determination of the stereochemistry of their 24-hydroxy analogs, the saringosterols
  作者：Cesar A. N. Catalan、W. C. M. C. Kokke、Carmenza Duque、Carl Djerassi

  DOI：10.1021/jo00174a011

  日期：1983.12
• 一种马尾藻甾醇的合成方法
  申请人：中国海洋大学

  公开号：CN113861258A

  公开（公告）日：2021-12-31

  本发明公开了一种马尾藻甾醇的合成方法，以猪去氧胆酸为原料进行酯化生成猪去氧胆酸酯或直接以猪去氧胆酸酯为原料，经磺酰化反应生成3，6‑二磺酰基猪去氧胆酸酯，再经亲核取代‑消除反应生成3β‑羟基胆‑5‑烯‑24‑酸酯，随后与N,O‑二甲基羟胺反应制备weinreb酰胺，再经两步格林尼亚反应，最终得到马尾藻甾醇。本发明的合成方法反应条件温和，反应时间较短，起始原料猪去氧胆酸和反应试剂价格低廉，最终产率较高，适用于马尾藻甾醇的大规模制备。
• “Dinoflagellate Sterols” in marine diatoms
  作者：José-Luis Giner、Gary H. Wikfors

  DOI：10.1016/j.phytochem.2011.05.002

  日期：2011.10

  Sterol compositions for three diatom species, recently shown to contain sterols with side chains typically found in dinoflagellates, were determined by HPLC and (1)H NMR spectroscopic analyses. The centric diatom Triceratium dubium (= Biddulphia sp., CCMP 147) contained the highest percentage of 23-methylated sterols (37.2% (24R)-23-methylergosta-5,22-dienol), whereas the pennate diatom Delphineis sp. (CCMP 1095) contained the cyclopropyl sterol gorgosterol, as well as the 27-norsterol occelasterol. The sterol composition of Ditylum brightwellii (CCMP 358) was the most complex, containing Delta(0)- and Delta(7)-sterols, in addition to the predominant Delta(5)-sterols. A pair of previously unknown sterols, stigmasta-5,24,28-trienol and stigmasta-24,28-dienol, were detected in D. brightwellii and their structures were determined by NMR spectroscopic analysis and by synthesis of the former sterol from saringosterol. Also detected in D. brightwellii was the previously unknown 23-methylcholesta-7,22-dienol. (C) 2011 Elsevier Ltd. All rights reserved.