di-β-sitosteryl ether | 25694-37-5

• 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: di-β-sitosteryl ether
• 英文别名: 3β,3'β-disitosteryl ether；di-(stigmasten-(5)-yl-(3β))-ether；Bis-[(10R)-10r.13c-dimethyl-17c-((1R:4R)-1.5-dimethyl-4-aethyl-hexyl)-(8cH.9tH.14tH)-Δ⁵-tetradecahydro-1H-cyclopenta[a]phenanthrenyl-(3c)]-aether；Bis-(24α_F-aethyl-cholesten-(5)-yl-(3β))-aether；Di-(stigmasten-(5)-yl-(3β))-aether
• CAS: 25694-37-5
• 化学式: C₅₈H₉₈O
• 分子量: 811.416
• InChiKey: ANCUQSSTCSIHDZ-BCZYIEQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.1
• 重原子数：
  59.0
• 可旋转键数：
  14.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  氯仿 、 di-β-sitosteryl ether 、 溴 生成 bis-(5.6β-dibromo-5α-stigmastanyl-(3β))-ether
  参考文献：
  名称：

  On the Dehydration of 22-Dihydrostigmasterol and Cholesterol with Iodine

  摘要：

  DOI：

  10.1021/ja01846a024
• 作为产物：
  描述：

  豆甾醇 在 montmorillonite K 10 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 di-β-sitosteryl ether
  参考文献：
  名称：

  富含固醇的样品经过高温处理后，合成并寻找3β，3'β-二硬脂基醚。

  摘要：

  已经证明，在升高的温度下，固醇会经历各种化学反应，例如氧化，脱氢，脱水和聚合。这项研究的目的是证明二聚体的存在并定量分析二聚体（3β，3'β-二硬脂基醚）。将富含甾醇的样品在180°C，200°C和220°C下加热1至5小时。使用液相萃取，固相萃取和气相色谱-质谱联用技术对3β，3'β-二十二烷基醚进行了定量分析。另外，为了进行分析，从天然甾醇中合成了合适的标准品。为了确定高温下3β，3'β-二叔丁基醚形成的机理，尝试使用提出的合成方法。另外，

  DOI：

  10.1016/j.foodchem.2020.127132

文献信息

• Montmorillonite Clay Catalysis I: An Efficient and Convenient Procedure for Preparation of 5(6)/5′(6′)-Unsaturated 3β-Disteryl Ethers
  作者：Tongshuang Li、Huizhang Li、Juanli Guo、Tongshou Jin

  DOI：10.1080/00397919608004562

  日期：1996.7

  Abstract In the presence of montmorillonite K 10, 5(6)-unsaturated sterols (1) were heated at refluxing temperature in dichloromethane to provide 5(6)/5′(6′)-unsaturated 3β,3′β-disteryl ethers (4) in 69–73% yield. The mechanism of the reaction was discussed.

  摘要 在蒙脱石 K 10 存在下，5(6)-不饱和甾醇 (1) 在二氯甲烷中回流加热，得到 5(6)/5'(6')-不饱和 3β,3'β-二十八烷基醚 ( 4) 69–73% 的产率。讨论了反应机理。
• Synthesis of triterpene and steroid glycosides
  作者：Nina I. Uvarova、Lyubov N. Atopkina、Georgi B. Elyakov

  DOI：10.1016/s0008-6215(00)85361-6

  日期：1980.8
• Characterisation of non-polar dimers formed during thermo-oxidative degradation of β-sitosterol
  作者：Ewa Sosińska、Roman Przybylski、Paul Hazendonk、Yuan Yuan Zhao、Jonathan M. Curtis

  DOI：10.1016/j.foodchem.2013.01.053

  日期：2013.8

  Thermo-oxidative degradation of sterols at temperature typical for frying leads to the formation of oxidised derivatives, fragmented sterols and oligomers. Recent research on sterol oxidation focuses mainly on the oxysterol derivatives formation to the exclusion of compounds with high molecular mass. The aim of this work was to decipher the chemical structure of non-polar dimers formed during beta-sitosterol oxidation at 180 degrees C in the presence of oxygen. The dimer fraction was separated by size-exclusion chromatography (SEC) after pre-fractionation on silica gel. The chemical structure of the dimers was assessed by 1D and 2D NMR, IR, Raman and MS spectroscopies. NMR data confirmed that the predominant non-polar dimer formed during beta-sitosterol oxidative degradation has a configuration of 3 beta,3 beta'-disitosteryl ether. Data from IR and Raman spectroscopies further proved it chemical structure. Applied analytical techniques also confirmed presence of dimers with different configuration than disteryl ethers. (C) 2013 Elsevier Ltd. All rights reserved.