β-sitosterol 3-O-(6'-octadecanoyl) β-D-glucopyranoside | 53657-30-0

• 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: β-sitosterol 3-O-(6'-octadecanoyl) β-D-glucopyranoside
• 英文别名: 6'-stearoyl-3-O-β-D-glucopyranosyl-β-sitosterol；(6’-O-palmitoyl)-sitosterol-3-O-β-D-glucoside；6'-stearoyl-3-O-β-glucopyranosyl-β-sitosterol；6-O-stearoyl-β-D-glucosyl-β-sitosterol；sitosterol-3-O-6-stearoyl-β-D-glucopyranoside；β-sitosterol 6'-stearylglucopyranoside；[(2R,3S,4S,5R,6R)-6-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl octadecanoate
• CAS: 53657-30-0
• 化学式: C₅₃H₉₄O₇
• 分子量: 843.325
• InChiKey: WHXVFRBDLSVIIH-RUCVJHJTSA-N

物化性质

• 沸点：
  828.0±65.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.2
• 重原子数：
  60
• 可旋转键数：
  27
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  β-sitosterol 3-O-(6'-octadecanoyl) β-D-glucopyranoside 在 sodium methylate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 2.0h， 生成 stigmast-5-en-3β-yl-(tetra-O-acetyl-β-D-glucopyranoside)
  参考文献：
  名称：

  一种来自车前草-水生泽泻的酰化谷甾醇葡萄糖苷

  摘要：

  摘要 从车前草根茎甲醇提取物中分离得到一种硬脂酸酰化的植物甾醇糖苷，及其提取物。

  DOI：

  10.1016/0031-9422(88)80475-8
• 作为产物：
  描述：

  植物甾醇 在 吡啶 、 magnesium sulfate 、 silver(l) oxide 作用下， 以 乙醚 、 苯 为溶剂， 反应 72.0h， 生成 β-sitosterol 3-O-(6'-octadecanoyl) β-D-glucopyranoside
  参考文献：
  名称：

  Suppressors of Cancer Cell Proliferation from Fig (Ficus carica) Resin:  Isolation and Structure Elucidation

  摘要：

  A mixture of 6-O-acyl-beta -D-glucosyl-beta -sitosterols, the acyl moeity being primarily palmitoyl and linoleyl with minor amounts of stearyl and oleyl, has been isolated as a potent cytotoxic agent from fig (Ficus carica) latex and soybeans. Identity was established by spectroscopic methods (NMR, MS) and confirmed by chemical synthesis. Both the natural and the synthetic compounds showed in vitro inhibitory effects on proliferation of various cancer cell lines.

  DOI：

  10.1021/np000592z

文献信息

• Suppressors of Cancer Cell Proliferation from Fig (<i>Ficus </i><i>c</i><i>arica</i>) Resin:  Isolation and Structure Elucidation
  作者：Shai Rubnov、Yoel Kashman、Ruth Rabinowitz、Michael Schlesinger、Raphael Mechoulam

  DOI：10.1021/np000592z

  日期：2001.7.1

  A mixture of 6-O-acyl-beta -D-glucosyl-beta -sitosterols, the acyl moeity being primarily palmitoyl and linoleyl with minor amounts of stearyl and oleyl, has been isolated as a potent cytotoxic agent from fig (Ficus carica) latex and soybeans. Identity was established by spectroscopic methods (NMR, MS) and confirmed by chemical synthesis. Both the natural and the synthetic compounds showed in vitro inhibitory effects on proliferation of various cancer cell lines.
• An acylated sitosterol glucoside from Alisma plantago-aquatica
  作者：Geng Pei-Wu、Yoshiyasu Fukuyama、Wang Rei、Bao Jinxian、Kazuyuki Nakagawa

  DOI：10.1016/0031-9422(88)80475-8

  日期：1988.1

  Abstract A phytosterol glucoside acylated with stearic acid has been isolated from the methanol extract of the rhizome of Alisma Plantago-aquatica , and its

  摘要 从车前草根茎甲醇提取物中分离得到一种硬脂酸酰化的植物甾醇糖苷，及其提取物。