austroinulin | 62868-75-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: austroinulin
• 英文别名: (1R,2S,3S,4R,4aS,8aS)-3,4a,8,8-tetramethyl-4-[(2Z)-3-methylpenta-2,4-dienyl]-2,4,5,6,7,8a-hexahydro-1H-naphthalene-1,2,3-triol
• CAS: 62868-75-1
• 化学式: C₂₀H₃₄O₃
• 分子量: 322.488
• InChiKey: JEZOMVOAWYLQAJ-ZHPNODNJSA-N

物化性质

• 沸点：
  408.5±30.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  austroinulin 、 甲氧基-三氟甲基苯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2S,3S,4R,4aS,8aS)-1,3-dihydroxy-3,4a,8,8-tetramethyl-4-((Z)-3-methyl-penta-2,4-dienyl)-decahydro-naphthalen-2-yl ester
  参考文献：
  名称：

  Isolation of Austroinulin Possessing Cell Cycle Inhibition Activity fromBlumea glomerataand Revision of Its Absolute Configuration

  摘要：

  A labdane-diterpene, austroinulin (1), together with several known flavonoids and sesquiterpenes were isolated from leaves of Blumea glomerata (Compositae). Austroinulin (1) and most of the flavonoids showed cytotoxicity against HeLa cells, while austroinulin (1) exhibited a cell cycle inhibition effect at the G1 stage at the concentration of 15.2 μg/mL (47.2 μM). The absolute configuration of 1 was revised as 5S,6R,7S,8S,9R,10R on the basis of the modified Mosher’s method.

  DOI：

  10.1055/s-2004-835847

文献信息

• Isolation of Austroinulin Possessing Cell Cycle Inhibition Activity from<i>Blumea glomerata</i>and Revision of Its Absolute Configuration
  作者：Takashi Ohtsuki、Takashi Koyano、Thaworn Kowithayakorn、Naoto Yamaguchi、Masami Ishibashi

  DOI：10.1055/s-2004-835847

  日期：2004.12

  A labdane-diterpene, austroinulin (1), together with several known flavonoids and sesquiterpenes were isolated from leaves of Blumea glomerata (Compositae). Austroinulin (1) and most of the flavonoids showed cytotoxicity against HeLa cells, while austroinulin (1) exhibited a cell cycle inhibition effect at the G1 stage at the concentration of 15.2 μg/mL (47.2 μM). The absolute configuration of 1 was revised as 5S,6R,7S,8S,9R,10R on the basis of the modified Mosher’s method.