3β-acetoxy-9,15-cyclo-GA₉-Me | 138213-41-9

• 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: 3β-acetoxy-9,15-cyclo-GA₉-Me
• 英文别名: methyl (1S,2S,5R,8S,9S,10R,11S,12S)-12-acetyloxy-11-methyl-6-methylidene-16-oxo-15-oxahexacyclo[9.3.2.15,8.01,10.02,7.02,8]heptadecane-9-carboxylate
• CAS: 138213-41-9
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: ZXLZFQAJCVIYSI-LYTKEIRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-9,15-cyclo-GA₉-Me 在 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 以2.5 mg的产率得到3β-hydroxy-9,15-cyclo-GA₉-Me
  参考文献：
  名称：

  Biosynthesis of antheridic acid, the principal antheridiogen in Anemia phyllitidis

  摘要：

  [(H2)-H-2]9,15-Cyclo-GA9 and [(H2)-H-2]3-alpha-hydroxy-9,15-cyclo-GA9 were fed to prothallia of the fern, Anemia phyllitidis. The metabolites from these feeds were subjected to full-scan GC-MS to confirm the conversion of [(H2)-H-2]9,15-cyclo-GA9 into [(H2)-H-2]3-alpha-hydroxy-9,15-cyclo-GA9 and [(H2)-H-2]antheridic acid, and of [(H2)-H-2]3-alpha-hydroxy-9,15-cyclo-GA9 into [(H2)-H-2]antheridic acid. These results indicated that antheridic acid is biosynthesized from 9,15-cyclo-GA9 via 3-alpha-hydroxy-9,15-cyclo-GA9 in A. phyllitidis. It was also shown that 3-alpha-hydroxy-9,15-cyclo-GA9 is a native antheridiogen in A. phyllitidis. Biological activity of 9,15-cyclo-GA9 and 3-alpha-hydroxy-9,15-cyclo-GA9 are also reported.

  DOI：

  10.1016/0031-9422(91)83186-o
• 作为产物：
  描述：

  ent-3α-Acetoxy-10β-hydroxy-16-oxo-17,20-dinor-9α,15α-cyclogibberell-1(10)-ene-7,19-dioic acid 7-(methyl ester) 19,10-lactone 在 rhodium on alumina 氢气 、 四氯化钛 、 锌 作用下， 以 乙酸乙酯 为溶剂， 反应 16.08h， 生成 3β-acetoxy-9,15-cyclo-GA₉-Me
  参考文献：
  名称：

  Biosynthesis of antheridic acid, the principal antheridiogen in Anemia phyllitidis

  摘要：

  [(H2)-H-2]9,15-Cyclo-GA9 and [(H2)-H-2]3-alpha-hydroxy-9,15-cyclo-GA9 were fed to prothallia of the fern, Anemia phyllitidis. The metabolites from these feeds were subjected to full-scan GC-MS to confirm the conversion of [(H2)-H-2]9,15-cyclo-GA9 into [(H2)-H-2]3-alpha-hydroxy-9,15-cyclo-GA9 and [(H2)-H-2]antheridic acid, and of [(H2)-H-2]3-alpha-hydroxy-9,15-cyclo-GA9 into [(H2)-H-2]antheridic acid. These results indicated that antheridic acid is biosynthesized from 9,15-cyclo-GA9 via 3-alpha-hydroxy-9,15-cyclo-GA9 in A. phyllitidis. It was also shown that 3-alpha-hydroxy-9,15-cyclo-GA9 is a native antheridiogen in A. phyllitidis. Biological activity of 9,15-cyclo-GA9 and 3-alpha-hydroxy-9,15-cyclo-GA9 are also reported.

  DOI：

  10.1016/0031-9422(91)83186-o