(6E,10E,14E,18E)-2,6,10,19,23-pentamethyl-tetracosa-2,6,10,14,18,22-hexaene | 59681-06-0

• 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: (6E,10E,14E,18E)-2,6,10,19,23-pentamethyl-tetracosa-2,6,10,14,18,22-hexaene
• 英文别名: 15-desmethylsqualene；demethylsqualene；(all-E)-2,6,10,19,23-pentamethyl-tetracosa-2,6,10,14,18,22-hexaene；10-demethyl-squalene；10-Desmethylsqualen；10-Demethylsqualen；10-Demethylsqualene；(6E,10E,14E,18E)-2,6,10,19,23-pentamethyltetracosa-2,6,10,14,18,22-hexaene
• CAS: 59681-06-0
• 化学式: C₂₉H₄₈
• 分子量: 396.7
• InChiKey: BBCQGYMUMKNTQE-BAIGTOHMSA-N

物化性质

• 沸点：
  483.3±40.0 °C(Predicted)
• 密度：
  0.847±0.06 g/cm3(Predicted)
• 保留指数：
  2859

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (6E,10E,14E,18E)-2,6,10,19,23-pentamethyl-tetracosa-2,6,10,14,18,22-hexaene 在 Alicyclobacillus acidocaldarius squalene-hopene cyclase 、 Triton X-100 作用下， 以 水 为溶剂， 反应 16.0h， 以16.8 mg的产率得到(1R,3aS,7aR)-1-[(1S,6aR)-4-((S)-1,5-Dimethyl-hex-4-enyl)-6a-methyl-1,2,3,5,6,6a-hexahydro-pentalen-1-yl]-4,4,7a-trimethyl-octahydro-indene
  参考文献：
  名称：

  Importance of the Methyl Group at C(10) of Squalene for Hopene Biosynthesis and Novel Carbocyclic Skeletons with 6/5 + 5/5 + (6) Ring System(s)

  摘要：

  [GRAPHICS]Incubation of (6E,10E,14E,18E)-2,6,10,19,23-pentamethyl-tetracosa-2,6,10,14,18,22-hexaene with Alicyclobacillus acidocaidarius hopene cyclase afforded four products having two types of carbocyclic skeletons, i.e., two hopane products and two products having an unprecedented carbocyclic skeleton of 6/5 + 5/5 +6 pentacyclic and 6/5 + 5/5 tetracyclic ring systems. The former two hopane skeletons were formed from the bioconversion of C(15)-desmethylsqualene and the latter two skeletons from that of C(10)-desmethylsqualene.

  DOI：

  10.1021/ol026180u
• 作为产物：
  描述：

  (2E,6E,10E)-7,11,15-trimethylhexadeca-2,6,10,14-tetraen-1-ol 在 四氢吡咯 、 吡啶 、 copper(l) iodide 、 正丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 苯 为溶剂， 反应 0.5h， 生成 (6E,10E,14E,18E)-2,6,10,19,23-pentamethyl-tetracosa-2,6,10,14,18,22-hexaene
  参考文献：
  名称：

  Importance of the Methyl Group at C(10) of Squalene for Hopene Biosynthesis and Novel Carbocyclic Skeletons with 6/5 + 5/5 + (6) Ring System(s)

  摘要：

  [GRAPHICS]Incubation of (6E,10E,14E,18E)-2,6,10,19,23-pentamethyl-tetracosa-2,6,10,14,18,22-hexaene with Alicyclobacillus acidocaidarius hopene cyclase afforded four products having two types of carbocyclic skeletons, i.e., two hopane products and two products having an unprecedented carbocyclic skeleton of 6/5 + 5/5 +6 pentacyclic and 6/5 + 5/5 tetracyclic ring systems. The former two hopane skeletons were formed from the bioconversion of C(15)-desmethylsqualene and the latter two skeletons from that of C(10)-desmethylsqualene.

  DOI：

  10.1021/ol026180u

文献信息

• Squalene biosynthesis. Role of the 3-methyl group in farnesyl pyrophosphate
  作者：Paul R. Ortiz de Montellano、Rafael Castillo、Wayne Vinson、Jeng Shu Wei

  DOI：10.1021/ja00426a060

  日期：1976.5
• Importance of the Methyl Group at C(10) of Squalene for Hopene Biosynthesis and Novel Carbocyclic Skeletons with 6/5 + 5/5 + (6) Ring System(s)
  作者：Tsutomu Hoshino、Shumi Ohashi

  DOI：10.1021/ol026180u

  日期：2002.7.1

  [GRAPHICS]Incubation of (6E,10E,14E,18E)-2,6,10,19,23-pentamethyl-tetracosa-2,6,10,14,18,22-hexaene with Alicyclobacillus acidocaidarius hopene cyclase afforded four products having two types of carbocyclic skeletons, i.e., two hopane products and two products having an unprecedented carbocyclic skeleton of 6/5 + 5/5 +6 pentacyclic and 6/5 + 5/5 tetracyclic ring systems. The former two hopane skeletons were formed from the bioconversion of C(15)-desmethylsqualene and the latter two skeletons from that of C(10)-desmethylsqualene.