3β-hydroxy-11-oxours-12-ene | 198413-78-4

• 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-hydroxy-11-oxours-12-ene
• CAS: 198413-78-4
• 化学式: C₃₀H₄₈O₂
• 分子量: 440.71
• InChiKey: UHBYXZSSQWLZHC-FJQLFFQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  32.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-11-oxours-12-ene 在 氢氧化钾 、 一水合肼 作用下， 生成 peruvianursenol C
  参考文献：
  名称：

  Effect of plant monofunctional pentacyclic triterpenes on the dynamic and structural properties of dipalmitoylphosphatidylcholine bilayers

  摘要：

  Fluorescence lifetime and rotational behaviour of 1,6-diphenyl-1,3-5-hexatriene (DPH) and 1-(4-trimethylammoniumphenyl)-6-phenyl-1,3,5 hexatriene (TMA-DPH) were used to study the influence of several monofunctional pentacyclic triterpenes on the structural and dynamic properties of dipalmitoylphosphatidylcholine (DPPC) bilayers. The plant monoalcohols alpha-amiryn, lupeol and taraxerol, the semisynthetic (H-18-alpha)-alpha-amiryn, and the ketone taraxerone were studied in comparison with cholesterol. Among them, only alpha-amiryn is incorporated at as high levels as cholesterol into DPPC bilayers. At 50 mol%, it results in the phase transition vanishing. Pentacyclic monoalcohols are more potent than cholesterol to decrease the DPPC gel phase order, but less potent than it to increase the liquid-crystalline state order. They also produce more packing defects than cholesterol in DPPC bilayers. These effects correlate with the absence of planarity in the pentacyclic skeleton, which would obstruct the 'all trans' packing of acyl chains in the gel state and Van der Waals interactions in the liquid-crystalline state. Taraxerone has little effect on DPPC bilayers, probably due to its difficulty to form hydrogen bonds. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00068-6
• 作为产物：
  描述：

  ALPHA-乙酸香树脂醇酯 在 N-溴代丁二酰亚胺(NBS) 、 三甲基氯硅烷 、 jones reagent 作用下， 以 1,4-二氧六环 、 三乙胺 为溶剂， 反应 28.0h， 生成 3β-hydroxy-11-oxours-12-ene
  参考文献：
  名称：

  Effect of plant monofunctional pentacyclic triterpenes on the dynamic and structural properties of dipalmitoylphosphatidylcholine bilayers

  摘要：

  Fluorescence lifetime and rotational behaviour of 1,6-diphenyl-1,3-5-hexatriene (DPH) and 1-(4-trimethylammoniumphenyl)-6-phenyl-1,3,5 hexatriene (TMA-DPH) were used to study the influence of several monofunctional pentacyclic triterpenes on the structural and dynamic properties of dipalmitoylphosphatidylcholine (DPPC) bilayers. The plant monoalcohols alpha-amiryn, lupeol and taraxerol, the semisynthetic (H-18-alpha)-alpha-amiryn, and the ketone taraxerone were studied in comparison with cholesterol. Among them, only alpha-amiryn is incorporated at as high levels as cholesterol into DPPC bilayers. At 50 mol%, it results in the phase transition vanishing. Pentacyclic monoalcohols are more potent than cholesterol to decrease the DPPC gel phase order, but less potent than it to increase the liquid-crystalline state order. They also produce more packing defects than cholesterol in DPPC bilayers. These effects correlate with the absence of planarity in the pentacyclic skeleton, which would obstruct the 'all trans' packing of acyl chains in the gel state and Van der Waals interactions in the liquid-crystalline state. Taraxerone has little effect on DPPC bilayers, probably due to its difficulty to form hydrogen bonds. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00068-6

文献信息

• Effect of plant monofunctional pentacyclic triterpenes on the dynamic and structural properties of dipalmitoylphosphatidylcholine bilayers
  作者：Sonia Rodrı́guez、Horacio A Garda、Horacio Heinzen、Patrick Moyna

  DOI：10.1016/s0009-3084(97)00068-6

  日期：1997.10

  Fluorescence lifetime and rotational behaviour of 1,6-diphenyl-1,3-5-hexatriene (DPH) and 1-(4-trimethylammoniumphenyl)-6-phenyl-1,3,5 hexatriene (TMA-DPH) were used to study the influence of several monofunctional pentacyclic triterpenes on the structural and dynamic properties of dipalmitoylphosphatidylcholine (DPPC) bilayers. The plant monoalcohols alpha-amiryn, lupeol and taraxerol, the semisynthetic (H-18-alpha)-alpha-amiryn, and the ketone taraxerone were studied in comparison with cholesterol. Among them, only alpha-amiryn is incorporated at as high levels as cholesterol into DPPC bilayers. At 50 mol%, it results in the phase transition vanishing. Pentacyclic monoalcohols are more potent than cholesterol to decrease the DPPC gel phase order, but less potent than it to increase the liquid-crystalline state order. They also produce more packing defects than cholesterol in DPPC bilayers. These effects correlate with the absence of planarity in the pentacyclic skeleton, which would obstruct the 'all trans' packing of acyl chains in the gel state and Van der Waals interactions in the liquid-crystalline state. Taraxerone has little effect on DPPC bilayers, probably due to its difficulty to form hydrogen bonds. (C) 1997 Elsevier Science Ireland Ltd.