peruvianursenol C | 198413-76-2

• 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: peruvianursenol C
• 英文别名: α-amyrin；(3S,4aR,6aR,6bS,8aR,11R,12S,12aS,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-ol
• CAS: 198413-76-2
• 化学式: C₃₀H₅₀O
• 分子量: 426.726
• InChiKey: FSLPMRQHCOLESF-WYWZMYMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  peruvianursenol C 在 palladium on activated charcoal 吡啶 、 chromium(VI) oxide 、 氢气 作用下， 以 甲醇 为溶剂， 生成 3-Oxo-ursan
  参考文献：
  名称：

  五环三萜烯羰基衍生物结构的ORD和CD研究

  摘要：

  已经通过ORD和CD方法研究了一系列五环三萜醇的单羰基和二羰基衍生物。确定了骨架类型，双键位置，羰基位置和其他乙酰氧基位置对ORD和CD谱的影响。

  DOI：

  10.1016/0040-4020(72)80159-5
• 作为产物：
  描述：

  ALPHA-乙酸香树脂醇酯 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 三甲基氯硅烷 、 一水合肼 作用下， 以 1,4-二氧六环 、 三乙胺 为溶剂， 反应 33.0h， 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

文献信息

• Ali; Ravinder; Ramachandram, Pharmazie, 2000, vol. 55, # 5, p. 385 - 389
  作者：Ali、Ravinder、Ramachandram

  DOI：——

  日期：——
• ORD and CD studies on the structure of carbonyl derivatives of pentacyclic triterpenes
  作者：J. Śliwowski、Z. Kasprzyk

  DOI：10.1016/0040-4020(72)80159-5

  日期：1972.1

  A series of mono- and di-carbonyl derivatives of pentacyclic triterpenic alcohols have been investigated by ORD and CD methods. The effect on ORD and CD spectra of backbone type, position of double bond, position of carbonyl groups and position of additional acetoxyl groups was determined.

  已经通过ORD和CD方法研究了一系列五环三萜醇的单羰基和二羰基衍生物。确定了骨架类型，双键位置，羰基位置和其他乙酰氧基位置对ORD和CD谱的影响。
• 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.