polyprenol-12 | 72690-19-8

• 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: polyprenol-12
• 英文别名: (2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E,42E)-3,7,11,15,19,23,27,31,35,39,43,47-dodecamethyloctatetraconta-2,6,10,14,18,22,26,30,34,38,42,46-dodecaen-1-ol
• CAS: 72690-19-8
• 化学式: C₆₀H₉₈O
• 分子量: 835.438
• InChiKey: BDMCAOBQLHJGBE-CTPVASEHSA-N

物化性质

• 沸点：
  819.6±34.0 °C(Predicted)
• 密度：
  0.891±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  21.5
• 重原子数：
  61
• 可旋转键数：
  34
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  polyprenol-12 在 sodium carbonate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.33h， 生成 trans-prenal-12
  参考文献：
  名称：

  Configuration of polyisoprenoids affects the permeability and thermotropic properties of phospholipid/polyisoprenoid model membranes

  摘要：

  The influence of alpha-cis- and alpha-trans-polyprenols on the structure and properties of model membranes was analyzed. The interaction of Ficaprenol-12 (alpha-cis-Prenol-12, alpha-Z-Prenol-12) and Alloprenol-12 (alpha-trans-Prenol-12, alpha-E-Prenol-12) with model membranes was compared using high performance liquid chromatography (HPLC), differential scanning calorimetry (DSC) and fluorescent methods. L-alpha-Phosphatidylcholine from egg yolk (EYPC) and 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) as the main lipid components of unilamellar (SUVs) and multilamellar (MLVs) vesicles were used. The two-step extraction procedure (n-pentane and hexane, respectively) allowed to separately analyze the fractions of polyprenol as non-incorporated (Prenol(NonInc)) and incorporated (Prenol(Inc)) into liposomes. Consequently, distribution coefficients, P. describing the equilibrium of prenol content between phospholipid (EYPC) membrane and the aqueous phase gave different log P for alpha-cis- and alpha-trans-Prenol-12, indicating that the configuration of the alpha-terminal residue significantly alters the hydrophobicity of the polyisoprenoid molecule and consequently the affinity of polyprenols for EYPC membrane. In fluorescence experiments alpha-trans-Pren-12 increased up to 1.7-fold the permeability of EYPC bilayer for glucose while the effect of alpha-cis-Pren-12 was almost negligible. Considerable changes of thermotropic behavior of DPPC membranes in the presence of both prenol isomers were observed. alpha-trans-Pren-12 completely abolished the pretransition while in the case of a-cis-Pren-12 it was noticeably reduced. Furthermore, for both prenol isomers, the temperature of the main phase transition (T-m) was shifted by about 1 degrees C to lower values and the height of the peak was significantly reduced. The DSC analysis profiles also showed a new peak at 38.7 degrees C. which may suggest the concomitant presence of more that one phase within the membrane.Results of these experiments and the concomitant occurrence of alloprenols and ficaprenols in plant tissues suggest that cis/trans isomerization of the a-residue of polyisoprenoid molecule might comprise a putative mechanism responsible for modulation of the permeability of cellular membranes. (C) 2011 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2011.03.004
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.67h， 生成 polyprenol-12 、 3,7,11,15,19,23,27,31,35,39,43,47-dodecamethyloctatetraconta-2E,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E,42E,46-dodecaen-1-ol
  参考文献：
  名称：

  Configuration of polyisoprenoids affects the permeability and thermotropic properties of phospholipid/polyisoprenoid model membranes

  摘要：

  The influence of alpha-cis- and alpha-trans-polyprenols on the structure and properties of model membranes was analyzed. The interaction of Ficaprenol-12 (alpha-cis-Prenol-12, alpha-Z-Prenol-12) and Alloprenol-12 (alpha-trans-Prenol-12, alpha-E-Prenol-12) with model membranes was compared using high performance liquid chromatography (HPLC), differential scanning calorimetry (DSC) and fluorescent methods. L-alpha-Phosphatidylcholine from egg yolk (EYPC) and 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) as the main lipid components of unilamellar (SUVs) and multilamellar (MLVs) vesicles were used. The two-step extraction procedure (n-pentane and hexane, respectively) allowed to separately analyze the fractions of polyprenol as non-incorporated (Prenol(NonInc)) and incorporated (Prenol(Inc)) into liposomes. Consequently, distribution coefficients, P. describing the equilibrium of prenol content between phospholipid (EYPC) membrane and the aqueous phase gave different log P for alpha-cis- and alpha-trans-Prenol-12, indicating that the configuration of the alpha-terminal residue significantly alters the hydrophobicity of the polyisoprenoid molecule and consequently the affinity of polyprenols for EYPC membrane. In fluorescence experiments alpha-trans-Pren-12 increased up to 1.7-fold the permeability of EYPC bilayer for glucose while the effect of alpha-cis-Pren-12 was almost negligible. Considerable changes of thermotropic behavior of DPPC membranes in the presence of both prenol isomers were observed. alpha-trans-Pren-12 completely abolished the pretransition while in the case of a-cis-Pren-12 it was noticeably reduced. Furthermore, for both prenol isomers, the temperature of the main phase transition (T-m) was shifted by about 1 degrees C to lower values and the height of the peak was significantly reduced. The DSC analysis profiles also showed a new peak at 38.7 degrees C. which may suggest the concomitant presence of more that one phase within the membrane.Results of these experiments and the concomitant occurrence of alloprenols and ficaprenols in plant tissues suggest that cis/trans isomerization of the a-residue of polyisoprenoid molecule might comprise a putative mechanism responsible for modulation of the permeability of cellular membranes. (C) 2011 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2011.03.004

文献信息

• Configuration of polyisoprenoids affects the permeability and thermotropic properties of phospholipid/polyisoprenoid model membranes
  作者：Ewa Ciepichal、Malgorzata Jemiola-Rzeminska、Jozefina Hertel、Ewa Swiezewska、Kazimierz Strzalka

  DOI：10.1016/j.chemphyslip.2011.03.004

  日期：2011.5

  The influence of alpha-cis- and alpha-trans-polyprenols on the structure and properties of model membranes was analyzed. The interaction of Ficaprenol-12 (alpha-cis-Prenol-12, alpha-Z-Prenol-12) and Alloprenol-12 (alpha-trans-Prenol-12, alpha-E-Prenol-12) with model membranes was compared using high performance liquid chromatography (HPLC), differential scanning calorimetry (DSC) and fluorescent methods. L-alpha-Phosphatidylcholine from egg yolk (EYPC) and 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) as the main lipid components of unilamellar (SUVs) and multilamellar (MLVs) vesicles were used. The two-step extraction procedure (n-pentane and hexane, respectively) allowed to separately analyze the fractions of polyprenol as non-incorporated (Prenol(NonInc)) and incorporated (Prenol(Inc)) into liposomes. Consequently, distribution coefficients, P. describing the equilibrium of prenol content between phospholipid (EYPC) membrane and the aqueous phase gave different log P for alpha-cis- and alpha-trans-Prenol-12, indicating that the configuration of the alpha-terminal residue significantly alters the hydrophobicity of the polyisoprenoid molecule and consequently the affinity of polyprenols for EYPC membrane. In fluorescence experiments alpha-trans-Pren-12 increased up to 1.7-fold the permeability of EYPC bilayer for glucose while the effect of alpha-cis-Pren-12 was almost negligible. Considerable changes of thermotropic behavior of DPPC membranes in the presence of both prenol isomers were observed. alpha-trans-Pren-12 completely abolished the pretransition while in the case of a-cis-Pren-12 it was noticeably reduced. Furthermore, for both prenol isomers, the temperature of the main phase transition (T-m) was shifted by about 1 degrees C to lower values and the height of the peak was significantly reduced. The DSC analysis profiles also showed a new peak at 38.7 degrees C. which may suggest the concomitant presence of more that one phase within the membrane.Results of these experiments and the concomitant occurrence of alloprenols and ficaprenols in plant tissues suggest that cis/trans isomerization of the a-residue of polyisoprenoid molecule might comprise a putative mechanism responsible for modulation of the permeability of cellular membranes. (C) 2011 Elsevier Ireland Ltd. All rights reserved.