2,4,13-(E,E,Z)-docosatrienoic acid | 190393-11-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,4,13-(E,E,Z)-docosatrienoic acid
• 英文别名: (2E,4E,13Z)-docosa-2,4,13-trienoic acid
• CAS: 190393-11-4
• 化学式: C₂₂H₃₈O₂
• 分子量: 334.543
• InChiKey: XLETUGRKBNQVPH-WFLRLSCMSA-N

物化性质

• 沸点：
  464.9±14.0 °C(Predicted)
• 密度：
  0.911±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  24
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-((4-methoxybenzyl)oxy)propane-1,2-diol 、 2,4,13-(E,E,Z)-docosatrienoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 以50%的产率得到1,2-bis[2,4,13-(E,E,Z)-docosatrienoyl]-3-(4-methoxybenzyl)-sn-glycerol
  参考文献：
  名称：

  Polymerization of the Inverted Hexagonal Phase

  摘要：

  The hydration of polar natural and synthetic lipids yields a variety of lipid phases including various inverted cubic phases and the inverted hexagonal (H-II) phase. The H-II phase can be considered as aqueous columns encased with a monolayer of lipids and arranged in a hexagonal pattern. The polar head groups are well-ordered at the water interface, whereas the lipid tails are disordered to fill the volume between the tubes of water. A particularly interesting characteristic of the H-II phase is the large temperature effect on the basis vector length d of the hexagonal lattice. Previous studies indicate that polymerization of the lipid region of the H-II phase might reduce the sensitivity of the basis vector to temperature. A phosphoethanolamine (PE) was designed and synthesized with dienoyl groups in each lipid tail in an attempt to cross-link the lipids around and along the water core of the H-II phase. The synthesis of the the PE was accomplished by acylation of 3-(4-methoxybenzyl)-sn-glycerol with 2,4,13-(E,E,Z)-docosatrienoic acid, followed by deprotection, then phosphorylation with dichloro-[[N-[(2,2,2-trichloroethoxy)carbonyl]-2-amino]ethyl]phosphinic acid to give the Troc-PE, which was converted to the PE with activated zinc and acetic acid, The hydrated PE (1/1 weight lipid/water) formed the H-II phase over an extended temperature range. Polymerization to high conversion was accomplished at 60 degrees C with the aid of redox initiators. Polymerization was followed in-situ using X-ray diffraction over a period of 48 h. The scattering, which weakened over the course of the reaction, remained consistent with a hexagonal phase. Temperature cycling of the polymerized H-II phase showed an unaltered pattern on decreasing temperature while maintaining the same lattice parameter, unlike that of the unpolymerized phase where the value increased with decreasing temperature. Thus it is possible to fix the dimensions of the H-II phase by cross-linking polymerization of appropriately designed reactive lipids.

  DOI：

  10.1021/ja970052x
• 作为产物：
  描述：

  油醇 在 氢氧化钾 、 重铬酸吡啶 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2,4,13-(E,E,Z)-docosatrienoic acid
  参考文献：
  名称：

  Polymerization of the Inverted Hexagonal Phase

  摘要：

  The hydration of polar natural and synthetic lipids yields a variety of lipid phases including various inverted cubic phases and the inverted hexagonal (H-II) phase. The H-II phase can be considered as aqueous columns encased with a monolayer of lipids and arranged in a hexagonal pattern. The polar head groups are well-ordered at the water interface, whereas the lipid tails are disordered to fill the volume between the tubes of water. A particularly interesting characteristic of the H-II phase is the large temperature effect on the basis vector length d of the hexagonal lattice. Previous studies indicate that polymerization of the lipid region of the H-II phase might reduce the sensitivity of the basis vector to temperature. A phosphoethanolamine (PE) was designed and synthesized with dienoyl groups in each lipid tail in an attempt to cross-link the lipids around and along the water core of the H-II phase. The synthesis of the the PE was accomplished by acylation of 3-(4-methoxybenzyl)-sn-glycerol with 2,4,13-(E,E,Z)-docosatrienoic acid, followed by deprotection, then phosphorylation with dichloro-[[N-[(2,2,2-trichloroethoxy)carbonyl]-2-amino]ethyl]phosphinic acid to give the Troc-PE, which was converted to the PE with activated zinc and acetic acid, The hydrated PE (1/1 weight lipid/water) formed the H-II phase over an extended temperature range. Polymerization to high conversion was accomplished at 60 degrees C with the aid of redox initiators. Polymerization was followed in-situ using X-ray diffraction over a period of 48 h. The scattering, which weakened over the course of the reaction, remained consistent with a hexagonal phase. Temperature cycling of the polymerized H-II phase showed an unaltered pattern on decreasing temperature while maintaining the same lattice parameter, unlike that of the unpolymerized phase where the value increased with decreasing temperature. Thus it is possible to fix the dimensions of the H-II phase by cross-linking polymerization of appropriately designed reactive lipids.

  DOI：

  10.1021/ja970052x

文献信息

• Polymerization of the Inverted Hexagonal Phase
  作者：Warunee Srisiri、Thomas M. Sisson、David F. O'Brien、K. M. McGrath、Yuqi Han、Sol M. Gruner

  DOI：10.1021/ja970052x

  日期：1997.5.1

  The hydration of polar natural and synthetic lipids yields a variety of lipid phases including various inverted cubic phases and the inverted hexagonal (H-II) phase. The H-II phase can be considered as aqueous columns encased with a monolayer of lipids and arranged in a hexagonal pattern. The polar head groups are well-ordered at the water interface, whereas the lipid tails are disordered to fill the volume between the tubes of water. A particularly interesting characteristic of the H-II phase is the large temperature effect on the basis vector length d of the hexagonal lattice. Previous studies indicate that polymerization of the lipid region of the H-II phase might reduce the sensitivity of the basis vector to temperature. A phosphoethanolamine (PE) was designed and synthesized with dienoyl groups in each lipid tail in an attempt to cross-link the lipids around and along the water core of the H-II phase. The synthesis of the the PE was accomplished by acylation of 3-(4-methoxybenzyl)-sn-glycerol with 2,4,13-(E,E,Z)-docosatrienoic acid, followed by deprotection, then phosphorylation with dichloro-[[N-[(2,2,2-trichloroethoxy)carbonyl]-2-amino]ethyl]phosphinic acid to give the Troc-PE, which was converted to the PE with activated zinc and acetic acid, The hydrated PE (1/1 weight lipid/water) formed the H-II phase over an extended temperature range. Polymerization to high conversion was accomplished at 60 degrees C with the aid of redox initiators. Polymerization was followed in-situ using X-ray diffraction over a period of 48 h. The scattering, which weakened over the course of the reaction, remained consistent with a hexagonal phase. Temperature cycling of the polymerized H-II phase showed an unaltered pattern on decreasing temperature while maintaining the same lattice parameter, unlike that of the unpolymerized phase where the value increased with decreasing temperature. Thus it is possible to fix the dimensions of the H-II phase by cross-linking polymerization of appropriately designed reactive lipids.