(E)-(9-hydroxy-12-oxodec-10-enoyl)-1-palmitoyl-sn-glycero-3-phosphatidylcholine | 215810-70-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: (E)-(9-hydroxy-12-oxodec-10-enoyl)-1-palmitoyl-sn-glycero-3-phosphatidylcholine
• 英文别名: 1-hexadecanoyl-2-(9-hydroxy-12-oxo-10(E)-dodecenoyl)-3-phosphatidylcholine；Phoda-PC；[(2R)-3-hexadecanoyloxy-2-[(E)-9-hydroxy-12-oxododec-10-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 215810-70-1
• 化学式: C₃₆H₆₈NO₁₀P
• 分子量: 705.91
• InChiKey: NLLIYSQDIWHBBB-IKSFTUCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  48
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  壬二酸氢甲酯 在 N-甲基咪唑 、 sodium tetrahydroborate 、 草酰氯 、 Porcine pancreatic lipase type II 、 水 、 4-甲基苯磺酸吡啶 、 2,6-二氯苯甲酰氯 、 sodium chloride 、 calcium chloride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 37.0h， 生成 (E)-(9-hydroxy-12-oxodec-10-enoyl)-1-palmitoyl-sn-glycero-3-phosphatidylcholine
  参考文献：
  名称：

  2-溶血磷脂酰胆碱的γ-羟基-α,β-不饱和醛酯的有效合成

  摘要：

  γ-羟基链烯醛磷脂的多种生物活性及其与疾病的关系是深入研究的主题。磷脂醛，例如 2-溶血磷脂酰胆碱的 4-羟基-7-氧代庚烷-5-烯酸酯 (HOHA-PC)、2-溶血-磷脂酰胆碱的 5-羟基-8-氧代-6-辛烯酸酯PC (HOOA-PC) 和 2-lyso-PC 的 9-羟基-12-oxododec-10-烯酸酯 (HODA-PC) 是通过多不饱和脂肪酰基磷脂的氧化裂解产生的。为了促进对其化学和生物学的研究，我们现在报告了 HOOA、HODA 和 HOHA 磷脂的有效全合成。因为目标 γ-羟基烯醛很容易通过醛基氧化成羧酸或环化成呋喃而分解，

  DOI：

  10.1016/j.bmc.2010.10.058

文献信息

• An ¹O₂ Route to γ-Hydroxyalkenal Phospholipids by Vitamin E-Induced Fragmentation of Hydroperoxydiene-Derived Endoperoxides
  作者：Xiaodong Gu、Wujuan Zhang、Jaewoo Choi、Wei Li、Xi Chen、James M. Laird、Robert G. Salomon

  DOI：10.1021/tx200093m

  日期：2011.7.18

  Biologically active phospholipids that incorporate an oxidatively truncated acyl chain terminated by a gamma-hydroxyalkenal are generated in vivo. The gamma-hydroxyalkenal moiety protrudes from lipid bilayers like whiskers that serve as ligands for the scavenger receptor CD36, fostering endocytosis, e.g., of oxidatively damaged photoreceptor cell outer segments by retinal pigmented endothelial cells. They also covalently modify proteins generating carboxyalkyl pyrroles incorporating the E-amino group of protein lysyl residues. We postulated that gamma-hydroxyalkenals could be generated, e.g., in the eye, through fragmentation of hydroperoxy endoperoxides produced in the retina through reactions of singlet molecular oxygen with polyunsaturated phospholipids. Since phospholipid esters are far more abundant in the retina than free fatty acids, we examined the influence of a membrane environment on the fate of hydroperoxy endoperoxides. We now report that linoleate hydroperoxy endoperoxides in thin films and their phospholipid esters in biomimetic membranes fragment to gamma-hydroxyalkenals, and fragmentation is stoichiometrically induced by vitamin E. The product distribution from fragmentation of the free acid in the homogeneous environment of a thin film is remarkably different from that from the corresponding phospholipid in a membrane. In the membrane, further oxidation of the initially formed gamma-hydroxyalkenal to a butenolide is disfavored. A conformational preference for the gamma-hydroxyalkenal, to protrude from the membrane into the aqueous phase, may protect it from oxidation induced by lipid hydroperoxides that remain buried in the lipophilic membrane core.
• An efficient synthesis of γ-hydroxy-α,β-unsaturated aldehydic esters of 2-lysophosphatidylcholine
  作者：Jaewoo Choi、James M. Laird、Robert G. Salomon

  DOI：10.1016/j.bmc.2010.10.058

  日期：2011.1

  4-hydroxy-7-oxohept-5-enoic acid ester of 2-lyso-phosphatidylcholine (HOHA-PC), the 5-hydroxy-8-oxo-6-octenoic acid ester of 2-lyso-PC (HOOA-PC), and the 9-hydroxy-12-oxododec-10-enoic acid ester of 2-lyso-PC (HODA-PC), are generated by oxidative cleavage of polyunsaturated fatty acyl phospholipids. To facilitate investigations of their chemistry and biology, we now report efficient total synthesis of HOOA, HODA

  γ-羟基链烯醛磷脂的多种生物活性及其与疾病的关系是深入研究的主题。磷脂醛，例如 2-溶血磷脂酰胆碱的 4-羟基-7-氧代庚烷-5-烯酸酯 (HOHA-PC)、2-溶血-磷脂酰胆碱的 5-羟基-8-氧代-6-辛烯酸酯PC (HOOA-PC) 和 2-lyso-PC 的 9-羟基-12-oxododec-10-烯酸酯 (HODA-PC) 是通过多不饱和脂肪酰基磷脂的氧化裂解产生的。为了促进对其化学和生物学的研究，我们现在报告了 HOOA、HODA 和 HOHA 磷脂的有效全合成。因为目标 γ-羟基烯醛很容易通过醛基氧化成羧酸或环化成呋喃而分解，