1-hexadecanoyl-2-(9-carboxynonanoyl)glycerophosphocholine | 117746-89-1

• 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: 1-hexadecanoyl-2-(9-carboxynonanoyl)glycerophosphocholine
• 英文别名: 1-palmitoyl-2-azelaoyl-sn-glycero-3-phosphocholine；1-palmitoyl-2-azelaoyl-sn-glycero-3-phophocholine；AzPC；PAzePC；1-palmitoyl-2-(9'-oxo-nonanoyl)-sn-glycero-3-phosphocholine；PAz-PC；[(2R)-2-(8-carboxyoctanoyloxy)-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 117746-89-1
• 化学式: C₃₃H₆₄NO₁₀P
• 分子量: 665.846
• InChiKey: GHQQYDSARXURNG-SSEXGKCCSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  45
• 可旋转键数：
  34
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  10

安全信息

• WGK Germany：
  3
• 储存条件：
  | 20°C |

制备方法与用途

1-Palmitoyl-2-azelaoyl-sn-glycero-3-phosphocholine (PazePC) is a stable lipid oxidation product that functions as an inter-H₂O₂ permeation promoter. It is a common target for antipsychotic and antimicrobial agents in cells experiencing oxidative stress at inflammatory sites.

反应信息

• 作为反应物：
  描述：

  N-[3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propyl]-4-formylbenzamide 、 1-hexadecanoyl-2-(9-carboxynonanoyl)glycerophosphocholine 在 N-羟基丁二酰亚胺 作用下， 以 1,2-二氯乙烷 为溶剂， 生成
  参考文献：
  名称：

  [EN] LIPIDS CAPABLE OF CONFORMATIONAL CHANGE AND THEIR USE IN FORMULATIONS TO DELIVER THERAPEUTIC AGENTS TO CELLS
  [FR] LIPIDES POUVANT SUPPORTER UN CHANGEMENT CONFORMATIONNEL ET UTILISATION DE CES DERNIERS DANS DES FORMULATIONS AFIN D'APPORTER DES AGENTS THÉRAPEUTIQUES À DES CELLULES

  摘要：

  公开号：

  WO2013032643A3
• 作为产物：
  描述：

  壬二酸 、 溶血磷脂酰胆碱(鸡蛋) 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， 生成 1-hexadecanoyl-2-(9-carboxynonanoyl)glycerophosphocholine
  参考文献：
  名称：

  [EN] LIPIDS CAPABLE OF CONFORMATIONAL CHANGE AND THEIR USE IN FORMULATIONS TO DELIVER THERAPEUTIC AGENTS TO CELLS
  [FR] LIPIDES POUVANT SUPPORTER UN CHANGEMENT CONFORMATIONNEL ET UTILISATION DE CES DERNIERS DANS DES FORMULATIONS AFIN D'APPORTER DES AGENTS THÉRAPEUTIQUES À DES CELLULES

  摘要：

  公开号：

  WO2013032643A3

文献信息

• Quantitative Evaluation on the Degradation Process of the Pulmonary Surfactant Monolayer When Exposed to Low-Level Ozone of Ambient Environment
  作者：Lin Qiao、Zhen Chen、Chunji Takada、Hitoshi Chiba、Ken-ichi Inoue、Shu-Ping Hui、Shen Ye

  DOI：10.1021/acs.analchem.2c00576

  日期：2022.6.21

  ocholine (POnPC) and a trace amount of an acid-type one of 1-palmitoyl-2-azelaoyl-sn-glycero-3-phosphocholine (PAzPC), as well as a pair of secondary ozonide (SOZ) isomers. Furthermore, with prolonged exposure, the SOZ stayed constant but the yield of PAzPC significantly increased with the decrease in POnPC. The low-level ozone-induced oxidation mechanisms for unsaturated lipids are discussed based

  臭氧是一种具有高化学反应性的强效环境氧化剂，在周围环境中的含量很低，仅为几十 ppb。然而，关于低水平臭氧对呼吸系统的影响，我们只知道有限的信息。在本研究中，我们系统地研究了 1-palmitoyl-2-oleoyl- sn的降解。-甘油-3-磷酸胆碱 (POPC)，它是肺表面活性剂 (PS) 的主要成分之一，使暴露于低环境臭氧水平 (40 ± 10 ppb) 的肺具有呼吸功能。使用液相色谱-质谱技术结合 Langmuir-Blodgett 方法，我们首先通过确定暴露于周围环境期间的降解产物来跟踪 POPC 分子的降解过程。结果，我们发现POPC分子可以在45分钟内从C=C部分轻松降解，产生1-palmitoyl-2-(9'-oxo-nonanoyl) -sn - glycero-的醛类产物。 3-磷酸​​胆碱 (POnPC) 和微量的 1-palmitoyl-2-azelaoyl- sn
• PROPHYLACTIC AGENT AND/OR THERAPEUTIC AGENT FOR CATARACT, MEDICINAL COMPOSITION FOR PREVENTING AND/OR TREATING CATARACT, USE OF PPAR ACTIVATOR FOR PRODUCING SAME, AND EYEDROPS
  申请人：University of Fukui

  公开号：EP3733203A1

  公开（公告）日：2020-11-04

  Provided are agents for prevention and therapeutic treatment of cataract that act by a different mechanism from conventional agents, and use of a PPAR activator for production of such agents. An agent for prevention and/or therapeutic treatment of cataract, containing a PPAR activator as an active ingredient, is used.

  本发明提供了预防和治疗白内障的药剂，其作用机理与传统药剂不同，还提供了使用 PPAR 激活剂生产此类药剂的方法。一种用于预防和/或治疗白内障的药剂含有 PPAR 激活剂作为活性成分。
• A simple method to generate oxidized phosphatidylcholines in amounts close to one milligram
  作者：Kristin Zschörnig、Jürgen Schiller

  DOI：10.1016/j.chemphyslip.2014.09.003

  日期：2014.12

  Oxidized (phospho)lipids are of paramount interest from different reasons: beside their significant in vivo relevance, these products are often needed in the laboratory to study the response of selected cells to oxidized lipids. Unfortunately, the commercial availability of oxidized lipids is limited and scientists interested in studying the physiological impact of oxidized lipids are normally forced to prepare the required compounds by themselves.We will show here that chain-shortened products of oxidized phosphatidylcholines (PCs) such as aldehydes and carboxylic acids can be easily (and in nearly quantitative yields) generated by the Fenton reaction (H2O2 + Fe2+) or the KMnO4-induced oxidation of the PC. Using the Fenton reaction and physiological saline, chlorinated oxidation products such as chlorohydrins are also readily available. Additionally, it will be shown that preparative thin-layer chromatography (TLC) is a convenient but simple method to isolate the individual oxidation products in reasonable yields and high purities: all relevant products could be successfully identified by matrix-assisted laser desorption and ionization (MALDI) mass spectrometry and the amounts of the oxidized products determined by a simple colorimetric assay. (C) 2014 Elsevier Ireland Ltd. All rights reserved.