lysophosphatidylcholine

• 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: lysophosphatidylcholine
• 英文别名: 1-palmitoyl-sn-glycero-3-phosphocholine；LPC；LPC 16:0；1-O-palmitoyl-sn-glycero-3-phosphocholine；2-[[(2R)-3-hexadecanoyloxy-2-hydroxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium
• 化学式: C₂₄H₅₁NO₇P
• 分子量: 496.645
• InChiKey: ASWBNKHCZGQVJV-HSZRJFAPSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  33
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  lysophosphatidylcholine 、 戊二酸酐 、 chloroform methanol 在 4-二甲氨基吡啶 1-棕榈酰基-2-戊二酰基-sn-甘油-3-磷酸胆碱 、 甲醇 、 水合甲醇 、 4-二甲氨基吡啶 、 乙醚 作用下， 以 二氯甲烷 为溶剂， 以afforded 32 mg of PGPC (42%, Rf=0.05)的产率得到1-棕榈酰基-2-戊二酰基-sn-甘油-3-磷酸胆碱
  参考文献：
  名称：

  Oxidized Phospholipids

  摘要：

  本发明涉及具有以下一般式(I)或(II)之一的氧化磷脂，其中A = O，C，NH或S; B = O，C，NH或S; R2从以下组中选择：-CO-（CH2）n-CH3; -CO-（CH2）b-CHO; 和-CO-（CH2）n-COOH，其中n = 3-7，但在一般式(I)中，R1从以下组中选择：-CH2-（CH2）n-X; -CO-（CH2）n-X，其中n = 5-11，X是荧光染料; 而在一般式(II)中，R1从以下组中选择：-CH═CH-（CH2）n-CH3，其中n = 9-15; -（CH2）n-CH3，其中n = 11-17; 和-CO-（CH2）n-CH3，其中n = 10-16; 而R3从以下组中选择：-CO-（CH2）n-X; 和-SO2-（CH2）n-X，其中n = 0-5，X是荧光染料。

  公开号：

  US20090130648A1
• 作为产物：
  描述：

  lecithin 在 氧气 作用下， 反应 24.0h， 生成 lysophosphatidylcholine 、 1-hexadecanoyl-2-(9'-oxononanoyl)glycerophosphocholine 、 1-hexadecanoyl-2-(9-carboxynonanoyl)glycerophosphocholine
  参考文献：
  名称：

  A simple method to generate oxidized phosphatidylcholines in amounts close to one milligram

  摘要：

  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.

  DOI：

  10.1016/j.chemphyslip.2014.09.003

文献信息

• Oxidized phospholipids
  申请人：——

  公开号：US07906674B2

  公开（公告）日：2011-03-15

  The invention relates to oxidized phospholipids having one of the general formulas (I) or (II) wherein A═O, C, NH, or S; B═O, C, NH, or S; and R2 is selected from the group consisting of —CO—(CH2)n—CH3; —CO—(CH2)n—CHO; and —CO—(CH2)n—COOH, with n=3-7, with the proviso that in general formula (I), R1 is selected from the group consisting of —CH2—(CH2)n—X; and —CO—(CH2)n—X with n=5-11, wherein X is a fluorophore; and in general formula (II), R1 is selected from the group consisting of —CH═CH—(CH2)n—CH3 with n=9-15; —(CH2)n—CH3 with n=11-17; and —CO—(CH2)n—CH3 with n=10—16; and R3 is selected from the group consisting of —CO—(CH2)n—X; and —SO2—(CH2)n—X, with n=0-5, wherein X is a fluorophore.

  本发明涉及具有以下通式(I)或(II)之一的氧化磷脂： 其中A = O，C，NH或S；B = O，C，NH或S；R2从以下组中选择：—CO—(CH2)n—CH3；—CO—( )n—CHO；和—CO—( )n—COOH，其中n = 3-7，但需注意，在通式(I)中，R1从以下组中选择：— —( )n—X；和—CO—( )n—X，其中n = 5-11，X是荧光分子；在通式(II)中，R1从以下组中选择：—CH═CH—( )n— ，其中n = 9-15；—( )n— ，其中n = 11-17；和—CO—( )n— ，其中n = 10-16；R3从以下组中选择：—CO—( )n—X；和—SO2—( )n—X，其中n = 0-5，X是荧光分子。
• PREVENTION AND TREATMENT OF INFLAMMATORY CONDITIONS
  申请人：GLYCOREGIMMUNE, INC.

  公开号：US20160158258A1

  公开（公告）日：2016-06-09

  In accordance with some embodiments herein, methods and compositions for prevention and treatment of inflammatory conditions are provided. In some embodiments, compositions comprising NKT-2 activators, for example miltefosine are provided. In some embodiments, the compositions further comprise sulfatide and/or a RAR agonist. In some embodiments, the compositions comprise activators of Type II NKT cells, and/or inhibitors of Type I NKT cells.
• Lipid Abnormalities and Association with Atopic Allergic Diseases
  申请人：National Jewish Health

  公开号：US20180224470A1

  公开（公告）日：2018-08-09

  The present invention is related to novel methods for identifying a population of subjects that are at risk for developing of atopic allergic diseases, such as atopic dermatitis, and to the prevention and treatment of these allergic diseases.
• US7501533B2
  申请人：——

  公开号：US7501533B2

  公开（公告）日：2009-03-10
• [EN] PREVENTION AND TREATMENT OF INFLAMMATORY CONDITIONS<br/>[FR] PRÉVENTION ET TRAITEMENT DE PATHOLOGIES INFLAMMATOIRES
  申请人：GLYCOREGIMMUNE INC

  公开号：WO2016094226A1

  公开（公告）日：2016-06-16

  In accordance with some embodiments herein, methods and compositions for prevention and treatment of inflammatory conditions are provided. In some embodiments, compositions comprising NKT-2 activators, for example miltefosine are provided. In some embodiments, the compositions further comprise sulfatide and/or a RAR agonist. In some embodiments, the compositions comprise activators of Type II NKT cells, and/or inhibitors of Type I NKT cells.