1-palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine | 70094-88-1

• 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-palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine
• 英文别名: 1-palmitoyl-2-linoleoylphosphatydylcholine；1-palmitoyl-2-linoleyl-sn-glycero-3-phosphocholine；[(2S)-3-hexadecanoyloxy-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 70094-88-1
• 化学式: C₄₂H₈₀NO₈P
• 分子量: 758.073
• InChiKey: JLPULHDHAOZNQI-GFEYFTFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  52
• 可旋转键数：
  40
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine 在 2,2’-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride 作用下， 生成 4-羟基-2,3-壬烯醛
  参考文献：
  名称：

  心磷脂氧化形成 4-羟基壬烯醛：分子内过氧自由基加成和分解。

  摘要：

  我们在此报告细胞色素 c 和 H(2)O(2) 氧化线粒体特异性磷脂四亚油酰心磷脂 (L(4)CL) 导致 4-羟基-2-壬烯醛 (4-HNE) 的形成一种涉及跨链过氧自由基加成和分解的新化学机制。作为最具生物活性的脂质亲电试剂之一，4-HNE 具有多种生物活性，从调节多种信号转导途径到诱导内在细胞凋亡。然而，人们对 4-HNE 在体内的形成位置和方式知之甚少。最近提出了一种新的化学机制，涉及脂肪酸通过过氧键形成的分子间二聚化；但这种机制的生物学相关性尚不清楚，因为大多数脂肪酸在细胞膜的磷脂中被酯化。我们假设心磷脂的氧化，尤其是 L(4)CL，可能会通过这种新机制导致 4-HNE 的形成。我们采用 L(4)CL 和二亚油酰磷脂酰胆碱 (DLPC) 作为模型化合物来测试这一假设。事实上，在旨在评估分子内机制的实验中，与 1-palmitoyl-2-linoleoylphosphatydylcholine

  DOI：

  10.1016/j.freeradbiomed.2010.10.709
• 作为产物：
  描述：

  1-Benzyl-glycerin-3-palmitinsaeureester 在 4-二甲氨基吡啶 、 水 、 三氯化硼 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 13.0h， 生成 1-palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine
  参考文献：
  名称：

  The efficient synthesis of mixed diacyl phospholipids with polyunsaturated fatty acid in sn-2 position of glycerol

  摘要：

  A convenient method for synthesis of the mixed-diacyl phospholipid using boron trichloride as an efficient reagent for the removal of benzyl protecting group from polyunsaturated diacylglycerols without affecting the double bond and acyl migration is described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00371-6

文献信息

• Iron-catalyzed reaction products of α-tocopherol with 1-palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine (13S)-hydroperoxide
  作者：Ryo Yamauchi、Keiko Ozaki、Makoto Shimoyamada、Koji Kato

  DOI：10.1016/s0009-3084(02)00004-x

  日期：2002.2

  alpha-Tocopherol was reacted with 1-palmitoyl-2-[(9Z,11E)-(S)-13-hydroperoxy-9,11-octadecadienoyl]-3-sn-phosphatidylcholine (13-PLPC-OOH) in the presence of a lipid-soluble iron chelate, Fe(III) acetylacetonate, in methanol at 37 degreesC. The reaction product was isolated and identified as a mixture of 1-palmitoyl-2-[(10E)-(12S,13S)-9-(8a-dioxy-alpha-tocopherone)-12,13-epoxy-10-octadecenoyl]-3-sn-phosphatidylcholine and 1-palmitoyl-2-[(9Z)-(12S,13S)-11-(8a-dioxy-alpha-tocopherone)-12,13-epoxy-9-octadecenoyl]-3-sn-phosphatidylcholine (TOO-epoxyPLPC), in which the 12,13-epoxyperoxyl radicals derived from 13-PLPC-OOH attacked the 8a-position of the alpha-tocopheroxyl radical. The iron and ascorbate-catalyzed reaction of 13-PLPC-OOH with alpha-tocopherol in phosphatidylcholine (PC) liposomes was assessed by measuring the reaction products of alpha-tocopherol. When 13- PLPC-OOH and alpha-tocopherol were added in saturated dimyristoyl-PC liposomes, the products were TOO-epoxyPLPC, alpha-tocopherylquinone, and epoxy-alpha-tocopherylquinones. In 1-palmitoyl-2-linoleoyl-PC (PLPC) liposomes, alpha-tocopherol could react with both the 13-PLPC-OOH derived 12,13-epoxyperoxyl radicals and the PLPC-derived peroxyl radicals and formed the addition products together with a-tocopherylquinone and epoxy-alpha-tocopherylquinones. Therefore, the iron-catalyzed decomposition of phospholipid hydroperoxides primarily produces epoxyperoxyl radicals, which react with the 8a-carbon centered radical of alpha-tocopherol in liposomal systems. (C) 2002 Elsevier Science Ireland Ltd. All rights reserved.
• RAMESHA, CHAKKODABYLU S.;PICKETT, WALTER C.;KRISHNA, MURTHY D. V., J. CHROMATOGR. BIOMED. APPL., 491,(1989) N, C. 37-48
  作者：RAMESHA, CHAKKODABYLU S.、PICKETT, WALTER C.、KRISHNA, MURTHY D. V.

  DOI：——

  日期：——
• The efficient synthesis of mixed diacyl phospholipids with polyunsaturated fatty acid in sn-2 position of glycerol
  作者：Jie Xia、Yong-Zheng Hui

  DOI：10.1016/s0957-4166(97)00371-6

  日期：1997.9

  A convenient method for synthesis of the mixed-diacyl phospholipid using boron trichloride as an efficient reagent for the removal of benzyl protecting group from polyunsaturated diacylglycerols without affecting the double bond and acyl migration is described. (C) 1997 Elsevier Science Ltd.
• Formation of 4-hydroxynonenal from cardiolipin oxidation: Intramolecular peroxyl radical addition and decomposition
  作者：Wei Liu、Ned A. Porter、Claus Schneider、Alan R. Brash、Huiyong Yin

  DOI：10.1016/j.freeradbiomed.2010.10.709

  日期：2011.1

  We report herein that oxidation of a mitochondria-specific phospholipid tetralinoleoyl cardiolipin (L(4)CL) by cytochrome c and H(2)O(2) leads to the formation of 4-hydroxy-2-nonenal (4-HNE) via a novel chemical mechanism that involves cross-chain peroxyl radical addition and decomposition. As one of the most bioactive lipid electrophiles, 4-HNE possesses diverse biological activities ranging from

  我们在此报告细胞色素 c 和 H(2)O(2) 氧化线粒体特异性磷脂四亚油酰心磷脂 (L(4)CL) 导致 4-羟基-2-壬烯醛 (4-HNE) 的形成一种涉及跨链过氧自由基加成和分解的新化学机制。作为最具生物活性的脂质亲电试剂之一，4-HNE 具有多种生物活性，从调节多种信号转导途径到诱导内在细胞凋亡。然而，人们对 4-HNE 在体内的形成位置和方式知之甚少。最近提出了一种新的化学机制，涉及脂肪酸通过过氧键形成的分子间二聚化；但这种机制的生物学相关性尚不清楚，因为大多数脂肪酸在细胞膜的磷脂中被酯化。我们假设心磷脂的氧化，尤其是 L(4)CL，可能会通过这种新机制导致 4-HNE 的形成。我们采用 L(4)CL 和二亚油酰磷脂酰胆碱 (DLPC) 作为模型化合物来测试这一假设。事实上，在旨在评估分子内机制的实验中，与 1-palmitoyl-2-linoleoylphosphatydylcholine