7-(1,3-dioxan-2-yl)-5-oxoheptanoic acid | 170710-94-8

• 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: 7-(1,3-dioxan-2-yl)-5-oxoheptanoic acid
• CAS: 170710-94-8
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: VSPGKJPERIDBHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(1,3-dioxan-2-yl)-5-oxoheptanoic acid 在 palladium on activated charcoal 盐酸 、 氢气 、 红铝 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 96.0h， 生成 (-)-(8aR)-octahydroindolizine
  参考文献：
  名称：

  An Asymmetric Route to Chiral, Nonracemic 2-Substituted Piperidines. Synthesis of (-)-Pipecoline, (+)-Coniine, and (-)-Coniceine

  摘要：

  DOI：

  10.1021/jo00127a005
• 作为产物：
  描述：

  4-氯甲酰基丁酸甲酯 在 氢氧化钾 作用下， 生成 7-(1,3-dioxan-2-yl)-5-oxoheptanoic acid
  参考文献：
  名称：

  An Asymmetric Route to Chiral, Nonracemic 2-Substituted Piperidines. Synthesis of (-)-Pipecoline, (+)-Coniine, and (-)-Coniceine

  摘要：

  DOI：

  10.1021/jo00127a005

文献信息

• Efficient Quantitative Analysis of Carboxyalkylpyrrole Ethanolamine Phospholipids: Elevated Levels in Sickle Cell Disease Blood
  作者：Junhong Guo、Hua Wang、Borys Hrinczenko、Robert G. Salomon

  DOI：10.1021/acs.chemrestox.6b00152

  日期：2016.7.18

  γ-Hydroxy-α,β-unsaturated aldehydes, generated by oxidative damage of polyunsaturated phospholipids, form pyrrole derivatives that incorporate the ethanolamine phospholipid (EP) amino group such as 2-pentylpyrrole (PP)-EP and 2-(ω-carboxyalkyl)pyrrole (CAP)-EP derivatives: 2-(ω-carboxyethyl)pyrrole (CEP)-EP, 2-(ω-carboxypropyl)pyrrole (CPP)-EP, and 2-(ω-carboxyheptyl)pyrrole (CHP)-EP. Because EPs occur in vivo in various forms, a complex mixture of pyrrole-modified EPs with different molecular weights is expected to be generated. To provide a sensitive index of oxidative stress, all of the differences in mass related to the glycerophospholipid moieties were removed by releasing a single CAP-ethanolamine (ETN) or PP-ETN from each mixture by treatment with phospholipase D. Accurate quantization was achieved using the corresponding ethanolamine-d4 pyrroles as internal standards. The product mixture obtained by phospholipolysis of total blood phospholipids from sickle cell disease (SCD) patients was analyzed by LC-MS/MS. The method was applied to measure CAP-EP and PP-EP levels in blood plasma from clinical monitoring of SCD patients. We found uniformly elevated blood levels of CEP-EP (63.9 ± 9.7 nM) similar to mean levels in blood from age-related macular degeneration (AMD) patients (56.3 ± 37.1 nM), and 2-fold lower levels (27.6 ± 3.6 nM, n = 5) were detected in plasma from SCD patients hospitalized to treat a sickle cell crisis, although mean levels remain higher than those (12.1 ± 10.5 nM) detected in blood from healthy controls. Plasma levels of CPP-EPs from SCD clinic patients were 4-fold higher than those of SCD patients hospitalized to treat a sickle cell crisis (45.1 ± 10.9 nM, n = 5 versus 10.9 ± 3.4 nM, n = 6; p < 0.002). PP-EP concentration in plasma from SCD clinic patients is nearly 4.8-fold higher than its level in plasma samples from SCD patients hospitalized to treat a sickle cell crisis (7.06 ± 4.05 vs 1.48 ± 0.92 nM; p < 0.05). Because CAP-EPs promote angiogenesis and platelet activation, the elevated levels present in SCD blood can contribute to the hypercoaguability and vaso-occlusive events that are critical pathophysiologic features of SCD.

  γ-羟基-α、β-不饱和醛类是由多不饱和磷脂氧化破坏产生的，形成了含有乙醇胺磷脂（EP）氨基的吡咯衍生物，如 2-戊基吡咯（PP）-EP 和 2-(ω-羧基烷基)吡咯（CAP）-EP 衍生物：2-(ω-羧乙基)吡咯（CEP）-EP、2-(ω-羧丙基)吡咯（CPP）-EP 和 2-(ω-羧庚基)吡咯（CHP）-EP。由于 EPs 在体内以各种形式存在，因此预计会产生分子量不同的吡咯修饰 EPs 的复杂混合物。为了提供一个灵敏的氧化应激指数，用磷脂酶 D 处理每种混合物，释放出单个 CAP-乙醇胺（ETN）或 PP-ETN，从而消除与甘油磷脂分子有关的所有质量差异。通过 LC-MS/MS 分析了镰状细胞病（SCD）患者总血液磷脂的磷脂分解产物混合物。该方法被用于检测镰状细胞病（SCD）患者临床监测血浆中 CAP-EP 和 PP-EP 的水平。我们发现，血液中的 CEP-EP 水平普遍升高（63.9 ± 9.7 nM），与老年性黄斑变性（AMD）患者血液中的平均水平（56.3 ± 37.1 nM）相似；在住院治疗镰状细胞危象的 SCD 患者血浆中检测到的 CEP-EP 水平低 2 倍（27.6 ± 3.6 nM，n = 5），但平均水平仍高于健康对照组血液中检测到的水平（12.1 ± 10.5 nM）。SCD门诊患者血浆中的CPP-EP水平比住院治疗镰状细胞危象的SCD患者高4倍（45.1 ± 10.9 nM，n = 5对10.9 ± 3.4 nM，n = 6；P < 0.002）。SCD门诊患者血浆中的PP-EP浓度比住院治疗镰状细胞危象的SCD患者血浆样本中的PP-EP浓度高出近4.8倍（7.06 ± 4.05 vs 1.48 ± 0.92 nM；p < 0.05）。由于 CAP-EPs 可促进血管生成和血小板活化，因此 SCD 血液中的 CAP-EPs 水平升高可导致高凝状态和血管闭塞事件，而这正是 SCD 的关键病理生理特征。
• DETECTION OF CARBOXYALKYLPYRROLE OR PENTYLPYRROLE ETHANOLAMINE PHOSPHOLIPIDS
  申请人：CASE WESTERN RESERVE UNIVERSITY

  公开号：US20170176470A1

  公开（公告）日：2017-06-22

  A method of detecting carboxyalkylpyrrole ethanolamine phospholipids (CAP-EPs) or pentylpyrrole ethanolamine phospholipids (CAP-EPs) in a bodily sample from a subject includes obtaining a bodily sample from a subject suspected of including carboxyalkylpyrrole ethanolamine phospholipids (CAP-EPs) or pentylpyrrole ethanolamine phospholipids (PP-EPs) extracting carboxyalkylpyrrole ethanolamine phospholipids or pentylpyrrole ethanolamine phospholipids from the bodily sample; hydrolyzing carboxyalkylpyrrole or pentylpyrrole ethanolamine phospholipids from the extracted with a phospholipase D to form carboxyalkylpyrrole ethanolamine (CAP-ETN) and pentylpyrrole ethanolamine (PP-ETN) derivatives; and determining the amount of carboxyalkylpyrrole ethanolamine (CAP-ETN) and pentylpyrrole ethanolamine (PP-ETN) by mass spectrometry.
• An Asymmetric Route to Chiral, Nonracemic 2-Substituted Piperidines. Synthesis of (-)-Pipecoline, (+)-Coniine, and (-)-Coniceine
  作者：Michael J. Munchhof、A. I. Meyers

  DOI：10.1021/jo00127a005

  日期：1995.11