9,12-dioxo-dodecanoic acid | 51551-01-0

• 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: 9,12-dioxo-dodecanoic acid
• 英文别名: Dodecanoic acid, 9,12-dioxo-；9,12-dioxododecanoic acid
• CAS: 51551-01-0
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: DRCRMCBLQUKXIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9,12-dioxo-dodecanoic acid 在 氢氧化钾 作用下， 生成 5-氧代环戊-1-烯-1-庚酸
  参考文献：
  名称：

  2-(6-CARBOXYHEXYL)CyclOPENT-2-EN-1-ONE 的新合成，一种前列腺素合成物

  摘要：

  描述了标题化合物 (1) 的新合成，它是合成各种前列腺素的有用中间体，它涉及酸催化的 9-环丙基-9-氧壬酸 (7) 的环丙烷重排作为关键步骤。环丙基酮7是由环丙基甲基酮通过三个步骤制备的。

  DOI：

  10.1246/cl.1977.1121
• 作为产物：
  描述：

  7-溴庚酸 在 Py*HClCrO₃ 、 硫酸 、 mercury(II) sulfate 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 9,12-dioxo-dodecanoic acid
  参考文献：
  名称：

  Mamdapur,V.R. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1979, vol. 17, p. 269 - 271

  摘要：

  DOI：

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。
• Recherches sur la synthese totale des alcaloides appartenant a la serie de la carpaine et de la cassine—V
  作者：E. Brown、A. Bourgouin

  DOI：10.1016/0040-4020(75)80125-6

  日期：——

  The total synthesis is described of (±) 6-(7-carboxy hept-1-yl) 3-hydroxy 2-methyl piperidine [(±) carpamic acid] in five steps from 1-ethoxycarbonyl 6-methyl hept-5-en-2-one.

  从1-乙氧羰基6-甲基庚基-5-烯分五个步骤描述了（±）6-（7-羧基庚基-1-基）3-羟基2-甲基哌啶[（±）棕榈酸]的总合成-2-一
• Improved processes for preparing 7-(2-hexyl-5-hydroxy-cyclopentyl)-heptanoic acid
  申请人：IBI- Istituto Biochimico Italiano Giovanni Lorenzini S.p.A.

  公开号：EP0155392A2

  公开（公告）日：1985-09-25

  The present invention concerns new processes for preparing the compound having prostanoic structure IBI-C83 [7-(2-hexyl-5-hydroxy-cyclopentyl)-heptanoic acid], with anti-ulcer action and of the pharmacologically acceptable salts thereof. Furthermore, some new intermediates are claimed, which are useful for preparing the compound ICI-C83.

  本发明涉及制备具有前列腺结构 IBI-C83 [7-(2-己基-5-羟基-环戊基)-庚酸]、具有抗溃疡作用的化合物及其药理上可接受的盐的新工艺。 此外，本发明还要求得到一些新的中间体，它们有助于制备化合物 ICI-C83。
• DIAGNOSTIC TOOLS FOR ALZHEIMER'S DISEASE
  申请人：Pharnext

  公开号：EP3028049B1

  公开（公告）日：2019-03-20
• Diagnostic methods for age related macular degeneration
  申请人：——

  公开号：US20040265924A1

  公开（公告）日：2004-12-30

  Diagnostic methods for identifying a test subject who has or is at risk of developing age-related macular degeneration (AMD) or an analogous disease associated with oxidation of DHA-containing lipids are provided. In one aspect, the methods comprise: assaying for the presence of elevated levels of 2-(&ohgr;-carboxyethyl) pyrrole (CEP) adducts in a bodily fluid which has been obtained from the test subject. In a preferred embodiment, such methods comprise providing an antibody that is immunospecific for CEP, contacting a bodily fluid from the subject with the anti-CEP antibody, and assaying for the formation of a complex between the antibody and an antigen in the sample. In another aspect, the methods comprise assaying for the presence of elevated levels of an antibody that binds to or is immunospecific for a CEP adduct in the bodily fluid of the test subject. The present invention also relates to CEP protein and peptide adducts, an antibody reactive with a CEP adduct and a diagnostic kit comprising such antibody.