(E)-9-hydroxy-12-oxo-10-dodecenoic acid | 74886-18-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (E)-9-hydroxy-12-oxo-10-dodecenoic acid
• 英文别名: 9-hydroxy-12-oxo-10E-dodecenoic acid；9-hydroxy-12-oxododec-10-enoic acid；(E)-9-hydroxy-12-oxododec-10-enoic acid；9-hydroxytraumatin；9-hydroxy-12-oxo-10-dodecenoic acid；10-Dodecenoic acid, 9-hydroxy-12-oxo-, (10E)-
• CAS: 74886-18-3
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: ADPDWAFVBDMZSV-SOFGYWHQSA-N

物化性质

• 沸点：
  385.6±37.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-9-hydroxy-12-oxo-10-dodecenoic acid 在 silver(II) oxide 作用下， 生成 (E)-4-hydroxydodec-2-enedioic acid
  参考文献：
  名称：

  Hydroperoxide lyase cascade in pea seedlings: Non-volatile oxylipins and their age and stress dependent alterations

  摘要：

  The profiles of non-volatile oxylipins of pea (Pisum sativum) seedlings were examined by gas chromatography-mass spectrometry after in vitro incubation with alpha-linolenic acid. The 13-lipoxygenase/hydroperoxide lyase (HPL) products were predominant in the leaves, while the roots possess both 13-and 9-HPL products. Allene oxide synthase (AOS) and divinyl ether synthase (DES) products were not detected in the leaves or in the roots of any age. The HPL cascade produces a diversity of oxylipins, including the compounds (2E)-4-hydroxy-traumatic, (10E)-9,12-dihydroxy-10-dodecenoic and 9,12-dihydroxydodecanoic acids, as well as (2E)-4-hydroxy-2-nonenoic acid, which has not yet been detected in plants. Oxylipin patterns were altered by infection, water deficit, as well as by plant age. Infection caused the specific strong accumulation of azelaic (nonane-1,9-dioic) acid in the leaves. The azelaic acid content in the aged (14 and 18 day-old) leaves was significantly higher than in the younger leaves. Water deficit induced the accumulation of (2E)-4-hydroxy-2-nonenoic acid and (2E)-traumatic acid in the roots. Results demonstrate that: (1) the HPL cascade is the predominant branch of the lipoxygenase pathway in pea seedlings; (2) the HPL products may have the regulatory role both in growth control and adaptation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2011.01.013
• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 sodium tetrahydroborate 、 氧气 、 lead(IV) tetraacetate 作用下， 生成 (E)-9-hydroxy-12-oxo-10-dodecenoic acid
  参考文献：
  名称：

  Hydroperoxide lyase cascade in pea seedlings: Non-volatile oxylipins and their age and stress dependent alterations

  摘要：

  The profiles of non-volatile oxylipins of pea (Pisum sativum) seedlings were examined by gas chromatography-mass spectrometry after in vitro incubation with alpha-linolenic acid. The 13-lipoxygenase/hydroperoxide lyase (HPL) products were predominant in the leaves, while the roots possess both 13-and 9-HPL products. Allene oxide synthase (AOS) and divinyl ether synthase (DES) products were not detected in the leaves or in the roots of any age. The HPL cascade produces a diversity of oxylipins, including the compounds (2E)-4-hydroxy-traumatic, (10E)-9,12-dihydroxy-10-dodecenoic and 9,12-dihydroxydodecanoic acids, as well as (2E)-4-hydroxy-2-nonenoic acid, which has not yet been detected in plants. Oxylipin patterns were altered by infection, water deficit, as well as by plant age. Infection caused the specific strong accumulation of azelaic (nonane-1,9-dioic) acid in the leaves. The azelaic acid content in the aged (14 and 18 day-old) leaves was significantly higher than in the younger leaves. Water deficit induced the accumulation of (2E)-4-hydroxy-2-nonenoic acid and (2E)-traumatic acid in the roots. Results demonstrate that: (1) the HPL cascade is the predominant branch of the lipoxygenase pathway in pea seedlings; (2) the HPL products may have the regulatory role both in growth control and adaptation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2011.01.013

文献信息

• Novel Acetylenic Oxylipins from the Moss Dicranum scoparium with Antifeeding Activity against Herbivorous Slugs
  作者：Martin Rempt、Georg Pohnert

  DOI：10.1002/anie.201000825

  日期：2010.6.28

  A slug stopper: The defensive properties of oxylipins from the moss Dicranum scoparium are far more active than required to fend off herbivory by a common slug. The precursor‐guided structure elucidation of seven novel and several known unusual oxylipins was supported by chemometric data mining.

  塞子塞：来自苔藓龙骨草（Dicranum scoparium）的脂环素的防御特性远比通过普通塞子抵御草食动物所需的活性高得多。化学计量学数据挖掘支持了对七个新颖的和几种已知的不寻常的脂蛋白的前体导向结构的阐明。
• NANOPARTICLE-BASED DELIVERY SYSTEM WITH OXIDIZED PHOSPHOLIPIDS AS TARGETING LIGANDS FOR THE PREVENTION, DIAGNOSIS AND TREATMENT OF ATHEROSCLEROSIS
  申请人：WANG Shu

  公开号：US20140287024A1

  公开（公告）日：2014-09-25

  Disclosed are nanoparticle-based medicine/nutrient delivery system that are coated or incorporated with oxidized phospholipids as targeting ligands. Such delivery systems can specifically target macrophages, which are determinant cells in the aortic wall for atherosclerotic lesion development, to significantly increase bioavailability and specificity for the prevention, diagnosis and treatment of atherosclerosis.

  揭示了一种基于纳米颗粒的医药/营养素传递系统，其涂有或包含氧化磷脂作为靶向配体。这样的传递系统可以特异性地靶向巨噬细胞，它们是动脉壁上动脉粥样硬化病变发展的决定性细胞，从而显着增加生物利用度和特异性，用于预防、诊断和治疗动脉粥样硬化。
• Compositions and methods for modulating toll-like receptor 2 activation
  申请人：THE CLEVELAND CLINIC FOUNDATION

  公开号：US10987408B2

  公开（公告）日：2021-04-27

  A method of promoting hair growth of a subject includes administering to follicle cells of the subject a therapeutically effective amount of a TLR2 agonist that promotes TLR2 activation and hair growth of the subject.

  一种促进受试者毛发生长的方法包括向受试者的毛囊细胞施用治疗有效量的 TLR2 激动剂，以促进受试者的 TLR2 激活和毛发生长。
• Myeloperoxidase, a risk indicator for cardiovascular disease
  申请人：——

  公开号：US20020164662A1

  公开（公告）日：2002-11-07

  Diagnostic tests for characterizing an individual's risk of developing or having a cardiovascular disease. In one embodiment the present diagnostic test comprises determining the level of myeloperoxidase (MPO) activity in a bodily sample obtained from the individual or test subject. In another embodiment, the diagnostic test comprises determining the level of MPO mass in a bodily sample obtained from the test subject. In another embodiment, the diagnostic test comprises determining the level of one or more select MPO-generated oxidation products in a bodily sample obtained from the test subject. The select MPO-generated oxidation products are dityrosine, nitrotyrosine, methionine sulphoxide or an MPO-generated lipid peroxidation products. Levels of MPO activity, MPO mass, or the select MPO-generated oxidation product in bodily samples from the test subject are then compared to a predetermined value that is derived from measurements of MPO activity, MPO mass, or the select MPO-generated oxidation product in comparable bodily samples obtained from the general population or a select population of human subjects. Such comparison characterizes the test subject's risk of developing CVD.

  用于确定个人罹患或患有心血管疾病风险的诊断测试。在一个实施方案中，本诊断测试包括确定从个体或测试对象处获取的身体样本中髓过氧化物酶（MPO）活性的水平。在另一个实施方案中，诊断检测包括确定从测试对象处获取的身体样本中 MPO 质量的水平。在另一个实施方案中，诊断检测包括确定从测试对象处获取的身体样本中一种或多种选择性 MPO 生成的氧化产物的水平。选择性 MPO 生成的氧化产物是指二酪氨酸、硝基酪氨酸、蛋氨酸亚砜或 MPO 生成的脂质过氧化产物。然后，将测试对象身体样本中的 MPO 活性、MPO 质量或所选 MPO 生成的氧化产物的水平与一个预定值进行比较，该预定值是通过测量从普通人群或特定人群中获得的可比身体样本中的 MPO 活性、MPO 质量或所选 MPO 生成的氧化产物而得出的。通过这种比较可以确定受试者患心血管疾病的风险。
• Systemic marker for monitoring anti-inflammatory and antioxidant actions of therapeutic agents
  申请人：The Cleveland Clinic Foundation

  公开号：US20030180218A1

  公开（公告）日：2003-09-25

  A diagnostic method of monitoring anti-inflammatory and/or antioxidant actions of therapeutic agents comprises determining the level of at least one systemic marker indicative of inflammation or oxidation in a bodily sample taken from a subject at base line or following administration of the therapeutic agent. The marker includes at least one of MPO activity, MPO mass, select MPO-generated oxidation products, and combinations thereof. The level of the systemic marker is compared with a predetermined value to monitor the anti-inflammatory and/or antioxidant actions of the therapeutic agent.

  一种监测治疗剂的抗炎和/或抗氧化作用的诊断方法包括确定在基线或服用治疗剂后从受试者体内采集的样本中至少一种指示炎症或氧化的全身标记物的水平。标记物包括 MPO 活性、MPO 质量、MPO 生成的特定氧化产物及其组合中的至少一种。将全身标记物的水平与预定值进行比较，以监测治疗剂的抗炎和/或抗氧化作用。