11,12-Epoxyeicosaquatraenoic acid

• 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: 11,12-Epoxyeicosaquatraenoic acid
• 英文别名: (±)-11,12-epoxy-5Z,8Z,14Z,17Z-eicosatetraenoic acid；11,12-epoxieicosatetraenoic acid；11,12-epoxyeicosatetraenoic acid；11,12-EETeTr；11,12-EEQ；(+/-)-11(12)-epoxy-5Z,8Z,14Z,17Z-eicosatetraenoic acid；11(12)-EpETE；(5Z,8Z)-10-[3-[(2Z,5Z)-octa-2,5-dienyl]oxiran-2-yl]deca-5,8-dienoic acid
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: QHOKDYBJJBDJGY-BVILWSOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  全顺式二十碳五烯酸 在 human recombinant cytochrome P₄₅₀ 2C₈ 作用下， 以41%的产率得到17,18-Epoxyeicosatetraenoic acid
  参考文献：
  名称：

  Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450

  摘要：

  Cytochromes P450 (CYPs) metabolize polyunsaturated long-chain fatty acids (PUFA-LC) to several classes of oxygenated metabolites. Through use of human recombinant CYPs, we recently showed that CYP1A1, -2C19, -2D6, -2E1, and -3A4 are mainly hydroxylases, whereas CYP1A2, -2C8, -2C9, and -2J2 are mainly epoxygenases of arachidonic acid (AA), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA), respectively. It is worth noting that the last double bond of these PUFAs, i.e., omega 6 in AA or omega 3 in EPA and DHA, respectively, was preferentially epoxidized. In this study, we have characterized the stereoselectivity of this epoxidation reaction by comparison with the PUFA-LC epoxide stereoisomers obtained from the enantioselective bacterial CYP102A1 F87V. The stereoselectivity of the epoxidation of the last olefin of AA (omega 6), EPA (omega 3), or DHA (omega 3) differed between the CYP isoforms but was similar for EPA and DHA. These data give additional insight into the PUFA-LC epoxide enantiomers generated by the hepatic CYPs.-Lucas, D., S. Goulitquer, J. Marienhagen, M. Fer, Y. Dreano, U. Schwaneberg, Y. Amet, and L. Corcos. Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450. J. Lipid Res. 2010. 51: 1125-1133.

  DOI：

  10.1194/jlr.m003061

文献信息

• Oils with anti-inflammatory activity containing natural specialized proresolving mediators and their precursors
  申请人：SOLUTEX NA LLC

  公开号：US10568858B2

  公开（公告）日：2020-02-25

  The present invention encompasses oils that have anti-inflammatory or resolution-stimulating activity that contain or are enriched with Specialized Proresolving Mediators (SPM) or SPM precursors, which originate from an oil obtained from organisms containing long chain omega-3 polyunsaturated fatty acids, such as fish, crustaceae, algae, and mollusks. The invention also encompasses a method for the production of these oils, and the utilization of the oils for nutritional supplements, pharmaceutical formulations, and cosmetic formulations, which can be employed for treating an inflammatory condition.

  本发明包括具有抗炎或刺激溶解活性的油类，这些油类含有或富含特化促溶解介质（SPM）或 SPM 前体，这些特化促溶解介质或 SPM 前体来源于从含有长链欧米加-3 多不饱和脂肪酸的生物（如鱼类、甲壳类、藻类和软体动物）中获得的油类。本发明还包括生产这些油的方法，以及将这些油用于营养补充剂、药物制剂和化妆品制剂的方法，这些制剂可用于治疗炎症。
• Methods of inhibiting pain
  申请人：The Regents of the University of California

  公开号：US10813894B2

  公开（公告）日：2020-10-27

  Provided are methods and compositions for preventing, reducing, mitigating and treating pain, particularly neuropathic pain by the combined administration of an agent that increases EETs and an agent that reduces/inhibits endoplasmic reticulum (ER) stress.

  本文提供了通过联合施用增加 EETs 的制剂和减少/抑制内质网（ER）应激的制剂来预防、减少、减轻和治疗疼痛，特别是神经性疼痛的方法和组合物。
• Oils with anti-inflammatory activity containing natural Specialized Proresolving Mediators and their precursors
  申请人：Solutex NA LLC

  公开号：US11077083B2

  公开（公告）日：2021-08-03

  The present invention encompasses oils that have anti-inflammatory or resolution-stimulating activity that contain or are enriched with Specialized Proresolving Mediators (SPM) or SPM precursors, which originate from an oil obtained from organisms containing long chain omega-3 polyunsaturated fatty acids, such as fish, crustaceae, algae, and mollusks. The invention also encompasses a method for the production of these oils, and the utilization of the oils for nutritional supplements, pharmaceutical formulations, and cosmetic formulations, which can be employed for treating an inflammatory condition.

  本发明包括具有抗炎或刺激溶解活性的油类，这些油类含有或富含特化促溶解介质（SPM）或 SPM 前体，这些特化促溶解介质或 SPM 前体来源于从含有长链欧米加-3 多不饱和脂肪酸的生物（如鱼类、甲壳类、藻类和软体动物）中获得的油类。本发明还包括生产这些油的方法，以及将这些油用于营养补充剂、药物制剂和化妆品制剂的方法，这些制剂可用于治疗炎症。
• Treatment of vulvar pain
  申请人：University of Rochester

  公开号：US11400057B2

  公开（公告）日：2022-08-02

  The present invention relates to methods of treating female reproductive tract irritation (such as pain and pruritus) or/and inflammation.

  本发明涉及治疗女性生殖道刺激（如疼痛和瘙痒）或/和炎症的方法。
• STABLE ANALOGS OF CYP450 LIPID METABOLITES AND INHIBITORS OF SOLUBLE EPOXIDE HYDROLASE
  申请人：Massachusetts Eye & Ear Infirmary

  公开号：EP3377056B1

  公开（公告）日：2020-09-23