(4Z,7Z,10Z,13E,15E,17R,19Z)-17-羟基-4,7,10,13,15,19-二十二碳六烯酸 | 155976-53-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (4Z,7Z,10Z,13E,15E,17R,19Z)-17-羟基-4,7,10,13,15,19-二十二碳六烯酸
• 英文名称: 17R-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid
• 英文别名: 17R-HDHA；17R-hydroxy DHA；(4Z,7Z,10Z,13Z,15E,17R,19Z)-17-hydroxydocosa-4,7,10,13,15,19-hexaenoic acid
• CAS: 155976-53-7
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: SWTYBBUBEPPYCX-NGHKTGSUSA-N

物化性质

• 沸点：
  505.1±50.0 °C(Predicted)
• 密度：
  0.995±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：可混溶； DMSO：可混溶；乙醇：可混溶； PBS（pH 7.2）：0.8 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4Z,7Z,10Z,13E,15E,17R,19Z)-17-羟基-4,7,10,13,15,19-二十二碳六烯酸 在 L-半胱氨酸 、 Sorangium cellulosum arachidonate 15R-lipoxygenase, wild type 作用下， 以 aq. buffer 为溶剂， 生成 7R,17R-dihydroxy-4Z,8E,10Z,13Z,15E,19Z-docosahexaenoic acid
  参考文献：
  名称：

  Biotransformation of C20- and C22-polyunsaturated fatty acids and fish oil hydrolyzates to R,R-dihydroxy fatty acids as lipid mediators using double-oxygenating 15R-lipoxygenase

  摘要：

  C20- 和 C22-二羟基脂肪酸（DiHFAs）是人体中具有生物活性的脂质介质（LMs）。

  DOI：

  10.1039/d4gc00308j
• 作为产物：
  描述：

  二十二碳六烯酸 在 L-半胱氨酸 、 Sorangium cellulosum arachidonate 15R-lipoxygenase, L₆₀₆F mutant 作用下， 以 aq. buffer 为溶剂， 生成 (4Z,7Z,10Z,13E,15E,17R,19Z)-17-羟基-4,7,10,13,15,19-二十二碳六烯酸
  参考文献：
  名称：

  Biotransformation of C20- and C22-polyunsaturated fatty acids and fish oil hydrolyzates to R,R-dihydroxy fatty acids as lipid mediators using double-oxygenating 15R-lipoxygenase

  摘要：

  C20- 和 C22-二羟基脂肪酸（DiHFAs）是人体中具有生物活性的脂质介质（LMs）。

  DOI：

  10.1039/d4gc00308j

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。
• 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。
• Use of Docosatrienes, Resolvins and Their Stable Analogs in the Treatment of Airway Diseases and Asthma
  申请人：Serhan N. Charles

  公开号：US20080096961A1

  公开（公告）日：2008-04-24

  The present invention is generally drawn to novel isolated therapeutic agents, termed resolving, generated from the interaction between a dietary omega-3 polyunsaturated fatty acid (PUFA) such as eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA), cyclooxygenase-II (COX-2) and an analgesic, such as aspirin (ASA). Surprisingly, careful isolation of compounds generated from the combination of components in an appropriate environment provide di- and tri-hydroxy EPA or DHA compounds having unique structural and physiological properties. The present invention therefore provides for many new useful therapeutic di- or tri-hydroxy derivatives of EPA or DHA (resolvins) that diminish, prevent, or eliminate inflammation or PMN migration, for example. The present invention also provides methods of use, methods of preparation, and packaged pharmaceuticals for use as medicaments for the compounds disclosed throughout the specification.
• USE OF DOCOSATRIENES, RESOLVINS, AND THEIR STABLE ANALOGS IN THE TREATMENT OF AIRWAY DISEASES AND ASTHMA
  申请人：Serhan Charles N.

  公开号：US20120264713A1

  公开（公告）日：2012-10-18

  The present invention is generally drawn to novel isolated therapeutic agents, termed resolvins, generated from the interaction between a dietary omega-3 polyunsaturated fatty acid (PUFA) such as eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA), cyclooxygenase-II (COX-2) and an analgesic, such as aspirin (ASA). Surprisingly, careful isolation of compounds generated from the combination of components in an appropriate environment provide di- and tri-hydroxy EPA or DHA compounds having unique structural and physiological properties. The present invention therefore provides for many new useful therapeutic di- or tri-hydroxy derivatives of EPA or DHA (resolvins) that diminish, prevent, or eliminate inflammation or PMN migration, for example. The present invention also provides methods of use, methods of preparation, and packaged pharmaceuticals for use as medicaments for the compounds disclosed throughout the specification.