(5Z,8Z,11Z,14Z,16E)-18-羟基-5,8,11,14,16-二十碳五烯酸 | 141110-17-0

• 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: (5Z,8Z,11Z,14Z,16E)-18-羟基-5,8,11,14,16-二十碳五烯酸
• 英文名称: 18-HEPE
• 英文别名: (±)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid；18-hydroxyeicosapentaenoic acid；18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid；(+/-)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid；(5Z,8Z,11Z,14Z,16E)-18-hydroxyicosa-5,8,11,14,16-pentaenoic acid
• CAS: 141110-17-0
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: LRWYBGFSVUBWMO-UXNZXXPISA-N

物化性质

• 沸点：
  488.0±45.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)
• 溶解度：
  0.1 M Na2CO3：2 mg/mL； 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)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  (5Z,8Z,11Z,14Z,16E)-18-羟基-5,8,11,14,16-二十碳五烯酸 在 5-lipoxygenase potato 作用下， 以 乙醇 、 水 为溶剂， 生成 5S-hydroperoxy, 18R/S-hydroxy-EPE
  参考文献：
  名称：

  [EN] USE OF DOCOSATRIENES, RESOLVINS AND THEIR STABLE ANALOGS IN THE TREATMENT OF AIRWAY DISEASES AND ASTHMA
  [FR] UTILISATION DE DOCOSATRIENES, RESOLVINES ET LEURS ANALOGUES STABLES POUR LE TRAITEMENT DE MALADIES DES VOIES RESPIRATOIRES ET DE L'ASTHME

  摘要：

  公开号：

  WO2005089744A3
• 作为产物：
  描述：

  methyl (5Z,8Z,11Z)-13-bromotrideca-5,8,11-trienoate 、 在 copper(l) iodide 、 potassium carbonate 、 sodium iodide 、 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (5Z,8Z,11Z,14Z,16E)-18-羟基-5,8,11,14,16-二十碳五烯酸
  参考文献：
  名称：

  1-三甲基甲硅烷基-1,2-环氧-3-烷醇与炔烃的反应及其在18-HEPE合成中的应用

  摘要：

  衍生自 (E)-TMS-CH=CHCH(OH)R 的环氧醇（反和/或顺异构体）与 TMS-C≡CLi 在 THF/HMPA 中立体选择性地得到 (E)-TMS-C≡C- CH=CHCH(OH)R。(E) 立体化学独立于反/顺式立体化学，但顺式异构体显示出比反异构体更高的反应性。该反应用于合成(18R)-和(18S)-HEPE。

  DOI：

  10.1055/s-0037-1610194

文献信息

• Compositions comprising omega-3 fatty acids, 17-HDHA and 18-HEPE and methods of using same
  申请人：Solutex NA LLC

  公开号：US10653703B2

  公开（公告）日：2020-05-19

  The present invention relates to a polyunsaturated fatty acid composition comprising Omega-3 fatty acids, 17-HDHA and 18-HEPE. The composition can furthermore comprise DPA and/or an acceptable carrier and can be present in a capsule or other suitable dosage unit. The invention also relates to the process of obtaining the composition and methods for using same.

  本发明涉及一种多不饱和脂肪酸组合物，该组合物由 Omega-3 脂肪酸、17-HDHA 和 18-HEPE 组成。该组合物还可进一步包含 DPA 和/或可接受的载体，并可以胶囊或其他合适的剂量单位形式存在。本发明还涉及获得该组合物的过程以及使用该组合物的方法。
• WO2006/78457
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] RESOLVINS: BIOTEMPLATES FOR THERAPEUTIC INTERVENTIONS<br/>[FR] LES RESOLVINES, DES GABARITS BIOLOGIQUES CONVENANT POUR DE NOUVELLES INTERVENTIONS THERAPEUTIQUES
  申请人：BRIGHAM & WOMENS HOSPITAL

  公开号：WO2004014835A3

  公开（公告）日：2004-04-15
• 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.