(4Z,7Z,10Z,12E,16Z,19Z)-14-羟基-4,7,10,12,16,19-二十二碳六烯酸 | 87042-40-8

• 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,12E,16Z,19Z)-14-羟基-4,7,10,12,16,19-二十二碳六烯酸
• 英文名称: 14-HDHA
• 英文别名: 14-hydroxy docosahexaenoic acid；(+/-)-14-hydroxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoic acid；(4Z,7Z,10Z,12E,16Z,19Z)-14-hydroxydocosa-4,7,10,12,16,19-hexaenoic acid
• CAS: 87042-40-8
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: ZNEBXONKCYFJAF-BGKMTWLOSA-N

物化性质

• 沸点：
  510.0±50.0 °C(Predicted)
• 密度：
  0.995±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)：
  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,12E,16Z,19Z)-14-羟基-4,7,10,12,16,19-二十二碳六烯酸 在 戴斯-马丁氧化剂 作用下， 生成 14-oxo-DoHE
  参考文献：
  名称：

  15-Hydroxyprostaglandin Dehydrogenase Generation of Electrophilic Lipid Signaling Mediators from Hydroxy Ω-3 Fatty Acids

  摘要：

  15-Hydroxyprostaglandin dehydrogenase (15PGDH) is the primary enzyme catalyzing the conversion of hydroxylated arachidonic acid species to their corresponding oxidized metabolites. The oxidation of hydroxylated fatty acids, such as the conversion of prostaglandin (PG) E-2 to 15-ketoPGE(2), by 15PGDH is viewed to inactivate signaling responses. In contrast, the typically electrophilic products can also induce anti-inflammatory and anti-proliferative responses. This study determined that hydroxylated docosahexaenoic acid metabolites (HDoHEs) are substrates for 15PGDH. Examination of 15PGDH substrate specificity was conducted in cell culture (A549 and primary human airway epithelia and alveolar macrophages) using chemical inhibition and shRNA knockdown of 15PGDH. Substrate specificity is broad and relies on the carbon position of the acyl chain hydroxyl group. 14-HDoHE was determined to be the optimal DHA substrate for 15PGDH, resulting in the formation of its electrophilic metabolite, 14-oxoDHA. Consistent with this, 14-HDoHE was detected in bronchoalveolar lavage cells of mild to moderate asthmatics, and the exogenous addition of 14-oxoDHA to primary alveolar macrophages inhibited LPS-induced proinflammatory cytokine mRNA expression. These data reveal that 15PGDH-derived DHA metabolites are biologically active and can contribute to the salutary signaling actions of Omega-3 fatty acids.

  DOI：

  10.1074/jbc.m114.635151

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。
• 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。
• 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。
• OILS WITH ANTI-INFLAMMATORY ACTIVITY CONTAINING NATURAL SPECIALIZED PRORESOLVING MEDIATORS AND THEIR PRECURSORS
  申请人：Solutex NA LLC

  公开号：EP2858496A2

  公开（公告）日：2015-04-15
• 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：US20200316086A1

  公开（公告）日：2020-10-08

  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.