5(S)-羟化二十烷四烯酸 | 92008-51-0

• 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: 5(S)-羟化二十烷四烯酸
• 英文名称: 5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid
• 英文别名: (5S,6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid
• CAS: 92008-51-0
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: FTAGQROYQYQRHF-GHWNLOBHSA-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

反应信息

• 作为产物：
  描述：

  5S-hydroperoxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid 在 乙二胺四乙酸 、 human 5-lipoxygenase 、 5’-三磷酸腺苷 、 sodium chloride 、 三甲氧基磷 作用下， 以 aq. phosphate buffer 为溶剂， 反应 2.0h， 生成 5(S)-羟化二十烷四烯酸
  参考文献：
  名称：

  15-脂氧合酶-1 与 5S-HETE 和 7S-HDHA 位置特异性改变的结构基础及其对 resolvin E4 生物合成的影响

  摘要：

  人类 15-脂氧合酶 (LOX) 是炎症过程中的关键酶，可产生各种促分解分子，例如脂氧素和分解素，但这两种 15-LOX 在这些生物合成途径中的确切作用仍不清楚。以前，观察到 h15-LOX-1 以非规范方式与 5S-HETE 反应，主要产生 5S,12S-diHETE 产物。为了确定 h15-LOX-1 在实现这种反应性方面的活性位点限制，研究了参与脂肪酸结合的氨基酸。据观察，R402L 对 5S-HETE 催化作用没有太大影响，但 F414 似乎与 5S-HETE 形成 π-π 堆叠，如 AA 所示结合，表明 5S-HETE 和 F414 的双键之间存在芳香族相互作用。减小 F352 和 I417 的大小将 5S-HETE 的氧化转移到 C12，而增加这些残基的大小则逆转了 5S-HETE 到 C15 的位置特异性。这些位置的突变体以 7S-HDHA 作为底物表现出类似的效果，表明活性

  DOI：

  10.1016/j.abb.2022.109317

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：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：US11077084B2

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

  公开号：US20150126602A1

  公开（公告）日：2015-05-07

  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.
• TREATMENT OF VULVAR PAIN
  申请人：University of Rochester

  公开号：US20200121617A1

  公开（公告）日：2020-04-23

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