(17R,18S)-dihydroxy-5Z,8Z,11Z,13E,15E-eicosapentaenoic acid | 1360805-64-6

• 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: (17R,18S)-dihydroxy-5Z,8Z,11Z,13E,15E-eicosapentaenoic acid
• 英文别名: (5Z,8Z,11Z,13E,15E,17R,18S)-17,18-dihydroxyicosa-5,8,11,13,15-pentaenoic acid；(18S)-resolvin E3；(17R,18S)-resolvin E3；(17R,18S)-17,18-dihydroxy-5Z,8Z,11Z,13E,15E-eicosapentaenoic acid；18S-Resolvin E3
• CAS: 1360805-64-6
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: WYCMUVNNXSREQB-BBJRFLMCSA-N

物化性质

• 沸点：
  538.7±50.0 °C(predicted)
• 密度：
  1.054±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 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：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-trimethylsilyl-1-pentyn-3-ol 在 吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 Noyori's catalyst 、 草酰氯 、 偶氮二甲酸二异丙酯 、 copper diacetate 、 sodium hexamethyldisilazane 、 silica gel 、 碳酸氢钠 、 potassium carbonate 、 对甲苯磺酸 、 silver nitrate 、 二甲基亚砜 、 叔丁胺 、 间氯过氧苯甲酸 、 三苯基膦 、 pyridinium chlorochromate 、 potassium hydroxide 、 lithium hydroxide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 异丙醇 、 苯 为溶剂， 反应 66.25h， 生成 (17R,18S)-dihydroxy-5Z,8Z,11Z,13E,15E-eicosapentaenoic acid
  参考文献：
  名称：

  通过钯催化将AcOH加到乙烯基环氧醇中来合成resolvin E3

  摘要：

  有效的消炎介质resolvin E3（RvE3）的（18 R）-和（18 S）-立体异构体是通过6 R，7 R-和6 R，7的碳酸盐的Wittig反应立体和对映选择性合成的S -dihydroxynona -2 E，4 E-二烯丙基，C12–C20部分，,盐对应于C1–C11部分。通过对3-（AcO）-6 R，7 R-或3-（AcO）-6 R，7 S-（二羟基碳酸酯）-4-壬烯-1-醇进行Swern氧化制备立体异构碳酸盐。一锅中自发消除AcO基团 （6 R（18 R）-RvE3的，7 R）-（二羟基碳酸酯）-醇依次由9-（TBS-氧基）nona-4 Z，6 E -dien-3 R -ol的立体选择性环氧化提供与米-CPBA和随后的Pd-催化加入AcOH到所得的顺式乙烯基环氧醇随后碳酸盐形成的VIC-SYN二醇和脱甲硅烷基TBS。合成乙烯基环氧醇的Mitsunobu转化反应得到反异构体，将其转变为3-（AcO）-6

  DOI：

  10.1039/c8ob03196g

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：US11020406B2

  公开（公告）日：2021-06-01

  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。
• Compositions and methods relating to salts of specialized pro-resolving mediators
  申请人：Thetis Pharmaceuticals LLC

  公开号：US11135298B2

  公开（公告）日：2021-10-05

  The present invention relates to compounds of Formulas I-IV and compositions comprising same, including pharmaceutical compositions. The compounds of Formulas I-IV represent new salt forms of specialized pro-resolving mediators (“SPMs”) which include lipoxins, resolvins, protectins, and their aspirin-triggered counterparts. The SPM salts described here contain at least one or two SPM molecules ionically bound to at least one basic function that is provided by a scaffold as described in Formulas I-IV. Also provided are methods for pharmaceutical and non-pharmaceutical uses of such compounds and compositions describing same.

  本发明涉及式 I-IV 的化合物和包含这些化合物的组合物，包括药物组合物。式 I-IV 的化合物代表了特异性促溶解介质（"SPMs"）的新盐形式，其中包括脂质素、溶血素、保护素及其阿司匹林触发的对应物。这里描述的 SPM 盐包含至少一个或两个 SPM 分子，它们与至少一个基本功能离子结合，该基本功能由式 I-IV 所述的支架提供。此外，还提供了此类化合物的制药和非制药用途方法，以及描述此类化合物的组合物。
• Total syntheses of four possible stereoisomers of resolvin E3
  作者：Daisuke Urabe、Hidenori Todoroki、Koji Masuda、Masayuki Inoue

  DOI：10.1016/j.tet.2012.02.045

  日期：2012.4

  Resolvin E3, 17,18-dihydroxy-5Z,8Z,11Z,13E,15E-eicosapentaenoic acid, is a potent anti-inflammatory lipid mediator. To determine the stereochemistries of the C17- and C18-hydroxy groups of resolvin E3 and to supply a sufficient amount of material for future biological studies, we developed a highly convergent and practical route to its four possible stereoisomers. The key reactions employed here were the Horner-Wadsworth-Emmons coupling, the two copper(I)-mediated reactions between the alkynes and the propargyl tosylates, and the simultaneous reduction of the three triple bonds to the three Z-olefins. (C) 2012 Elsevier Ltd. All rights reserved.
• COMPOSITIONS AND METHODS RELATING TO SALTS OF SPECIALIZED PRO-RESOLVING MEDIATORS
  申请人：Thetis Pharmaceuticals LLC

  公开号：US20180110751A1

  公开（公告）日：2018-04-26

  The present invention relates to compounds of Formulas I-IV, which are salts of special lipid mediators of inflammation, compositions containing same, and methods of using same in the treatment of various diseases and disorders characterized by chronic or excessive inflammation, or both.
• 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.