(±)-15-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid | 88852-33-9

• 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: (±)-15-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid
• 英文别名: 15-hydroxy-eicosa-5Z,8Z,11Z,13E,17Z-pentaenoic acid；15-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid；15-hydroxyeicosa-5Z,8Z,11Z,13E,17Z-pentaenoic acid；15-hydroxyeicosapentaenoic acid；hydroxyeicosapentaenoic acid；15-OHEPA；(+/-)-15-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid；(5Z,8Z,11Z,13E,17Z)-15-hydroxyicosa-5,8,11,13,17-pentaenoic acid
• CAS: 88852-33-9
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: WLKCSMCLEKGITB-XWJJKCKWSA-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)：
  4.5
• 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

• 储存条件：
  -20°C，密封保存，置于干燥处。

制备方法与用途

(±)-15-HEPE是由非酶促氧化作用从EPA生成的。

反应信息

• 作为产物：
  描述：

  全顺式二十碳五烯酸 在 soybean 15-lipoxygenase 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 (±)-15-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid
  参考文献：
  名称：

  Controlled formation of mono- and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase

  摘要：

  Resolvins and protectins are important anti-inflammatory and pro-resolution compounds derived from the enzymatic oxidation of omega-3 fatty acids all-cis-5,8,11,14,17-eicosapentaenoic acid (EPA) and all-cis-4,7,10,13,16,19-docosahexaenoic acid (DHA). We have developed a simple, controlled method to synthesize an array of resolvin and protectin analogs from fatty acid starting materials using soybean 15-lipoxygenase. The conditions were optimized for the production of both mono-and dihydroxy derivatives, with enzyme concentration and pH found to have a significant effect on the reaction products. The methods were applied to five biologically important omega-3 and omega-6 fatty acid substrates. Mono-and dihydroxy compounds were successfully synthesized from all substrates and the products were characterized by normal phase (NP) HPLC, GC-MS, TOF-MS, UV-visible (UV-vis) spectroscopy, and NMR spectroscopy. The methods could be further applied to any polyunsaturated fatty acids containing the cis-1,4,7,10-undecatetraene moiety to produce a range of novel compounds with potential biological activity.-Dobson, E. P., C. J. Barrow, J. A. Kralovec, and J. L. Adcock. Controlled formation of mono-and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase. J. Lipid Res. 2013. 54: 1439-1447.

  DOI：

  10.1194/jlr.m036186

文献信息

• NOVEL ANTI-INFLAMMATORY METABOLITE DERIVED FROM OMEGA-3-TYPE FATTY ACID
  申请人：Arita Makoto

  公开号：US20130274327A1

  公开（公告）日：2013-10-17

  The purpose is to provide a compound which can overcomes the disadvantages of conventional steroid drugs and NSAID. It is found that specific epoxy monohydroxy forms of eicosapentaenoic acid, docosahexaenoic acid and docosapentaenoic acid which are independently represented by formulae [chemical formula 1], [chemical formula 5] and the like have an inhibitory activity on neutrophils. This compound can inhibit the invasion of neutrophils into tissues and the activation of neutrophils which are observed in acute inflammations.
• COMPOSITIONS COMPRISING 15-HEPE AND/OR 15-HETrE AND METHODS OF TREATING OR PREVENTING CARDIOMETABOLIC DISEASE, METABOLIC SYNDROME, AND/OR RELATED DISEASES
  申请人：Afimmune Limited

  公开号：US20200360331A1

  公开（公告）日：2020-11-19

  The present disclosure relates to methods of treating or preventing metabolic syndrome and/or cardiometabolic disease by administration of 15-HEPE, 15-HETrE, or compositions thereof.
• COMPOSITIONS COMPRISING 15-HEPE AND METHODS OF TREATING OR PREVENTING HEMATOLOGIC DISORDERS, AND/OR RELATED DISEASES
  申请人：Afimmune Limited

  公开号：US20210315851A1

  公开（公告）日：2021-10-14

  The present disclosure relates to methods of treating or preventing hematologic disorders by administration of 15-HEPE or compositions thereof.
• Methods for Predicting Patient Response to DMARDs
  申请人：Queen Mary University of London

  公开号：US20220349886A1

  公开（公告）日：2022-11-03

  The present invention provides a method for predicting whether a patient having, suspected of having, or at risk of developing an inflammatory condition will respond to treatment with a disease-modifying antirheumatic drug (DMARD) comprising measuring the level of at least one specialized pro-resolving mediator (SPM) in a DMARD naïve patient sample and classifying the patient as a predicted DMARD responder or a predicted DMARD non-responder. The present invention also provides a method of assessing the efficacy of a disease-modifying antirheumatic drug (DMARD) for use in the treatment of an inflammatory condition in a patient. The present invention also provides a method of predicting which rheumatoid arthritis pathotype a patient having, suspected of having, or at risk of developing rheumatoid arthritis will develop.
• US9238634B2
  申请人：——

  公开号：US9238634B2

  公开（公告）日：2016-01-19