(±)-5,6-dihydroxy-8Z,11Z,14Z,17Z-eicosatetraenoic acid | 845673-97-4

• 物质功能分类: 生物化工 - 生化试剂
• 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: (±)-5,6-dihydroxy-8Z,11Z,14Z,17Z-eicosatetraenoic acid
• 英文别名: 5,6-DiHETE；(8Z,11Z,14Z,17Z)-5,6-dihydroxyicosa-8,11,14,17-tetraenoic acid
• CAS: 845673-97-4
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: VPXVODYVPILPRC-LTKCOYKYSA-N

物化性质

• 沸点：
  515.8±50.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：30mg/mL； DMSO：30mg/mL；乙醇：30mg/mL； PBS（pH 7.2）：0.5 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (±)-5,6-dihydroxy-8Z,11Z,14Z,17Z-eicosatetraenoic acid 在 sodium periodate 、 甲醇 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以63%的产率得到(3Z,6Z,9Z,12Z)-pentadeca-3,6,9,12-tetraen-1-ol
  参考文献：
  名称：

  [EN] FATTY ACID DERIVATIVES FOR TREATING NON-ALCOHOLIC STEATOHEPATITIS
  [FR] DÉRIVÉS D'ACIDE GRAS POUR LE TRAITEMENT DE LA STÉATOHÉPATITE NON ALCOOLIQUE

  摘要：

  本公开提供了一种用于治疗和/或预防非酒精性脂肪肝炎（NASH）和/或酒精性脂肪肝炎（ASH）的化合物。根据本发明使用的化合物是一种在β位含有氧原子的不饱和脂肪酸，并且还包含一个α-取代基。更具体地说，本发明提供了一种用于治疗NASH和/或ASH的化合物以及使用该方法，其中该化合物是公式（II），其中R1、R2、R3、X和Y如说明书中所定义；并且该化合物可以单独使用或与另一种活性剂结合使用。

  公开号：

  WO2019111048A1
• 作为产物：
  描述：

  6-[(3Z,6Z,9Z,12Z)-1-iodopentadeca-3,6,9,12-tetraen-1-yl]-tetrahydro-2H-pyran-2-one 在 lithium hydroxide monohydrate 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 以99%的产率得到(±)-5,6-dihydroxy-8Z,11Z,14Z,17Z-eicosatetraenoic acid
  参考文献：
  名称：

  Synthesis of All-Z-1,6,9,12,15-Octadecapenten-3-one, A Vinyl Ketone Polyunsaturated Marine Natural Product Isolated from Callysponga sp.

  摘要：

  海洋天然产物 1,6Z,9Z,12Z,15Z-octadecapentaen-3-one (1) 的合成是通过两种不同的路线从二十碳五烯酸 (EPA) 和二十二碳六烯酸 (DHA) 乙酯开始合成的，分别。使用EPA乙酯作为起始原料，以17%的总产率获得多不饱和乙烯基酮脂质1。

  DOI：

  10.3390/molecules19033804

文献信息

• [EN] FATTY ACID DERIVATIVES FOR TREATING NON-ALCOHOLIC STEATOHEPATITIS<br/>[FR] DÉRIVÉS D'ACIDE GRAS POUR LE TRAITEMENT DE LA STÉATOHÉPATITE NON ALCOOLIQUE
  申请人：BASF AS

  公开号：WO2019111048A1

  公开（公告）日：2019-06-13

  The present disclosure provides a compound for use in therapeutic and/or prophylactic treatment of non-alcoholic steatohepatitis (NASH) and/or alcoholic steatohepatitis (ASH). The compound for use according to the invention, is an unsaturated fatty acid with an oxygen incorporated in the β-position, and further comprising an α-substituent. More particularly, the invention provides a compound for use in treatment of NASH and/or ASH, and a method using this, wherein the compound is of Formula (II), wherein R1, R2, R3, X, and Y are as defined in the specification; and wherein this compound may be administered alone or in combination with an additional active agent.

  本公开提供了一种用于治疗和/或预防非酒精性脂肪肝炎（NASH）和/或酒精性脂肪肝炎（ASH）的化合物。根据本发明使用的化合物是一种在β位含有氧原子的不饱和脂肪酸，并且还包含一个α-取代基。更具体地说，本发明提供了一种用于治疗NASH和/或ASH的化合物以及使用该方法，其中该化合物是公式（II），其中R1、R2、R3、X和Y如说明书中所定义；并且该化合物可以单独使用或与另一种活性剂结合使用。
• Syntheses of some polyunsaturated trifluoromethyl ketones as potential phospholipase A2 inhibitors
  作者：Anne Kristin Holmeide、Lars Skattebøl

  DOI：10.1039/b001944p

  日期：——

  Starting from (all-Z)-icosa-5,8,11,14,17-pentaenoic acid [(all-Z)-eicosa-5,8,11,14,17-pentaenoic acid, EPA] and (all-Z)-docosa-4,7,10,13,16,19-hexaenoic acid (DHA) several trifluoromethyl ketones, containing sulfur or oxygen atoms at the β-position, have been synthesized as potential inhibitors of cytosolic phospholipase A2. As part of this work EPA and DHA have been oxidatively degraded to (all-Z)-pentadeca-3,6,9,12-tetraenal and (all-Z)-octadeca-3,6,9,12,15-pentaenal, respectively, in 75% overall yields.

  从（全-Z）-5,8,11,14,17-二十碳五烯酸[（全-Z）-5,8,11,14,17-二十碳五烯酸，EPA]和（全-Z）-4,7,10,13,16,19-二十二碳六烯酸（DHA）出发，已经合成了几种含有硫或氧原子在β位的三氟甲基酮，这些化合物被认为是细胞质磷脂酶A2的潜在抑制剂。作为这项工作的一部分，EPA和DHA分别被氧化降解为（全-Z）-3,6,9,12-十五碳四烯醛和（全-Z）-3,6,9,12,15-十八碳五烯醛，总产率均为75%。
• FATTY ACID DERIVATIVES FOR TREATING NON-ALCOHOLIC STEATOHEPATITIS
  申请人：BASF AS

  公开号：US20210177794A1

  公开（公告）日：2021-06-17

  The present disclosure provides a compound for use in therapeutic and/or prophylactic treatment of non-alcoholic steatohepatitis (NASH) and/or alcoholic steatohepatitis (ASH). The compound for use according to the invention, is an unsaturated fatty acid with an oxygen incorporated in the β-position, and further comprising an α-substituent. More particularly, the invention provides a compound for use in treatment of NASH and/or ASH, and a method using this, wherein the compound is of Formula (II), wherein RI, R2, R3, X, and Y are as defined in the specification; and wherein this compound may be administered alone or in combination with an additional active agent.
• BIOMARKERS FOR DETECTION OF CORONARY ARTERY DISEASE AND ITS MANAGEMENT
  申请人：Oregon State University

  公开号：US20210223269A1

  公开（公告）日：2021-07-22

  The present disclosure provides biomarkers for the detection of coronary artery disease. The biomarkers comprise oxylipins and the detection, identification, and quantification can provide a means to diagnose, prognose, and manage subject at risk for cardiovascular disease. Methods of also provided for the detection and quantification of the oxylipins, for treating, and for predicting the survival of a subject at high risk for coronary artery disease.
• 5,6-DIHETE LACTONE FOR TREATMENT OF MICROVASCULAR DYSFUNCTION
  申请人：MIGAL GALILEE RESEARCH INSTITUTE LTD.

  公开号：US20220241233A1

  公开（公告）日：2022-08-04

  The present invention provides 5,6 dihydroxyeicosatetraenoic acid (5,6-diHETE) lactone or a pharmaceutical composition comprising 5,6-diHETE lactone and a pharmaceutically acceptable carrier, and uses thereof for inducing vasodilation, for treating a disease, disorder or condition associated with microvascular dysfunction, or for preventing, or reducing the risk of, developing a cardiac condition associated with microvascular dysfunction.