(5Z,8Z,11Z,13E)-(R)-15-Hydroxy-icosa-5,8,11,13-tetraenoic acid methyl ester | 118013-72-2

• 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: (5Z,8Z,11Z,13E)-(R)-15-Hydroxy-icosa-5,8,11,13-tetraenoic acid methyl ester
• CAS: 118013-72-2
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: ZGQAWLCSJFHXDF-TXCHIZOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  24.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5Z,8Z,11Z,13E)-(R)-15-Hydroxy-icosa-5,8,11,13-tetraenoic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 15(R)-HETE
  参考文献：
  名称：

  立体控制的（5 Z，8 Z 11 Z，13 E）（15 S）-15-hydroxyeicosa-5,8,11,13-丁烯酸（15 S -HETE）及其类似物的全合成

  摘要：

  描述了一种新颖且立体选择性的15 S -HETE和许多基于Cu I -Pd 0偶联反应的类似物的合成方法。

  DOI：

  10.1039/c39850001580
• 作为产物：
  描述：

  (5Z,8Z,11Z,13E)-(R)-15-(tert-Butyl-dimethyl-silanyloxy)-icosa-5,8,11,13-tetraenoic acid methyl ester 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 (5Z,8Z,11Z,13E)-(R)-15-Hydroxy-icosa-5,8,11,13-tetraenoic acid methyl ester
  参考文献：
  名称：

  立体控制的（5 Z，8 Z 11 Z，13 E）（15 S）-15-hydroxyeicosa-5,8,11,13-丁烯酸（15 S -HETE）及其类似物的全合成

  摘要：

  描述了一种新颖且立体选择性的15 S -HETE和许多基于Cu I -Pd 0偶联反应的类似物的合成方法。

  DOI：

  10.1039/c39850001580

文献信息

• Identification and absolute configuration of dihydroxy-arachidonic acids formed by oxygenation of 5S-HETE by native and aspirin-acetylated COX-2
  作者：Surafel Mulugeta、Takashi Suzuki、Noemi Tejera Hernandez、Markus Griesser、William E. Boeglin、Claus Schneider

  DOI：10.1194/jlr.m001719

  日期：2010.3

  Biosynthesis of the prostaglandin endoperoxide by the cyclooxygenase (COX) enzymes is accompanied by formation of a small amount of 11R-hydroxyeicosatetraenoic acid (HETE), 15R-HETE, and 15S-HETE as by-products. Acetylation of COX-2 by aspirin abrogates prostaglandin synthesis and triggers formation of 15R-HETE as the sole product of oxygenation of arachidonic acid. Here, we investigated the formation of by-products of the transformation of 5S-HETE by native COX-2 and by aspirin-acetylated COX-2 using HPLC-ultraviolet, GC-MS, and LC-MS analysis. 5S,15S- dihydroxy (di)HETE, 5S,15R-diHETE, and 5S,11R-diHETE were identified as by-products of native COX-2, in addition to the previously described di-endoperoxide (5S,15S-dihydroxy-9S,11R,8S,12S-diperoxy-6E,13E-eicosadienoic acid) as the major oxygenation product. 5S,15R-diHETE was the only product formed by aspirin-acetylated COX-2. Both 5,15-diHETE and 5,11-diHETE were detected in CT26 mouse colon carcinoma cells as well as in lipopolysaccharide-activated RAW264.7 cells incubated with 5S-HETE, and their formation was attenuated in the presence of the COX-2 specific inhibitor, NS-398. Aspirin-treated CT26 cells gave 5,15-diHETE as the most prominent product formed from 5S-HETE. 5S,15S-diHETE has been described as a product of the cross-over of 5-lipoxygenase (5-LOX) and 15-LOX activities in elicited rat mononuclear cells and human leukocytes, and our studies implicate crossover of the 5-LOX and COX-2 pathways as an additional bio-synthetic route.-Mulugeta, S., T. Suzuki, N. T. Hernandez, M. Griesser, W. E. Boeglin, and C. Schneider. Identification and absolute configuration of dihydroxy-arachidonic acids formed by oxygenation of 5S-HETE by native and aspirin-acetylated COX-2. J. Lipid Res. 2010. 51: 575-585.