(5S,12S)-二羟基-(6E,8E,10E,14Z)-二十碳四烯酸 | 71548-19-1

• 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: (5S,12S)-二羟基-(6E,8E,10E,14Z)-二十碳四烯酸
• 英文名称: (5S,12S)-6-trans-leukotriene B
• 英文别名: (5S,12S,6E,8E,10E,14Z)-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid；6-trans-12-epi-leukotriene B4；6-trans-12-epi-LTB₄；6E,8E,10E,14Z,5S,12S-diHETE；(5S,6E,8E,10E,12S,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
• CAS: 71548-19-1
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: VNYSSYRCGWBHLG-CTOJTRLNSA-N

物化性质

• 沸点：
  536.4±50.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：50 mg/ml； DMSO：50 mg/ml；乙醇：50 mg/ml； PBS pH 7.2：1 mg/ml
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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

安全信息

• 危险品标志：
  F,Xi
• 安全说明：
  S16,S26,S36
• 危险类别码：
  R11
• 危险品运输编号：
  UN 1170 3
• 储存条件：
  -20°C保存。

制备方法与用途

反式-12-表位白三烯B4是一种花生四烯酸的代谢产物，它具有显著的抗炎作用。

反应信息

• 作为产物：
  描述：

  在 lithium hydroxide 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 7.5h， 生成 (5S,12S)-二羟基-(6E,8E,10E,14Z)-二十碳四烯酸
  参考文献：
  名称：

  6-白三烯B的12-（）-和12- （）-形式的立体特异性全合成

  摘要：

  白三烯B（）的生物遗传前体白三烯A（）的非酶促水合除其他产品外，提供了两种2的非对映异构6-异构体，本文记录了它们的第一立体定向和有效合成。

  DOI：

  10.1016/s0040-4039(01)90384-3

文献信息

• Stabilized leukotriene B4 (LTB4) agent pharmaceutical formulation
  申请人：Borgeat Pierre

  公开号：US20060063837A1

  公开（公告）日：2006-03-23

  The present invention relates to a novel pharmaceutical formulation comprising an LTB4 agent at an alkaline pH effective to stabilize the LTB4 agent and provide a formulation with an increased shelf-life. The formulation of the present invention has an increased shelf-life of at least 24 months.

  本发明涉及一种新型药物制剂，该制剂包含一种LTB4制剂，其碱性pH值可有效稳定LTB4制剂，并提供一种保质期更长的制剂。本发明制剂的保质期至少延长了 24 个月。
• COX-2-dependent and -independent biosynthesis of dihydroxy-arachidonic acids in activated human leukocytes
  作者：Noemi Tejera、William E. Boeglin、Takashi Suzuki、Claus Schneider

  DOI：10.1194/jlr.m017822

  日期：2012.1

  Biosynthesis of 5,15-dihydroxyeicosatetraenoic acid (5,15-diHETE) in leukocytes involves consecutive oxygenation of arachidonic acid by 5-lipoxygenase (LOX) and 15-LOX in either order. Here, we analyzed the contribution of cyclooxygenase (COX)-2 to the biosynthesis of 5,15-di-HETE and 5,11-diHETE in isolated human leukocytes activated with lipopolysaccharide and calcium ionophore A23187. Transformation of arachidonic acid was initiated by 5-LOX providing 5S-HETE as a substrate for COX-2 forming 5S,15S-diHETE, 5S,15R-diHETE, and 5S,11R-di-HETE as shown by LC/MS and chiral phase HPLC analyses. The levels of 5,15-diHETE were 0.45 +/- 0.2 ng/10(6) cells (mean +/- SEM, n = 6), reaching about half the level of LTB(4) (1.3 +/- 0.5 ng/10(6) cells, n = 6). The COX-2 specific inhibitor NS-398 reduced the levels of 5,15-diHETE to below 0.02 ng/10(6) cells in four of six samples. Similar reduction was achieved by MK-886, an inhibitor of 5-LOX activating protein but the above differences were not statistically significant. Aspirin treatment of the activated cells allowed formation of 5,15-diHETE (0.1 +/- 0.05 ng/10(6) cells, n = 6) but, as expected, abolished formation of 5,11-diHETE. The mixture of activated cells also produced 5S,12S-diHETE with the unusual 6E,8Z,10E double bond configuration, implicating biosynthesis by 5-LOX and 12-LOX activity rather than by hydrolysis of the leukotriene A(4)-epoxide. Exogenous octadeuterated 5S-HETE and 15S-HETE were converted to 5,15-diHETE, implicating that multiple oxygenation pathways of arachidonic acid occur in activated leukocytes. The contribution of COX-2 to the biosynthesis of dihydroxylated derivatives of arachidonic acid provides evidence for functional coupling with 5-LOX in activated human leukocytes.-Tejera, N., W. E. Boeglin, T. Suzuki, and C. Schneider. COX-2-dependent and -independent biosynthesis of dihydroxy-arachidonic acids in activated human leukocytes. J. Lipid Res. 2012. 53: 87-94.
• Pathways for migration and cleavage of the S-peptide unit of the leukotrienes
  作者：E.J. Corey、Hunseung Oh、Alan E. Barton

  DOI：10.1016/s0040-4039(00)87643-1

  日期：1982.1
• TRUDELL, JAMES R.;GUT, JOSEF, FREE RADIC. BIOL. AND MED., 7,(1989) N, C. 275-284
  作者：TRUDELL, JAMES R.、GUT, JOSEF

  DOI：——

  日期：——
• STABILIZED LEUKOTRIENE B4 (LTB4) AGENT PHARMACEUTICAL
  申请人：LTB4 Sweden AB

  公开号：EP1796730A2

  公开（公告）日：2007-06-20