(E)-8-氧代十八碳-9-烯酸 | 99640-10-5

• 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: (E)-8-氧代十八碳-9-烯酸
• 英文名称: trans-8-oxooctadec-9-enoic acid
• 英文别名: (9E)-8-oxo-9-octadecenoic acid；(E)-8-oxooctadec-9-enoic acid；8-oxo-9(E)-octadecenoic acid；8-oxooctadec-9(E)-enoic acid；9-octadecenoic acid, 8-oxo-, (9E)-
• CAS: 99640-10-5
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: PHIXKQDGLSTYQU-SDNWHVSQSA-N

物化性质

• 沸点：
  438.5±28.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-8-氧代十八碳-9-烯酸 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 8-oxooctadecanoic acid
  参考文献：
  名称：

  Anti-inflammatory Constituents of the Red Alga Gracilaria verrucosa and Their Synthetic Analogues

  摘要：

  A chemical study on the anti-inflammatory components of the red alga Gracilaria verrucosa led to the isolation of new 11 -deoxyprostaglandins (1-4), a ceramide (5), and a C-16 keto fatty acid (6), along with known oxygenated fatty acids (7-14). Their structures were elucidated on the basis of NMR and MS data. The absolute configurations of compounds 1-5 were determined by Mosher's method. The anti-inflammatory activity of the isolated compounds (1-14) was evaluated by determining their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-alpha) in lipopolysaccharide (LPS)-activated RAW 264.7 murine macrophage cells. Compounds 9 and 10 exhibited the most potent activity. In the evaluation of these two compounds and derivatized analogues (15-40), the anti-inflammatory activity was enhanced in some synthetic analogues. These enone fatty acids were investigated as potential anti-inflammatory leads for the first time.

  DOI：

  10.1021/np070452q
• 作为产物：
  描述：

  (E)-8-Oxo-octadec-9-enoic acid ethyl ester 在 phosphate buffer 、 lipase from Pseudomonas sp 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以68%的产率得到(E)-8-氧代十八碳-9-烯酸
  参考文献：
  名称：

  Aldehyde Dehydrogenase Inhibitors from the Mushroom Clitocybe clavipes

  摘要：

  Five fatty acid derivatives including three novel compounds were isolated from the mushroom Clitocybe clavipe. Their structures were elucidated by spectral analyses. These compounds inhibited aldehyde dehydrogenase in vitro.

  DOI：

  10.1021/np020200j

文献信息

• Knothe, Gerhard; Bagby, Marvin O.; Weisleder, David, Journal of the Chemical Society. Perkin transactions II, 1994, # 7, p. 1661 - 1670
  作者：Knothe, Gerhard、Bagby, Marvin O.、Weisleder, David、Peterson, Robert E.

  DOI：——

  日期：——
• Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads
  作者：Hung The Dang、Gyeoung Jin Kang、Eun Sook Yoo、Jongki Hong、Jae Sue Choi、Hyung Sik Kim、Hae Young Chung、Jee H. Jung

  DOI：10.1016/j.bmc.2010.12.046

  日期：2011.2

  A series of endogenous fatty acid amides and their analogues (1-78) were prepared, and their inhibitory effects on pro-inflammatory mediators (NO, IL-1 beta, IL-6, and TNF-alpha) in LPS-activated RAW264.7 cells were evaluated. Their inhibitory activity on the pro-inflammatory chemokine MDC in IFN-gamma-activated HaCaT cells was also examined. The results showed that the activity is strongly dependent on the nature of the fatty acid part of the molecules. As expected, the amides derived from enone fatty acids showed significant activity and were more active than those derived from other types of fatty acids. A variation of the amine headgroup also altered bioactivity profile remarkably, possibly by modulating cell permeability. Regarding the amine part of the molecules, N-acyl dopamines exhibited the most potent activity (IC50 similar to 2 mu M). This is the first report of the inhibitory activity of endogenous fatty acid amides and their analogues on the production of nitric oxide, cytokines (IL-1 beta, IL-6, and TNF-alpha) and the chemokine MDC. This study suggests that the enone fatty acid-derived amides (such as N-acyl ethanolamines and N-acyl amino acids) and N-acyl dopamines may be potential anti-inflammatory leads. (C) 2010 Elsevier Ltd. All rights reserved.
• PORTER, NED A.;WUJEK, JACQUELINE SULLIVAN, J. ORG. CHEM., 52,(1987) N 23, 5085-5089
  作者：PORTER, NED A.、WUJEK, JACQUELINE SULLIVAN

  DOI：——

  日期：——
• Anti-inflammatory Constituents of the Red Alga <i>Gracilaria verrucosa</i> and Their Synthetic Analogues
  作者：Hung The Dang、Hye Ja Lee、Eun Sook Yoo、Pramod B. Shinde、Yoon Mi Lee、Jongki Hong、Dong Kyoo Kim、Jee H. Jung

  DOI：10.1021/np070452q

  日期：2008.2.1

  A chemical study on the anti-inflammatory components of the red alga Gracilaria verrucosa led to the isolation of new 11 -deoxyprostaglandins (1-4), a ceramide (5), and a C-16 keto fatty acid (6), along with known oxygenated fatty acids (7-14). Their structures were elucidated on the basis of NMR and MS data. The absolute configurations of compounds 1-5 were determined by Mosher's method. The anti-inflammatory activity of the isolated compounds (1-14) was evaluated by determining their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-alpha) in lipopolysaccharide (LPS)-activated RAW 264.7 murine macrophage cells. Compounds 9 and 10 exhibited the most potent activity. In the evaluation of these two compounds and derivatized analogues (15-40), the anti-inflammatory activity was enhanced in some synthetic analogues. These enone fatty acids were investigated as potential anti-inflammatory leads for the first time.
• Aldehyde Dehydrogenase Inhibitors from the Mushroom <i>Clitocybe </i><i>c</i><i>lavipes</i>
  作者：Hirokazu Kawagishi、Toshiyuki Miyazawa、Hiroko Kume、Yasushi Arimoto、Takahiro Inakuma

  DOI：10.1021/np020200j

  日期：2002.11.1

  Five fatty acid derivatives including three novel compounds were isolated from the mushroom Clitocybe clavipe. Their structures were elucidated by spectral analyses. These compounds inhibited aldehyde dehydrogenase in vitro.

表征谱图