(E)-9-oxooctadec-10-enol | 1011286-75-1

• 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: (E)-9-oxooctadec-10-enol
• 英文别名: (E)-1-hydroxyoctadec-10-en-9-one
• CAS: 1011286-75-1
• 化学式: C₁₈H₃₄O₂
• 分子量: 282.467
• InChiKey: QHGSKKVKEKAREH-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-9-oxooctadec-10-enol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 1-羟基-9-十八烷酮
  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：

  油醇 在 manganese triacetate 叔丁基过氧化氢 、 3 A molecular sieve 作用下， 以 癸烷 、 乙酸乙酯 为溶剂， 生成 (E)-9-oxooctadec-10-enol 、 (E)-10-oxooctadec-8-enol 、 (E)-8-oxooctadec-9-enol 、 (E)-11-oxooctadec-9-enol
  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

文献信息

• 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.