methyl-(E)-8-oxooctadec-9-enoate | 91363-64-3

• 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: methyl-(E)-8-oxooctadec-9-enoate
• 英文别名: (9E)-8-oxo-9-octadecenoate methyl ester；methyl (E)-8-oxooctadec-9-enoate
• CAS: 91363-64-3
• 化学式: C₁₉H₃₄O₃
• 分子量: 310.477
• InChiKey: HORQKYODZYHRHA-NTCAYCPXSA-N

物化性质

• 沸点：
  402.1±28.0 °C(Predicted)
• 密度：
  0.922±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl-(E)-8-oxooctadec-9-enoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 methyl 8-oxooctadecanoate
  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：

  methyl (E)-8-hydroperoxyoctadec-9-enoate 生成 methyl-(E)-8-oxooctadec-9-enoate
  参考文献：
  名称：

  CAPELLA, P.;CABONI, M. F.;BONAGA, G.;LERCKER, G., RIV. ITAL. SOSTANZE GRASSE, 65,(1988) N0, C. 629-631

  摘要：

  DOI：

文献信息

• Design and Synthesis of Pro-Apoptotic Compounds Inspired by Diatom Oxylipins
  作者：Giovanna Romano、Emiliano Manzo、Gian Russo、Giuliana d'Ippolito、Adele Cutignano、Maria Russo、Angelo Fontana

  DOI：10.3390/md11114527

  日期：——

  Oxylipins are a large and diverse family of fatty acid derivatives exhibiting different levels of oxidation of the carbon chain. They are involved in many biological functions in mammals, plants and diatoms. In this last group of organisms, they are suggested to play a role in the reproductive failure of copepod predators, showing clear pro-apoptotic effects on newborn nauplii. In this work, these compounds were tested for the ability to induce mitotic arrest in sea urchin embryos. We show for the first time that oxylipins have an increased efficacy in their corresponding methylated form. Natural oxylipins were also used as an inspiration for the rational design and synthesis of stable chemical analogs with apoptotic activity against tumor cell lines. This approach led to the synthesis of the linear C15-ketol (22) that was shown to induce apoptosis in human leukemia U-937 cells. These results are proof of the concept of the use of eco-physiological considerations as a platform to guide the search for novel drug candidates.

  氧脂质是一大类多样的脂肪酸衍生物，具有不同程度的碳链氧化。它们参与哺乳动物、植物和硅藻等多种生物功能。在这最后一类生物中，氧脂质被认为在 copepod 捕食者的繁殖失效中起着作用，对新生的 nauplii 显示出明显的促凋亡效应。在这项工作中，测试了这些化合物对海胆胚胎诱导有丝分裂停滞的能力。我们首次显示，氧脂质在相应的甲基化形式下具有更高的效能。天然氧脂质也用于理性设计和合成具有针对肿瘤细胞系凋亡活性的稳定化学类似物。这一方法导致合成了线性 C15-酮醇（22），其已被证明能够诱导人类白血病 U-937 细胞的凋亡。这些结果证明了以生态生理学考虑为平台来指导新药候选物搜索的概念的有效性。
• CAPELLA, P.;CABONI, M. F.;BONAGA, G.;LERCKER, G., RIV. ITAL. SOSTANZE GRASSE, 65,(1988) N0, C. 629-631
  作者：CAPELLA, P.、CABONI, M. F.、BONAGA, G.、LERCKER, G.

  DOI：——

  日期：——
• US5869709A
  申请人：——

  公开号：US5869709A

  公开（公告）日：1999-02-09
• US6111118A
  申请人：——

  公开号：US6111118A

  公开（公告）日：2000-08-29
• US6384251B1
  申请人：——

  公开号：US6384251B1

  公开（公告）日：2002-05-07