8-(2-Furyl)octansaeure | 27609-57-0

• 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: 8-(2-Furyl)octansaeure
• 英文别名: 8-(2-furyl)octanoic Acid；8-(furan-2-yl)octanoic acid
• CAS: 27609-57-0
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: SXQRVQKQTIWUKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-(2-Furyl)octansaeure 在 硫酸 、 碳酸氢钠 作用下， 以 甲醇 、 ice-water 为溶剂， 生成 8-(2-Furyl)octansaeure-methylester
  参考文献：
  名称：

  8-(5-Formyl-2-furyl)-octanoic acid

  摘要：

  本发明涉及具有治疗价值的新型辛酸衍生物，以及制备它们的方法。

  公开号：

  US04009187A1
• 作为产物：
  描述：

  8-(2-furyl)octan-1-ol 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以78%的产率得到8-(2-Furyl)octansaeure
  参考文献：
  名称：

  新型生物活性磷脂：2-溶血磷脂酰胆碱（1）的花生四烯酸和亚油酸酯氧化产物的实用全合成。

  摘要：

  完成了九种新型磷脂的总合成，以简化对低密度脂蛋白中两种最丰富的多不饱和磷脂的2-溶血磷脂酰胆碱的花生四烯酸酯和亚油酸酯的氧化裂解后生成的化合物的鉴定和生物学测试。利用2-硫代呋喃作为4-氧代-2-丁烯酰基碳负离子等效物的有效通用合成提供了含有γ-酮-α，β-不饱和羰基官能团的磷脂。通过利用容易的顺式-反式异构化，可以将两种市售的顺式烯烃（2Z）-2-丁烯-1,4-二醇和2,5-二氢呋喃用作制备霍纳-沃兹沃思-埃蒙斯试剂4的原料。 -（二乙氧基磷酰基）-2E-丁烯醛，是合成2,4-二烯醛的重要组成部分。

  DOI：

  10.1021/jo0105383

文献信息

• NANOPARTICLE-BASED DELIVERY SYSTEM WITH OXIDIZED PHOSPHOLIPIDS AS TARGETING LIGANDS FOR THE PREVENTION, DIAGNOSIS AND TREATMENT OF ATHEROSCLEROSIS
  申请人：WANG Shu

  公开号：US20140287024A1

  公开（公告）日：2014-09-25

  Disclosed are nanoparticle-based medicine/nutrient delivery system that are coated or incorporated with oxidized phospholipids as targeting ligands. Such delivery systems can specifically target macrophages, which are determinant cells in the aortic wall for atherosclerotic lesion development, to significantly increase bioavailability and specificity for the prevention, diagnosis and treatment of atherosclerosis.

  揭示了一种基于纳米颗粒的医药/营养素传递系统，其涂有或包含氧化磷脂作为靶向配体。这样的传递系统可以特异性地靶向巨噬细胞，它们是动脉壁上动脉粥样硬化病变发展的决定性细胞，从而显着增加生物利用度和特异性，用于预防、诊断和治疗动脉粥样硬化。
• Kern, Werner; Spiteller, Gerhard, Liebigs Annalen der Chemie, 1985, # 5, p. 1168 - 1174
  作者：Kern, Werner、Spiteller, Gerhard

  DOI：——

  日期：——
• Total Syntheses of Bioactive Oxidized Ethanolamine Phospholipids
  作者：Bogdan G. Gugiu、Robert G. Salomon

  DOI：10.1021/ol034729z

  日期：2003.8.1

  GraphicsTruncated ethanolamine phospholipids containing aldehyde functionality, e.g. OVPE, and the corresponding acids, are generated by oxidative cleavage of polyunsaturated phospholipids. To confirm their identities and facilitate studies of the chemistry and biological actions of these analogues of biologically active phosphatidylcholines, e.g. OVPC, total syntheses were developed. An efficient general strategy was used that features selective N-protection of 2-lysophosphatidylethanolamine, and generation of the target compounds by mild deprotection of stable precursors.
• Gruber, Chemische Berichte, 1955, vol. 88, p. 178,184
  作者：Gruber

  DOI：——

  日期：——
• An ¹O₂ Route to γ-Hydroxyalkenal Phospholipids by Vitamin E-Induced Fragmentation of Hydroperoxydiene-Derived Endoperoxides
  作者：Xiaodong Gu、Wujuan Zhang、Jaewoo Choi、Wei Li、Xi Chen、James M. Laird、Robert G. Salomon

  DOI：10.1021/tx200093m

  日期：2011.7.18

  Biologically active phospholipids that incorporate an oxidatively truncated acyl chain terminated by a gamma-hydroxyalkenal are generated in vivo. The gamma-hydroxyalkenal moiety protrudes from lipid bilayers like whiskers that serve as ligands for the scavenger receptor CD36, fostering endocytosis, e.g., of oxidatively damaged photoreceptor cell outer segments by retinal pigmented endothelial cells. They also covalently modify proteins generating carboxyalkyl pyrroles incorporating the E-amino group of protein lysyl residues. We postulated that gamma-hydroxyalkenals could be generated, e.g., in the eye, through fragmentation of hydroperoxy endoperoxides produced in the retina through reactions of singlet molecular oxygen with polyunsaturated phospholipids. Since phospholipid esters are far more abundant in the retina than free fatty acids, we examined the influence of a membrane environment on the fate of hydroperoxy endoperoxides. We now report that linoleate hydroperoxy endoperoxides in thin films and their phospholipid esters in biomimetic membranes fragment to gamma-hydroxyalkenals, and fragmentation is stoichiometrically induced by vitamin E. The product distribution from fragmentation of the free acid in the homogeneous environment of a thin film is remarkably different from that from the corresponding phospholipid in a membrane. In the membrane, further oxidation of the initially formed gamma-hydroxyalkenal to a butenolide is disfavored. A conformational preference for the gamma-hydroxyalkenal, to protrude from the membrane into the aqueous phase, may protect it from oxidation induced by lipid hydroperoxides that remain buried in the lipophilic membrane core.