8-(5-己基-2-呋喃基)辛酸 | 4179-44-6

• 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: 8-(5-己基-2-呋喃基)辛酸
• 英文名称: 9,12-epoxy-9,11-octadecadienoic acid
• 英文别名: 8-(5-Hexylfuran-2-yl)octanoic acid
• CAS: 4179-44-6
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: SZNVIDWMWMWUCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 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-(5-己基-2-呋喃基)辛酸 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 9,12-二氧代十八烷酸
  参考文献：
  名称：

  Buchta,E.; Huhn,C., Justus Liebigs Annalen der Chemie, 1965, vol. 686, p. 77 - 87

  摘要：

  DOI：

文献信息

• Hydroxyl Radical Scavenging Activity of Naturally Occurring Furan Fatty Acids.
  作者：Youji OKADA、Michikazu KANEKO、Haruo OKAJIMA

  DOI：10.1248/bpb.19.1607

  日期：——

  As a part of our work on the antioxidant properties of naturally occurring furan fatty acids (F acids), we evaluated their hydroxyl radical (HO·) scavenging activity by an electron spin resonance (ESR) spin trapping technique with 5, 5-dimethyl-1-pyrroline-N-oxide (DMPO). The additions of F acids to the incubation mixture of Fe2+-diethylenetriaminepentaacetic acid complex, H2O2 and DMPO decreased the intensity of the DMPO-OH adduct signal in a dose-dependent way. This decrease was not attributed to the destruction of DMPO-OH adduct by F acids. Kinetic competition studies indicated that the decrease in DMPO-OH signal intensity was mainly due to the competition of F acids with DMPO for HO·, and not to the inhibition of the HO· generation system itself.F acids were found to react rapidly with HO· at approximately a diffusion-controlled rate (1.7×1010M-1s-1).Comparison with the common HO· scavengers indicated that the rate constant of F acids is higher than those of mannitol and ethanol, and is compatible with those of histidine and dimethylsulfoxide, demonstrating that F acids are a potent HO· scavenger. It is suggested that F acids may serve as antioxidants in biological systems through their ability to scavenge HO·.

  作为我们研究天然呋喃脂肪酸（F酸）抗氧化性质的一部分，我们通过电子自旋共振（ESR）自捕获技术与5,5-二甲基-1-吡咯啉-N-氧化物（DMPO）评估了它们对羟基自由基（HO·）的清除活性。将F酸添加到含有Fe2+-二乙三胺五乙酸络合物、H2O2和DMPO的培养混合物中，以剂量依赖性方式降低了DMPO-OH加合物的信号强度。这种降低并非由于F酸破坏DMPO-OH加合物所致。动力学竞争研究表明，DMPO-OH信号强度的降低主要是因为F酸与DMPO对HO·的竞争，而不是对HO·生成系统本身的抑制。研究发现，F酸与HO·反应迅速，接近扩散控制速率（1.7×1010M-1s-1）。与常见的HO·清除剂相比，F酸的速率常数高于甘露醇和乙醇，并与组氨酸和二甲基亚砜相当，表明F酸是一种强效的HO·清除剂。建议F酸可能通过其清除HO·的能力在生物系统中作为抗氧化剂。
• PRODUCTION METHODS OF FURAN FATTY ACIDS
  申请人：KIM Hak ryul

  公开号：US20120302774A1

  公开（公告）日：2012-11-29

  Disclosed is a method for preparing a furan fatty acid, more particularly a method for preparing a furan fatty acid by heat-treating 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) in hexane. The present disclosure provides a simple method for producing 7,10-EODA from a dihydroxyl fatty acid precursor. Considering the difficulties in purifying natural furan fatty acids because of easy attack by peroxyl radicals and small quantity and the complicated multiple steps for chemical synthesis, the present disclosure provides a useful way to produce the biologically activity F-acid cost-effectively in large scale.

  本公开涉及一种制备呋喃脂肪酸的方法，更具体地说，是通过在己烷中热处理7,10-二羟基-8(E)-十八碳烯酸（DOD）来制备呋喃脂肪酸的方法。本公开提供了一种从二羟基脂肪酸前体中简单制备7,10-EODA的方法。考虑到天然呋喃脂肪酸易受过氧自由基攻击、数量较少且化学合成的多个步骤复杂，本公开提供了一种在大规模上经济实用地生产生物活性F酸的有用方法。
• Singlet oxygen quenching activity of furan fatty acids: Kinetic and thermodynamics study
  作者：Kensuke Seki、Youji Okada

  DOI：10.1002/aocs.12693

  日期：——

  We have undertaken a detailed study of the reactivity of furan fatty acids (F-acids) with singlet oxygen (1O2) produced by thermal decomposition of endoperoxide and photosensitizer reaction of rose bengal in ethanol. Accordingly, we measured the second order rate constant (kQ) for the reaction of F-acids with 1O2. As a result, the reactivity of F-acids against 1O2 exhibited a decrease in the order

  我们对呋喃脂肪酸 (F-acids) 与单线态氧 ( 1 O 2 ) 的反应性进行了详细研究，单线态氧 ( 1 O 2 ) 由内过氧化物的热分解和玫瑰红在乙醇中的光敏剂反应产生。因此，我们测量了 F-酸与1 O 2反应的二阶速率常数 ( k Q ) 。结果，F-酸对1 O 2的反应性按四烷基 F-酸 (F 3 ) > 三烷基 F-酸 (F 2) > 二烷基 F-酸 (NMF)。此外，我们还采用密度泛函理论 (DFT) 和量子化学计算来预测 F-酸与猝灭1 O 2相关的化学反应性、稳定性和热力学性质。因此，很明显，F 酸的 log k Q值与最高占据分子轨道 ( E HOMO )的能级相关，F 酸的 HOMO 可能与1的最低未占据分子轨道 (LUMO) 反应哦2。此外，F-酸与1 O 2的反应根据热力学方法计算，在乙醇中自发进行。这些结果表明，F-酸可能通过猝灭1 O 2有助于保护动物体内的氧化损伤。
• Improved processes for preparing 7-(2-hexyl-5-hydroxy-cyclopentyl)-heptanoic acid
  申请人：IBI- Istituto Biochimico Italiano Giovanni Lorenzini S.p.A.

  公开号：EP0155392A2

  公开（公告）日：1985-09-25

  The present invention concerns new processes for preparing the compound having prostanoic structure IBI-C83 [7-(2-hexyl-5-hydroxy-cyclopentyl)-heptanoic acid], with anti-ulcer action and of the pharmacologically acceptable salts thereof. Furthermore, some new intermediates are claimed, which are useful for preparing the compound ICI-C83.

  本发明涉及制备具有前列腺结构 IBI-C83 [7-(2-己基-5-羟基-环戊基)-庚酸]、具有抗溃疡作用的化合物及其药理上可接受的盐的新工艺。 此外，本发明还要求得到一些新的中间体，它们有助于制备化合物 ICI-C83。
• Process for the production of delta 5-unsaturated fatty acids in transgenic organisms
  申请人：BASF Plant Science GmbH

  公开号：EP1790731A2

  公开（公告）日：2007-05-30

  A process for the production of Δ5-unsaturated fatty acids in transgenic organisms comprises transforming an organism with nucleic acid encoding a Δ5-desaturase.

  一种在转基因生物体中生产Δ5-不饱和脂肪酸的工艺，包括用编码Δ5-去饱和酶的核酸转化生物体。