顺式8-十八碳烯酸 | 5684-71-9

• 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: 顺式8-十八碳烯酸
• 英文名称: (8Z)-octadec-8-enoic acid
• 英文别名: cis-octadec-8-enoic acid；oleic acid；octadec-8c-enoic acid；Octadec-8c-ensaeure；8c-Octadecensaeure；8-Oelsaeure；cis-8-Octadecenoic acid；(Z)-octadec-8-enoic acid
• CAS: 5684-71-9
• 化学式: C₁₈H₃₄O₂
• 分子量: 282.467
• InChiKey: WRIDQFICGBMAFQ-KHPPLWFESA-N

物化性质

• 沸点：
  403.7±24.0 °C(Predicted)
• 密度：
  0.899±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：30mg/mL； DMSO：30mg/mL；乙醇：30mg/mL；乙醇:PBS (pH 7.2) (1:1): 0.25 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 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：

  顺式8-十八碳烯酸 在 ammonium hydroxide 、 草酰氯 作用下， 生成 cis-8,9-octadecenamide
  参考文献：
  名称：

  Structure Determination of an Endogenous Sleep-Inducing Lipid, cis-9-Octadecenamide (Oleamide):  A Synthetic Approach to the Chemical Analysis of Trace Quantities of a Natural Product

  摘要：

  The pursuit of endogenous sleep-inducing substances has been the focus of an extensive, complicated body of research. Several compounds, including Delta-sleep-inducing peptide and prostaglandin D-2, have been suggested to play a role in sleep induction, and yet, the molecular mechanisms of this physiological process remain largely unknown. In recent efforts, the cerebrospinal fluid of deep-deprived cats was analyzed in search of compounds that accumulated during sleep deprivation. An agent with the chemical formula C18H35NO was found to cycle with sleep-wake patterns, increasing in concentration with sleep deprivation and decreasing in amount upon recovery sleep. Since the material was generated in minute quantities and only under the special conditions of sleep deprivation, efforts to isolate sufficient material for adequate characterization, structure identification, and subsequent detailed evaluation of its properties proved unrealistic. With the trace amounts of the impure endogenous compound available, extensive MS studies on the agent were completed, revealing key structural features of the molecule including two degrees of unsaturation, a long alkyl chain, and a nitrogen substituent capable of fragmenting as ammonia. Additionally, HPLC traces suggested a weak UV absorbance for the unknown material. With this data in hand and encouraged by the relatively small size of the molecule, MW = 281, a synthetic approach toward the structural identification of the natural compound was initiated. Herein, we report the full details of the synthesis and comparative characterization of candidate structures for this endogenous agent that led to the unambiguous structural correlation with synthetic cis-9-octadecenamide.

  DOI：

  10.1021/ja9532345
• 作为产物：
  描述：

  ethyl 8-oxo-octanoate 在 水 、 sodium hexamethyldisilazane 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 顺式8-十八碳烯酸
  参考文献：
  名称：

  Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2

  摘要：

  It has been demonstrated previously that the endogenous compound N-arachidonyl-glycine inhibits the glycine transporter GlyT2, stimulates glycinergic neurotransmission, and provides analgesia in animal models of neuropathic and inflammatory pain. However, it is a relatively weak inhibitor with an IC50, of 9 mu M and is subject to oxidation via cyclooxygenase, limiting its therapeutic value. In this paper we describe the synthesis and testing of a novel series of monounsaturated C18 and C16 acyl-glycine molecules as inhibitors of the glycine transporter GIyT2. We demonstrate that they are up to 28 fold more potent that N-arachidonyl-glycine with no activity at the closely related GlyT1 transporter at concentrations up to 30 mu M. This novel class of compounds show considerable promise as a first generation of GIyT2 transport inhibitors.

  DOI：

  10.1021/acschemneuro.7b00105

文献信息

• Biochemical Characterization of the Oxygenation of Unsaturated Fatty Acids by the Dioxygenase and Hydroperoxide Isomerase of Pseudomonas aeruginosa 42A2
  作者：Eriel Martínez、Mats Hamberg、Montse Busquets、Pilar Díaz、Angeles Manresa、Ernst H. Oliw

  DOI：10.1074/jbc.m109.078147

  日期：2010.3

  hydrogen at C-8 was lost in the biosynthesis of (10S)-HPODE, whereas the pro-S hydrogen was lost and the pro-R hydrogen was retained at C-7 during biosynthesis of the 7,10-dihydroxy metabolites. Analysis of the fatty acid composition of P. aeruginosa revealed relatively large amounts of (9E/Z)-16:1 and (11E/Z)-18:1 and only traces of 18:1n-9. We found that (11Z)-18:1 (vaccenic acid) was transformed to (11S

  我们研究了铜绿假单胞菌 42A2 细胞提取物对脂肪酸的氧化作用。油酸（(9Z)-18:1）转化为（10S）-氢过氧-（8E）-十八碳烯酸（（10S）-HPOME）和（7S，10S）-二羟基-（8E）-十八碳烯酸（ 7,10-DiHOME)。在oxy-18下的实验表明，7,10-DiHOME含有空气中的氧，并且由(10S)-HPOME通过异构化顺序形成。 (10R)-HPOME 未异构化。 (10S)-双加氧酶和氢过氧化物异构酶活性在离子交换色谱和凝胶过滤上共洗脱，表观分子大小约为 50 kDa。 16:1n-7、18:2n-6和20:1n-11也被氧化成7,10-二羟基脂肪酸，(8Z)-18:1被氧化成6,9-二羟基-(7E) -十八碳烯酸。一系列双键位置更靠近（(6Z)-18:1、(5Z,9Z)-18:2）或更远离羧基的脂肪酸（(11Z)-、(13Z)-和(15Z)-18:1) 是较差的
• OXIDIZED AND MALEATED DERIVATIVE COMPOSITIONS
  申请人：Hurd Phillip W.

  公开号：US20090194731A1

  公开（公告）日：2009-08-06

  Oxidized and maleated derivative compositions, such as chemically modified oxidized and maleated tall oil fatty acid compositions, can be prepared and used in a variety of industrial applications, including as emulsifiers, corrosion inhibitors, concrete admixtures, and in reverse flotation mining applications.

  氧化和马来化衍生物组合物，例如经化学改性的氧化和马来化松香油脂酸组合物，可以制备并用于各种工业应用，包括作为乳化剂、防腐剂、混凝土外加剂，以及逆浮选矿业应用中。
• Introduction of a Fixed-Charge, Photolabile Derivative for Enhanced Structural Elucidation of Fatty Acids
  作者：Venkateswara R. Narreddula、Nathan R. Boase、Ramesh Ailuri、David L. Marshall、Berwyck L.J. Poad、Michael J. Kelso、Adam J. Trevitt、Todd W. Mitchell、Stephen J. Blanksby

  DOI：10.1021/acs.analchem.9b01566

  日期：2019.8.6

  enyl)pyridin-1-ium (3-I-AMPP+) derivatives reveal structurally diagnostic product ions. These spectra feature radical-directed dissociation of the carbon–carbon bonds within the fatty acyl chain, enabling structural assignments of fatty acids and discrimination of isomers that differ in site(s) of unsaturation, methyl branching or cyclopropanation. These derivatives are shown to be suitable for hyphenated

  脂肪酸是具有多种生化功能的脂质在结构上的多样性，包括其作为更复杂脂质（例如甘油磷脂和三酰基甘油）的结构单元的作用。脂肪酸的分析越来越多地使用液相色谱-质谱法（LC-MS）进行，这是因为它具有广泛的浓度范围以及分子结构和质量的多样性，可以检测脂质。先前的工作表明，固定电荷的吡啶鎓衍生物可有效增强LC-MS工作流程中脂肪酸的检测。在这里，我们描述了两种新型的吡啶鎓固定电荷衍生化试剂的开发，这些试剂结合了光不稳定的芳基碘，该芳基碘被质谱仪内部的激光辐照选择性激活。+）和1-（4-（氨基甲基）-3-碘苯基）吡啶-1-鎓（3-I-AMPP +）衍生物揭示了结构诊断产物离子。这些光谱的特征是脂肪酰基链中碳-碳键的自由基定向解离，使脂肪酸的结构分配和对不饱和，甲基支化或环丙烷化位点不同的异构体的区分成为可能。这些衍生物被证明适用于联用LC-MS方法，其可预测的光解离行为使得可以从生物学角度重新鉴定不寻常的脂肪酸。
• [EN] NOVEL GLYCINE TRANSPORT INHIBITORS FOR THE TREATMENT OF PAIN<br/>[FR] NOUVEAUX INHIBITEURS DE TRANSPORT DE GLYCINE POUR LE TRAITEMENT DE LA DOULEUR
  申请人：UNIV SYDNEY

  公开号：WO2018132876A1

  公开（公告）日：2018-07-26

  The present invention relates to novel glycine transport inhibitor compounds and their use for treating pain.

  本发明涉及新型甘氨酸转运抑制剂化合物及其用于治疗疼痛的用途。
• Method of making coated articles
  申请人：THE SECANT GROUP, LLC

  公开号：US10329448B2

  公开（公告）日：2019-06-25

  A method of preparing a coated article includes providing an article and coating a surface of the article with a polymeric composition comprising poly(glycerol sebacate). In some embodiments, the composition is a poly(glycerol sebacate) copolymer.

  制备涂层制品的方法包括提供一种制品，并用包含聚（甘油癸二酸酯）的聚合物组合物涂覆该制品的表面。在某些实施例中，该组合物是一种聚（甘油癸二酸酯）共聚物。