10-十九碳烯酸 | 73033-09-7

• 物质功能分类: 分析化学 - 食品安全 - 脂肪酸、脂肪酸甲酯
• 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: 10-十九碳烯酸
• 中文别名: 十九碳烯酸(顺-10)
• 英文名称: cis-10-nonadecenoic acid
• 英文别名: 10(Z)-nonadecenoic acid；(Z)-nonadec-10-enoic acid
• CAS: 73033-09-7
• 化学式: C₁₉H₃₆O₂
• 分子量: 296.494
• InChiKey: BBOWBNGUEWHNQZ-KTKRTIGZSA-N

物化性质

• 熔点：
  11-12 °C
• 沸点：
  184-186 °C(Press: 0.5 Torr)
• 密度：
  0.897±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：30mg/mL； DMSO：30mg/mL；乙醇：30mg/mL；乙醇:PBS (pH7.2) (1:7): 0.25 mg/ml
• 物理描述：
  Solid
• 保留指数：
  2256

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2916190090
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  -20°C

制备方法与用途

生物活性

10Z-Nonadecenoic 酸是一种具有抗肿瘤活性的长链脂肪酸，能够抑制 p53 活性。

目标分子

Human Endogenous Metabolite

体外研究

10Z-Nonadecenoic 酸不仅表现出抗肿瘤活性，还能抑制 p53 的活性。

反应信息

• 作为反应物：
  描述：

  10-十九碳烯酸 在 六甲基磷酰三胺 、 氧气 、 lithium diisopropyl amide 作用下， 生成 2-hydroxy-10(Z)-nonadecenoic acid
  参考文献：
  名称：

  Inhibition of Oleamide Hydrolase Catalyzed Hydrolysis of the Endogenous Sleep-Inducing Lipid cis-9-Octadecenamide

  摘要：

  Oleamide (1, cis-9-octadecenamide) is a naturally occurring brain constituent that. has been shown to accumulate and disappear under conditions of sleep deprivation and sleep recovery, respectively. Synthetic 1 has been found to induce sleep in a structurally specific manner at nanomolar quantities. Hydrolysis of 1 by an enzyme (oleamide hydrolase) present in the cell membrane rapidly degrades oleamide to oleic acid (cis-9-octadecenoic acid). Such observations suggest 1 may constitute a prototypical member of a class of fatty acid primary amide biological signaling molecules in which the diversity and selectivity of function are derived from the length of the alkane chain as well as the position, stereochemistry, and degree of unsaturation. A series of inhibitors of oleamide hydrolase were designed and prepared which were expected to derive their properties through interactions with the putative active site cysteine residue within oleamide hydrolase. This approach yielded a series of rapid, selective, and highly potent inhibitors (K-i = 13 mu M to 1 nM) which in addition to their potential therapeutic value may serve as useful tools to define the biological role of oleamide.

  DOI：

  10.1021/ja954064z
• 作为产物：
  描述：

  1,10-癸二醇 在 chromium(VI) oxide 、 硫酸 、 水 、 氢溴酸 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 丙酮 、 甲苯 为溶剂， 反应 77.0h， 生成 10-十九碳烯酸
  参考文献：
  名称：

  Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl-4(1H)-quinolones

  摘要：

  A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.060

文献信息

• Vanilloids. 1. Analogs of capsaicin with antinociceptive and antiinflammatory activity
  作者：John M. Janusz、Brian L. Buckwalter、Patricia A. Young、Thomas R. LaHann、Ralph W. Farmer、Gerald B. Kasting、Maurice E. Loomans、Gary A. Kerckaert、Cherie S. Maddin

  DOI：10.1021/jm00070a002

  日期：1993.9

  As part of a program to establish structure-activity relationships for vanilloids, analogs of the pungent principle capsaicin, the alkyl chain portion of the parent structure (and related compounds derived from homovanillic acid) was varied. In antinociceptive and antiinflammatory assays (rat and mouse hot plate and croton oil-inflamed mouse ear), compounds with widely varying alkyl chain structures

  作为建立香草醛的结构活性关系的程序的一部分，辛辣成分辣椒素的类似物，母体结构的烷基链部分（以及衍生自高香草酸的相关化合物）发生了变化。在抗伤害感受和抗炎试验（大鼠和小鼠热板以及巴豆油刺激的小鼠耳朵）中，具有广泛变化的烷基链结构的化合物具有活性。短链化合物在上述测定中通过全身给药具有活性，但它们保留了辣椒素的高刺激性和急性毒性特征。相比之下，长链顺式不饱和物NE-19550（香草基油酰胺）和NE-28345（油基单香草酰胺）具有口服活性，刺激性较低，并且比辣椒素的急性毒性小。
• Different roles for the acyl chain and the amine leaving group in the substrate selectivity of <i>N</i>-Acylethanolamine acid amidase
  作者：Andrea Ghidini、Laura Scalvini、Francesca Palese、Alessio Lodola、Marco Mor、Daniele Piomelli

  DOI：10.1080/14756366.2021.1912035

  日期：2021.1.1

  length is still lacking. In this report, we combined enzymatic and molecular modelling approaches to determine the effects of acyl chain and polar head modifications on substrate recognition and hydrolysis by NAAA. The results show that, in both saturated and monounsaturated FAEs, the catalytic efficiency is strictly dependent upon fatty acyl chain length, whereas there is a wider tolerance for modifications

  摘要 N-酰基乙醇胺酸酰胺酶 (NAAA) 是一种N-末端亲核试剂 (Ntn) 水解酶催化内源性镇痛和抗炎剂棕榈酰乙醇酰胺 (PEA) 的细胞内失活。NAAA 抑制剂可以抵消这一过程，并在疼痛、炎症和神经退行性疾病的动物模型中发挥显着的治疗作用。虽然已知 NAAA 优先水解饱和脂肪酸乙醇酰胺 (FAE)，但仍缺乏催化效率与脂肪酸链长度之间关系的详细概况。在本报告中，我们结合酶促和分子建模方法来确定酰基链和极性头部修饰对 NAAA 底物识别和水解的影响。结果表明，在饱和和单不饱和 FAE 中，催化效率严格取决于脂肪酰基链长，而对极头的修改有更广泛的容忍度。这种关系反映了酶-底物复合物在分子动力学模拟中的相对稳定性。
• 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] COMPOSITIONS AND METHODS OF DELIVERY OF DEUBIQUITINASE INHIBITORS<br/>[FR] COMPOSITIONS ET MÉTHODES D'ADMINISTRATION D'INHIBITEURS DE DÉUBIQUITINASE
  申请人：PHARMAKEA INC

  公开号：WO2015183987A1

  公开（公告）日：2015-12-03

  Described herein are compositions comprising deubiquitinase inhibitors in combination with albumin, methods of making such compositions, and methods of using such compositions in the treatment of conditions, diseases, or disorders that would benefit from inhibition of deubiquitinase activity.

  本文描述了含有去泛素化酶抑制剂与白蛋白组合的组合物，制备这种组合物的方法，以及利用这种组合物治疗需要抑制去泛素化酶活性的病症、疾病或紊乱的方法。
• Functional associative coatings for nanoparticles
  申请人：Hainfeld James F.

  公开号：US20080089836A1

  公开（公告）日：2008-04-17

  Described herein are nanoparticles that are coated with a bilayer of molecules formed from surface binding molecules and amphiphatic molecules. The bilayer coating self assembles on the nanoparticles from readily available materials/molecules. The modular design of the bilayer coated nanoparticles provides a means for readily and efficiently optimizing the properties of the bilayer coated nanoparticle compositions. Also described herein are uses of such nanoparticles in medicine, laboratory techniques, industrial and commerical applications.

  本文描述了一种纳米颗粒，其表面涂覆有由表面结合分子和两亲分子形成的双层分子层。该双层涂层可以自组装在纳米颗粒上，使用易得的材料/分子。双层涂层纳米颗粒的模块化设计提供了一种方便和高效地优化其性质的方法。此外，本文还描述了这种纳米颗粒在医学、实验室技术、工业和商业应用中的用途。