palmitoleoyl chloride | 40426-22-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酰卤
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: palmitoleoyl chloride
• 英文别名: (Z)-hexadec-9-enoyl chloride
• CAS: 40426-22-0
• 化学式: C₁₆H₂₉ClO
• 分子量: 272.859
• InChiKey: VZQFJZYVQNXVRY-FPLPWBNLSA-N

物化性质

• 沸点：
  347.2±21.0 °C(Predicted)
• 密度：
  0.925±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：10mg/mL； DMSO：10mg/mL；乙醇：10mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  3
• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  palmitoleoyl chloride 在 四氮唑 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 dibenzyl (4-((Z)-9-hexadecenoylamino)phenyl) phosphate
  参考文献：
  名称：

  Structure−Activity Relationships of Lysophosphatidic Acid:  Conformationally Restricted Backbone Mimetics

  摘要：

  Lysophosphatidic acid (LPA) has associated with it an intriguing cell biology that is thought to be mediated through its interaction with G-protein coupled receptor(s). In an effort to extend the structure-activity relationships of LPA, we have produced a series of LPA analogues in which the glycerol core in LPA was replaced with conformationally restricted aryl substructures. The aryl substructures encompassed aminophenol, resorcinol, dihydroxy benzophenone, and tocopherol systems. The benzophenone moiety was investigated both as a conformationally restricting substructure for LPA and as a possible photoreactive alkylating agent for the LPA receptor(s). All LPA analogues were evaluated for their potency and efficacy in mobilizing calcium ions from internal stores in MDA MB-231 cells. Ten of the 14 analogues exhibited activity in this assay at doses up to 5 mu M; none of the compounds exhibited nonreceptor-mediated lytic activity at this maximal concentration. The receptor response showed surprising tolerance for manipulation in the backbone region of LPA, although none of the compounds were equipotent to LPA. This tolerance for a variety of structures has given us new leads into the realization of novel agonists and antagonists of the LPA receptor(s).

  DOI：

  10.1021/jm970809v
• 作为产物：
  描述：

  (9Z)-9-十六碳烯-1-醇 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 草酰氯 、 三氧化硫吡啶 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 5.5h， 生成 palmitoleoyl chloride
  参考文献：
  名称：

  来自海洋玫瑰细菌群细菌的N-酰化氨基酸甲酯。

  摘要：

  玫瑰细菌群（Rhodobacteraceae）的细菌是许多海洋生态系统的重要成员。与其他革兰氏阴性细菌相似，许多玫瑰细菌都产生N-酰基高丝氨酸内酯（AHL），以通过群体感应系统进行通讯。AHL调节细胞分裂或抗生素产生等不同特征。也已经报道了相关的N-酰基丙氨酸甲酯（NAMEs），但到目前为止仅来自耐受性玫瑰茄。在筛选从大型藻类中分离出的各种玫瑰细菌时，我们遇到了四种菌株，即玫瑰酵母。D12_1.68，Loktanella sp.。产生名称新衍生物和类似物的F13，F14和D3，即N-酰基-2-氨基丁酸甲酯（NABME），N-酰基甘氨酸甲酯（NAGME），N-酰基缬氨酸甲酯（NAVME）第一次是甲基支链的名称，N-（13-甲基十四烷酰基）丙氨酸甲酯。通过GC-MS分析检测了这些化合物，并从质谱和衍生化获得了结构方案。通过合成进行化合物结构的验证。NABME，NAVME和NAGME仅少量生产，

  DOI：

  10.3762/bjoc.14.276

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。
• Improved LC−MS Method for the Determination of Fatty Acids in Red Blood Cells by LC−Orbitrap MS
  作者：Xingnan Li、Adrian A. Franke

  DOI：10.1021/ac103093w

  日期：2011.4.15

  We report a new method for fast and sensitive analyses of biologically relevant fatty acids (FAs) in red blood cells (RBC) by liquid chromatography mass spectrometry (LC−MS). A new chemical derivatization approach was developed forming picolylamides from FAs in a quantitative reaction. Fourteen derivatized FA standards, including saturated and unsaturated FAs from C14 to C22, were efficiently separated within 15 min. In addition, the use of a recently introduced benchtop orbitrap mass spectrometer under positive electrospray ionization (ESI) full scan mode showed a 2−10-fold improvement in sensitivity compared with a conventional tandem MS method, with a limit of detection in the low femtomole range for saturated and unsaturated FAs. The developed method was applied to determine FA concentrations in RBC with intra- and interday coefficients of variation below 10%.

  我们报告了一种通过液相色谱质谱联用（LC−MS）快速且灵敏分析红细胞（RBC）中生物学相关的脂肪酸（FAs）的新方法。该方法开发了一种形成吡啶甲酰胺的新化学衍生化途径，通过定量反应从FAs中生成。包括从C14到C22的饱和及不饱和FAs在内的14种衍生化FA标准品，在15分钟内得以高效分离。此外，采用最近推出的台式轨道阱质谱仪在正离子电喷雾电离（ESI）全扫描模式下进行检测，相较于传统串联MS方法，灵敏度提高了2至10倍，对饱和及不饱和FAs的检测限达到了低飞摩尔水平。所开发的方法被应用于测定RBC中的FA浓度，其日内和日间变异系数均低于10%。
• Structure/Activity Relationships in Lysophosphatidic Acid: The 2-Hydroxyl Moiety
  作者：Kevin R. Lynch、Darrin W. Hopper、Steven J. Carlisle、John G. Catalano、Ming Zhang、Timothy L. Macdonald

  DOI：10.1124/mol.52.1.75

  日期：1997.7.1

  Although lipid phosphoric acid mediators such as lysophosphatidic acid (LPA) are now recognized widely as intercellular signaling molecules, the medicinal chemistry of these mediators is poorly developed. With the goal of achieving a better understanding of the structure activity relationships in LPA, we have synthesized and tested a series of LPA analogs that lack the 2-hydroxyl moiety. Our series consisted of compounds with 2, 3, or 4 carbon diol or amino alcohol backbones and oleoyl or palmitoleoyl acyl groups. These molecules cannot be acylated further to form phosphatidic acids, nor do they have chiral centers. The rank order potency of these compounds in mobilization of calcium in MDA MB-231 cells suggested a maximum optimal chain length of 24–25 atoms. However, high potency for the inhibition of adenylyl cyclase in these cells was achieved only by one compound that also contained a dissociable proton five bond lengths from the phosphorus atom. That compound, N -oleoyl-2-hydroxyethyl-1-phosphate, was nearly equipotent to 1-oleoyl LPA in both assays. The striking mimicry of LPA by the ethanolamine-based compound and the presence of fatty acid amides in tissue prompts us to propose that phosphorylated N -acyl ethanolamides occur naturally.

  尽管脂磷酸类介质如溶血磷脂酸（LPA）现已被广泛认可为细胞间信号分子，但这些介质的药物化学研究尚处于起步阶段。为了更好地理解LPA结构活性关系，我们合成并测试了一系列缺乏2-羟基部分的LPA类似物。我们的研究系列包括具有2、3或4个碳的二醇或氨基醇骨架以及油酰或棕榈油酰酰基的化合物。这些分子不能进一步酰化形成磷脂酸，也不具有手性中心。这些化合物在MDA MB-231细胞中动员钙的活性排序提示了最大最佳链长度为24-25个原子。然而，在这些细胞中抑制腺苷酸环化酶的高效活性仅由一种化合物实现，该化合物在磷原子五键长度处含有一个可解离的质子。该化合物，即N-油酰-2-羟乙基-1-磷酸，在两种检测中与1-油酰LPA几乎等效。基于这种以乙醇胺为基础的化合物对LPA的惊人模拟及组织中脂肪酸酰胺的存在，我们推测自然界中存在磷酸化的N-酰基乙醇酰胺。
• Antiproliferative 3-deoxysphingomyelin analogs: Design, synthesis, biological evaluation and molecular docking of pyrrolidine-based 3-deoxysphingomyelin analogs as anticancer agents
  作者：Ahmed H.E. Hassan、Hye Rim Park、Yoon Mi Yoon、Hye In Kim、Sung Yeun Yoo、Kun Won Lee、Yong Sup Lee

  DOI：10.1016/j.bioorg.2018.11.040

  日期：2019.3

  phospholipids. Nevertheless, glycerophospholipids analogs are known as antitumor agents while sphingomyelin analogs were reported as cytoprotective agents. Herein, we have addressed the development of 3-deoxysphingomyelin analogs as cytotoxic agents possessing modified sphingobases. Thus, pyrrolidine-based 3-deoxysphingomyelin analogs were synthesized and evaluated against a panel of cell lines representing

  鞘磷脂和甘油磷脂是结构上相关的磷脂。然而，甘油磷脂类似物被称为抗肿瘤剂，而鞘磷脂类似物被报告为细胞保护剂。在这里，我们已经解决了3-脱氧鞘磷脂类似物作为具有修饰的鞘氨醇碱基的细胞毒剂的开发。因此，合成了基于吡咯烷的3-脱氧鞘磷脂类似物，并针对代表四种主要类型癌症的一组细胞系进行了评估。化合物3d，4d和6d的GI50值优于FDA批准的药物米替福辛。作为这类化合物的抗增殖活性的可能机制，它们对Akt磷酸化的影响的研究表明，这些化合物可能通过在较低浓度下抑制Akt磷酸化而引发浓度依赖性的机制。分子对接预测它们与Akt的结合模式涉及与Pleckstrin同源结构域的极性头结合和疏水尾延伸至连接Pleckstrin同源结构域和激酶结构域的疏水口袋中。总体而言，上述工作表明化合物3d，4d和6d是有前途的基于吡咯烷的3-deoxysphingomyelin类似物，可用于开发新的癌症疗法。分子对接预测
• Compositions containing lysophosphatidic acids which inhibit apoptosis and uses thereof
  申请人：Goddard John G.

  公开号：US06949528B1

  公开（公告）日：2005-09-27

  The invention provides anti-apoptotic compositions lysophosphatidic acids and methods for making and using the compositions. Such compositions can also contain LPA potentiating agents, including proteins, lipid membrane structures and polymers such as polyethylene glycols. The compositions can additionally contain other pharmaceutically effective agents such as drugs, antibiotics, wound healing agents and antioxidants.

  该发明提供了抗凋亡组合物溶磷脂酸及其制备和使用方法。这种组合物还可以包含增强LPA作用的剂，包括蛋白质、脂质膜结构和聚合物，如聚乙二醇。该组合物还可以额外含有其他药用有效剂，如药物、抗生素、伤口愈合剂和抗氧化剂。