十六碳-9-炔酸 | 89155-39-5

• 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: 十六碳-9-炔酸
• 英文名称: .9-hexadecynoic acid
• 英文别名: hexadec-9-ynoic acid；Hexadec-9-insaeure；9-Hexadecynoic acid
• CAS: 89155-39-5
• 化学式: C₁₆H₂₈O₂
• 分子量: 252.397
• InChiKey: PUVMMVZJPHBIGN-UHFFFAOYSA-N

物化性质

• 熔点：
  59.1°C (estimate)
• 沸点：
  409.64°C (rough estimate)
• 密度：
  0.9310 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  十六碳-9-炔酸 在 硫酸 、 氢气 、 乙二胺 作用下， 以 乙醇 、 水 为溶剂， 生成 棕榈油酸甲酯
  参考文献：
  名称：

  Efficient Synthesis of Unsaturated 1-Monoacyl Glycerols for in meso Crystallization of Membrane Proteins

  摘要：

  建立了高度有效的未饱和1-单酰甘油合成方法，以满足膜蛋白结晶中使用的脂质介晶材料迫切需要。

  DOI：

  10.1055/s-0030-1259912
• 作为产物：
  描述：

  N,N-Dimethyl-decin-9-saeure-1-amid 在 氢氧化钾 作用下， 以 乙二醇甲醚 为溶剂， 生成 十六碳-9-炔酸
  参考文献：
  名称：

  144.长链酸的合成。第三部分 炔酸的合成

  摘要：

  DOI：

  10.1039/jr9630000775

文献信息

• Antibacterial Activity of Hexadecynoic Acid Isomers toward Clinical Isolates of Multidrug‐Resistant <scp> <i>Staphylococcus aureus</i> </scp>
  作者：David J. Sanabria‐Ríos、Christian Morales‐Guzmán、Joseph Mooney、Solymar Medina、Tomás Pereles‐De‐León、Ashley Rivera‐Román、Carlimar Ocasio‐Malavé、Damarith Díaz、Nataliya Chorna、Néstor M. Carballeira

  DOI：10.1002/lipd.12213

  日期：2020.3

  In the present study, the structural characteristics that impart antibacterial activity to C16 alkynoic fatty acids (aFA) were further investigated. The syntheses of hexadecynoic acids (HDA) containing triple bonds at C‐3, C‐6, C‐8, C‐9, C‐10, and C‐12 were carried out in four steps and with an overall yield of 34–78%. In addition, HDA analogs containing a sulfur atom at either C‐4 or C‐5 were also

  在本研究中，进一步研究了赋予C 16炔属脂肪酸（aFA）抗菌活性的结构特征。四个步骤进行了在C-3，C-6，C-8，C-9，C-10和C-12处含有三键的十六碳烯酸（HDA）的合成，总产率为34- 78％。此外，还分别制备了C-4或C-5含硫原子的HDA类似物，总产率分别为69-77％。这项研究的结果表明，C-2处的三键对于2-HDA所显示的抗菌活性至关重要，而三键距羰基的位置越远，其对革兰氏阳性细菌的杀菌活性就越低，包括耐甲氧西林金黄色葡萄球菌的临床分离株（CIMRSA）菌株。还对五种对环丙沙星（Cipro）耐药的CIMRSA菌株评估了2-HDA作为抗菌剂的潜力，证明与单独使用Cipro或等摩尔组合Cipro相比，2-HDA是抑制其生长的最有效方法。和2‐HDA。此外，已证明金黄色葡萄球菌DNA促旋酶的抑制作用可能与2-HDA表现出的抗菌活性有关。最后，确定了HDA类似物形成胶束的能力可
• Depot preparations
  申请人：——

  公开号：US20030114352A1

  公开（公告）日：2003-06-19

  The present invention relates to depot preparations for the targeted release of an aldehyde together with two carboxylic acids, where the released aldehydes are organoleptic substances, specifically fragrances or flavorings, and these depot preparations are prepared by reacting aldehydes with carboxylic anhydrides.

  本发明涉及用于有针对性地释放一种醛和两种羧酸的仓库制剂，其中释放的醛是感官物质，具体来说是香料或调味料，这些仓库制剂是通过将醛与羧酸酐反应制备而成的。
• Rubber composition, crosslinked rubber molded product and golf ball
  申请人：Dunlop Sports Co. Ltd.

  公开号：US10293215B2

  公开（公告）日：2019-05-21

  An object of the present invention is to provide a rubber composition from which a crosslinked rubber molded product excellent in the resilience performance can be obtained. The present invention provides a rubber composition containing (a) a base rubber, (b) a co-crosslinking agent and (c) a crosslinking initiator, wherein (b) the co-crosslinking agent contains a complex represented by a general formula (1). [In the formula (1), M is a metal atom, and L is a carboxylate represented by the general formula (2). In the formula (2), R is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms or an alkynyl group having 2 to 18 carbon atoms, and the dotted line shows a resonance structure. In the formula (1), a plurality of R may be identical to or different from each other, and at least one of R is the alkenyl group having 2 to 18 carbon atoms or the alkynyl group having 2 to 18 carbon atoms.]

  本发明的目的是提供一种橡胶组合物，通过该组合物可获得回弹性能优异的交联橡胶模塑产品。本发明提供了一种橡胶组合物，其中包含（a）基础橡胶、（b）共交联剂和（c）交联引发剂，其中（b）共交联剂包含通式（1）表示的复合物。 [在式 (1) 中，M 是金属原子，L 是通式 (2) 所代表的羧酸盐。式（2）中，R 是氢原子、具有 1 至 18 个碳原子的烷基、具有 2 至 18 个碳原子的烯基或具有 2 至 18 个碳原子的炔基，虚线表示共振结构。在式 (1) 中，多个 R 可以彼此相同或不同，且至少一个 R 是具有 2 至 18 个碳原子的烯基或具有 2 至 18 个碳原子的炔基。］
• Complex and process for preparing complex
  申请人：SUMITOMO RUBBER INDUSTRIES, LTD.

  公开号：US10562919B2

  公开（公告）日：2020-02-18

  An object of the present invention is to provide a novel complex having at least one carbon-carbon double bond and/or carbon-carbon triple bond. The present invention provides a complex represented by formula (1): ((RCOO)8M5(OH)2)n   (1) wherein in the formula (1), M is a metal atom, R is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms or an alkynyl group having 2 to 18 carbon atoms, a plurality of R may be identical to or different from each other, at least one of R is the alkenyl group having 2 to 18 carbon atoms or the alkynyl group having 2 to 18 carbon atoms, and n is an integer of 1 or more.

  本发明的目的是提供一种新型络合物，该络合物至少具有一个碳碳双键和/或碳碳三键。本发明提供了一种由式（1）表示的络合物： ((RCOO)8M5(OH)2)n (1) 其中，在式 (1) 中，M 是金属原子，R 是氢原子、具有 1 至 18 个碳原子的烷基、具有 2 至 18 个碳原子的烯基或具有 2 至 18 个碳原子的炔基，多个 R 可以彼此相同或不同，R 中至少有一个是具有 2 至 18 个碳原子的烯基或具有 2 至 18 个碳原子的炔基，n 是 1 或 1 以上的整数。
• 2-Hexadecynoic acid inhibits plasmodial FAS-II enzymes and arrests erythrocytic and liver stage Plasmodium infections
  作者：Deniz Tasdemir、David Sanabria、Ina L. Lauinger、Alice Tarun、Rob Herman、Remo Perozzo、Mire Zloh、Stefan H. Kappe、Reto Brun、Néstor M. Carballeira

  DOI：10.1016/j.bmc.2010.08.055

  日期：2010.11

  Acetylenic fatty acids are known to display several biological activities, but their antimalarial activity has remained unexplored. In this study, we synthesized the 2-, 5-, 6-, and 9-hexadecynoic acids (HDAs) and evaluated their in vitro activity against erythrocytic (blood) stages of Plasmodium falciparum and liver stages of Plasmodium yoelii infections. Since the type II fatty acid biosynthesis pathway (PfFAS-II) has recently been shown to be indispensable for liver stage malaria parasites, the inhibitory potential of the HDAs against multiple P. falciparum FAS-II (PfFAS-II) elongation enzymes was also evaluated. The highest antiplasmodial activity against blood stages of P. falciparum was displayed by 5-HDA (IC(50) value 6.6 mu g/ml), whereas the 2-HDA was the only acid arresting the growth of liver stage P. yoelii infection, in both flow cytometric assay (IC(50) value 2-HDA 15.3 mu g/ml, control drug atovaquone 2.5 ng/ml) and immunofluorescence analysis (IC(50) 2-HDA 4.88 mu g/ml, control drug atovaquone 0.37 ng/ml). 2-HDA showed the best inhibitory activity against the PfFAS-II enzymes PfFabI and PfFabZ with IC(50)values of 0.38 and 0.58 mu g/ml (IC(50)control drugs 14 and 30 ng/ml), respectively. Enzyme kinetics and molecular modeling studies revealed valuable insights into the binding mechanism of 2-HDA on the target enzymes. All HDAs showed in vitro activity against Trypanosoma brucei rhodesiense (IC(50) values 3.7-31.7 mu g/ml), Trypanosoma cruzi (only 2-HDA, IC(50) 20.2 mu g/ml), and Leishmania donovani (IC(50) values 4.1-13.4 mu g/ml) with generally low or no significant toxicity on mammalian cells. This is the first study to indicate therapeutic potential of HDAs against various parasitic protozoa. It also points out that the malarial liver stage growth inhibitory effect of the 2-HDA may be promoted via PfFAS-II enzymes. The lack of cytotoxicity, lipophilic nature, and calculated pharmacokinetic properties suggests that 2-HDA could be a useful compound to study the interaction of fatty acids with these key P. falciparum enzymes. (C) 2010 Elsevier Ltd. All rights reserved.