methyl 16-hydroxy-10-oxohexadecanoate | 77441-82-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 16-hydroxy-10-oxohexadecanoate
• 英文别名: 16-Hydroxy-10-oxo-hexadecansaeuremethylester；Methyl 16-hydroxy-10-oxohexadecanoate
• CAS: 77441-82-8
• 化学式: C₁₇H₃₂O₄
• 分子量: 300.439
• InChiKey: ICLNGTPGGPAQMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 16-hydroxy-10-oxohexadecanoate 在 咪唑 、 碘 、 三苯基膦 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以3.5 g的产率得到
  参考文献：
  名称：

  Bifunctional Fatty Acid Chemical Reporter for Analyzing S-Palmitoylated Membrane Protein–Protein Interactions in Mammalian Cells

  摘要：

  Studying the functions of S-palmitoylated proteins in cells can be challenging due to the membrane targeting property and dynamic nature of protein S-palmitoylation. New strategies are therefore needed to specifically capture S-palmitoylated protein complexes in cellular membranes for dissecting their functions in vivo. Here we present a bifunctional fatty acid chemical reporter, x-alk-16, which contains an alkyne and a diazirine, for metabolic labeling of S-palmitoylated proteins and photo-cross-linking of their involved protein complexes in mammalian cells. We demonstrate that x-alk-16 can be metabolically incorporated into known S-palmitoylated proteins such as H-Ras and IFITM3, a potent antiviral protein, and induce covalent cross-linking of IFITM3 oligomerization as well as its specific interactions with other membrane proteins upon in-cell photoactivation. Moreover, integration of x-alk-16-induced photo-cross-linking with label-free quantitative proteomics allows identification of new IFITM3 interacting proteins.

  DOI：

  10.1021/ja502109n
• 作为产物：
  描述：

  10-氯-10-氧代癸酸甲酯 在 对甲苯磺酸 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 methyl 16-hydroxy-10-oxohexadecanoate
  参考文献：
  名称：

  Bifunctional Fatty Acid Chemical Reporter for Analyzing S-Palmitoylated Membrane Protein–Protein Interactions in Mammalian Cells

  摘要：

  Studying the functions of S-palmitoylated proteins in cells can be challenging due to the membrane targeting property and dynamic nature of protein S-palmitoylation. New strategies are therefore needed to specifically capture S-palmitoylated protein complexes in cellular membranes for dissecting their functions in vivo. Here we present a bifunctional fatty acid chemical reporter, x-alk-16, which contains an alkyne and a diazirine, for metabolic labeling of S-palmitoylated proteins and photo-cross-linking of their involved protein complexes in mammalian cells. We demonstrate that x-alk-16 can be metabolically incorporated into known S-palmitoylated proteins such as H-Ras and IFITM3, a potent antiviral protein, and induce covalent cross-linking of IFITM3 oligomerization as well as its specific interactions with other membrane proteins upon in-cell photoactivation. Moreover, integration of x-alk-16-induced photo-cross-linking with label-free quantitative proteomics allows identification of new IFITM3 interacting proteins.

  DOI：

  10.1021/ja502109n

文献信息

• A General Approach to Intermolecular Olefin Hydroacylation through Light‐Induced HAT Initiation: An Efficient Synthesis of Long‐Chain Aliphatic Ketones and Functionalized Fatty Acids
  作者：Subhasis Paul、Joyram Guin

  DOI：10.1002/chem.202004946

  日期：2021.3

  hydroacylation protocol applies to a wide array of substrates bearing numerous functional groups and many complex structural units. The reaction proves to be scalable (up to 5 g). Different functionalized fatty acids, petrochemicals and naturally occurring alkanes can be synthesized with this protocol. A radical chain mechanism is implicated in the process.

  本文介绍了一种通过使用光诱导氢原子转移（HAT）引发对未活化底物进行分子间自由基加氢酰化的操作简单，对环境无害且有效的方法。使用可商购和廉价的光引发剂（Ph 2 CO和NHPI）使该方法具有吸引力。烯烃加氢酰化方案适用于多种带有许多官能团和许多复杂结构单元的底物。该反应证明是可扩展的（最大5 g）。可以使用该方案合成不同的官能化脂肪酸，石化产品和天然存在的烷烃。自由基链机制与该过程有关。
• Plant extract compositions and methods of preparation thereof
  申请人：Apeel Technology, Inc.

  公开号：US10959442B2

  公开（公告）日：2021-03-30

  Embodiments described herein relate generally to plant extract compositions and methods to isolate cutin-derived monomers, oligomers, and mixtures thereof for application in agricultural coating formulations, and in particular, to methods of preparing plant extract compositions that include functionalized and non-functionalized fatty acids and fatty esters (as well as their oligomers and mixtures thereof), which are substantially free from accompanying plant-derived compounds (e.g., proteins, polysaccharides, phenols, lignans, aromatic acids, terpenoids, flavonoids, carotenoids, alkaloids, alcohols, alkanes, and aldehydes) and can be used in agricultural coating formulations.

  本文描述的实施方案一般涉及植物提取物组合物和分离角质衍生单体、低聚物及其混合物以应用于农用涂料配方的方法，特别是涉及制备植物提取物组合物的方法，该组合物包括官能化和非官能化脂肪酸和脂肪酯（以及它们的低聚物和混合物），它们基本上不含伴随的植物衍生化合物（例如，蛋白质、多糖、酚、木质素、芳香酸、萜类化合物、类黄酮、类胡萝卜素和生物碱）、蛋白质、多糖、酚、木脂素、芳香酸、萜类化合物、类黄酮、类胡萝卜素、生物碱、醇、烷和醛），可用于农用涂料配方。
• PLANT EXTRACT COMPOSITIONS AND METHODS OF PREPARATION THEREOF
  申请人：Apeel Technology, Inc.

  公开号：EP3298024B1

  公开（公告）日：2020-04-01
• US9743679B2
  申请人：——

  公开号：US9743679B2

  公开（公告）日：2017-08-29
• Bifunctional Fatty Acid Chemical Reporter for Analyzing S-Palmitoylated Membrane Protein–Protein Interactions in Mammalian Cells
  作者：Tao Peng、Howard C. Hang

  DOI：10.1021/ja502109n

  日期：2015.1.21

  Studying the functions of S-palmitoylated proteins in cells can be challenging due to the membrane targeting property and dynamic nature of protein S-palmitoylation. New strategies are therefore needed to specifically capture S-palmitoylated protein complexes in cellular membranes for dissecting their functions in vivo. Here we present a bifunctional fatty acid chemical reporter, x-alk-16, which contains an alkyne and a diazirine, for metabolic labeling of S-palmitoylated proteins and photo-cross-linking of their involved protein complexes in mammalian cells. We demonstrate that x-alk-16 can be metabolically incorporated into known S-palmitoylated proteins such as H-Ras and IFITM3, a potent antiviral protein, and induce covalent cross-linking of IFITM3 oligomerization as well as its specific interactions with other membrane proteins upon in-cell photoactivation. Moreover, integration of x-alk-16-induced photo-cross-linking with label-free quantitative proteomics allows identification of new IFITM3 interacting proteins.