3-(acetylsulfanyl)-2-hydroxypropyl oleate | 1321603-34-2

• 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: 3-(acetylsulfanyl)-2-hydroxypropyl oleate
• 英文别名: (3-acetylsulfanyl-2-hydroxypropyl) (Z)-octadec-9-enoate
• CAS: 1321603-34-2
• 化学式: C₂₃H₄₂O₄S
• 分子量: 414.65
• InChiKey: SBQXMQWKLWOEQT-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  28
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(acetylsulfanyl)-2-hydroxypropyl oleate 在 三乙基硅烷 、 palladium on carbon 作用下， 以 丙酮 为溶剂， 以92%的产率得到2-hydroxy-3-mercaptopropyl oleate
  参考文献：
  名称：

  Efficient synthesis of 3-O-thia-cPA and preliminary analysis of its biological activity toward autotaxin

  摘要：

  The efficient synthesis of 3-O-thia-cPAs (4a-d), sulfur analogues of cyclic phosphatidic acid (cPA), has been achieved. The key step of the synthesis is an intramolecular Arbuzov reaction to construct the cyclic thiophosphate moiety. The present synthetic route enables the synthesis of 4a-d in only four steps from the commercially available glycidol. Preliminary biological experiments showed that 4a-d exhibited a similar inhibitory effect on autotaxin (ATX) as original cPA. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.083
• 作为产物：
  描述：

  1-monooleoyl glycerol 以 吡啶 、 丙酮 为溶剂， 反应 22.5h， 生成 3-(acetylsulfanyl)-2-hydroxypropyl oleate
  参考文献：
  名称：

  Design and Synthesis of Lipids for the Fabrication of Functional Lipidic Cubic-Phase Biomaterials

  摘要：

  A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of alpha-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.

  DOI：

  10.1021/jo301659c

文献信息

• Design and Synthesis of Lipids for the Fabrication of Functional Lipidic Cubic-Phase Biomaterials
  作者：Yazmin M. Osornio、Peter Uebelhart、Silvan Bosshard、Fabian Konrad、Jay S. Siegel、Ehud M. Landau

  DOI：10.1021/jo301659c

  日期：2012.12.7

  A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of alpha-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.
• Efficient synthesis of 3-O-thia-cPA and preliminary analysis of its biological activity toward autotaxin
  作者：Ryo Tanaka、Masaru Kato、Takahiro Suzuki、Atsuo Nakazaki、Emi Nozaki、Mari Gotoh、Kimiko Murakami-Murofushi、Susumu Kobayashi

  DOI：10.1016/j.bmcl.2011.05.083

  日期：2011.7

  The efficient synthesis of 3-O-thia-cPAs (4a-d), sulfur analogues of cyclic phosphatidic acid (cPA), has been achieved. The key step of the synthesis is an intramolecular Arbuzov reaction to construct the cyclic thiophosphate moiety. The present synthetic route enables the synthesis of 4a-d in only four steps from the commercially available glycidol. Preliminary biological experiments showed that 4a-d exhibited a similar inhibitory effect on autotaxin (ATX) as original cPA. (C) 2011 Elsevier Ltd. All rights reserved.