1,3-Dihydroxy-2-myristyloxy-propan | 17174-69-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,3-Dihydroxy-2-myristyloxy-propan
• 英文别名: 2-Tetradecyloxy-propandiol-(1,3)；2-myristyl-glycerol；2-tetradecyloxy-propane-1,3-diol；2-(tetradecyloxy)-1,3-propanediol；2-O-Tetradecylglycerol；2-tetradecoxypropane-1,3-diol
• CAS: 17174-69-5
• 化学式: C₁₇H₃₆O₃
• 分子量: 288.471
• InChiKey: PBIJAKQGWLSALJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-Dihydroxy-2-myristyloxy-propan 在 sodium hydride 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Terjung, Andreas; Jung, Karl-Heinz; Schmidt, Richard R., Liebigs Annalen, 1996, # 8, p. 1313 - 1321

  摘要：

  DOI：
• 作为产物：
  描述：

  溴代十四烷 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 1,3-Dihydroxy-2-myristyloxy-propan
  参考文献：
  名称：

  Berecoechea,J.; Anatol,J., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1969, vol. 268, p. 434 - 437

  摘要：

  DOI：

文献信息

• Studies of the mesomorphic behavior of bivalent carbohydrate amphiphiles
  作者：Narayanaswamy Jayaraman、Madan Kumar Singh、D. S. Shankar Rao、S. K. Prasad

  DOI：10.1039/b618753f

  日期：——

  A homologous series of bivalent glycolipids constituted of 1,3-bis-O-(β-D-glucopyranosyl)-2-O-alkyl glycerol, bearing two sugar head groups and one alkyl chain on a glycerol backbone, was synthesized. The mesomorphic behaviour was investigated with the aid of polarizing optical microscopy, differential scanning calorimetry and X-ray diffraction methods. The homologous members exhibit a smectic A phase, consistently with a partial bilayer structure. From experimental d-spacing and computationally derived length of the molecules, it is suggested that a partial interdigitation of the molecules is present in the bilayer structure.

  合成了一系列由1,3-双-O-(β-D-吡喃葡萄糖基)-2-O-烷基甘油组成的同源二价糖脂，在甘油主链上带有两个糖头基团和一个烷基链。借助于偏光光学显微镜、差示扫描量热法和X射线衍射方法研究了介晶行为。同源成员表现出近晶A相，与部分双层结构一致。根据实验的 d 间距和计算得出的分子长度，表明双层结构中存在分子的部分叉指。
• Sterol-Modified Phospholipids: Cholesterol and Phospholipid Chimeras with Improved Biomembrane Properties
  作者：Zhaohua Huang、Francis C. Szoka

  DOI：10.1021/ja8065557

  日期：2008.11.19

  We synthesized a family of sterol-modified glycerophospholipids (SML) in which the sn-1 or sn-2 position is covalently attached to cholesterol and the alternative position contains an aliphatic chain. The SML were used to explore how anchoring cholesterol to a phospholipid affects cholesterol behavior in a bilayer. Notably, cholesterol in the SML retains the membrane condensing properties of free cholesterol regardless of the chemistry or position of its attachment to the glycerol moiety of the phospholipid. SMLs by themselves formed liposomes upon hydration and in mixtures between an SML and diacylglycerophospholipids (C14 to C18 chain length) the thermotropic phase transition is eliminated at the SML equivalent of about 30 mol % free cholesterol. Osmotic-induced contents leakage from SML (C14-C18) liposomes depends upon the linkage and position of cholesterol but in general is similar to that observed in 3/2 diacylphosphatidylcholine/cholesterol (mole ratio) liposomes. SML liposomes are exceptionally resistant to contents release in the presence of serum at 37 degrees C. This is probably due to the fact that SML exchange between bilayers is more than 100 fold less than the exchange rate of free cholesterol in the same conditions. Importantly, SML liposomes containing doxorubicin are as effective in treating the murine C26 colon carcinoma as Doxil, a commercial liposome doxorubicin formulation. SMLs stabilize bilayers but do not exchange and hence provide a new tool for biophysical studies on membranes. They may improve liposomal drug delivery in organs predisposed to the extraction of free cholesterol from bilayers, such as the skin, lung, or blood.
• STEROL-MODIFIED AMPHIPHILIC LIPIDS
  申请人：The Regents of the University of California

  公开号：EP2219587A1

  公开（公告）日：2010-08-25
• Sterol-Modified Amphiphilic Lipids
  申请人：Szoka, JR. Francis C.

  公开号：US20110177156A1

  公开（公告）日：2011-07-21

  Disclosed are sterol-modified amphiphilic lipid compounds having two or more hydrophobic tails of which at least one is a sterol. Also disclosed are the processes for the synthesis of these compounds, compositions comprising such compounds, and the use of such compounds in delivery of an agent of interest, e.g., therapeutics, imaging agents, contrast materials for ultrasound applications, vaccines, biosensors, nutritional supplements and skin care products.
• [EN] STEROL-MODIFIED AMPHIPHILIC LIPIDS<br/>[FR] LIPIDES AMPHIPHILES MODIFIÉS PAR UN STÉROL
  申请人：UNIV CALIFORNIA

  公开号：WO2009064696A1

  公开（公告）日：2009-05-22

  Disclosed are sterol-modified amphiphilic lipid compounds having two or more hydrophobic tails of which at least one is a sterol. Also disclosed are the processes for the synthesis of these compounds, compositions comprising such compounds, and the use of such compounds in delivery of an agent of interest, e.g., therapeutics, imaging agents, contrast materials for ultrasound applications, vaccines, biosensors, nutritional supplements and skin care products.