1,3-benzylidene-2-myristyl-glycerol | 1085528-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 1,3-benzylidene-2-myristyl-glycerol
• 英文别名: 2-Phenyl-5-tetradecoxy-1,3-dioxane；2-phenyl-5-tetradecoxy-1,3-dioxane
• CAS: 1085528-35-3
• 化学式: C₂₄H₄₀O₃
• 分子量: 376.58
• InChiKey: QLQXBHOKYUFVGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  27
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-benzylidene-2-myristyl-glycerol 在 palladium on activated charcoal 吡啶 、 lithium aluminium tetrahydride 、 三氯化铝 、 氢气 、 四丁基碘化铵 、 sodium hydride 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 生成 2-[2-(2-{3-[(3aS,4R,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxy]-2-tetradecyloxy-propoxy}-ethoxy)-ethoxy]-ethanol
  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：

  十四烷基碘化物 、 2-苯基-1,3-二氧六环-5-醇 在 sodium hydride 作用下， 以 甲苯 、 mineral oil 为溶剂， 反应 0.5h， 生成 1,3-benzylidene-2-myristyl-glycerol
  参考文献：
  名称：

  Sterol-Modified Phospholipids: Cholesterol and Phospholipid Chimeras with Improved Biomembrane Properties

  摘要：

  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.

  DOI：

  10.1021/ja8065557

文献信息

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

  DOI：——

  日期：——
• 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.