1,3-benzylidene-2-oleylglycerol | 291312-49-7

• 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-oleylglycerol
• 英文别名: 2-(9-octadecenyl)-1,3-benzylideneglycerol；5-[(9Z)-9-Octadecen-1-yloxy]-2-phenyl-1,3-dioxane；5-[(Z)-octadec-9-enoxy]-2-phenyl-1,3-dioxane
• CAS: 291312-49-7
• 化学式: C₂₈H₄₆O₃
• 分子量: 430.671
• InChiKey: CGMMVQPBUJBHBM-KTKRTIGZSA-N

物化性质

• 沸点：
  533.5±50.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  31
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 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-oleylglycerol 在 硼酸三甲酯 、 硼酸 作用下， 反应 0.33h， 以52%的产率得到2-O-(9-十八碳烯基)甘油
  参考文献：
  名称：

  内源性大麻素受体配体2-花生四烯酰甘油及其代谢稳定的醚连接类似物的合成及生物学活性。

  摘要：

  我们合成了内源性大麻素受体配体2-花生四烯酸甘油酯（1）及其代谢稳定的醚连接类似物。在N，N′-二环己基碳二亚胺和4-二甲基氨基吡啶的存在下，由1，3-亚苄基甘油（6）和花生四烯酸合成化合物1，然后用硼酸和硼酸三甲酯处理。由6和5,8,11,14-二十碳四烯基碘（9）合成了2-花生四烯酰基甘油的醚连接类似物（2）。2-棕榈酰甘油（4）和2-油甘油（5）的醚连接类似物分别由碘化十六烷基碘（12）和碘化十八烷基碘（14）合成。我们证实1通过CB1受体依赖性机制刺激NG108-15细胞诱导细胞内游离Ca2 +浓度快速瞬时升高。明显地，尽管2的活性明显低于1的活性，但2却显示出明显的激动活性。化合物2将是探索1的生理学意义的有用工具，因为与1相比，该化合物对水解酶具有抗性。 4或5的醚连接类似物不能充当CB1受体激动剂。在使用2的实验中，化合物4和5作为对照分子也将是有价值的。

  DOI：

  10.1248/cpb.48.903
• 作为产物：
  描述：

  油醇 在 甲基三苯氧基碘磷 、 四丁基碘化铵 、 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.33h， 生成 1,3-benzylidene-2-oleylglycerol
  参考文献：
  名称：

  内源性大麻素受体配体2-花生四烯酰甘油及其代谢稳定的醚连接类似物的合成及生物学活性。

  摘要：

  我们合成了内源性大麻素受体配体2-花生四烯酸甘油酯（1）及其代谢稳定的醚连接类似物。在N，N′-二环己基碳二亚胺和4-二甲基氨基吡啶的存在下，由1，3-亚苄基甘油（6）和花生四烯酸合成化合物1，然后用硼酸和硼酸三甲酯处理。由6和5,8,11,14-二十碳四烯基碘（9）合成了2-花生四烯酰基甘油的醚连接类似物（2）。2-棕榈酰甘油（4）和2-油甘油（5）的醚连接类似物分别由碘化十六烷基碘（12）和碘化十八烷基碘（14）合成。我们证实1通过CB1受体依赖性机制刺激NG108-15细胞诱导细胞内游离Ca2 +浓度快速瞬时升高。明显地，尽管2的活性明显低于1的活性，但2却显示出明显的激动活性。化合物2将是探索1的生理学意义的有用工具，因为与1相比，该化合物对水解酶具有抗性。 4或5的醚连接类似物不能充当CB1受体激动剂。在使用2的实验中，化合物4和5作为对照分子也将是有价值的。

  DOI：

  10.1248/cpb.48.903

文献信息

• 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.
• Acid-Triggered Transformation of Diortho Ester Phosphocholine Liposome
  作者：Zhaohua Huang、Xin Guo、Weijun Li、J. Andrew MacKay、Francis C. Szoka

  DOI：10.1021/ja057024w

  日期：2006.1.1

  The use of pH-sensitive liposomes for acid-triggered site-specific drug delivery is one of the more promising approaches to improve the therapeutic index of drugs. Here, we report the synthesis, assembly, and hydrolysis of the first ortho ester phosphocholine (OEPC). The acid hydrolysis of OEPC liposomes consists of a lag phase and a burst phase. The lag time is pH-dependent-the lower the pH, the shorter the time. Upon acid hydrolysis, the OEPC liposomes were transformed into leaky metastable vesicles that rapidly collapsed in the presence of albumin. OEPC, when formulated with cationic lipid, significantly enhanced the transfection efficiency compared with that of the pH-insensitive formulation.
• Homologues and isomers of noladin ether, a putative novel endocannabinoid: interaction with rat cannabinoid CB1 receptors
  作者：Giovanni Appendino、Alessia Ligresti、Alberto Minassi、Nives Daddario、Tiziana Bisogno、Vincenzo Di Marzo

  DOI：10.1016/s0960-894x(02)00839-9

  日期：2003.1

  Two regioisomers and 13 analogues of the putative endocannabinoid noladin ether (2-arachidonyl glyceryl ether, 2-AGE, 1) were synthesized and tested for their interaction with CB1 receptors in rat brain membranes. The results showed that a C-20 tetra-unsaturated moiety is necessary for high affinity, and that a series of alkyl glyceryl ethers of potential occurrence in brain tissues have less affinity than 2-AGE for CB1 receptors. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.