Methyl 4-pentadecoxybenzoate | 40654-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 4-pentadecoxybenzoate
• CAS: 40654-34-0
• 化学式: C₂₃H₃₈O₃
• 分子量: 362.553
• InChiKey: OMSGVGNQIOVWHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  溴代十五烷 、 对羟基苯甲酸甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 Methyl 4-pentadecoxybenzoate
  参考文献：
  名称：

  NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer

  摘要：

  The development of "molecular rulers" would allow one to quantitatively locate intercalants within the liposomal bilayer. To this end, we have attempted to correlate the C-13 NMR chemical shift of a polarizable "reporter" carbon (e.g., carbonyl) of the intercalant-with the E-T(30) polarity it experiences, and with its Angstrom distance from the interface. This requires families of molecules with the same two "reporter carbons" separated by a fixed distance, residing at various depths/polarities within the bilayer. The families studied included 4,4-dialkylcyclohexa-2,5-dienones 1, benzenediacetic esters 15, benzenedipropionic esters 17, 4-alkoxybenzaldehydes 19 and methyl 4-alkoxybenzoates 22. These compounds possessed the following characteristics: (1) a planar backbone; (2) polar/hydrophilic "head" groups: (3) modular hydrophobic tails; (4) large changes in the C-13 NMR chemical shift (Delta delta) of the reporter atoms with sol- vent polarity. These studies revealed a fifth requirement, namely: (5) the reporter carbons must not be strongly conjugated, lest it reflect the charge build-up at another site within the conjugated system. (C) 2008 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2008.07.004

文献信息

• 5-(Tetradecyloxy)-2-furancarboxylic acid and related hypolipidemic fatty acid-like alkyloxyarylcarboxylic acids
  作者：Roger A. Parker、Takashi Kariya、J. Martin Grisar、Vladimir Petrow

  DOI：10.1021/jm00216a009

  日期：1977.6

  5-(Tetradecyloxy)-2-furancarboxylic acid (91, RMI 14514) was found to lower blood lipids and to inhibit fatty acid synthesis with minimal effects on liver weight and liver fat content. This fatty acid-like compound represents a new class of hypolipidemic agent; it is effective in rats and monkeys. The compound resulted from discovery of hypolipidemic activity in certain beta-keto esters, postulation

  发现5-（四氢癸氧基）-2-呋喃羧酸（91，RMI 14514）可以降低血脂并抑制脂肪酸合成，对肝脏重量和肝脏脂肪含量的影响最小。这种类似脂肪酸的化合物代表了一类新的降血脂药。对大鼠和猴子有效。该化合物的产生是由于发现了某些β-酮酸酯的降血脂活性，假定和确认了相应的苯甲酸作为活性代谢物以及系统地研究了结构-活性关系。
• NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer
  作者：Yael Cohen、Efrat Bodner、Michal Richman、Michal Afri、Aryeh A. Frimer

  DOI：10.1016/j.chemphyslip.2008.07.004

  日期：2008.10

  The development of "molecular rulers" would allow one to quantitatively locate intercalants within the liposomal bilayer. To this end, we have attempted to correlate the C-13 NMR chemical shift of a polarizable "reporter" carbon (e.g., carbonyl) of the intercalant-with the E-T(30) polarity it experiences, and with its Angstrom distance from the interface. This requires families of molecules with the same two "reporter carbons" separated by a fixed distance, residing at various depths/polarities within the bilayer. The families studied included 4,4-dialkylcyclohexa-2,5-dienones 1, benzenediacetic esters 15, benzenedipropionic esters 17, 4-alkoxybenzaldehydes 19 and methyl 4-alkoxybenzoates 22. These compounds possessed the following characteristics: (1) a planar backbone; (2) polar/hydrophilic "head" groups: (3) modular hydrophobic tails; (4) large changes in the C-13 NMR chemical shift (Delta delta) of the reporter atoms with sol- vent polarity. These studies revealed a fifth requirement, namely: (5) the reporter carbons must not be strongly conjugated, lest it reflect the charge build-up at another site within the conjugated system. (C) 2008 Elsevier Ireland Ltd. All rights reserved.