肉豆蔻酰基色胺 | 21469-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 肉豆蔻酰基色胺
• 英文名称: N-2-(3-indolyl)ethyl-tetradecanoyl carboxamide
• 英文别名: 3-(2-Tetradecanoylamino-ethyl)-indol；Myristoyl tryptamine；N-[2-(1H-indol-3-yl)ethyl]tetradecanamide
• CAS: 21469-16-9
• 化学式: C₂₄H₃₈N₂O
• 分子量: 370.579
• InChiKey: WKHRRBLLYDJXAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  27
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  色胺 、 肉豆蔻酰氯 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 肉豆蔻酰基色胺
  参考文献：
  名称：

  Fatty acid-indole fluorescent derivatives as probes to measure the polarity of interfaces containing gangliosides

  摘要：

  The fluorescence emission properties of three indole derivative probes N-2-(3-indolyl)ethyl-tetradecanoyl carboxamide (N-myrTAM), 2-tetradecanoyl carboxamidyl-3-(3-indolyl)propanoic acid (N-myrTRP) and 11-N(2-[3-indolyl]ethylamino)-9-en-methyloxy carbonyldecenate (11-TAMundec) were studied in solvents of different polarities in pure lysophosphatidylcholine micelles (lysoPC) and in total brain gangliosides (TBG) micelles using steady-state and phase-modulation fluorometry. By comparing the fluorescence emission spectra in solvent mixtures with the spectra in lipid micelles it is concluded that the probes detect a more polar environment in TBG compared to lysoPC micelles. Quenching experiments with acrylamide indicate that the indole group of N-myrTRP and N-myrTAM are more exposed to the aqueous medium than the indole group of 11-TAMundec both in lysoPC and TBG micelles. Quenching of the indole fluorescence with brominated fatty acid at the position 9-10 of the acyl chain is in the following order: 11-TAMundec > N-MyrTAM > N-MyrTRP in lysoPC micelles whereas in TBG micelles only 11-TAMundec fluorescence is quenched. Based on the results of accessibility of the probes to the aqueous quencher and the dielectric constant calculated for their environment, we estimated the surface to core polarity gradient of the micelles. The polarity gradient is higher in TBG micelles compared to lysoPC micelles.

  DOI：

  10.1016/0009-3084(95)02499-9

文献信息

• Fatty acid-indole fluorescent derivatives as probes to measure the polarity of interfaces containing gangliosides
  作者：Luis A. Bagatolli、Guillermo G. Montich、Mario Ravera、Jorge D. Perez、Gerardo D. Fidelio

  DOI：10.1016/0009-3084(95)02499-9

  日期：1995.11

  The fluorescence emission properties of three indole derivative probes N-2-(3-indolyl)ethyl-tetradecanoyl carboxamide (N-myrTAM), 2-tetradecanoyl carboxamidyl-3-(3-indolyl)propanoic acid (N-myrTRP) and 11-N(2-[3-indolyl]ethylamino)-9-en-methyloxy carbonyldecenate (11-TAMundec) were studied in solvents of different polarities in pure lysophosphatidylcholine micelles (lysoPC) and in total brain gangliosides (TBG) micelles using steady-state and phase-modulation fluorometry. By comparing the fluorescence emission spectra in solvent mixtures with the spectra in lipid micelles it is concluded that the probes detect a more polar environment in TBG compared to lysoPC micelles. Quenching experiments with acrylamide indicate that the indole group of N-myrTRP and N-myrTAM are more exposed to the aqueous medium than the indole group of 11-TAMundec both in lysoPC and TBG micelles. Quenching of the indole fluorescence with brominated fatty acid at the position 9-10 of the acyl chain is in the following order: 11-TAMundec > N-MyrTAM > N-MyrTRP in lysoPC micelles whereas in TBG micelles only 11-TAMundec fluorescence is quenched. Based on the results of accessibility of the probes to the aqueous quencher and the dielectric constant calculated for their environment, we estimated the surface to core polarity gradient of the micelles. The polarity gradient is higher in TBG micelles compared to lysoPC micelles.