2-Amino-palmitinsaeureamid | 13880-25-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Amino-palmitinsaeureamid
• 英文别名: Aminostearamide；2-aminooctadecanamide
• CAS: 13880-25-6
• 化学式: C₁₈H₃₈N₂O
• 分子量: 298.513
• InChiKey: CHKKUAYZLGNROD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  69.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Amino-palmitinsaeureamid 在 lithium aluminium tetrahydride 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 72.5h， 生成 2,2'azo[2-(2-imidiazolin-2-yl)propane]{2-[2-(4-n-hexadecyl)imidazolin-2-yl]propane}
  参考文献：
  名称：

  Unsymmetrical Azo Initiators Increase Efficiency of Radical Generation in Aqueous Dispersions, Liposomal Membranes, and Lipoproteins

  摘要：

  Lipid peroxidation studies often employ the use of azo initiators to produce a slow, steady source of free radicals, but the lack of initiators capable of efficiently generating radicals in lipid aggregates such as micelles and membranes has created persistent problems in these investigations. We report here the synthesis and study of unsymmetrically substituted (hydrophilic/hydrophobic) azo initiators C-8, C-12, and C-16 that increase the efficiency of radical generation in lipophilic regions of aqueous emulsions such as micelles and liposomes. Radical generation from these initiators was monitored in micelles? liposomes, and lipoproteins by the use of two radical scavengers, one that scavengers lipophilic peroxyl radicals and one that scavenges hydrophilic peroxyls. The lipophilic radical scavenger used was the well-known antioxidant alpha-tocopherol and thr hydrophilic radical scavenger used was uric acid. Two peroxyl radicals are trapped by each of these scavengers, tocopherol presumably being biased toward reacting with lipid soluble radicals, uric acid presumably reacting preferentially with water-soluble radicals. In Triton X-100 micelles the unsymmetrical initiators C-8 and C-16 display an increase in both alpha-TOH (alpha-tocopherol) trapping and in overall radical generation efficiency compared to the symmetrical initiators C-0 (hydrophilic) and MeOAMVN (lipophilic). The unsymmetrical azo initiators performance in liposomes was excellent (increased cage escape with lipid compartment access). In low-density lipoprotein oxidations, the initiators C-8, C-12, and C-16 also provided advantages over C-0 and MeOAMVN. The hydrophilic/hydrophobic character of the two radicals generated from the unsymmetrical initiators is an important factor for separating the geminate radical pair, These initiators, when compared to the widely used symmetrical azo initiators, provide an advantage of free radical production, lipophilic access, and constant radical generation in the investigation of lipid peroxidation in various media.

  DOI：

  10.1021/ja9934605
• 作为产物：
  描述：

  溴代十六烷 在 氯化亚砜 、 乙醇 、 氨 、 sodium 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 168.0h， 生成 2-Amino-palmitinsaeureamid
  参考文献：
  名称：

  Unsymmetrical Azo Initiators Increase Efficiency of Radical Generation in Aqueous Dispersions, Liposomal Membranes, and Lipoproteins

  摘要：

  Lipid peroxidation studies often employ the use of azo initiators to produce a slow, steady source of free radicals, but the lack of initiators capable of efficiently generating radicals in lipid aggregates such as micelles and membranes has created persistent problems in these investigations. We report here the synthesis and study of unsymmetrically substituted (hydrophilic/hydrophobic) azo initiators C-8, C-12, and C-16 that increase the efficiency of radical generation in lipophilic regions of aqueous emulsions such as micelles and liposomes. Radical generation from these initiators was monitored in micelles? liposomes, and lipoproteins by the use of two radical scavengers, one that scavengers lipophilic peroxyl radicals and one that scavenges hydrophilic peroxyls. The lipophilic radical scavenger used was the well-known antioxidant alpha-tocopherol and thr hydrophilic radical scavenger used was uric acid. Two peroxyl radicals are trapped by each of these scavengers, tocopherol presumably being biased toward reacting with lipid soluble radicals, uric acid presumably reacting preferentially with water-soluble radicals. In Triton X-100 micelles the unsymmetrical initiators C-8 and C-16 display an increase in both alpha-TOH (alpha-tocopherol) trapping and in overall radical generation efficiency compared to the symmetrical initiators C-0 (hydrophilic) and MeOAMVN (lipophilic). The unsymmetrical azo initiators performance in liposomes was excellent (increased cage escape with lipid compartment access). In low-density lipoprotein oxidations, the initiators C-8, C-12, and C-16 also provided advantages over C-0 and MeOAMVN. The hydrophilic/hydrophobic character of the two radicals generated from the unsymmetrical initiators is an important factor for separating the geminate radical pair, These initiators, when compared to the widely used symmetrical azo initiators, provide an advantage of free radical production, lipophilic access, and constant radical generation in the investigation of lipid peroxidation in various media.

  DOI：

  10.1021/ja9934605

文献信息

• Kempter,G.; Moser,G., Journal fur praktische Chemie (Leipzig 1954), 1966, vol. 34, p. 104 - 111
  作者：Kempter,G.、Moser,G.

  DOI：——

  日期：——
• Unsymmetrical Azo Initiators Increase Efficiency of Radical Generation in Aqueous Dispersions, Liposomal Membranes, and Lipoproteins
  作者：Sean M. Culbertson、Ned A. Porter

  DOI：10.1021/ja9934605

  日期：2000.5.1

  Lipid peroxidation studies often employ the use of azo initiators to produce a slow, steady source of free radicals, but the lack of initiators capable of efficiently generating radicals in lipid aggregates such as micelles and membranes has created persistent problems in these investigations. We report here the synthesis and study of unsymmetrically substituted (hydrophilic/hydrophobic) azo initiators C-8, C-12, and C-16 that increase the efficiency of radical generation in lipophilic regions of aqueous emulsions such as micelles and liposomes. Radical generation from these initiators was monitored in micelles? liposomes, and lipoproteins by the use of two radical scavengers, one that scavengers lipophilic peroxyl radicals and one that scavenges hydrophilic peroxyls. The lipophilic radical scavenger used was the well-known antioxidant alpha-tocopherol and thr hydrophilic radical scavenger used was uric acid. Two peroxyl radicals are trapped by each of these scavengers, tocopherol presumably being biased toward reacting with lipid soluble radicals, uric acid presumably reacting preferentially with water-soluble radicals. In Triton X-100 micelles the unsymmetrical initiators C-8 and C-16 display an increase in both alpha-TOH (alpha-tocopherol) trapping and in overall radical generation efficiency compared to the symmetrical initiators C-0 (hydrophilic) and MeOAMVN (lipophilic). The unsymmetrical azo initiators performance in liposomes was excellent (increased cage escape with lipid compartment access). In low-density lipoprotein oxidations, the initiators C-8, C-12, and C-16 also provided advantages over C-0 and MeOAMVN. The hydrophilic/hydrophobic character of the two radicals generated from the unsymmetrical initiators is an important factor for separating the geminate radical pair, These initiators, when compared to the widely used symmetrical azo initiators, provide an advantage of free radical production, lipophilic access, and constant radical generation in the investigation of lipid peroxidation in various media.