(2R,3S,4R,5S)-2,3,4,5-Tetrakis-octanoyloxy-hexanedioic acid | 511529-52-5

• 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: (2R,3S,4R,5S)-2,3,4,5-Tetrakis-octanoyloxy-hexanedioic acid
• 英文别名: (2S,3R,4S,5R)-2,3,4,5-tetra(octanoyloxy)hexanedioic acid
• CAS: 511529-52-5
• 化学式: C₃₈H₆₆O₁₂
• 分子量: 714.935
• InChiKey: VOLFWWHOJKSUAN-IYMPVJEUSA-N

物化性质

• 沸点：
  772.1±60.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  50
• 可旋转键数：
  37
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  180
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  meso-galactaric acid 、 辛酰氯 在 zinc(II) chloride 作用下， 以70%的产率得到(2R,3S,4R,5S)-2,3,4,5-Tetrakis-octanoyloxy-hexanedioic acid
  参考文献：
  名称：

  Amphiphilic Scorpion-like Macromolecules:  Design, Synthesis, and Characterization

  摘要：

  A series of novel amphiphilic scorpion-like macromolecules (AScMs) were designed for optimized drug encapsulation and transport. The branched hydrophobic domains were prepared by acylation of mucic acid with varying chain lengths of acyl chlorides. Monohydroxylated poly(ethylene glycol) (PEG) was conjugated onto the hydrophobic domain to form the final polymers. Fluorescence spectroscopy and dynamic light scattering were performed to determine the critical micelle concentrations (cmc) and aggregation particle sizes, respectively. By changing the length of PEG and acyl chains, the physicochemical properties (e.g., M-w, HLB, T-m, cmc) of AScMs are controlled. Low emc values (10(-5)-10(-7) mol/L) and small particle sizes (10-20 nm) of AScMs are potentially applicable for lipophilic drug delivery applications.

  DOI：

  10.1021/ma030411a

文献信息

• Amphiphilic Scorpion-like Macromolecules:  Design, Synthesis, and Characterization
  作者：Lu Tian、Larry Yam、Nan Zhou、Henry Tat、Kathryn E. Uhrich

  DOI：10.1021/ma030411a

  日期：2004.1.1

  A series of novel amphiphilic scorpion-like macromolecules (AScMs) were designed for optimized drug encapsulation and transport. The branched hydrophobic domains were prepared by acylation of mucic acid with varying chain lengths of acyl chlorides. Monohydroxylated poly(ethylene glycol) (PEG) was conjugated onto the hydrophobic domain to form the final polymers. Fluorescence spectroscopy and dynamic light scattering were performed to determine the critical micelle concentrations (cmc) and aggregation particle sizes, respectively. By changing the length of PEG and acyl chains, the physicochemical properties (e.g., M-w, HLB, T-m, cmc) of AScMs are controlled. Low emc values (10(-5)-10(-7) mol/L) and small particle sizes (10-20 nm) of AScMs are potentially applicable for lipophilic drug delivery applications.