ascorbyl caprate | 10583-71-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ascorbyl caprate
• 英文别名: 6-O-n-Decanoyl-ascorbinsaeure；5-(2-decanoyloxy-1-hydroxy-ethyl)-3,4-dihydroxy-5H-furan-2-one；decanoic acid 2-(3,4-dihydroxy-5-oxo-2,5-dihydro-furan-2-yl)-2-hydroxy-ethyl ester；[2-(3,4-dihydroxy-5-oxo-2H-furan-2-yl)-2-hydroxyethyl] decanoate
• CAS: 10583-71-8
• 化学式: C₁₆H₂₆O₇
• 分子量: 330.378
• InChiKey: NXNYZMCJEATBKA-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  439.7±45.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  正癸酸 、 异抗坏血酸 在 Staphylococcus xylosus lipase immobilized onto silica aerogel 作用下， 以 乙腈 、 叔丁醇 为溶剂， 反应 72.0h， 生成 ascorbyl caprate
  参考文献：
  名称：

  Lipophilization of Ascorbic Acid: A Monolayer Study and Biological and Antileishmanial Activities

  摘要：

  Ascorbyl lipophilic derivatives (Asc-C2 to Asc-C(18:1)) were synthesized in a good yield using lipase from Staphylococcus xylosus produced in our laboratory and immobilized onto silica aerogel. Results showed that esterification had little effect on radical-scavenging capacity of purified ascorbyl esters using DPPH assay in ethanol. However, long chain fatty acid esters displayed higher protection of target lipids from oxidation. Moreover, compared to ascorbic acid, synthesized derivatives exhibited an antibacterial effect. Furthermore, ascorbyl derivatives were evaluated, for the first time, for their antileishmanial effects against visceral (Leishmania infantum) and cutaneous parasites (Leishmania major). Among all the tested compounds, only Asc-C10, Asc-C12, and Asc-C(18:1) exhibited antileishmanial activities. The interaction of ascorbyl esters with a phospholipid monolayer showed that only medium and unsaturated long chain (Asc-C10 to Asc-C(18:1)) derivative esters were found to interact efficiently with mimetic membrane of leishmania. These properties would make ascorbyl derivatives good candidates to be used in cosmetic and pharmaceutical lipophilic formulations.

  DOI：

  10.1021/jf5029398