[(R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-yloxy]-acetic acid decyl ester | 126100-79-6

• 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: [(R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-yloxy]-acetic acid decyl ester
• CAS: 126100-79-6
• 化学式: C₂₁H₃₄O₈
• 分子量: 414.496
• InChiKey: FQIRERGCSGJMNC-CRAIPNDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  29.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [(R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-yloxy]-acetic acid decyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以52%的产率得到[(R)-2-((R)-1,2-Dihydroxy-ethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-yloxy]-acetic acid decyl ester
  参考文献：
  名称：

  3-O-Alkylascorbic acids as free-radical quenchers: synthesis and inhibitory effect on lipid peroxidation

  摘要：

  A novel series of 3-O-alkylascorbic acids (3-RASA, 3a-n) was synthesized to act as radical scavengers for active oxygen species and free radicals, and their redox potentials and inhibitory effects on lipid peroxidation in rat liver microsomes were evaluated. The redox potentials of the 3-RASA compounds were increased by the substituent group to 90-190 mV above the potential for ascorbic acid (i.e., 3-RASA compounds were harder to oxidize). Although 3-O-dodecylascorbic acid (3c) and 3-O-(decylcarbomethyl)ascorbic acid (3i) differed in their redox potentials, they both markedly inhibited lipid peroxidation in rat liver microsomes to a similar extent (IC50 = 3.1 and 3.3 x 10(-6) M, respectively). Structure-activity relationship studies demonstrated that the anti lipid peroxidation activity of the 3-RASA compounds was markedly dependent upon their hydrophobicity.

  DOI：

  10.1021/jm00111a034
• 作为产物：
  描述：

  D-异抗坏血酸 在 碳酸氢钠 、 乙酰氯 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 [(R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-yloxy]-acetic acid decyl ester
  参考文献：
  名称：

  3-O-Alkylascorbic acids as free-radical quenchers: synthesis and inhibitory effect on lipid peroxidation

  摘要：

  A novel series of 3-O-alkylascorbic acids (3-RASA, 3a-n) was synthesized to act as radical scavengers for active oxygen species and free radicals, and their redox potentials and inhibitory effects on lipid peroxidation in rat liver microsomes were evaluated. The redox potentials of the 3-RASA compounds were increased by the substituent group to 90-190 mV above the potential for ascorbic acid (i.e., 3-RASA compounds were harder to oxidize). Although 3-O-dodecylascorbic acid (3c) and 3-O-(decylcarbomethyl)ascorbic acid (3i) differed in their redox potentials, they both markedly inhibited lipid peroxidation in rat liver microsomes to a similar extent (IC50 = 3.1 and 3.3 x 10(-6) M, respectively). Structure-activity relationship studies demonstrated that the anti lipid peroxidation activity of the 3-RASA compounds was markedly dependent upon their hydrophobicity.

  DOI：

  10.1021/jm00111a034