3-O-n-octadecyl isoascorbic acid | 88306-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-O-n-octadecyl isoascorbic acid
• 英文别名: (2R)-2-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-3-octadecoxy-2H-furan-5-one
• CAS: 88306-82-5
• 化学式: C₂₄H₄₄O₆
• 分子量: 428.61
• InChiKey: OZXPGWNBRLSTAI-IFMALSPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  30
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-异抗坏血酸 在 盐酸 、 碳酸氢钠 、 乙酰氯 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 3-O-n-octadecyl isoascorbic acid
  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

文献信息

• US4552888A
  申请人：——

  公开号：US4552888A

  公开（公告）日：1985-11-12
• 3-O-Alkylascorbic acids as free-radical quenchers: synthesis and inhibitory effect on lipid peroxidation
  作者：Yasunori Nihro、Hideki Miyataka、Tadamitsu Sudo、Hitoshi Matsumoto、Toshio Satoh

  DOI：10.1021/jm00111a034

  日期：1991.7

  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.