2-O-octadecylisoascorbic acid | 107707-32-4

• 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: 2-O-octadecylisoascorbic acid
• 英文别名: (2R)-2-[(1R)-1,2-dihydroxyethyl]-3-hydroxy-4-octadecoxy-2H-furan-5-one
• CAS: 107707-32-4
• 化学式: C₂₄H₄₄O₆
• 分子量: 428.61
• InChiKey: OIRQROBVKNWIIW-IFMALSPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 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 、 potassium carbonate 、 乙酰氯 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 21.0h， 生成 2-O-octadecylisoascorbic 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

• Pharmaceutical compositions containing ascorbic acid derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0202589A2

  公开（公告）日：1986-11-26

  wherein R1 is organic residue having molecular weight of from 15 to 700, R2 is hydrogen or hydroxyl, R3 is hydrogen, acyl, optionally substituted phosphono or sulfo, and R3 and hydroxyl of R2 may form acetal residue or ketal residue, and a salt thereof are provided. The compound (I) and salts thereof have excellent prophylactic and improving actions on disorders of circulatory functions, and they are useful as agents of prophylaxis and improvement of circulatory functional disorders.

  其中 R1 是分子量为 15 至 700 的有机残基，R2 是氢或羟基，R3 是氢、酰基、任选取代的膦酰基或磺酰基，R3 和 R2 的羟基可形成缩醛残基或酮缩残基。 化合物(I)及其盐对循环功能紊乱有很好的预防和改善作用，可作为预防和改善循环功能紊乱的药物。
• Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids
  作者：Kaneyoshi Kato、Shinji Terao、Norio Shimamoto、Minoru Hirata

  DOI：10.1021/jm00399a019

  日期：1988.4

  A novel series of 2-O-alkylascorbic acids (5a-u) was synthesized, and their scavenging activities against active oxygen species as well as their suppressive effects on the arrhythmias in rat heart ischemia-reperfusion models were evaluated. Some 2-O-alkylascorbic acids (5e-1) exhibited potent inhibiting activities against lipid peroxidation in rat brain homogenates and in alleviating effects in the ischemia-reperfusion models. Studies on the structure-activity relationship demonstrated that a free 3-enolic hydroxyl group and the longer alkyl chains substituted on the 2-hydroxyl group of ascorbic acid were beneficial for the biological and pharmacological activities. 2-O-Octadecylascorbic acid (5k, CV-3611), one of the most potent and promising compounds, markedly inhibited lipid peroxidation (IC50 = 4.3 X 10(-6) M) and alleviated myocardial lesions induced by ischemia-reperfusion at an oral dose of 1 mg/kg in rats.
• KATO, KANEYOSHI;TERAO, SHINJI;SHIMAMOTO, NORIO;HIRATA, MINORU, J. MED. CHEM., 31,(1988) N 4, 793-798
  作者：KATO, KANEYOSHI、TERAO, SHINJI、SHIMAMOTO, NORIO、HIRATA, MINORU

  DOI：——

  日期：——
• US4959362A
  申请人：——

  公开号：US4959362A

  公开（公告）日：1990-09-25
• 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.