2-O-octadecyl-3-O-benzyl-ascorbic acid | 98829-11-9

• 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-octadecyl-3-O-benzyl-ascorbic acid
• 英文别名: 3-O-benzyl-2-O-octadecylascorbic acid；(2R)-2-[(1S)-1,2-dihydroxyethyl]-4-octadecoxy-3-phenylmethoxy-2H-furan-5-one
• CAS: 98829-11-9
• 化学式: C₃₁H₅₀O₆
• 分子量: 518.734
• InChiKey: SAZWNRKPPNMWPC-WUFINQPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  37
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-O-octadecyl-3-O-benzyl-ascorbic acid 在 钯 ethyl acetate diisopropyl ether 作用下， 以 乙酸乙酯 为溶剂， 以to give 2-O-octadecylascorbic acid (1.5 g)的产率得到2-O-octadecylascorbic acid
  参考文献：
  名称：

  Ascorbic acid derivatives and their production

  摘要：

  一种抗坏血酸衍生物的化学式如下：## STR1 ## 其中R.sub.1是具有分子量从58到400的有机残基，是一种新化合物，可用作食品抗氧化剂。

  公开号：

  US04780549A1
• 作为产物：
  描述：

  5,6-O-isopropylidene-L-ascorbic acid 在 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 2-O-octadecyl-3-O-benzyl-ascorbic acid
  参考文献：
  名称：

  Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids

  摘要：

  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.

  DOI：

  10.1021/jm00399a019

文献信息

• Novel antioxidant agents deriving from molecular combinations of vitamins C and E analogues: 3,4-dihydroxy-5(R)-[2(R,S)-(6-hydroxy-2,5,7,8-tetramethyl-chroman-2(R,S)-yl-methyl)-[1,3]dioxolan-4(S)-yl]-5H-furan-2-one and 3-O-octadecyl derivatives
  作者：Stefano Manfredini、Silvia Vertuani、Barbara Manfredi、Giuseppe Rossoni、Gabriella Calviello、Paola Palozza

  DOI：10.1016/s0968-0896(00)00205-4

  日期：2000.12

  Molecular combinations of two antioxidants (i.e., ascorbic acid and the pharmacophore of alpha-tocopherol), namely the 2,3-dihydroxy-2,3-enono-1,4-lactone and the chromane residues, have been designed and tested for their radical scavenging activities. When evaluated for their capability to inhibit malondialdehyde (MDA) production in rat liver microsomal membranes, the 3,4-dihydroxy-5R-2(R,S)-(6-hydroxy-2

  设计并测试了两种抗氧化剂（即抗坏血酸和α-生育酚的药效基团）的分子组合，即2,3-二羟基-2,3-enono-1,4-内酯和苯甲醚残基彻底的清除活动。当评估它们抑制大鼠肝微粒体膜中丙二醛（MDA）产生的能力时，3,4-二羟基-5R-2（R，S）-（6-羟基-2,5,7,8-四甲基苯并二氢呋喃-2 （R，S）基-甲基）-1，3]二氧戊环-4S-基] -5H-呋喃-2-酮（11a-d）表现出有趣的活性。尤其是5R，2R，2R，4S和5R，2R，2S，4S异构体（11c，d）与相应的合成α-生育酚类似物（5）和天然α-生育酚或抗坏血酸相比，显示出有效的抗氧化作用，单独或组合使用。此外，立体异构体11a-d的混合物也被证明可有效地防止离体兔心脏再灌注引起的损害，特别是在300 microM的较高浓度下。鉴于这些结果，我们的研究代表了一种潜在治疗剂的新方法，可用于涉及自由基损伤的病理事件。讨论了设计，合成和初步生物学活性。
• Pharmaceutical compositions containing certain ascorbic acid derivatives
  申请人：Takeda Chemical Industries, Inc.

  公开号：US04959362A1

  公开（公告）日：1990-09-25

  An ascorbic acid derivative of the formula: ##STR1## wherein R.sup.1 is organic residue having molecular weight of from 15 to 700, R.sup.2 is hydrogen or hydroxyl, R.sup.3 is hydrogen, acyl, optionally substituted phosphono or sulfo, and R.sup.3 and hydroxyl or R.sup.2 may form acetal residue or ketal residue, and a salt thereof are provided. The compound [I] and salts thereof have antioxidant activity and excellent prophylactic and improving actions on disorders of circulatory functions, and they are usefule as antioxidant agent for food and as agents of prophylaxis and improvement of circulatory functional disorders.

  提供一种抗坏血酸衍生物的公式：##STR1##其中，R.sup.1是具有分子量在15到700之间的有机残基，R.sup.2是氢或羟基，R.sup.3是氢、酰基、可选取代的磷酸酯或磺酸酯，且R.sup.3和羟基或R.sup.2可以形成缩醛残基或缩酮残基，以及其盐。化合物[I]及其盐具有抗氧化活性，对循环功能紊乱具有优异的预防和改善作用，它们可用作食品抗氧化剂和循环功能紊乱预防和改善剂。
• Ascorbic acid ethers and their production
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0146121A2

  公开（公告）日：1985-06-26

  An ascorbic acid derivative of the formula: wherein R1 is an organic residue having a molecular weight of from 58 to 400 is novel compound and is useful as antioxidant agent for food.

  式中的抗坏血酸衍生物是一种新型化合物，可用作食品抗氧化剂： 其中 R1 是分子量为 58 至 400 的有机残留物，是一种新型化合物，可用作食品抗氧化剂。
• 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。
• Cardioselective Ammonium, Phosphonium, and Sulfonium Analogs of .alpha.-Tocopherol and Ascorbic Acid That Inhibit in Vitro and ex Vivo Lipid Peroxidation and Scavenge Superoxide Radicals
  作者：J. Martin Grisar、Gilbert Marciniak、Frank N. Bolkenius、Joelle Verne-Mismer、Eugene R. Wagner

  DOI：10.1021/jm00015a010

  日期：1995.7

  Analogues of alpha-tocopherol and ascorbic acid with permanently cationic substituents, i.e., phosphonium (8, 9), sulfonium (11), acylhydrazinium (13, 14), and ammonium (1, 16, 21), were synthesized, and the 2R and 2S enantiomers of the alpha-tocopherol analogues 1, 8, 11, and 13 were separated. The compounds were found to scavenge lipoperoxyl and superoxide radicals in vitro and accumulate in heart tissue (cardioselectivity) as demonstrated by measurement of ex vivo inhibition of lipid peroxidation in mouse heart homogenates and confirmed by HPLC determination of drug concentrations for 1 and 11. The 2R and 2S enantiomers of 1 inhibited ex vivo lipid peroxidation to an equal extent. Thus the in vivo uptake into myocytes (cardioselectivity) is independent of the geometry at the chiral center and common to permanently cationic compounds.