3-O-octadecylascorbic acid | 88306-73-4

• 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: 3-O-octadecylascorbic acid
• 英文别名: 3-O-octadecyl-L-ascorbic acid；(2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-3-octadecoxy-2H-furan-5-one
• CAS: 88306-73-4
• 化学式: C₂₄H₄₄O₆
• 分子量: 428.61
• InChiKey: OZXPGWNBRLSTAI-RBBKRZOGSA-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：

  5,6-O-isopropylidene-L-ascorbic acid 在 盐酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-O-octadecylascorbic 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

• Regio- and Chemoselective One-Step 3-O-Alkylenation of Unprotected Ascorbic Acid Using ω-Iodoalkanols
  作者：Bang Luu、Thierry Muller、Paul Heuschling

  DOI：10.1055/s-0028-1087662

  日期：——

  A regio- and chemoselective alkylenation employing unprotected ascorbic acid and a series of unprotected iodoalkanols in the presence of sodium hydrogen carbonate in dimethyl sulfoxide is described. This atom economic high yielding procedure delivers the corresponding 3-O-alkylene ethers in a single step without prior protection. Specific 3-O-etherification was also observed with ­unprotected 16-iodohexadecanoic acid and with 2-(10-iododecyl)isoindole-1,3-dione. Furthermore, an 2-O-alkylene derivative was obtained when 3-O-benzyl ascorbic acid was reacted with unprotected 10-iododecanol under slightly modified conditions. Finally, the antioxidative activity of all compounds was determined and compared to vitamin C and E.

  描述了一种使用未保护的抗坏血酸和一系列未保护的碘烷醇，在碳酸氢钠存在下于二甲基亚砜中进行的区域和化学选择性烷基化。这种原子经济、高产率的程序在无需事先保护的情况下，单步合成了相应的3-O-烷基醚。同时，未保护的16-碘十六酸和2-(10-碘十烷基)异吲哚-1,3-二酮也观察到了特定的3-O-醚化。此外，当3-O-苄基抗坏血酸与未保护的10-碘癸醇在稍微修改的条件下反应时，获得了一个2-O-烷基衍生物。最后，所有化合物的抗氧化活性被测定并与维生素C和E进行了比较。
• EXTERNAL PREPARATION FOR SKIN
  申请人：Ishihara Tatsuya

  公开号：US20130309188A1

  公开（公告）日：2013-11-21

  The present invention has an object to provide an external dermal agent with a sustainable anti-wrinkle action, which has both the action of enhancing the proliferation and differentiation of keratinocytes in the skin and the action of enhancing the collagen production in the skin, and which assists the maintenance and the improvement of tissue structures and physiological functions of the epidermis and the dermis, whereby providing a remarkable skin improvement effect. The present invention solves the above abject by providing an external dermal agent containing α-D-glucopyranosyl-(1→3′)-adenosine and/or α-D-glucopyranosyl-(1→5′)-adenosine as an effective ingredient(s).

  本发明的目的是提供一种具有持续抗皱作用的外用皮肤制剂，该制剂具有促进皮肤角质细胞增殖和分化以及促进皮肤胶原蛋白产生的作用，有助于维持和改善表皮和真皮组织结构和生理功能，从而提供显著的皮肤改善效果。本发明通过提供含有α-D-葡萄糖吡喃糖基-(1→3′)-腺苷和/或α-D-葡萄糖吡喃糖基-(1→5′)-腺苷作为有效成分的外用皮肤制剂来解决上述问题。
• Antiallergic Activity of 3-O-Dodecyl-l-ascorbic Acid
  作者：Takeru Koga、Naoaki Kawahara、Mei Aburada、Asako Ono、Shiori Mae、Aina Yoshida、Yuji Iwaoka、Hideyuki Ito、Akihiro Tai

  DOI：10.3390/molecules29010069

  日期：——

  synthesized, and their degranulation inhibitory activities were evaluated. Among ascorbic acid derivatives with butyl, octyl, dodecyl, hexadecyl, and octadecyl groups introduced at the C-2 or C-3 positions, an AA derivative with a dodecyl group introduced at the C-3 position, 3-O-dodecyl-l-ascorbic acid (compound 8), showed the strongest inhibitory activity against antigen-stimulated degranulation. Compound

  合成了2-O-烷基-L-抗坏血酸和3-O-烷基-L-抗坏血酸，并评价了它们的脱颗粒抑制活性。在C-2或C-3位引入丁基、辛基、十二烷基、十六烷基和十八烷基的抗坏血酸衍生物中，在C-3位引入十二烷基的AA衍生物为3-O-十二烷基-1 -抗坏血酸（化合物8），对抗原刺激的脱颗粒表现出最强的抑制活性。化合物8还抑制钙离子载体刺激的脱颗粒。将化合物8的C-6位的羟基替换为氨基的化合物11和将化合物8的C-3位的十二烷氧基替换为十二烷氨基的化合物12合成的，这些衍生物对抗原刺激的脱粒的抑制活性比化合物8弱。此外，口服化合物8抑制小鼠被动皮肤过敏反应，其效力与抗过敏剂奥沙米特相同。这些结果表明化合物8可能是抗过敏治疗的候选药物。
• Ascorbic acid ethers and related compounds
  申请人：ELI LILLY AND COMPANY

  公开号：EP0086554A1

  公开（公告）日：1983-08-24

  Ethers of ascorbic acid, isoascorbic acid, dihydroascorbic acid, dihydroisoascorbic acid, deoxyascorbic acid, and scorbamic acid, and ketals and acetals thereof, having angiogenesis and arthritis inhibiting properties, are provided.

  本研究提供了具有血管生成和关节炎抑制特性的抗坏血酸、异抗坏血酸、二氢抗坏血酸、二氢异抗坏血酸、脱氧抗坏血酸和氨基甲酸的醚及其酮和乙缩醛。
• Selective etherification
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0379968A2

  公开（公告）日：1990-08-01

  There is disclosed an improved process for substitution of the hydroxy group at 2-position of an ascorbic acid derivative according to the following reaction scheme: wherein R⁰ is hydrogen, alkyl having 1 to 6 carbon atoms, phenyl or a group of the formula (wherein X is two hydrogen atoms, or acetal or ketal residue); R¹ is an alkyl or alkenyl group having up to 22 carbon atoms which may be substituted with phenyl or alkoxy having 1 to 22 carbon atoms; Y is halogen or optionally substituted sulfonyloxy; R is hydrogen, or primary, secondary or tertiary alkyl having 1 to 10 carbon atoms; and Z is an alkali metal or an alkali earth metal. There is also disclosed hydrolysis of the following scheme: wherein R¹ is as defined above; and X is acetal or ketal residue.

  根据以下反应方案，公开了一种抗坏血酸衍生物 2-位羟基取代的改进工艺： 其中 R⁰ 是氢、具有 1 至 6 个碳原子的烷基、苯基或式中的基团 (其中 X 是两个氢原子，或缩醛或缩酮残基）；R¹ 是具有最多 22 个碳原子的烷基或烯基，可被具有 1 至 22 个碳原子的苯基或烷氧基取代；Y 是卤素或任选取代的磺酰氧基；R 是氢，或具有 1 至 10 个碳原子的伯、仲或叔烷基；Z 是碱金属或碱土金属。还公开了以下方案的水解： 其中 R¹ 如上定义；X 为缩醛或缩酮残基。