cinnamoyl 2,3-di-O-acetyl-β-D-xylopyranoside | 1587708-90-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: cinnamoyl 2,3-di-O-acetyl-β-D-xylopyranoside
• 英文别名: [(2S,3R,4S,5R)-3,4-diacetyloxy-5-hydroxyoxan-2-yl] (E)-3-phenylprop-2-enoate
• CAS: 1587708-90-4
• 化学式: C₁₈H₂₀O₈
• 分子量: 364.352
• InChiKey: DUMJXLWVPOQQJW-NFUHTBTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  cinnamoyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 在 甲醇 作用下， 以 甲基叔丁基醚 为溶剂， 反应 24.0h， 以85%的产率得到cinnamoyl 2,3-di-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  Synthesis of hydroxycinnamoyl β-d-xylopyranosides and evaluation of their antioxidant properties

  摘要：

  Various hydroxycinnamoyl beta-D-xylopyranosides were efficiently prepared from 2,3,4-tri-O-acetyl-alpha-D-xylopyranosyl bromide (TAXB) with amine by amine-promoted glycosylation. The resulted acetylated hydroxycinnamoyl beta-D-xylopyranosides with acetoxy groups at C-2, C-3, and C-4 were regioselectively deacetylated at C-4 position with Novozym 435. Antioxidant activities of free hydroxycinnamic acids and the respective beta-D-xylopyranosides were evaluated by DPPH center dot radical scavenging activity as well as their inhibitory effect on autoxidation of bulk methyl linoleate. The radical scavenging activity on 1, 1-diphenyl-2-picrylhydrazyl (DPPH center dot) decreased in the order ferulic acid > caffeic acid approximate to caffeoyl beta-D-xylopyranosides approximate to sinapinic acid > sinapoyl beta-D-xylopyranosides approximate to feruloyl beta-D-xylopyranosides > p-coumaric acid > p-coumaroyl beta-D-xylopyranosides. In bulk methyl linoleate, the antioxidant activity order against autoxidation was almost consistent with the scavenging activity order. The results showed that caffeoyl beta-D-xylopyranosides and sinapoyl beta-D-xylopyranosides were as effective as free caffeic acid, sinapinic acid, and ferulic acid. Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2013.12.014