2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl (trans)-sinapinate | 1053615-45-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl (trans)-sinapinate
• 英文别名: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl (trans)-sinapate；(2S,3R,4S,5R,6R)-3,4,5-Tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-YL (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate；[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl] (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• CAS: 1053615-45-4
• 化学式: C₂₅H₃₀O₁₄
• 分子量: 554.505
• InChiKey: OVDHLKVANAGJCA-BKLNSXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl (trans)-sinapinate 在 甲醇 、 immobilized lipase from Candida Antarctica 作用下， 以 甲基叔丁基醚 为溶剂， 反应 24.0h， 以90%的产率得到2,3-di-O-acetyl-β-D-glucopyranosyl trans-sinapinate
  参考文献：
  名称：

  Synthesis of glycosyl ferulate derivatives by amine-promoted glycosylation with regioselective hydrolysis using Novozym 435 and evaluation of their antioxidant properties

  摘要：

  Various glycosyl ferulates were efficiently synthesized from 2,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide (TAGB) with amine by amine-promoted glycosylation without using heavy metal. The resulted acetylated glycosyl ferulates with acetoxyl groups at C-2, C-3 and C-4 were regioselectively deacetylated at C-4 and C-6 positions with Novozym 435. Antioxidant abilities of free ferulic acids and its synthetic glycosyl ferulates were evaluated by inhibitory effect on autoxidation of bulk methyl linoleate as well as their radical scavenging activity. The radical scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH.) decreased in the order ferulic acid > sinapinic acid approximate to glycosyl sinapinates approximate to glycosyl ferulates > p-coumaric acid > glycosyl p-coumarates. In bulk methyl linoleate, the antioxidant activity order against autoxidation was very consistent with the scavenging activity order. The results showed that glycosyl ferulates and sinapinates were effective as well as free carboxylic acid forms. Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2012.06.019
• 作为产物：
  描述：

  3,5-二甲氧基-4-羟基肉桂酸 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以73%的产率得到2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl (trans)-sinapinate
  参考文献：
  名称：

  Synthesis of glycosyl ferulate derivatives by amine-promoted glycosylation with regioselective hydrolysis using Novozym 435 and evaluation of their antioxidant properties

  摘要：

  Various glycosyl ferulates were efficiently synthesized from 2,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide (TAGB) with amine by amine-promoted glycosylation without using heavy metal. The resulted acetylated glycosyl ferulates with acetoxyl groups at C-2, C-3 and C-4 were regioselectively deacetylated at C-4 and C-6 positions with Novozym 435. Antioxidant abilities of free ferulic acids and its synthetic glycosyl ferulates were evaluated by inhibitory effect on autoxidation of bulk methyl linoleate as well as their radical scavenging activity. The radical scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH.) decreased in the order ferulic acid > sinapinic acid approximate to glycosyl sinapinates approximate to glycosyl ferulates > p-coumaric acid > glycosyl p-coumarates. In bulk methyl linoleate, the antioxidant activity order against autoxidation was very consistent with the scavenging activity order. The results showed that glycosyl ferulates and sinapinates were effective as well as free carboxylic acid forms. Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2012.06.019