methyl 4-[(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl]coumarate | 66642-77-1

• 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: methyl 4-[(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl]coumarate
• 英文别名: 4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamic acid；4-(Tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-zimtsaeure；methyl 4-[(2',3',4',6'-tetra-O-acetyl)-beta-D-glucopyranosyl]coumarate；(E)-3-[4-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid
• CAS: 66642-77-1
• 化学式: C₂₃H₂₆O₁₂
• 分子量: 494.452
• InChiKey: ROAJFWNOTCXYMP-XVOHNCCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 4-[(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl]coumarate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以90%的产率得到E-4-O-β-D-glucopyranosyl-p-coumaric acid
  参考文献：
  名称：

  Chemical Synthesis of Hydroxycinnamic Acid Glucosides and Evaluation of Their Ability To Stabilize Natural Colors via Anthocyanin Copigmentation

  摘要：

  This work describes the chemical synthesis of O-aryi-beta-D-glucosides and 1 -O-beta-D-glucosyl esters of hydroxycinnamic acids. In particular, OLaryl-beta-D-glucosides were efficiently prepared via a simple diastereoselective glycosylation procedure using phase transfer conditions. Despite the lability of its ester linkage, 1-O-beta-D-caffeoylglucose could also be obtained using a Lewis acid catalyzed glycosylation step and a set of protective groups that can be removed under neutral conditions. Hydroxycinnamic acid O-aryl-beta-D-glucosides were then quantitatively investigated for their affinity for the naturally occurring anthocyanin malvin (pigment). Formation of the pi-stacking molecular complexes (copigmentation) was characterized in terms of binding constants and enthalpy and entropy changes. The glucosyl moiety did not significantly alter these thermodynamic parameters, in line with a binding process solely involving the polyphenolic nuclei.

  DOI：

  10.1021/jf071205v
• 作为产物：
  描述：

  丙二酸 、 4-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 哌啶 、 吡啶 作用下， 生成 methyl 4-[(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl]coumarate
  参考文献：
  名称：

  Kratzl; Billek, Holzforschung, 1953, vol. 7, p. 66,69

  摘要：

  DOI：

文献信息

• Chemical Synthesis of Hydroxycinnamic Acid Glucosides and Evaluation of Their Ability To Stabilize Natural Colors via Anthocyanin Copigmentation
  作者：Stephanie Galland、Nathalie Mora、Maryline Abert-Vian、Njara Rakotomanomana、Olivier Dangles

  DOI：10.1021/jf071205v

  日期：2007.9.1

  This work describes the chemical synthesis of O-aryi-beta-D-glucosides and 1 -O-beta-D-glucosyl esters of hydroxycinnamic acids. In particular, OLaryl-beta-D-glucosides were efficiently prepared via a simple diastereoselective glycosylation procedure using phase transfer conditions. Despite the lability of its ester linkage, 1-O-beta-D-caffeoylglucose could also be obtained using a Lewis acid catalyzed glycosylation step and a set of protective groups that can be removed under neutral conditions. Hydroxycinnamic acid O-aryl-beta-D-glucosides were then quantitatively investigated for their affinity for the naturally occurring anthocyanin malvin (pigment). Formation of the pi-stacking molecular complexes (copigmentation) was characterized in terms of binding constants and enthalpy and entropy changes. The glucosyl moiety did not significantly alter these thermodynamic parameters, in line with a binding process solely involving the polyphenolic nuclei.
• Kratzl; Billek, Holzforschung, 1953, vol. 7, p. 66,69
  作者：Kratzl、Billek

  DOI：——

  日期：——