methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate | 23598-08-5

• 分子结构分类: 有机化合物
• 英文名称: methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate
• 英文别名: 3-methoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamic acid；3-Methoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-zimtsaeure
• CAS: 23598-08-5
• 化学式: C₂₄H₂₈O₁₃
• 分子量: 524.479
• InChiKey: FOPQUCXLABOXGC-SQNDRUCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  170.19
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate 在 1,4-二氧六环 、 lithium aluminium tetrahydride 、 氯化亚砜 、 乙醚 、 苯 作用下， 生成 (E)-松柏苷
  参考文献：
  名称：

  Die Synthese des mit C14 markierten Coniferins

  摘要：

  DOI：

  10.1007/bf00899204
• 作为产物：
  描述：

  4-(beta-D-葡萄糖基)-3-甲氧基苯甲醛 在 吡啶 、 苯胺 作用下， 生成 methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate
  参考文献：
  名称：

  Helferich; Vorsatz, Journal fur praktische Chemie (Leipzig 1954), 1936, vol. <2> 145, p. 270

  摘要：

  DOI：

文献信息

• Constituents of pollen. XI. Constituents of Cryptomeria japonica D. Don.
  作者：TAICHI OHMOTO、OHGI YOSHIDA

  DOI：10.1248/cpb.31.919

  日期：——

  A new biflavone, 5'''-hydroxyamentoflavone, was isolated, together with naringenin, apigenin, luteolin, 2, 3-dihydroamentoflavone, amentoflavone, afzelin, cosmosiin, quercitrin, and 4-β-D-glucopyranosyloxyferulic acid, from pollen grains of Cryptomeria japonica D. DON.

  从花粉粒中分离出一种新的双黄酮，5'''-羟基amentoflavone，以及柚皮素、芹菜素、木犀草素、2, 3-二氢amentoflavone、amentoflavone、afzelin、cosmosiin、槲皮苷和4-β-D-glucopyranosyloxyferulic Acid。日本柳杉 D. DON。
• 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.
• Glucosidodihydroferulic Acid'
  作者：Nelson Richtmyer、Raymond Hann

  DOI：10.1021/ja01304a064

  日期：1935.1