methyl 4-O-β-glucopyranosyl-(E)-caffeate | 499-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-β-glucopyranosyl-(E)-caffeate
• 英文别名: methyl 4-O-(β-D-glucopyranosyl)-caffeate；methyl-4-O-(β-D-glucopyranosyl)caffeate；methyl 4-(β-D-glucopyranosyl)caffeate；methyl 4-O-β-D-glucopyranosylcaffeate；methyl 4-β-D-glucopyranosylcaffeate；4-β-D-glucopyranosyloxy-3-hydroxy-trans-cinnamic acid methyl ester；methyl (E)-3-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoate
• CAS: 499-21-8
• 化学式: C₁₆H₂₀O₉
• 分子量: 356.329
• InChiKey: RHLLCIWGXNNMLI-BJGSYIFTSA-N

物化性质

• 沸点：
  644.2±55.0 °C(Predicted)
• 密度：
  1.510±0.06 g/cm3(Predicted)
• 熔点：
  208 °C(Solv: methanol (67-56-1))

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 4-O-β-glucopyranosyl-(E)-caffeate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以85%的产率得到4-O-(β-D-glucopyranosyl)-trans-caffeic 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：

  methyl pentaacetyl-4-O-β-D-glucopyranosylcaffeate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 methyl 4-O-β-glucopyranosyl-(E)-caffeate
  参考文献：
  名称：

  Heavenly blue anthocyanin II -4-0-(6-0-(-3-0-(β -d-glucopyranosyl)caffeyl)-β-d-glucopyranosyl)- caffeic acid, a novel component in heavenly blue anthocyanin

  摘要：

  DOI：

  10.1016/s0040-4039(01)81866-9

文献信息

• Structure of anthocyanin from the blue petals of Phacelia campanularia and its blue flower color development
  作者：Mihoko Mori、Tadao Kondo、Kenjiro Toki、Kumi Yoshida

  DOI：10.1016/j.phytochem.2005.12.024

  日期：2006.3

  The dicaffeoyl anthocyanin, phacelianin, was isolated from blue petals of Phacelia campanularia. Its structure was determined to be 3-O-(6-O-(4'-O-(6-O-(4'-O-beta-d-glucopyranosyl-(E)-caffeoyl)-beta-d-glucopyranosyl)-(E)-caffeoyl)-beta-d-glucopyranosyl)-5-O-(6-O-malonyl-beta-d-glucopyranosyl)delphinidin. The CD of the blue petals of the phacelia showed a strong negative Cotton effect and that of the

  双咖啡酰花青素，phacelianin，是从Phacelia campanularia 的蓝色花瓣中分离出来的。其结构被确定为 3-O-(6-O-(4'-O-(6-O-(4'-O-β-d-吡喃葡萄糖基-(E)-caffeoyl)-β-d-吡喃葡萄糖基)-(E)-咖啡酰)-β-d-吡喃葡萄糖基)-5-O-(6-O-丙二酰-β-d-吡喃葡萄糖基)飞燕草素。phacelia蓝色花瓣的CD显示出强烈的负Cotton效应，有色原生质体悬浮液的CD相同，表明phacelianin的生色团可能在蓝色液泡中以逆时针堆积的方式进行分子间堆积. 在弱酸性水溶液中，phacelianin 在 CD 中显示出与花瓣相同的蓝色和负棉花效应。然而，在没有金属离子的情况下逐渐形成蓝黑色沉淀。可能需要极少量的 Al(3+) 或 Fe(3+) 来稳定蓝色溶液。Phacelianin 可能同时采取分子间和分子内堆积的形式，通
• Structure of cinerarin, a tetra-acylated anthocyanin isolated from the blue garden cineraria,
  作者：Toshio Goto、Tadao Kondo、Takatoshi Kawai、Hirotoshi Tamura

  DOI：10.1016/s0040-4039(01)81749-4

  日期：1984.1
• The Glucosides of Flaxseed. II. Linocaffein¹
  作者：Harold J. Klosterman、Robert Z. Muggli

  DOI：10.1021/ja01518a043

  日期：1959.5
• Structure of platyconin, a diacylated anthocyanin isolated from the chinese bell-flower platycodon grandiflorum
  作者：Toshio Goto、TadaoKondo、Hirotoshi Tamura、Kiyoko Kawahori、Hiroyuki Hattori

  DOI：10.1016/s0040-4039(00)81877-8

  日期：——
• 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.