neochlorogenic acid methyl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: neochlorogenic acid methyl ester
• 英文别名: 3-O-caffeoylquinic acid methyl ester；methyl 5-O-caffeoyl quinate；5-caffeoylquinic acid methyl ester；methyl (1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylate
• 化学式: C₁₇H₂₀O₉
• 分子量: 368.34
• InChiKey: MZNIJRAPCCELQX-NYCIAPANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2S,3S,4aR,6S,8R,8aR)-八氢-6,8-二羟基-2,3-二甲氧基-2,3-二甲基-1,4-苯并二氧杂环己-6-羧酸甲酯 在 吡啶 、 盐酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 neochlorogenic acid methyl ester
  参考文献：
  名称：

  Essential structure of co-pigment for blue sepal-color development of hydrangea

  摘要：

  Blue sepal-color of Hydrangea macrophylla might be due to a supramolecular metal-complex pigment consisting of delphinidin 3-glucoside (1), co-pigments (5-O-caffeoylquinic acid (2), and/or 5-O-p-coumaroylquinic acid (3)) and Al3+ in an aqueous solution around pH 4.0. To clarify the mechanism of blue sepal-color development of hydrangea, we tried to reproduce the blue color in vitro by mixing 1 with designed synthetic co-pigments in the presence of Al3+ at pH 4.0. We at first succeeded in clarifying the essential functional structure in the co-pigment that could form the stable blue solution. Here, we present the structure of the blue pigment caused by an Al-complex coordinating of I at ortho-dihydroxyl groups of the B-ring, 1-hydroxy, 1-carboxylic acid, and the carbonyl residue in the ester at 5-position of 2 and/or 3. The hydrophobic interaction between the aromatic acyl residue at 5-position and the nucleus of 1 may also contribute to stabilize the complex. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.146

文献信息

• Synthesis of Designed Acylquinic Acid Derivatives Involved in Blue Color Development of Hydrangea and Their Co-pigmentation Effect
  作者：Kumi Yoshida、Yuki Toyama-Kato、Tadao Kondo

  DOI：10.3987/com-06-s(k)6

  日期：——
• Essential structure of co-pigment for blue sepal-color development of hydrangea
  作者：Tadao Kondo、Yuki Toyama-Kato、Kumi Yoshida

  DOI：10.1016/j.tetlet.2005.07.146

  日期：2005.9

  Blue sepal-color of Hydrangea macrophylla might be due to a supramolecular metal-complex pigment consisting of delphinidin 3-glucoside (1), co-pigments (5-O-caffeoylquinic acid (2), and/or 5-O-p-coumaroylquinic acid (3)) and Al3+ in an aqueous solution around pH 4.0. To clarify the mechanism of blue sepal-color development of hydrangea, we tried to reproduce the blue color in vitro by mixing 1 with designed synthetic co-pigments in the presence of Al3+ at pH 4.0. We at first succeeded in clarifying the essential functional structure in the co-pigment that could form the stable blue solution. Here, we present the structure of the blue pigment caused by an Al-complex coordinating of I at ortho-dihydroxyl groups of the B-ring, 1-hydroxy, 1-carboxylic acid, and the carbonyl residue in the ester at 5-position of 2 and/or 3. The hydrophobic interaction between the aromatic acyl residue at 5-position and the nucleus of 1 may also contribute to stabilize the complex. (c) 2005 Elsevier Ltd. All rights reserved.