3-p-coumaroylquinic acid | 87099-71-6

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-p-coumaroylquinic acid
• 英文别名: 3-O-p-coumaroylquinic acid；p-coumaroylquinic acid；5-O-p-coumaroylquinic acid；5-O-coumaroylquinic acid；3‐p‐coumaroylquinic acid；trans-3-p-coumaroylquinic acid；5-coumaroylquinic acid；(1R,3R,4S,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
• CAS: 87099-71-6
• 化学式: C₁₆H₁₈O₈
• 分子量: 338.314
• InChiKey: BMRSEYFENKXDIS-QHAYPTCMSA-N

物化性质

• 沸点：
  613.2±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  247-248°C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-p-coumaroylquinic acid 在 sulfatase 作用下， 反应 3.0h， 生成 4-羟基肉桂酸 、 4-香豆酸
  参考文献：
  名称：

  Identification and Quantification of Phenolic Compounds from the Forage Legume Sainfoin (Onobrychis viciifolia)

  摘要：

  Phenolic compounds of sainfoin (Onobrychis viciifolia) variety Cotswold Common are assumed to contribute to its nutritive value and bioactive properties. A purified acetone/water extract was separated by Sephadex LH-20 gel chromatography. Sixty-three phenolic and other aromatic compounds were identified by means of chemical, chromatographic, and spectroscopic methods. Reverse phase HPLC with diode array and chemical reaction detection was used to investigate the phenolic composition of different plant organs. All plant parts showed specific phenolic profiles. Moreover, there were considerable variations in the phenolic content among individual plants of the same variety. The three most abundant phenolic compounds were found to be arbutin [predominant in petiols, 17.7 mg/g of dry weight (DW)], rutin (predominant in leaves, 19.9 mg/g of DW), and catechin (predominant flavanol in petiols, 3.5 mg/g of DW). The present study reveals that the phenolic profile of sainfoin is even more complex than hitherto assumed.

  DOI：

  10.1021/jf900625r
• 作为产物：
  描述：

  (2'S,3'S)-methyl 3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate 在 五甲基苯 、 四丁基氟化铵 、 三氯化硼 、 caesium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 对甲苯磺酰氯 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.75h， 生成 3-p-coumaroylquinic acid
  参考文献：
  名称：

  以对甲氧基苄基奎宁酸酯为关键中间体，通过直接酯化反应高效合成5- O-酰基奎宁酸

  摘要：

  从市售（-）-奎宁酸完成了5- O-酰基奎宁酸的有效和通用合成。我们设计了对甲氧基苄基奎宁酸酯作为关键中间体，并解决了两个问题，即空间位阻的5-OH基团的酯化，以实现简洁的发散合成和最终脱保护步骤的收率低。对于第一个问题，我们通过添加i -Pr 2 NEt改进了田边的方法，即使用游离羧酸的TsCl / NMI介导的酯化反应。对于第二个问题，我们为最终的脱保护步骤建立了TFA或BCl 3 / C 6 HMe 5催化的脱保护反应。5 Ø-酰基奎尼酸通过七个步骤合成，总收率为45-60％。

  DOI：

  10.1016/j.tet.2014.08.064

文献信息

• CYCLOHEXANECARBOXYLIC ACIDS FOR SELECTIVE TASTE MASKING
  申请人：International Flavors & Fragrances Inc.

  公开号：EP3524062A2

  公开（公告）日：2019-08-14

  The use of cyclohexanecarboxylic acids in a consumable to provide taste specific masking effect is provided.

  在消费品中使用环己烷羧酸可提供特定口味的掩蔽效果。
• 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.
• Identification and Quantification of Phenolic Compounds from the Forage Legume Sainfoin (Onobrychis viciifolia)
  作者：Ionela Regos、Andrea Urbanella、Dieter Treutter

  DOI：10.1021/jf900625r

  日期：2009.7.8

  Phenolic compounds of sainfoin (Onobrychis viciifolia) variety Cotswold Common are assumed to contribute to its nutritive value and bioactive properties. A purified acetone/water extract was separated by Sephadex LH-20 gel chromatography. Sixty-three phenolic and other aromatic compounds were identified by means of chemical, chromatographic, and spectroscopic methods. Reverse phase HPLC with diode array and chemical reaction detection was used to investigate the phenolic composition of different plant organs. All plant parts showed specific phenolic profiles. Moreover, there were considerable variations in the phenolic content among individual plants of the same variety. The three most abundant phenolic compounds were found to be arbutin [predominant in petiols, 17.7 mg/g of dry weight (DW)], rutin (predominant in leaves, 19.9 mg/g of DW), and catechin (predominant flavanol in petiols, 3.5 mg/g of DW). The present study reveals that the phenolic profile of sainfoin is even more complex than hitherto assumed.
• Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate
  作者：Kin-ichi Oyama、Noriyuki Watanabe、Tomomi Yamada、Masako Suzuki、Yukiko Sekiguchi、Tadao Kondo、Kumi Yoshida

  DOI：10.1016/j.tet.2014.08.064

  日期：2015.5

  An efficient and versatile synthesis of 5-O-acylquinic acids from commercially available (−)-quinic acid was accomplished. We designed p-methoxybenzyl quinate as a key intermediate, and two problems, the esterification of the sterically hindered 5-OH group for the concise divergent synthesis and the low yield of the final deprotection step, were solved. For the first problem, we improved Tanabe's method

  从市售（-）-奎宁酸完成了5- O-酰基奎宁酸的有效和通用合成。我们设计了对甲氧基苄基奎宁酸酯作为关键中间体，并解决了两个问题，即空间位阻的5-OH基团的酯化，以实现简洁的发散合成和最终脱保护步骤的收率低。对于第一个问题，我们通过添加i -Pr 2 NEt改进了田边的方法，即使用游离羧酸的TsCl / NMI介导的酯化反应。对于第二个问题，我们为最终的脱保护步骤建立了TFA或BCl 3 / C 6 HMe 5催化的脱保护反应。5 Ø-酰基奎尼酸通过七个步骤合成，总收率为45-60％。