neochlorogenic acid | 342811-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: neochlorogenic acid
• 英文别名: 5-O-caffeoylquinic acid ；trans-5-O-caffeoyl-D-quinic acid；3-O-caffeoyl-quinic acid；5-O-caffeoyl quinic acid；5-O-caffeoyl-quinic acid；5-p-coumaroylquinic acid；(1R,3R,4S,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• CAS: 342811-68-1
• 化学式: C₁₆H₁₈O₉
• 分子量: 354.314
• InChiKey: CWVRJTMFETXNAD-UNIGVISCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  25
• 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：
  165
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  neochlorogenic acid 在 Candida antarctica lipase B 作用下， 40.0~80.0 ℃ 、101.33 kPa 条件下， 反应 28.0h， 生成 3-cyclohexylpropyl caffeate
  参考文献：
  名称：

  Synthesis of 3-cyclohexylpropyl caffeate from 5-caffeoylquinic acid with consecutive enzymatic conversions in ionic liquid

  摘要：

  We developed a convenient one-pot procedure for conversion of 5-caffeoylquinic acid to 3-cyclohexylpropyl caffeate, which exhibits an antiproliferative effect toward various human tumor cells. The procedure was comprised of two consecutive reactions by chlorogenate hydrolase (EC 3.1.1.42) from Aspergillus japonicus and Candida antarctica lipase B, and was performed using an ionic liquid, 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, as the reaction solvent. When various caffeoylquinic acids from coffee beans, namely, 3-caffeoylquinic acid, 4-caffeoylquinic acid, 5-caffeoylquinic acid,3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid were used, the first alcoholysis reaction with methanol using chlorogenate hydrolase produced methyl caffeate with conversion yields of 60.0%, 61.3%, 86.0%, 92.7%, and 114.0%, respectively, to each individual substrate. Two caffeoyl groups of dicaffeoylquinic acids would be used for the synthesis of methyl caffeate. In the subsequent transesterification reaction by C. antarctica lipase B with 3-cyclohexyl-1-propanol, the methyl caffeate produced was converted to 3-cyclohexylpropyl caffeate under reduced pressure to remove the by-product methanol. In the one-pot synthesis, the methyl caffeate was transesterified efficiently to 3-cyclohexylpropyl caffeate by C. antarctica lipase B with deactivation of chlorogenate hydrolase by taking advantage of the difference between the optimum temperatures for the two enzymes. This system provided 12.8 mM 3-cyclohexylpropyl caffeate from 15 mM 5-caffeoylquinic acid with conversion yield of 85.3%. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.01.012

文献信息

• Direct Observation of Hydrangea Blue-Complex Composed of 3-O-Glucosyldelphinidin, Al3+ and 5-O-Acylquinic Acid by ESI-Mass Spectrometry
  作者：Takaaki Ito、Kin-ichi Oyama、Kumi Yoshida

  DOI：10.3390/molecules23061424

  日期：——

  hydrangea is due to a metal complex anthocyanin composed of 3-O-glucosyldelphinidin (1) and an aluminum ion with the co-pigments 5-O-caffeoylquinic acid (2) and/or 5-O-p-coumaroylquinic acid (3). The three components, namely anthocyanin, Al3+ and 5-O-acylquinic acids, are essential for blue color development, but the complex is unstable and only exists in an aqueous solution. Furthermore, the complex did not

  绣球的蓝色萼片颜色归因于由3-O-葡糖基飞燕草素（1）和铝离子与共色素5-O-咖啡酰奎尼酸（2）和/或5-Op-香豆酰基奎尼丁组成的金属络合物花色苷（3）。花色苷，Al3 +和5-O-酰基奎宁酸这三个成分对于蓝色显影至关重要，但该配合物不稳定，仅存在于水溶液中。此外，该络合物没有给出可分析的NMR光谱或晶体。因此，迄今为止，许多确定绣球蓝复合物详细化学结构的试验尚未成功。相反，通过在pH 4.0的缓冲溶液中混合1，Al3 +和2或3的实验，我们获得了源自萼片的相同蓝色溶液。然而，该比率不是化学计量的而是波动的。为了确定复合物的组成，我们尝试使用电喷雾电离质谱法直接观察配合物的分子离子。在pH 4.0的低浓度缓冲溶液（2.0 mM）中，我们通过以1：1：1、1：2：1和1：3：1的比例混合1、2和Al3 +来再现绣球蓝色。所有溶液在m / z = 843时均给出相同的分子离子峰，表明蓝色溶液
• How to identify and discriminate between the methyl quinates of chlorogenic acids by liquid chromatography-tandem mass spectrometry
  作者：Rakesh Jaiswal、Nikolai Kuhnert

  DOI：10.1002/jms.1889

  日期：2011.3

  The methyl esters of chlorogenic acids, methyl quinates, are widely distributed in plant materials and frequently appear as extraction artifacts in plant samples. This is the first time when liquid chromatography–tandem mass spectrometry methods have been used for the identification and characterization of the methyl quinates. For this purpose, methyl quinates of mono caffeoylquinic acids and mono feruloylquinic

  绿原酸的甲酯，奎宁酸甲酯，广泛分布在植物材料中，经常作为提取物出现在植物样品中。这是液相色谱串联质谱法首次用于奎宁酸甲酯的鉴定和表征。为此目的，合成了单咖啡酰奎尼酸和单阿魏酰奎尼酸的奎宁甲酯作为真实的标准品。单和二酰基绿原酸的甲基奎宁酸酯在其串联质谱中显示出特征性的断裂模式。二酰基绿原酸的甲基奎宁酸的MS n +1光谱与单酰基衍生物的MS n光谱相同。这些奎宁酸酯在以下位置不产生任何奎宁甲酯峰m / z 205（与负离子模式下m / z 191处的奎宁酸峰相比）。在这些奎宁酸盐的MS n光谱中，肉桂酸部分或肉桂酰基部分被检测为负离子模式的基础峰。与针对绿原酸开发的LC-MS n方法相比，保留时间，洗脱顺序和碎片模式完全不同。这些LC-MS Ñ方法已经被应用于在马黛茶和半圆绿原酸类的甲基奎尼的鉴定和表征的区域异构体（猪殃玉竹）。两种咖啡因酰基奎宁酸甲酯（2和4）被鉴定为3-咖啡因酰基奎宁酸甲
• Polyphenols Are Intensively Metabolized in the Human Gastrointestinal Tract after Apple Juice Consumption
  作者：Kathrin Kahle、Wolfgang Huemmer、Michael Kempf、Wolfgang Scheppach、Thomas Erk、Elke Richling

  DOI：10.1021/jf071942r

  日期：2007.12.1

  Polyphenols are secondary plant compounds showing anticarcinogenic effects both in vitro and in animal experiments and may thus reduce the risk of colorectal cancer in man. The identification of polyphenol metabolites formed via their passage through the small intestine of healthy ileostomy subjects after apple juice consumption is presented. Identification and quantification of polyphenols and their metabolites were performed using HPLC-DAD as well as HPLC-ESI-MS/MS. Total procyanidin content (TPA) was measured, and additionally the mean degree of polymerization (DPm) of the procyanidins was determined in the apple juice and ileostomy effluents. As products of polyphenol metabolism, D-(-)-quinic acid and methyl esters of caffeic acid and p-coumaric acid are liberated from the corresponding hydroxycinnamic acid esters. 1-Caffeoylquinic acid and 3-caffeoylquinic acid were determined as products of isomerization. Phloretin 2'-O-glucoside (phloridzin) and phloretin 2'-O-xyloglucoside were metabolized into the corresponding aglycons phloretin and phloretin 2'-O-glucuronide and all were found in the ileostomy effluent. Ninety percent of the consumed procyanidins were recovered in the ileostomy effluent and therefore would reach the colon under physiologic circumstances. The DPm was reduced (DPm of apple juice = 5.7) and varied depending on the time point of excretion. The gastrointestinal passage seems to play an important role in the colonic availability of apple polyphenols.
• CYCLOHEXANECARBOXYLIC ACIDS FOR SELECTIVE TASTE MASKING
  申请人：International Flavors & Fragrances Inc.

  公开号：EP3169166A1

  公开（公告）日：2017-05-24
• COOLING AND FLAVOR BOOSTING COMPOSITIONS
  申请人：Firmenich SA

  公开号：EP3658109B1

  公开（公告）日：2022-12-07