(-)-1,3,5-tri-O-caffeoylquinic acid | 1073897-80-9

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-1,3,5-tri-O-caffeoylquinic acid
• 英文别名: 1,3,5-tri-O-caffeoylquinic acid
• CAS: 1073897-80-9
• 化学式: C₃₄H₃₀O₁₅
• 分子量: 678.603
• InChiKey: MSKVJEAKVWAQTA-UPHZGLEOSA-N

物化性质

• 沸点：
  960.4±65.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  49.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  257.81
• 氢给体数：
  8.0
• 氢受体数：
  14.0

制备方法与用途

生物活性化合物1,3,5-三咖啡酰奎宁酸是从胡枝子中分离出来的一种tricaffeoylquinic酸衍生物，展现出抗HIV的作用。

反应信息

• 作为产物：
  描述：

  在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (-)-1,3,5-tri-O-caffeoylquinic acid
  参考文献：
  名称：

  天然存在的 (-)-1,3,5-Tri-O-Caffeoylquinic 酸的合成

  摘要：

  核糖核酸酶 H (RNase H) 是人类免疫缺陷病毒 (HIV) 复制的重要组成部分，并且只有少数这种酶的抑制剂是已知的。Millenia Hope Pharmaceuticals Inc. 发现 (-)-1,3,5-tri-O-caffeoylquinic 酸是一种有效的 RNase H 抑制剂和抗病毒剂。其中报道了一种从市售 (-)-奎尼酸制备该抑制剂的简便途径。

  DOI：

  10.1055/s-0029-1217183

文献信息

• Characterization and Quantification of Hydroxycinnamate Derivatives in Stevia rebaudiana Leaves by LC-MS^<i>n</i>
  作者：Hande Karaköse、Rakesh Jaiswal、Nikolai Kuhnert

  DOI：10.1021/jf202185m

  日期：2011.9.28

  Stevia rebaudiana leaves are used as a zero-calorie natural sweetener in a variety of food products in Asian countries, especially in Japan. In this study, the hydroxycinnamate derivatives of S. rebaudiana have been investigated qualitatively and quantitatively by LC-MSn. Twenty-four hydroxycinnainic acid derivatives of quinic and shikimic acid were detected, and 19 of them were successfully characterized to regioisomeric levels; 23 are reported for the first time from this source. These comprise three monocaffeoylquinic acids (M-r 354), seven dicaffeoylquinic acids (M-r 516), one p-coumaroylquinic acid (M-r 338), one feruloylquinic acid (M-r 368), two caffeoyl-feruloylquinic acids (M-r 530), three caffeoylshildmic acids (M-r 336), and two tricaffeoylquinic acids (M-r 678). Cis isomers of di- and tricaffeoylquinic acids were observed as well. Three tricaffeoylquinic acids identified in stevia leaves are reported for the first time in nature. These phenolic compounds identified in stevia might affect the organoleptic properties and add additional beneficial health effects to stevia-based products.
• Synthesis of the Naturally Occurring (-)-1,3,5-Tri-<i>O</i>-Caffeoylquinic Acid
  作者：Kay Brummond、Jolie DeForrest

  DOI：10.1055/s-0029-1217183

  日期：——

  and only a few inhibitors of this enzyme are known. Millenia Hope Pharmaceuticals Inc. found that (-)-1,3,5-tri-O-caffeoylquinic acid is a potent RNase H inhibitor and antiviral agent. A facile route leading to this inhibitor from commercially available (-)-quinic acid is reported within.

  核糖核酸酶 H (RNase H) 是人类免疫缺陷病毒 (HIV) 复制的重要组成部分，并且只有少数这种酶的抑制剂是已知的。Millenia Hope Pharmaceuticals Inc. 发现 (-)-1,3,5-tri-O-caffeoylquinic 酸是一种有效的 RNase H 抑制剂和抗病毒剂。其中报道了一种从市售 (-)-奎尼酸制备该抑制剂的简便途径。