1-O-trans-caffeoyl-5-O-trans-p-coumaroylquinic acid | 1401532-34-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-trans-caffeoyl-5-O-trans-p-coumaroylquinic acid
• 英文别名: (1S,3R,4R,5R)-1-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
• CAS: 1401532-34-0
• 化学式: C₂₅H₂₄O₁₁
• 分子量: 500.459
• InChiKey: SZQUAPJIXVTPBU-ZQQDKFTKSA-N

物化性质

• 沸点：
  778.3±60.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  191
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  甲醇 、 1-O-trans-caffeoyl-5-O-trans-p-coumaroylquinic acid 在 potassium hydroxide 作用下， 反应 2.0h， 以3 mg的产率得到右旋奎宁酸
  参考文献：
  名称：

  Quinic acid derivatives from Pimpinella brachycarpa exert anti-neuroinflammatory activity in lipopolysaccharide-induced microglia

  摘要：

  Five new quinic acid derivatives (1-5), together with 10 known quinic acid derivatives (6-15), were isolated from the MeOH extract of Pimpinella brachycarpa (Umbelliferae). Their structures were established on the basis of spectroscopic analyses including extensive 2D NMR studies (COSY, HMQC and HMBC). Isolated compounds 1-15 were evaluated for their inhibitory activities on nitric oxide (NO) production in an activated murine microglial cell line. Compounds 2, 3, 8 and 11 significantly inhibited NO production without high cell toxicity in lipopolysaccharide (LPS)-activated BV-2 cells, a microglia cell line (IC50 = 4.66, 12.52, 9.04 and 12.11 mu M, respectively). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.115

文献信息

• Quinic acid derivatives from Pimpinella brachycarpa exert anti-neuroinflammatory activity in lipopolysaccharide-induced microglia
  作者：Seung Young Lee、Eunjung Moon、Sun Yeou Kim、Kang Ro Lee

  DOI：10.1016/j.bmcl.2013.01.115

  日期：2013.4

  Five new quinic acid derivatives (1-5), together with 10 known quinic acid derivatives (6-15), were isolated from the MeOH extract of Pimpinella brachycarpa (Umbelliferae). Their structures were established on the basis of spectroscopic analyses including extensive 2D NMR studies (COSY, HMQC and HMBC). Isolated compounds 1-15 were evaluated for their inhibitory activities on nitric oxide (NO) production in an activated murine microglial cell line. Compounds 2, 3, 8 and 11 significantly inhibited NO production without high cell toxicity in lipopolysaccharide (LPS)-activated BV-2 cells, a microglia cell line (IC50 = 4.66, 12.52, 9.04 and 12.11 mu M, respectively). (C) 2013 Elsevier Ltd. All rights reserved.