neochlorogenic acid | 928005-87-2

• 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: 1-O-(trans-caffeoyl)quinic acid；1-O-caffeoyl quinic acid；1-O-caffeoylquinic acid；1-O-caffeyolquinic acid；1-caffeoylquinic acid；1-trans-O-caffeoylquinic acid
• CAS: 928005-87-2
• 化学式: C₁₆H₁₈O₉
• 分子量: 354.314
• InChiKey: GWTUHAXUUFROTF-JUHZACGLSA-N

物化性质

• 沸点：
  636.2±55.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.65
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  164.75
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  1,3-di-O-caffeoylquinic acid 在 盐酸 作用下， 反应 2.0h， 生成 neochlorogenic acid
  参考文献：
  名称：

  Discriminating between the Six Isomers of Dicaffeoylquinic Acid by LC-MSⁿ

  摘要：

  The fragmentation behavior of all six dicaffeoylquinic acids (diCQA) has been investigated using LC-MS4. It is possible to discriminate between each of the isomers including those for which commercial standards are not available. For diCQA, the ease of removal of the caffeoyl residue during fragmentation is 1 approximate to 5 > 3 > 4. The distinctive fragmentation observed for the little-studied 1,4- dicaffeoylquinic acid involves elimination of the C1 caffeoyl residue, repeated dehydrations leading to the aromatization of the quinic acid moiety, and its decarboxylation. It is suggested that this process is initiated by the C1 carboxyl protonating the C5 hydroxyl in the inverted chair conformer, followed by its protonating the C1 caffeoyl residue in the favored chair conformation. The fragmentation of 1-caffeoylquinic acid is indistinguishable from that of the commercially available 5-caffeoylquinic acid, but these two isomers can be distinguished easily by their facile chromatographic resolution on reversed phase packings. The hierarchical key previously developed for characterizing chlorogenic acids has been extended to accommodate 1-caffeoylquinic acid and the 1-acyl dicaffeoylquinic acids.

  DOI：

  10.1021/jf050046h

文献信息

• First Efficient Syntheses of 1-, 4-, and 5-Caffeoylquinic Acid
  作者：Michael Sefkow、Alexandra Kelling、Uwe Schilde

  DOI：10.1002/1099-0690(200107)2001:14<2735::aid-ejoc2735>3.0.co;2-i

  日期：2001.7
• Scarpati et al., Annali di Chimica, 1958, vol. 48, p. 997,1003
  作者：Scarpati et al.

  DOI：——

  日期：——
• [EN] SESQUITERPENE LACTONES AS POTENT AND BROAD SPECTRUM ANTIVIRAL COMPOUNDS AGAINST ALL GENOTYPES OF HEPATITIS C VIRUS (HCV)<br/>[FR] LACTONES SESQUITERPÉNIQUES EN TANT QUE COMPOSÉS ANTIVIRAUX PUISSANTS ET À LARGE SPECTRE CONTRE TOUS LES GÉNOTYPES DU VIRUS DE L'HÉPATITE C (VHC)
  申请人：ELSEBAI MAHMOUD FAHMI

  公开号：WO2016169573A1

  公开（公告）日：2016-10-27

  The present invention relates to potent HCV entry inhibitors (cynaropicrin and grosheimol), in addition to mono-caffoeylquinic acid derivatives which have also anti-HCV activity but less than cynaropicrin and grosheimol.
• Discriminating between the Six Isomers of Dicaffeoylquinic Acid by LC-MS<i>ⁿ</i>
  作者：Michael N. Clifford、Susan Knight、Nikolai Kuhnert

  DOI：10.1021/jf050046h

  日期：2005.5.1

  The fragmentation behavior of all six dicaffeoylquinic acids (diCQA) has been investigated using LC-MS4. It is possible to discriminate between each of the isomers including those for which commercial standards are not available. For diCQA, the ease of removal of the caffeoyl residue during fragmentation is 1 approximate to 5 > 3 > 4. The distinctive fragmentation observed for the little-studied 1,4- dicaffeoylquinic acid involves elimination of the C1 caffeoyl residue, repeated dehydrations leading to the aromatization of the quinic acid moiety, and its decarboxylation. It is suggested that this process is initiated by the C1 carboxyl protonating the C5 hydroxyl in the inverted chair conformer, followed by its protonating the C1 caffeoyl residue in the favored chair conformation. The fragmentation of 1-caffeoylquinic acid is indistinguishable from that of the commercially available 5-caffeoylquinic acid, but these two isomers can be distinguished easily by their facile chromatographic resolution on reversed phase packings. The hierarchical key previously developed for characterizing chlorogenic acids has been extended to accommodate 1-caffeoylquinic acid and the 1-acyl dicaffeoylquinic acids.