angelic acid | 117425-95-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: angelic acid
• 英文别名: 4-oxo-pentanoic acid; 3-enol form；4-hydroxy-pent-3-enoic acid；Laevulinsaeure；3-Pentenoic acid,4-hydroxy-(9ci)；4-hydroxypent-3-enoic acid
• CAS: 117425-95-3
• 化学式: C₅H₈O₃
• mdl: MFCD18834738
• 分子量: 116.117
• InChiKey: FZBYZQPNENFBLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 angelic acid 以 四氢呋喃 为溶剂， 生成 (Z)-4-Hydroxy-pent-3-enoic acid methyl ester
  参考文献：
  名称：

  Structure−Cytoprotective Activity Relationship of Simple Molecules Containing an α,β-Unsaturated Carbonyl System

  摘要：

  In previous reports we attributed the cytoprotective activity of several sesquiterpene lactones to the presence of a nonhindered electrophilic acceptor in their structure. We suggested that the mechanism of protection would be, at least in part, mediated through a reaction between the electrophilic acceptor and the sulfhydryl-containing groups of the mucosa. We report here the gastric cytoprotective effect of simple molecules containing an alpha,beta-unsaturated carbonyl group. In the present paper, we undertake the study of molecular accessibility and molecular shape, in addition to conformational, electronic, and steric factors. Our results helped to establish two important facts connecting chemical structure with cytoprotective effect. Firstly, an adequate molecular accessibility appears to be necessary to produce the biological response, and secondly, the alpha,beta-unsaturated carbonyl system has to be included in a cyclic structure or, at least, in the proximity of a cyclic system.

  DOI：

  10.1021/jm960280m
• 作为产物：
  描述：

  惕格酸 在 二苯二硫醚 作用下， 以 苯 为溶剂， 反应 24.0h， 以23%的产率得到angelic acid
  参考文献：
  名称：

  Structure−Cytoprotective Activity Relationship of Simple Molecules Containing an α,β-Unsaturated Carbonyl System

  摘要：

  In previous reports we attributed the cytoprotective activity of several sesquiterpene lactones to the presence of a nonhindered electrophilic acceptor in their structure. We suggested that the mechanism of protection would be, at least in part, mediated through a reaction between the electrophilic acceptor and the sulfhydryl-containing groups of the mucosa. We report here the gastric cytoprotective effect of simple molecules containing an alpha,beta-unsaturated carbonyl group. In the present paper, we undertake the study of molecular accessibility and molecular shape, in addition to conformational, electronic, and steric factors. Our results helped to establish two important facts connecting chemical structure with cytoprotective effect. Firstly, an adequate molecular accessibility appears to be necessary to produce the biological response, and secondly, the alpha,beta-unsaturated carbonyl system has to be included in a cyclic structure or, at least, in the proximity of a cyclic system.

  DOI：

  10.1021/jm960280m

文献信息

• Structure−Cytoprotective Activity Relationship of Simple Molecules Containing an α,β-Unsaturated Carbonyl System
  作者：Ana M. Rodríguez、Ricardo D. Enriz、Luis N. Santagata、Esteban A. Jáuregui、Mauricio J. Pestchanker、Oscar S. Giordano

  DOI：10.1021/jm960280m

  日期：1997.6.1

  In previous reports we attributed the cytoprotective activity of several sesquiterpene lactones to the presence of a nonhindered electrophilic acceptor in their structure. We suggested that the mechanism of protection would be, at least in part, mediated through a reaction between the electrophilic acceptor and the sulfhydryl-containing groups of the mucosa. We report here the gastric cytoprotective effect of simple molecules containing an alpha,beta-unsaturated carbonyl group. In the present paper, we undertake the study of molecular accessibility and molecular shape, in addition to conformational, electronic, and steric factors. Our results helped to establish two important facts connecting chemical structure with cytoprotective effect. Firstly, an adequate molecular accessibility appears to be necessary to produce the biological response, and secondly, the alpha,beta-unsaturated carbonyl system has to be included in a cyclic structure or, at least, in the proximity of a cyclic system.