N-(4'-hydroxy-3'-methoxy-(E)-cinnamoyl)-5-hydroxy-4-methoxyanthranilic acid | 154992-25-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-(4'-hydroxy-3'-methoxy-(E)-cinnamoyl)-5-hydroxy-4-methoxyanthranilic acid
• 英文别名: avenanthramide 3f；Avenanthramide 2；5-hydroxy-2-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]amino]-4-methoxybenzoic acid
• CAS: 154992-25-3
• 化学式: C₁₈H₁₇NO₇
• 分子量: 359.335
• InChiKey: YDAKMIMUVCLFIN-GQCTYLIASA-N

物化性质

• 熔点：
  263-264 °C (decomp)
• 沸点：
  649.9±55.0 °C(Predicted)
• 密度：
  1.444±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-硝基-4-甲氧基-5-羟基苯甲酸 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 β-丙氨酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 5.83h， 生成 N-(4'-hydroxy-3'-methoxy-(E)-cinnamoyl)-5-hydroxy-4-methoxyanthranilic acid
  参考文献：
  名称：

  Quantitation and Taste Contribution of Sensory Active Molecules in Oat (Avena sativa L.)

  摘要：

  A total of 59 taste-active molecules were quantitated and then rated for their individual taste impact on the basis of dose-over-threshold factors in oat flour (Avena sativa L.). A sensitive high-performance liquid chromatography-tandem mass spectrometry method was developed to quantitate bitter-tasting steroidal and furostanol saponins as well as avenanthramides. Four monoglycerides, five free fatty acids and four saponins were confirmed for the first time to be major contributors to the bitter off-taste of oats, among them 1-linoleoyl-rac-glycerol, 1-stearoyl-rac-glycerol, 1-oleoyl-rac-glycerol, 1-palmitoyl-rac-glycerol, linoleic acid, linolenic acid, oleic acid, palmitic acid, and stearic acid as well as avenacosides A and B and the recently identified furostanosides 3(O-alpha-L-rhamnopyranosyl(1 -> 2)-[beta-D-glucopyranosyl(1 -> 3)-beta-D-glucopyranosyl(1 -> 4)]-beta-D-glucopyranosid)-26-O-beta-D-glucopyranosyl-(25R)-furost-5-ene-3 beta,22,26-triol and 3-(O-alpha-L-rhamnopyranosyl(1 -> 2)-[beta-D-glucopyranosyl(1 -> 4)]-beta-D-glucopyranosid)-26-O-beta-D-glucopyranosyl-(25R)-furost-5-ene-3 beta,22,26-triol. By means of a stable isotope dilution assay, quantitated avenanthramides 2c, 2p, 2f, 1p, 1c, 1f, and 3f were found in concentrations below their thresholds and, therefore, did not contribute to the bitter sensation of the tested oat flour.

  DOI：

  10.1021/acs.jafc.0c04022

文献信息

• Quantitation and Taste Contribution of Sensory Active Molecules in Oat (<i>Avena sativa</i> L.)
  作者：Kirsten Günther-Jordanland、Corinna Dawid、Thomas Hofmann

  DOI：10.1021/acs.jafc.0c04022

  日期：2020.9.16

  A total of 59 taste-active molecules were quantitated and then rated for their individual taste impact on the basis of dose-over-threshold factors in oat flour (Avena sativa L.). A sensitive high-performance liquid chromatography-tandem mass spectrometry method was developed to quantitate bitter-tasting steroidal and furostanol saponins as well as avenanthramides. Four monoglycerides, five free fatty acids and four saponins were confirmed for the first time to be major contributors to the bitter off-taste of oats, among them 1-linoleoyl-rac-glycerol, 1-stearoyl-rac-glycerol, 1-oleoyl-rac-glycerol, 1-palmitoyl-rac-glycerol, linoleic acid, linolenic acid, oleic acid, palmitic acid, and stearic acid as well as avenacosides A and B and the recently identified furostanosides 3(O-alpha-L-rhamnopyranosyl(1 -> 2)-[beta-D-glucopyranosyl(1 -> 3)-beta-D-glucopyranosyl(1 -> 4)]-beta-D-glucopyranosid)-26-O-beta-D-glucopyranosyl-(25R)-furost-5-ene-3 beta,22,26-triol and 3-(O-alpha-L-rhamnopyranosyl(1 -> 2)-[beta-D-glucopyranosyl(1 -> 4)]-beta-D-glucopyranosid)-26-O-beta-D-glucopyranosyl-(25R)-furost-5-ene-3 beta,22,26-triol. By means of a stable isotope dilution assay, quantitated avenanthramides 2c, 2p, 2f, 1p, 1c, 1f, and 3f were found in concentrations below their thresholds and, therefore, did not contribute to the bitter sensation of the tested oat flour.