(1-acetoxy-4-oxo-cyclohexa-2,5-dienyl)-acetic acid methyl ester | 60508-82-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1-acetoxy-4-oxo-cyclohexa-2,5-dienyl)-acetic acid methyl ester
• 英文别名: (1-Acetoxy-4-oxo-cyclohexa-2,5-dienyl)-essigsaeure-methylester；Methyl 2-(1-acetyloxy-4-oxocyclohexa-2,5-dien-1-yl)acetate
• CAS: 60508-82-9
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: ZXWNQJATHXGTLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  152 °C(Press: 3 Torr)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1-acetoxy-4-oxo-cyclohexa-2,5-dienyl)-acetic acid methyl ester 、 alkaline earth salt of/the/ methylsulfuric acid 生成 尿黑酸
  参考文献：
  名称：

  Quinol Intermediates in the Oxidation of Phenols and Their Rearrangements¹

  摘要：

  DOI：

  10.1021/ja01558a049
• 作为产物：
  描述：

  对苯醌 在 4-二甲氨基吡啶 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 4.16h， 生成 (1-acetoxy-4-oxo-cyclohexa-2,5-dienyl)-acetic acid methyl ester
  参考文献：
  名称：

  Isolation and structure–activity relationship studies of jacaranones: Anti-inflammatory quinoids from the Cuban endemic plant Jacaranda arborea (Bignoniaceae)

  摘要：

  The Cuban endemic plant Jacaranda arborea (Bignoniaceae) has been traditionally used in folk medicine as an acaricide and for acne treatment. Two known quinoids, methyl (1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetate (jacaranone) (1) and its ethyl ester 2 were isolated from this species as anti-inflammatory substances. Compound 1 prominently inhibited the production of TNF-alpha in both LPS-treated macrophages and mice, with low toxicity. Structure-activity relationship studies revealed that the high electrophilicity of 1 as a Michael acceptor played an important role in these effects. Unlike in previous studies, such as those on antitumor, anti-oxidant, and anti-malarial activities, ester derivatives of 1 retained their potent anti-inflammatory activity. Our results suggest that jacaranones may target specific biomacromolecule(s) at lower concentrations than hitherto expected to exhibit potent activities. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.152005

文献信息

• Isolation and structure–activity relationship studies of jacaranones: Anti-inflammatory quinoids from the Cuban endemic plant Jacaranda arborea (Bignoniaceae)
  作者：Minako Hirukawa、Menghua Zhang、Lazaro M. Echenique–Diaz、Koji Mizota、Satoshi D. Ohdachi、Gerardo Begué–Quiala、Jorge L. Delgado–Labañino、Jorgelino Gámez–Díez、José Alvarez–Lemus、Leandro Galano Machado、Miguel Suárez Núñez、Takahiro Shibata、Hideo Kigoshi、Masaki Kita

  DOI：10.1016/j.tetlet.2020.152005

  日期：2020.6

  The Cuban endemic plant Jacaranda arborea (Bignoniaceae) has been traditionally used in folk medicine as an acaricide and for acne treatment. Two known quinoids, methyl (1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetate (jacaranone) (1) and its ethyl ester 2 were isolated from this species as anti-inflammatory substances. Compound 1 prominently inhibited the production of TNF-alpha in both LPS-treated macrophages and mice, with low toxicity. Structure-activity relationship studies revealed that the high electrophilicity of 1 as a Michael acceptor played an important role in these effects. Unlike in previous studies, such as those on antitumor, anti-oxidant, and anti-malarial activities, ester derivatives of 1 retained their potent anti-inflammatory activity. Our results suggest that jacaranones may target specific biomacromolecule(s) at lower concentrations than hitherto expected to exhibit potent activities. (C) 2020 Elsevier Ltd. All rights reserved.
• Quinol Intermediates in the Oxidation of Phenols and Their Rearrangements¹
  作者：Sidney Goodwin、Bernhard Witkop

  DOI：10.1021/ja01558a049

  日期：1957.1