4-(4-hydroxyphenethoxy)-4-oxobutanoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(4-hydroxyphenethoxy)-4-oxobutanoic acid
• 英文别名: tyrosol succinate；succinic acid mono-(4-hydroxy-phenethyl ester)；Bernsteinsaeure-mono-(4-hydroxy-phenaethylester)；4-(4-Hydroxyphenethoxy)-4-oxobutanoic acid；4-[2-(4-hydroxyphenyl)ethoxy]-4-oxobutanoic acid
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: CVLYVXSOQKJPAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(4{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanol 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-(4-hydroxyphenethoxy)-4-oxobutanoic acid
  参考文献：
  名称：

  Cytotoxic naphthoquinone and a new succinate ester from the soil fungus Fusarium solani PSU-RSPG227

  摘要：

  A new naphthoquinone, solaninaphthoquione (1), and a new succinate ester derivative, 4-(4-hydroxyphenethoxy)-4-oxobutanoic acid (2), were isolated from the soil fungus Fusarium solani PSU-RSPG227 together with five previously reported compounds; javanicin (3), monaspilosin (4), aspergillol B (5), tyrosol (6) and 4- hydroxyphenylacetic acid (7). Their structures were elucidated primarily by NMR spectroscopic data. Due to paucity of materials, compounds 2, 4 and 5 as well as analogues of 5 were prepared for biological activity evaluation. Compound 1 showed significant cytotoxic activity against breast cancer (MCF-7) cells and mild cytotoxic activity against oral human carcinoma (KB) cells (IC50 values of 21.3 and 22.6 mu M, respectively) compared to standard compounds. Compound 1 also displayed weak antimalarial activity (IC50 of 26.1 mu M). (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2014.11.018

文献信息

• Pistschimuka, Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1916, vol. 48, p. 39
  作者：Pistschimuka

  DOI：——

  日期：——
• Cytotoxic naphthoquinone and a new succinate ester from the soil fungus Fusarium solani PSU-RSPG227
  作者：Kwanruthai Tadpetch、Chatsuda Chukong、Laksamee Jeanmard、Aticha Thiraporn、Vatcharin Rukachaisirikul、Souwalak Phongpaichit、Jariya Sakayaroj

  DOI：10.1016/j.phytol.2014.11.018

  日期：2015.3

  A new naphthoquinone, solaninaphthoquione (1), and a new succinate ester derivative, 4-(4-hydroxyphenethoxy)-4-oxobutanoic acid (2), were isolated from the soil fungus Fusarium solani PSU-RSPG227 together with five previously reported compounds; javanicin (3), monaspilosin (4), aspergillol B (5), tyrosol (6) and 4- hydroxyphenylacetic acid (7). Their structures were elucidated primarily by NMR spectroscopic data. Due to paucity of materials, compounds 2, 4 and 5 as well as analogues of 5 were prepared for biological activity evaluation. Compound 1 showed significant cytotoxic activity against breast cancer (MCF-7) cells and mild cytotoxic activity against oral human carcinoma (KB) cells (IC50 values of 21.3 and 22.6 mu M, respectively) compared to standard compounds. Compound 1 also displayed weak antimalarial activity (IC50 of 26.1 mu M). (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.