3-(2,4-Dihydroxy-phenyl)-propionic acid isopropyl ester | 55144-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(2,4-Dihydroxy-phenyl)-propionic acid isopropyl ester
• 英文别名: 3-(2,4-Dihydroxyphenyl)-propionic acid isopropylester；propan-2-yl 3-(2,4-dihydroxyphenyl)propanoate
• CAS: 55144-50-8
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: ULEKMXRXAWNLHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(2,4-二羟基苯)丙酸 、 异丙醇 在 硫酸 作用下， 反应 2.0h， 生成 3-(2,4-Dihydroxy-phenyl)-propionic acid isopropyl ester
  参考文献：
  名称：

  Enhanced Substituted Resorcinol Hydrophobicity Augments Tyrosinase Inhibition Potency

  摘要：

  The objective of the present study was to investigate to what extent the addition of hydrophobic residues to a 2,4-resorcinol derivative would contribute to their tyrosinase inhibitory potency. Hence, 3-(2,4-dihydroxyphenyl)propionic acid, isolated from Ficus carica, was transformed into esters, and the relationship between the structure of these esters to their mushroom tyrosinase inhibition activity was explored. The enzyme crystallographic structure, published recently (Matoba, Y. et al. J. Biol. Chem. 2006, 281, 8981-8990) was docked with the new esters, and their calculated free energy (FE) and docking energy (DE) were compared with the experimental IC50 values, providing good correlations. The observed IC50 of the isopropyl ester was 0.07 mu M, and its interaction with the enzyme binding site appears to be composed of four hydrogen bonds and two hydrophobic interactions. It may be concluded that the addition of a hydrophobic moiety to 2,4-resorcinol derivatives augments tyrosinase inhibitory potency as was predicted from the modeling study.

  DOI：

  10.1021/jm061361d

文献信息

• Utilisation de dérivés de la resorcine substitués en position(s)4,4 et 5 ou 4 et 6 dans des compositions cosmétiques ou dermopharmaceutiques à action dépigmentante
  申请人：L'OREAL

  公开号：EP0623339B1

  公开（公告）日：1997-07-23
• Enhanced Substituted Resorcinol Hydrophobicity Augments Tyrosinase Inhibition Potency
  作者：Soliman Khatib、Ohad Nerya、Ramadan Musa、Snait Tamir、Tal Peter、Jacob Vaya

  DOI：10.1021/jm061361d

  日期：2007.5.1

  The objective of the present study was to investigate to what extent the addition of hydrophobic residues to a 2,4-resorcinol derivative would contribute to their tyrosinase inhibitory potency. Hence, 3-(2,4-dihydroxyphenyl)propionic acid, isolated from Ficus carica, was transformed into esters, and the relationship between the structure of these esters to their mushroom tyrosinase inhibition activity was explored. The enzyme crystallographic structure, published recently (Matoba, Y. et al. J. Biol. Chem. 2006, 281, 8981-8990) was docked with the new esters, and their calculated free energy (FE) and docking energy (DE) were compared with the experimental IC50 values, providing good correlations. The observed IC50 of the isopropyl ester was 0.07 mu M, and its interaction with the enzyme binding site appears to be composed of four hydrogen bonds and two hydrophobic interactions. It may be concluded that the addition of a hydrophobic moiety to 2,4-resorcinol derivatives augments tyrosinase inhibitory potency as was predicted from the modeling study.