5-((S)-2′-oxo-4′-hydroxypentyl)-2-(β-D-glucopyranosyloxy-methyl)chromone | 1431323-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-((S)-2′-oxo-4′-hydroxypentyl)-2-(β-D-glucopyranosyloxy-methyl)chromone
• 英文别名: 5-((S)-2'-oxo-4'-hydroxypentyl)-2-(β-glucopyranosyl-oxy-methyl)chromone；5-[(4S)-4-hydroxy-2-oxopentyl]-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]chromen-4-one
• CAS: 1431323-49-7
• 化学式: C₂₁H₂₆O₁₀
• 分子量: 438.431
• InChiKey: DZCNGNCJKIPWRH-KPPYGAHPSA-N

物化性质

• 沸点：
  700.7±60.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-((S)-2′-oxo-4′-hydroxypentyl)-2-(β-D-glucopyranosyloxy-methyl)chromone 在 吡啶 、 盐酸 、 水 作用下， 反应 20.17h， 生成
  参考文献：
  名称：

  Mushroom tyrosinase inhibitors from Aloe barbadensis Miller

  摘要：

  Two new chromones, 5-((S)-2'-oxo-4'-hydroxypentyl)-2-(beta-glucopyranosyl-oxy-methyl) chromone (1) and 5-((S)-2'-oxo-4'-hydroxypentyl)-2-methoxychromone (2), together with four known analogues, 8-C-glucosyl-7-O-methyl-(S)-aloesol (3), isoaloeresin D (4), 8-C-glucosyl-(R)-aloesol (5), and aloesin (6) were isolated from the aqueous extract of Aloe barbadensis Miller. Their structures were determined on the basis of spectroscopic evidences (1-D and 2-D NMR, HRMS, UV, and IR data), chemical methods and the literature data. The Mosher's method was applied to establish the absolute configuration of compounds 1 and 2. The inhibitory effects of these chromones on the activity of mushroom tyrosinase were examined, and compound 6 was identified as a noncompetitive tyrosinase inhibitor with an IC50 value of 108.62 mu g.mL(-1). (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2012.09.028

文献信息

• Mushroom tyrosinase inhibitors from Aloe barbadensis Miller
  作者：Xiaofang Wu、Sheng Yin、Jiasheng Zhong、Wenjing Ding、Jinzhi Wan、Zhiyong Xie

  DOI：10.1016/j.fitote.2012.09.028

  日期：2012.12

  Two new chromones, 5-((S)-2'-oxo-4'-hydroxypentyl)-2-(beta-glucopyranosyl-oxy-methyl) chromone (1) and 5-((S)-2'-oxo-4'-hydroxypentyl)-2-methoxychromone (2), together with four known analogues, 8-C-glucosyl-7-O-methyl-(S)-aloesol (3), isoaloeresin D (4), 8-C-glucosyl-(R)-aloesol (5), and aloesin (6) were isolated from the aqueous extract of Aloe barbadensis Miller. Their structures were determined on the basis of spectroscopic evidences (1-D and 2-D NMR, HRMS, UV, and IR data), chemical methods and the literature data. The Mosher's method was applied to establish the absolute configuration of compounds 1 and 2. The inhibitory effects of these chromones on the activity of mushroom tyrosinase were examined, and compound 6 was identified as a noncompetitive tyrosinase inhibitor with an IC50 value of 108.62 mu g.mL(-1). (C) 2012 Elsevier B.V. All rights reserved.