4-(hydroxymethyl)-6-(8-methylprop-7-enyl)-5,6-dihydro-2H-pyran-2-one-11-O-β-D-glucopyranoside | 1312762-55-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(hydroxymethyl)-6-(8-methylprop-7-enyl)-5,6-dihydro-2H-pyran-2-one-11-O-β-D-glucopyranoside
• 英文别名: aruncide A；2-(2-methylprop-1-enyl)-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-6-one
• CAS: 1312762-55-2
• 化学式: C₁₆H₂₄O₈
• 分子量: 344.362
• InChiKey: MKXVLYPJBLBGIO-LQPVRJLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(hydroxymethyl)-6-(8-methylprop-7-enyl)-5,6-dihydro-2H-pyran-2-one-11-O-β-D-glucopyranoside 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 5-(hydroxymethyl)-2-(2-methylprop-1-enyl)-2,3-dihydropyran-6-one
  参考文献：
  名称：

  Monoterpenoids from the aerial parts of Aruncus dioicus var. kamtschaticus and their antioxidant and cytotoxic activities

  摘要：

  The aerial parts of Aruncus dioicus var. kamtschaticus afforded five new monoterpenoids (1-5): 4-(erythro-6,7-dihydroxy-9-methylpent-8-enyl)furan-2(5H)-one (1, aruncin A), 2-(8-ethoxy-8-methylpropylidene)-5-hydroxy-3,6-dihydro-2H-pyran-4-carboxylic acid (2, aruncin B), 4-(hydroxymethyl)-6-(8methylprop-7-enyl)-5,6-dihydro-2H-pyran-2-one-11-O-beta-D-glucopyranoside (3, aruncide A), (3S,4S,5R,10R)-3-(10-ethoxy-11-hydroxyethyl)-4-(5-hydroxy-7-methylbut-6-enyl)oxetan-2-one-11-O-beta-D-glucopyranoside (4, aruncide B), and (3S,4S,5R,7R)-5-(9-methylprop-8-enyl)-1,6-dioxabicyclo[3,2,0]heptan-2-one-7-(hydroxymethyl)-12-O-beta-D-glucopyranoside (5, aruncide C). Compound 2 showed potent cytotoxicity against Jurkat T cells with an IC50 value of 17.15 mu g/mL. In addition, compounds 7 and 10 exhibited-moderate antioxidant activity with IC50 values of 46.3 and 11.7 mu M, respectively. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.043