(1'S,2'S)-1'-syringylglycerol 3'-O-β-D-glucopyranoside | 189456-38-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (1'S,2'S)-1'-syringylglycerol 3'-O-β-D-glucopyranoside
• 英文别名: (7S,8S)-syringylglycerol 9-O-β-D-glucopyranoside；(2R,3R,4S,5S,6R)-2-[(2S,3S)-2,3-dihydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 189456-38-0
• 化学式: C₁₇H₂₆O₁₁
• 分子量: 406.387
• InChiKey: AWSHGBLBAKCDSY-FPDPAFLCSA-N

物化性质

• 沸点：
  757.3±60.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (1'S,2'S)-1'-syringylglycerol 3'-O-β-D-glucopyranoside 在 ammonium formate 、 溶剂黄146 、 β-glucosidase 作用下， 以 水 为溶剂， 以67%的产率得到(+)-threo-syringylglycerol
  参考文献：
  名称：

  Isolation of α-glusosidase inhibitors from hyssop ( Hyssopus officinalis )

  摘要：

  alpha-Glucosidase inhibitory activity was found in aqueous methanol extracts of dried hyssop (Hyssopus officinalis) leaves. Active principles against alpha-glucosidase, prepared from rat small intestine acetone powders, were isolated and characterized. The structures of these isolated compounds were determined to be (7S, 8S)-syringoylglycerol-9-O-(6'-O-cinnamoyl)-beta-D-glucopyranoside and (7S, 8S)-syringoylglycerol 9-O-beta-D-glucopyranoside by analysis of physical and spectroscopic data (FDMS, H-1 NMR, C-13 NMR, HMQC. and HMBC experiments) together with chemical syntheses. (C) 2003 Elsevier Ltd. All rights, reserved.

  DOI：

  10.1016/j.phytochem.2003.10.009
• 作为产物：
  描述：

  [(2R,3S,4S,5R,6R)-6-[(2S,3S)-2,3-dihydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-phenylprop-2-enoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以76%的产率得到(1'S,2'S)-1'-syringylglycerol 3'-O-β-D-glucopyranoside
  参考文献：
  名称：

  Isolation of α-glusosidase inhibitors from hyssop ( Hyssopus officinalis )

  摘要：

  alpha-Glucosidase inhibitory activity was found in aqueous methanol extracts of dried hyssop (Hyssopus officinalis) leaves. Active principles against alpha-glucosidase, prepared from rat small intestine acetone powders, were isolated and characterized. The structures of these isolated compounds were determined to be (7S, 8S)-syringoylglycerol-9-O-(6'-O-cinnamoyl)-beta-D-glucopyranoside and (7S, 8S)-syringoylglycerol 9-O-beta-D-glucopyranoside by analysis of physical and spectroscopic data (FDMS, H-1 NMR, C-13 NMR, HMQC. and HMBC experiments) together with chemical syntheses. (C) 2003 Elsevier Ltd. All rights, reserved.

  DOI：

  10.1016/j.phytochem.2003.10.009

文献信息

• Isolation of α-glusosidase inhibitors from hyssop ( Hyssopus officinalis )
  作者：Hideyuki Matsuura、Hiroyuki Miyazaki、Chikako Asakawa、Midori Amano、Teruhiko Yoshihara、Junya Mizutani

  DOI：10.1016/j.phytochem.2003.10.009

  日期：2004.1

  alpha-Glucosidase inhibitory activity was found in aqueous methanol extracts of dried hyssop (Hyssopus officinalis) leaves. Active principles against alpha-glucosidase, prepared from rat small intestine acetone powders, were isolated and characterized. The structures of these isolated compounds were determined to be (7S, 8S)-syringoylglycerol-9-O-(6'-O-cinnamoyl)-beta-D-glucopyranoside and (7S, 8S)-syringoylglycerol 9-O-beta-D-glucopyranoside by analysis of physical and spectroscopic data (FDMS, H-1 NMR, C-13 NMR, HMQC. and HMBC experiments) together with chemical syntheses. (C) 2003 Elsevier Ltd. All rights, reserved.