(4S)-α-terpineol 8-O-β-D-(6-O-galloyl)glucopyranoside

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S)-α-terpineol 8-O-β-D-(6-O-galloyl)glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-[(1S)-4-methylcyclohex-3-en-1-yl]propan-2-yloxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• 化学式: C₂₃H₃₂O₁₀
• 分子量: 468.501
• InChiKey: SGZVUALRBMIRIV-ZEGKYRDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (4S)-α-terpineol 8-O-β-D-(6-O-galloyl)glucopyranoside 在 单宁酶 、 Aspergillus oryzae 、 水 、 β-glucosidase 作用下， 反应 27.0h， 生成 α-松油醇
  参考文献：
  名称：

  Galloylglucosides from Berries of Pimenta dioica

  摘要：

  Three new galloylglucosides, (4S)-alpha-terpineol 8-O-beta-D-(6-O-galloyl)glucopyranoside (1); (4R)-alpha-terpineol 8-O-beta-D-(6-O-galloyl)glucopyranoside (2), and 3-(4-hydroxy-3-methoxyphenyl)propane-1,2-O-beta-D-(6-O-galloyl)glucopyranoside (3), were isolated from the berries of Pimenta dioica together with three known compounds, gallic acid (4), pimentol (5), and eugenol 4-O-beta-D-(6-O-galloyl)glucopyranoside (6). The structures of 1-3 were elucidated on the basis of MS and NMR spectral data and enzymatic hydrolysis. These galloylglucosides (1-3, 5, and 6) showed radical-scavenging activity nearly equivalent to that of gallic acid (4) against 1,1-diphenyl-2-picrylhydrazyl radical.

  DOI：

  10.1021/np9906121

文献信息

• Galloylglucosides from Berries of <i>Pimenta dioica</i>
  作者：Hiroe Kikuzaki、Akemi Sato、Yoko Mayahara、Nobuji Nakatani

  DOI：10.1021/np9906121

  日期：2000.6.1

  Three new galloylglucosides, (4S)-alpha-terpineol 8-O-beta-D-(6-O-galloyl)glucopyranoside (1); (4R)-alpha-terpineol 8-O-beta-D-(6-O-galloyl)glucopyranoside (2), and 3-(4-hydroxy-3-methoxyphenyl)propane-1,2-O-beta-D-(6-O-galloyl)glucopyranoside (3), were isolated from the berries of Pimenta dioica together with three known compounds, gallic acid (4), pimentol (5), and eugenol 4-O-beta-D-(6-O-galloyl)glucopyranoside (6). The structures of 1-3 were elucidated on the basis of MS and NMR spectral data and enzymatic hydrolysis. These galloylglucosides (1-3, 5, and 6) showed radical-scavenging activity nearly equivalent to that of gallic acid (4) against 1,1-diphenyl-2-picrylhydrazyl radical.