(4R)-α-terpineol O-β-D-glucopyranoside | 114673-99-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R)-α-terpineol O-β-D-glucopyranoside
• 英文别名: α-terpinyl-O-β-D-glucoside；beta-D-Glucopyranoside, 1-methyl-1-[(1R)-4-methyl-3-cyclohexen-1-yl]ethyl；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-yloxy]oxane-3,4,5-triol
• CAS: 114673-99-3
• 化学式: C₁₆H₂₈O₆
• 分子量: 316.395
• InChiKey: NZNWCYFBFHHMLM-MTWVNVMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-α-terpineol O-β-D-glucopyranoside 在 水 、 β-glucosidase 作用下， 反应 24.0h， 以0.5 mg的产率得到(+)-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
• 作为产物：
  描述：

  (4R)-α-terpineol 8-O-β-D-(6-O-galloyl)glucopyranoside 在 单宁酶 、 Aspergillus oryzae 、 水 作用下， 反应 3.0h， 以2.5 mg的产率得到(4R)-α-terpineol O-β-D-glucopyranoside
  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.