(1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentyl β-D-(6-O-galloyl)glucopyranoside | 844818-41-3

• 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'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentyl β-D-(6-O-galloyl)glucopyranoside
• 英文别名: 2-[(1R,2R)-3-oxo-2-[(Z)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyl)oxymethyl]oxan-2-yl]oxypent-2-enyl]cyclopentyl]acetic acid
• CAS: 844818-41-3
• 化学式: C₂₅H₃₂O₁₃
• 分子量: 540.521
• InChiKey: YNGJOPKAULIOQY-QUZKLYMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  221
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentyl β-D-(6-O-galloyl)glucopyranoside 在 水 作用下， 反应 1.5h， 生成 没食子酸 、 [(1R,2R)-2-{(2Z)-5-[(6,7-二脱氧-β-D-葡萄-七吡喃糖基)氧代]戊-2-烯-1-基}-3-羰基环戊基]乙酸
  参考文献：
  名称：

  Phenolic Glycosides from Berries of Pimenta dioica

  摘要：

  Four new phenolic glycosides, (27hydroxy-3-methoxy-5-allyl)phenyl beta-D-(6-O-E-sinapoyl)glucopyranoside (1), (1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-galloyl)glucopyranoside (2), (S)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1 -> 6)-beta-D-glucopyranoside (3), and (R)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1 -> 6)-beta-D-glucopyranoside (4), were isolated from the berries of Pimenta dioica together with eight known flavonoids. The structures of 1-4 were elucidated on the basis of MS and NMR data and enzymatic hydrolysis. All four glycosides showed radical - scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals.

  DOI：

  10.1021/np0705615

文献信息

• Phenolic Glycosides from Berries of <i>Pimenta dioica</i>
  作者：Hiroe Kikuzaki、Yoshiko Miyajima、Nobuji Nakatani

  DOI：10.1021/np0705615

  日期：2008.5.1

  Four new phenolic glycosides, (27hydroxy-3-methoxy-5-allyl)phenyl beta-D-(6-O-E-sinapoyl)glucopyranoside (1), (1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-galloyl)glucopyranoside (2), (S)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1 -> 6)-beta-D-glucopyranoside (3), and (R)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1 -> 6)-beta-D-glucopyranoside (4), were isolated from the berries of Pimenta dioica together with eight known flavonoids. The structures of 1-4 were elucidated on the basis of MS and NMR data and enzymatic hydrolysis. All four glycosides showed radical - scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals.