quercetin-3-O-α-L-rhamnopyranosyl-(1 → 2)-[6-O-(3-hydroxy-3-methylglutaryl)-β-D-galactopyranoside] | 1392831-75-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: quercetin-3-O-α-L-rhamnopyranosyl-(1 → 2)-[6-O-(3-hydroxy-3-methylglutaryl)-β-D-galactopyranoside]
• 英文别名: quercetin-3-O-α-rhamnosyl-(1->2)-[(6-O-3-hydroxy-3-methylglutaryl)-β-galactoside]；5-[[(2R,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
• CAS: 1392831-75-2
• 化学式: C₃₃H₃₈O₂₀
• 分子量: 754.653
• InChiKey: ASOAXQKETNAUHE-JCULEJJSSA-N

物化性质

• 沸点：
  1118.0±65.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  53
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  329
• 氢给体数：
  11
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  quercetin-3-O-α-L-rhamnopyranosyl-(1 → 2)-[6-O-(3-hydroxy-3-methylglutaryl)-β-D-galactopyranoside] 在 盐酸 、 水 作用下， 以 二甲基亚砜 为溶剂， 反应 1.5h， 生成 D-吡喃葡萄糖 、 L-rhamnopyranose
  参考文献：
  名称：

  Flavonol glycosides acylated with 3-hydroxy-3-methylglutaric acid as systematic characters in Rosa

  摘要：

  LC-UV-MS/MS analysis of leaf extracts from 146 accessions of 71 species of Rosa revealed that some taxa accumulated flavonol O-glycosides acylated with 3-hydroxy-3-methylglutaric acid, which are relatively uncommon in plants. The structures of two previously unrecorded examples isolated from Rosa spinosissima L. (syn. Rosa pimpinellifolia L) were elucidated using spectroscopic and chemical methods as the 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[6-O-(3-hydroxy-3-methylglutaryl)-beta-D-galactopyranosides] of kaempferol (3,5,7,4'-tetrahydroxyflavone) and quercetin (3,5,7,3',4'-pentahydroxyflavone). The corresponding 3-O-[6-O-(3-hydroxy-3-methylglutaryl)-beta-D-galactopyranoside] of quercetin was also present in R. spinasissima, but at lower levels, together with 17 other flavonol O-glycosides for which structures were assigned using LC-UV-MS/MS. The distribution of flavonol 3-hydroxy-3-methylglutarylgalactosides in Rosa was limited to some species of subgenus Rosa section Pimpinellifoliae and Rosa roxburghii Sw. of the monotypic subgenus Platyrhodon, indicating that this character could be of value in phylogenetic analyses of the genus. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.phytochem.2012.05.006