7-(β-D-galactopyranosyloxy)-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one

• 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: 7-(β-D-galactopyranosyloxy)-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one
• 英文别名: chrysin-β-D-galactopyranoside；5-hydroxy-7-O-galactosylflavone；7-O-β-D-galactopyranosylchrysine
• 化学式: C₂₁H₂₀O₉
• 分子量: 416.384
• InChiKey: PIJHQWMTZXDYER-OBJCFNGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  149.82
• 氢给体数：
  5.0
• 氢受体数：
  9.0

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  白杨素	5,7-dihydroxy-2-phenyl-chromen-4-one	480-40-0	C15H10O4	254.242

反应信息

• 作为产物：
  描述：

  白杨素 在 氢氧化钾 、 三(3,6-二氧杂庚基)胺 、 potassium chloride 、 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 75.0h， 生成 7-(β-D-galactopyranosyloxy)-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Acylated Flavone Glucosides: Synthesis, Conformational Investigation, and Complexation Properties

  摘要：

  Acylated flavonoid glycosides are ubiquitous in plants; however, the possible influence of the acyl groups on the typical properties of flavonoids is rather poorly documented. In this work, a series of chrysin (= 5,7-dihydroxyflavone) glucosides acylated with aromatic and aliphatic acid residues has been synthesized in a simple three-step procedure. Aromatic acyl groups are shown to impose folded conformations on the chrysin glucosides owing to their ability to stack on the polyphenolic nucleus. The: acyl groups may also cause significant changes in the ability of the flavonoid glucosides to bind hard metal ions and proteins, as demonstrated in this work in the case of Al3+ and bovine serum albumin.

  DOI：

  10.1002/(sici)1522-2675(19991215)82:12<2201::aid-hlca2201>3.0.co;2-4

文献信息

• Preparation and activity evaluation of chrysin-β-d-galactopyranoside
  作者：Zhen-Yuan Zhu、Ling Chen、Fei Liu、Li-Jing Chen、Meng Meng、Hui-Qing Sun、Yong-Min Zhang

  DOI：10.1007/s12272-016-0800-2

  日期：2016.10

  efficiently synthesized, evaluated for its inhibitory activities against H22 cell lines compared with chrysin, the scavenging of hydroxyl radical, DPPH radical and superoxide anion, inhibitory effect against bacteria and fungi. The structures of all compounds were fully characterized by spectroscopic data (NMR, MS). The anti-tumor, antioxidant and antimicrobial activities of chrysin-β-d-galactopyranoside were

  白杨素-β-d-吡喃半乳糖苷被有效合成，与白杨素相比，其对H22细胞系的抑制活性，羟基自由基，DPPH自由基和超氧阴离子的清除，对细菌和真菌的抑制作用被评估。所有化合物的结构都通过光谱数据（NMR、MS）进行了充分表征。与白杨素相比，白杨素-β-d-吡喃半乳糖苷的抗肿瘤、抗氧化和抗菌活性被证明显着增强。
• Acylated Flavone Glucosides: Synthesis, Conformational Investigation, and Complexation Properties
  作者：Bertrand Alluis、Olivier Dangles

  DOI：10.1002/(sici)1522-2675(19991215)82:12<2201::aid-hlca2201>3.0.co;2-4

  日期：1999.12.15

  Acylated flavonoid glycosides are ubiquitous in plants; however, the possible influence of the acyl groups on the typical properties of flavonoids is rather poorly documented. In this work, a series of chrysin (= 5,7-dihydroxyflavone) glucosides acylated with aromatic and aliphatic acid residues has been synthesized in a simple three-step procedure. Aromatic acyl groups are shown to impose folded conformations on the chrysin glucosides owing to their ability to stack on the polyphenolic nucleus. The: acyl groups may also cause significant changes in the ability of the flavonoid glucosides to bind hard metal ions and proteins, as demonstrated in this work in the case of Al3+ and bovine serum albumin.