apigenin 4'-O-β-D-glucopyranoside | 20486-34-4

• 物质功能分类: 生物化工 - 核苷类药物
• 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: apigenin 4'-O-β-D-glucopyranoside
• 英文别名: 5,7-dihydroxy-2-[4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
• CAS: 20486-34-4
• 化学式: C₂₁H₂₀O₁₀
• 分子量: 432.384
• InChiKey: ICLVCWSZHUZEFT-RQUKQETFSA-N

物化性质

• 熔点：
  173-174 °C(Solv: ethanol (64-17-5))
• 沸点：
  763.3±60.0 °C(Predicted)
• 密度：
  1.642±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  7-O-tert-butyldimethylsilylnaringenin 在 2,6-二叔丁基-4-甲基吡啶 、 三氟化硼乙醚 、 sodium methylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 氯苯 为溶剂， 反应 31.0h， 生成 apigenin 4'-O-β-D-glucopyranoside
  参考文献：
  名称：

  Total synthesis of apigenin 7,4′-di-O-β-glucopyranoside, a component of blue flower pigment of Salvia patens, and seven chiral analogues

  摘要：

  We have succeeded in the first total synthesis of apigenin 7,4'-di-O-beta-D-glucopyranoside (1a), a component of blue pigment, protodelphin, from naringenin (2). Glycosylation of 2 according to Koenigs-Knorr reaction provided a monoglucoside 4a in 80% yield, and this was followed by DDQ oxidation to give apigenin 7-O-glucoside (12a). Further glycosylation of 4'-OH of 12a with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl fluoride (5a) was achieved using a Lewis acid-and-base promotion system (BF3.Et2O, 2,6-di-tert-butyl-4-methylpyridine, and 1,1,3,3-tetramethylguanidine) in 70% yield, and subsequent deprotection produced 1a. Synthesis of three other chiral isomers of 1a, with replacement Of D-glucose at 7 and/or 4'-OH by L-glucose (1b-d), and four chiral isomers of apigenin 7-O-beta-glucosides (6a,b) and 4'-O-beta-glucosides (7a,b) also proved possible. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.001

文献信息

• Chiral Molecular Recognition on Formation of a Metalloanthocyanin: A Supramolecular Metal Complex Pigment from Blue Flowers ofSalvia patens
  作者：Tadao Kondo、Kin-ichi Oyama、Kumi Yoshida

  DOI：10.1002/1521-3773(20010302)40:5<894::aid-anie894>3.0.co;2-8

  日期：2001.3.2

  The chirality of the sugar moiety is responsible for the chiral molecular recognition on formation of a metalloanthocyanin from Salvia patens. This mechanism was revealed by using the synthetic apigenin 7,4'-diglucosides derived from D- or L-glucose. The supermolecule consists of six malonylawobanin molecules (blue) coordinated to two Mg2+ ions (red) with an M-helical arrangement of six 7,4'-diglucoside molecules (yellow) intercalated.