4-甲氧基牡荆素 | 2326-34-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 4-甲氧基牡荆素
• 英文名称: apigenin 4'-methoxy-8-C-β-D-glucopyranoside
• 英文别名: 4'-O-methyl vitexin；4'-O-methylvitexin；cytisoside；8-β-D-glucopyranosyl-5,7-dihydroxy-2-(4-methoxy-phenyl)-chromen-4-one；8-β-D-Glucopyranosyl-5,7-dihydroxy-2-(4-methoxy-phenyl)-chromen-4-on；5,7-dihydroxy-2-(4-methoxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• CAS: 2326-34-3
• 化学式: C₂₂H₂₂O₁₀
• 分子量: 446.411
• InChiKey: ADCCDGCXRFALSQ-PGPONNFDSA-N

物化性质

• 熔点：
  280-282 °C
• 沸点：
  735.5±60.0 °C(Predicted)
• 密度：
  1.583±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Acetic acid (3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 、 4-甲氧基牡荆素 在 lithium methanolate 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 6-C-cellobiosylcytisoside
  参考文献：
  名称：

  Structural determination of 6-C-diglycosyl-8-C-glycosyl-flavones and 6-C-glycosyl-8-C-diglycosylflavones by mass spectrometry of their permethyl ethers

  摘要：

  DOI：

  10.1016/s0031-9422(00)84119-9
• 作为产物：
  描述：

  8-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one 在 盐酸 作用下， 反应 1.0h， 生成 4-甲氧基牡荆素
  参考文献：
  名称：

  Four flavonoid glycosides from Peganum harmala

  摘要：

  The aerial parts of Peganum harmala yielded four new flavonoids: acacetin 7-O-rhamnoside, 7-O-[6 ''-O-glucosyl-2 ''-O-(3'''-acetylrhamnosyl)glucoside and 7-0-(2'''-0-rhamnosyl-2 ''-O-glucosylglucoside) and the glycoflavone 2'''-O-rhamnosyl-2 ''-O-glucosylcytisoside. Copyright (C) 1997 Elsevier Science Ltd

  DOI：

  10.1016/s0031-9422(96)00531-6

文献信息

• Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins
  作者：B. Hao、J.C. Caulfield、M.L. Hamilton、J.A. Pickett、C.A.O. Midega、Z.R. Khan、J. Wang、A.M. Hooper

  DOI：10.1016/j.phytochem.2016.02.013

  日期：2016.5

  The rice C-glycosyltransferase (OsCGT) is one of only a small number of characterised plant C-glycosyltransferases (CGT) known. The enzyme C-glucosylates a 2-hydroxyflavanone substrate with UDP-glucose as the sugar donor to produce C-glucosyl-2-hydroxyflavanones. We tested substrate specificity of the enzyme, using synthetic 2-hydroxyflavanones, and showed it has the potential to generate known natural CGFs that have been isolated from rice and also other plants. In addition, we synthesised novel, unnatural 2-hydroxyflavanone substrates to test the B-ring chemical space of substrate accepted by the OsCGT and demonstrated the OsCGT capacity as a synthetic reagent to generate significant quantities of known and novel CGFs. Many B-ring analogues are tolerated within a confined steric limit. Finally the OsCGT was used to generate novel mono-C-glucosyl-2-hydroxyflavanones as putative biosynthetic intermediates to examine the potential of Desmodium incanum biosynthetic CGTs to produce novel di-C-glycosylflavones, compounds implicated in the allelopathic biological activity of Desmodium against parasitic weeds from the Striga genus. (C) 2016 The Authors. Published by Elsevier Ltd.
• Four flavonoid glycosides from Peganum harmala
  作者：Mohamed Sharaf、Mohamed A. El-Ansari、Stephen A. Matlin、Nabiel A.M. Saleh

  DOI：10.1016/s0031-9422(96)00531-6

  日期：1997.2

  The aerial parts of Peganum harmala yielded four new flavonoids: acacetin 7-O-rhamnoside, 7-O-[6 ''-O-glucosyl-2 ''-O-(3'''-acetylrhamnosyl)glucoside and 7-0-(2'''-0-rhamnosyl-2 ''-O-glucosylglucoside) and the glycoflavone 2'''-O-rhamnosyl-2 ''-O-glucosylcytisoside. Copyright (C) 1997 Elsevier Science Ltd
• Structural determination of 6-C-diglycosyl-8-C-glycosyl-flavones and 6-C-glycosyl-8-C-diglycosylflavones by mass spectrometry of their permethyl ethers
  作者：M.L. Bouillant、F.Ferreres de Arce、J. Favre-Bonvin、J. Chopin、A. Zoll、G. Mathieu

  DOI：10.1016/s0031-9422(00)84119-9

  日期：1984.1