linarin heptaacetate | 124904-19-4

• 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: linarin heptaacetate
• 英文别名: [(2S,3S,4R,5R,6R)-4,5-diacetyloxy-2-methyl-6-[[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[5-acetyloxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]oxan-3-yl] acetate
• CAS: 124904-19-4
• 化学式: C₄₂H₄₆O₂₁
• 分子量: 886.815
• InChiKey: MUMANURGQYVFQI-YUBUJKQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  63.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  260.46
• 氢给体数：
  0.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  linarin heptaacetate 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 Acetic acid 3-bromo-2-(4-methoxy-phenyl)-4-oxo-7-[(2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-4H-chromen-5-yl ester
  参考文献：
  名称：

  Synthesis and anti-tubulin evaluation of chromone-based analogues of combretastatins

  摘要：

  Twenty new hybrid compounds with both combretastatin and flavone moieties were synthesized. These derivatives are classified according to the position of the trimethoxyphenyl ring at C-2 or C-3 of the chromone and presence or absence of a carbonyl as a linker between C-3 and the aryl ring. Most of these compounds were prepared from hesperidin or naringin, two natural and abundant Citrus flavonoids. Seven of these combretastatin analogues revealed anti-tubulin activity but in a medium range. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.024
• 作为产物：
  描述：

  乙酸酐 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 作用下， 生成 linarin heptaacetate
  参考文献：
  名称：

  Baker et al., Journal of the Chemical Society, 1951, p. 691,694

  摘要：

  DOI：

文献信息

• Linarin monoacetate from Thalictrum aquilegifolium
  作者：Hiroji Ina、Hideo Iida

  DOI：10.1016/0031-9422(81)83064-6

  日期：1981.1

  Abstract Linarin monoacetate, a new flavonoid glycoside, has been isolated from Thalictrum aquilegifolium and the position of the acetyl group has been determined by 13 C NMR spectral data.

  摘要 单乙酸利那林是一种新的黄酮苷，已从沉香木中分离得到，乙酰基的位置已通过 13 C NMR 光谱数据确定。
• Semisynthesis of Linarin, Acacetin, and 6-Iodoapigenin Derivatives from Diosmin
  作者：Jérôme Quintin、Guy Lewin

  DOI：10.1021/np040079b

  日期：2004.9.1

  Semisynthesis of linarin and acacetin from the Citrus flavonoid diosmin was performed via, as first intermediate, the 3'-O-phenyltetrazolyl ether of diosmin. This paper relates also a semisynthetic access to 6-iodoapigenin derivatives, which are key compounds in the synthesis of some biflavonoids such as robustaflavone.
• Zemplen; Bognar, Chemische Berichte, 1941, vol. 74, p. 1818,1821
  作者：Zemplen、Bognar

  DOI：——

  日期：——
• Photoprotective activity of Buddleja scordioides
  作者：J.G. Avila Acevedo、C.M.C. Castañeda、F.J.C. Benitez、D.A. Durán、V.R. Barroso、C.G. Martínez、L.J.L. Muñoz、C.A. Martínez、A. Romo de Vivar

  DOI：10.1016/j.fitote.2005.03.009

  日期：2005.6

  The purpose of this study was to determine the photoprotective properties of the methanolic extract of Buddleja scordioides, as well as verbascoside and linarin which were isolated from this extract, and linarin acetate prepared in the laboratory. The photoprotective effect of substances against UV-B induced cellular death was evaluated by challenge experiments using Escherichia coli. Verbascoside and linarin acetate showed the highest protection. The sun protection factor (SPF) of the methanolic extract, linarin, linarin acetate, and verbascoside was evaluated by guinea pig bioassays. Verbascoside showed the largest SPF measurement. (c) 2005 Elsevier B.V. All rights reserved.
• Über die Glykoside der Blüten von Linaria vulgaris L.: Die Konstitution des Linarins und des Pektolinarins
  作者：K. W. Merz、Y. H. Wu

  DOI：10.1002/ardp.19362740205

  日期：——