3',4',5,7-tetralauroyloxyflavone | 1399385-16-0

• 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: 3',4',5,7-tetralauroyloxyflavone
• CAS: 1399385-16-0
• 化学式: C₆₃H₉₈O₁₀
• 分子量: 1015.47
• InChiKey: RSVHYDIHJGRQAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.77
• 重原子数：
  73.0
• 可旋转键数：
  45.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  135.41
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  月桂酰氯 、 木犀草素 在 吡啶 作用下， 反应 25.0h， 生成 3',4',5,7-tetralauroyloxyflavone
  参考文献：
  名称：

  UV-ABC screens of luteolin derivatives compared to edelweiss extract

  摘要：

  Pure luteolin is a remarkably heat (200 degrees C/6 days) and UV stable UV-A screen, however, native luteolin enriched to 37% in an edelweiss extract lost its UV-A screen properties upon UV irradiation (similar to 4 MJ m(-2)). This contrasting behavior led to the examination of a series of purified luteolin derivatives as UV screen candidates. 3',4',5,7-Tetralipoyloxyflavones were synthesized from luteolin (3',4',5,7-tetrahydroxyflavone) and fatty acid chlorides. These acylated semi-biomolecules show a hypsochromic shift in UV-Vis spectra of about Delta lambda(A -> B) = 58 nm and absorbed in the centre of the harmful UV-B band (lambda(max) = 295 nm). Luteolin was also hydroxyethylated with Br(CH2)(2)OH. This substitution has no effect on the lambda(max) = 330 nm absorption of luteolin (UV-A band). Finally the natural 4'-O-beta-glucosyl-3',5,7-trihydroxyflavone was extracted from edelweiss and used as a purified natural benchmark. Glycosylated and hydroxyethylated luteolin are both UV stable. Fully acylated luteolin derivatives degrade upon UV exposure to a stable UV-C screen with a hypsochroic shift Delta lambda(B -> C) = 35 nm. All in all, three molecular structures based on luteolin with sunscreen properties were found, distinguishable in: UV-A, UV-B, and UV-C filters. The natural product based UV-absorbers show promise as alternatives to synthetic molecules and nanoparticles in sunscreen products. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotobiol.2011.01.005