fringelite D | 157301-83-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: fringelite D
• 英文别名: hypericin；5,7,11,13,16,18,22,24-Octahydroxyoctacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(26),2,4(25),5,7,10,12,14(28),15(27),16,18,21,23-tridecaene-9,20-dione
• CAS: 157301-83-2
• 化学式: C₂₈H₁₂O₁₀
• 分子量: 508.397
• InChiKey: LKAUISSMFREDQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  38
• 可旋转键数：
  0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  196
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,3,6,8-四羟基蒽-9,10-二酮 在 potassium tert-butylate 、 对苯二酚 作用下， 反应 20.0h， 生成 fringelite D
  参考文献：
  名称：

  Acidic properties of hypericin and its octahydroxy analogue in the ground and excited states

  摘要：

  金丝桃素 1 及其八羟基类似物 3 的吸收光谱和荧光光谱与 pH 值有关，这表明它们具有酸性，在基态和激发态，它们的去质子化作用分别来自海湾区和羰基周围位置的 OH；通过 X 射线衍射，确定了晶体态 1 阴离子的存在。

  DOI：

  10.1039/c39940000891

文献信息

• Synthesis and properties of fringelite D (1,3,4,6,8,10,11,13-octahydroxy-phenanthro[1,10,9,8,o,p,q,r,a]perylene-7,14-dione)
  作者：H. Falk、E. Mayr

  DOI：10.1007/bf00807161

  日期：——

  Fringelite D was synthesized from 1,3,6,8-tetramethoxyanthracen-9-ol via two different efficient routes. The first one involved demethylation and subsequent dimerization. The other one started with dimerization to yield octamethylfringelite D and subsequent demethylation. The starting material was prepared in four steps from commercially available educts, the key step being a benzamide ortho-lithiation. The spectroscopic properties of fringelite D were measured and are discussed. The dissociation, deprotonation, and protonation equilibria of fringelite D were characterized by their respective pK values in ground and excited states and compared with those of hypericin. Homo- and heteroassociation properties of fringelite D were found to be similar to those of hypericin.
• Hypericin, Hypocrellin, and Model Compounds:  Steady-State and Time-Resolved Fluorescence Anisotropies
  作者：K. Das、E. Dertz、J. Paterson、W. Zhang、G. A. Kraus、J. W. Petrich

  DOI：10.1021/jp973059+

  日期：1998.2.1

  Steady-state and time-resolved fluorescence anisotropies of hypericin, hypocrellin, and five other analogues have been measured. The steady-state excitation anisotropies for each of these compounds has a broad minimum at similar to 400 nm with a negative value. At the blue and red edges of the spectrum the value of the anisotropy is positive. Time-resolved fluorescence anisotropy measurements were performed for both hypericin and hypocrellin at excitation wavelengths of 300 and 570 nm. The limiting anisotropies are in excellent agreement with the corresponding steady-state values. These results are discussed in terms of the directions of the transition dipoles connecting the ground state to various excited states. The role of conformational isomers and tautomers in the ground and excited states is also considered.
• NECROSIS AVID TRACER AGENT
  申请人：K.U.Leuven Research & Development

  公开号：EP1651201A1

  公开（公告）日：2006-05-03
• Necrosis avid tracer agent
  申请人：Yicheng Ni

  公开号：US20070122340A1

  公开（公告）日：2007-05-31

  The present invention concerns to the use of phenanthro[1,10,9,8-opqra]perylene-7,14-dione derivatives, and more specifically hypericin or its derivatives, as necrosis or infarct specific agents. The phenanthro[1,10,9,8-opqra]perylene-7,14-dione derivatives can be labeled with a radionuclide, a radiopaque material or a material enhancing the effects magnetic resonance imaging.
• [EN] NECROSIS AVID TRACER AGENT<br/>[FR] AGENT TRACEUR PRESENTANT UNE AVIDITE POUR LA NECROSE
  申请人：LEUVEN K U RES & DEV

  公开号：WO2005009423A1

  公开（公告）日：2005-02-03

  The present invention concerns to the use of phenanthro[1,10,9,8-opqra]perylene-7,14-dione derivatives, and more specifically hypericin or its derivatives, as necrosis or infarct specific agents. The phenanthro[1,10,9,8-opqra]perylene-7,14-dione derivatives can be labeled with a radionuclide, a radiopaque material or a material enhancing the effects magnetic resonance imaging.