2,4,6-trihydroxyphenanthrene | 70205-57-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2,4,6-trihydroxyphenanthrene
• 英文别名: 2,4,6-Phenanthrenetriol；phenanthrene-2,4,6-triol
• CAS: 70205-57-1
• 化学式: C₁₄H₁₀O₃
• 分子量: 226.232
• InChiKey: AFINAJGJCNBZEO-UHFFFAOYSA-N

物化性质

• 沸点：
  535.3±19.0 °C(Predicted)
• 密度：
  1.479±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  白藜芦醇 在 盐酸 、 sodium hydride 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 45.5h， 生成 2,4,6-trihydroxyphenanthrene
  参考文献：
  名称：

  Theoretical and experimental exploration of the photochemistry of resveratrol: beyond the simple double bond isomerization

  摘要：

  resveratrol的光化学异构化过程是近期研究的主题，其中报告了相互矛盾的结果。这一反应的光产物混合物需要被认为比顺反异构体的共存更为复杂。尽管其性质未知，但在不同研究中已检测到至少一种未鉴定的第三种产物。在这项工作中，我们的目标是通过实验和计算方法的协同结合，对这一反应的光化学过程进行详尽的描述。

  DOI：

  10.1039/c2ob26241j

文献信息

• Effects of orchinol and related phenanthrenes on the enzymic degradation of indole-3-acetic acid
  作者：Tsung T. Lee、Gerald L. Rock、Albert Stoessl

  DOI：10.1016/s0031-9422(00)88680-x

  日期：1978.1

  Abstract Orchinol, hircinol, loroglossol and certain related phenanthrenes inhibited horseradish peroxidase-catalysed IAA degradation to a varied degree. Among

  摘要 Orchinol、hircinol、loroglossol 和某些相关的菲在不同程度上抑制辣根过氧化物酶催化的 IAA 降解。之中
• 2,4,6-Trihydroxyphenanthrene, a trans-resveratrol photoreaction byproduct: First evidences of genotoxic risk
  作者：Antonio Francioso、Luciana Mosca、Ivette María Menéndez-Perdomo、Sergio Fanelli、Mario Fontana、Maria D’Erme、Fabiana Fuentes-Leon、Angel Sanchez-Lamar

  DOI：10.1016/j.phytol.2019.02.025

  日期：2019.4

  2,4,6-trihydroxyphenanthrene (THP), derived from trans-resveratrol photochemical isomerization and electrocyclization. To achieve this goal, we used Caulobacter crescentus as the experimental model for evaluating the colony-forming ability and the SOS response induction of cells exposed to THP. DNA-strand breaks and oxidative damage were assessed by the cell-free pCMut plasmid. The obtained data demonstrated

  白藜芦醇是一种具有众所周知的多种有益作用的天然产品，已被广泛用作开发抗衰老局部植物产品的生物活性成分。这些产品通常应用于经常长时间暴露在太阳光下的皮肤，从而导致潜在有害的白藜芦醇衍生物。 在这项研究中，我们研究了由反式白藜芦醇光化学异构化和电环化衍生的2,4,6-三羟基菲（THP）的细胞毒性和遗传毒性。为了实现这个目标，我们使用新月形杆菌作为评估暴露于THP的细胞的集落形成能力和SOS应答诱导的实验模型。用无细胞的pCMut质粒评估DNA链断裂和氧化损伤。 所获得的数据表明，即使在亚微摩尔浓度下，THP也会通过促氧化剂机制导致DNA损伤而诱导THP的细胞毒性和遗传毒性作用。
• Effect of Natural Deep Eutectic Solvents on trans-Resveratrol Photo-Chemical Induced Isomerization and 2,4,6-Trihydroxyphenanthrene Electro-Cyclic Formation
  作者：Roberto Mattioli、Daniel Di Risola、Rodolfo Federico、Alessia Ciogli、Francesco Gasparrini、Claudio Villani、Mario Fontana、Anna Maggiore、Maria d’Erme、Luciana Mosca、Antonio Francioso

  DOI：10.3390/molecules27072348

  日期：——

  trans/cis isomerization and a 6π electrochemical cyclization with the subsequent formation of 2,4,6-trihydroxyphenanthrene (THP). THP is a potentially harmful compound which can exert genotoxic effects. In this work we improved the chromatographic separation and determination of the two resveratrol isomers and of THP by using a non-commercial pentafluorophenyl stationary phase. We assessed the effect of natural

  反式-白藜芦醇是一种具有公认的健康促进作用的天然生物活性化合物。当暴露在紫外光下时，该化合物可发生光化学诱导的反式/顺式异构化和 6π 电化学环化，随后形成 2,4,6-三羟基菲 (THP)。THP 是一种潜在的有害化合物，可发挥遗传毒性作用。在这项工作中，我们通过使用非商用五氟苯基固定相改进了两种白藜芦醇异构体和 THP 的色谱分离和测定。我们通过评估cis评估了天然低共熔溶剂 (NaDES) 作为可能的光保护剂的效果-白藜芦醇异构体和不同紫外光照射条件下THP的形成，目的是增强白藜芦醇的光稳定性并抑制THP的产生。我们的研究结果表明，含甘油的 NaDES，特别是脯氨酸/甘油 NaDES 具有显着的光保护作用，对白藜芦醇的光化学异构化具有很强的抑制作用，并显着限制了有毒衍生物 THP 的形成。考虑到各种商业产品中存在白藜芦醇，鉴于与其光化学降解产物相关的潜在遗传毒性风险以及开发绿色、生态
• Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues
  作者：De-Jun Ding、Xiao-Yan Cao、Fang Dai、Xiu-Zhuang Li、Guo-Yun Liu、Dong Lin、Xing Fu、Xiao-Ling Jin、Bo Zhou

  DOI：10.1016/j.foodchem.2012.05.074

  日期：2012.12

  Five hydroxylated phenanthrenes as "cis-configuration-fixed" resveratrol analogues differing in the number and position of the hydroxyl groups were designed and synthesized. Their antioxidant activity was studied by ferric reducing antioxidant power, 2,2-diphenyl-1-picrylhydrazyl free radical-scavenging, and DNA strand breakage-inhibiting assays, corresponding to their electron-donating, hydrogen-transfer and DNA-protecting abilities, respectively. In the above assays, their activity depends significantly on the number and position of the hydroxyl groups, and most of them are more effective than resveratrol. Noticeably, compound 9b (2,4,6-trihydroxyl phenanthrene) with the same hydroxyl group substitutions as resveratrol, is superior to the reference compound, highlighting the importance of extension of the conjugation over multiple aromatic-rings. Similar activity sequences were obtained in different experimental models, but the appreciable differences could contribute detailed insights into antioxidant mechanisms. Based on these results, the hydroxylated phenanthrenes may be considered as a novel type of resveratrol-directed antioxidants. (C) 2012 Elsevier Ltd. All rights reserved.
• Photo-induced chemical reaction of trans-resveratrol
  作者：Yue Zhao、Meng Shi、Jian-Hui Ye、Xin-Qiang Zheng、Jian-Liang Lu、Yue-Rong Liang

  DOI：10.1016/j.foodchem.2014.08.130

  日期：2015.3

  Photo-induced chemical reaction of trans-resveratrol has been studied. UV B, liquid state and sufficient exposure time are essential conditions to the photochemical change of trans-resveratrol. Three principal compounds, cis-resveratrol, 2,4,6-phenanthrenetriol and 2-(4-hydroxyphenyl)-5,6-benzofurandione, were successively generated in the reaction solution of trans-resveratrol (0.25 mM, 100% ethanol) under 100 mu W cm(-2) UV B radiation for 4 h. cis-Resveratrol, originated from isomerization of trans-resveratrol, resulted in 2,4,6-phenanthrenetriol through photocyclisation reaction meanwhile loss of 2 H. 2,4, 6-Phenanthrenetriol played a role of photosensitizer producing singlet oxygen in the reaction pathway. The singlet oxygen triggered [4+2] cycloaddition reaction of trans-resveratrol, and then resulted in the generation of 2-(4-hydroxyphenyl)-5,6-benzofurandione through photorearrangement and oxidation reaction. The singlet oxygen reaction was closely related to the substrate concentration of trans-resveratrol in solution. (C) 2014 Elsevier Ltd. All rights reserved.

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