2-(3,4,5-三羟基苯基)乙酸 | 29511-09-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-(3,4,5-三羟基苯基)乙酸
• 英文名称: 2-(3,4,5-trihydroxyphenyl)acetic acid
• 英文别名: 3,4,5-trihydroxyphenylacetic acid
• CAS: 29511-09-9
• 化学式: C₈H₈O₅
• 分子量: 184.149
• InChiKey: DOUMISZLKFGEAX-UHFFFAOYSA-N

物化性质

• 沸点：
  504.8±45.0 °C(Predicted)
• 密度：
  1.641±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3,4,5-三羟基苯基)乙酸 在 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Bioactivity and Structural Properties of Novel Synthetic Analogues of the Protozoan Toxin Climacostol

  摘要：

  Climacostol（5-[(2Z)-non-2-en-1-yl]苯-1,3-二醇）是一种由原生动物Climacostomum virens产生的间苯二酚，用于防御捕食者。它对细菌和真菌病原体具有强大的抗微生物活性，抑制了多种人类和啮齿动物肿瘤细胞的生长，并且现在可以通过化学合成获得。在本研究中，我们化学合成了两种新型的climacostol类似物，即2-甲基-5-[(2Z)-non-2-en-1-yl]苯-1,3-二醇（AN1）和5-[(2Z)-non-2-en-1-yl]苯-1,2,3-三醇（AN2），目的是增强天然毒素的活性，评估它们对原核生物、自由生活的原生生物和哺乳动物肿瘤细胞的影响。结果表明，在芳香环上带有甲基的类似物（AN1）对病原微生物和原生生物的毒性明显高于climacostol。另一方面，在芳香环上带有额外羟基的类似物（AN2）显示出诱导原生生物细胞程序性死亡的能力。总的来说，收集的数据表明，在climacostol的芳香环上引入甲基或羟基基团可以有效地调节其效力和作用机制。

  DOI：

  10.3390/toxins11010042
• 作为产物：
  描述：

  3,4-二羟基苯乙酸 在 sodium dihydrogenphosphate 作用下， 反应 0.25h， 以98%的产率得到2-(3,4,5-三羟基苯基)乙酸
  参考文献：
  名称：

  p-Hydroxyphenylacetate 3-Hydroxylase as a Biocatalyst for the Synthesis of Trihydroxyphenolic Acids

  摘要：

  Trihydroxyphenolic acids such as 3,4,5-trihydroxycinnamic acid (3,4,5-THCA) 4c and 2-(3,4,5-trihydroxyphenyl)acetic acid (3,4,5-THPA) 2c are strong antioxidants that are potentially useful as medicinal agents. Our results show that p-hydroxyphenylacetate (HPA) 3-hydroxylase (HPAH) from Acinetobacter baumannii can catalyze the syntheses of 3,4,5-THPA 2c and 3,4,5-THCA 4c from 4-HPA 2a and p-coumaric acid 4a, respectively. The wild-type HPAH can convert 4-HPA 2a completely into 3,4,5-THPA 2c within 100 min (total turnover number (TTN) of 100). However, the wild-type enzyme cannot efficiently synthesize 3,4,5-THCA 4c. To improve the efficiency, the oxygenase component of HPAH (C-2) was rationally engineered in order to maximize the conversion of p-coumaric acid 4a to 3,4,5-THCA 4c. Results from site-directed mutagenesis studies showed that Y398S is significantly more effective than the wildtype enzyme for the synthesis of 3,4,5-THCA 4c; it can catalyze the complete bioconversion of p-coumaric acid 4a to 3,4,5-THCA 4c within 180 min (TTN similar to 23 at 180 min). The yield and stability of 3,4,5-THPA 2c and 3,4,5-THCA 4c were significantly improved in the presence of ascorbic acid. Thermostability studies showed that the wild-type C-2 was very stable and remained active after incubation at 30, 35, and 40 degrees C for 24 h. Y398S was moderately stable because its activity was retained for 24 h at 30 degrees C and for 15 h at 35 degrees C. Transient kinetic studies using stopped-flow spectrophotometry indicated that the key improvement in the reaction of Y398S with p-coumaric acid 4a lies within the protein-ligand interaction. Y398S binds to p-coumaric acid 4a with higher affinity than the wild-type enzyme, resulting in a shift in equilibrium toward favoring the productive coupling path instead of the path leading to wasteful flavin oxidation.

  DOI：

  10.1021/acscatal.5b00439

文献信息

• Conversion of oxiranes and CO2 to organic cyclic carbonates using a recyclable, bifunctional polystyrene-supported organocatalyst
  作者：Christopher J. Whiteoak、Andrea H. Henseler、Carles Ayats、Arjan W. Kleij、Miquel A. Pericàs

  DOI：10.1039/c3gc41919c

  日期：——

  The development of a heterogeneous one-component bifunctional catalyst system able to catalyse the conversion of carbon dioxide and oxiranes to organic cyclic carbonates at low temperature (45 °C) is reported. The bifunctional system can be easily recycled and reactivated when required. When compared with other heterogeneous organocatalysts for the same transformation, the reported catalyst is active at much milder temperatures, thus emphasising the optimal sustainability profile of the new catalyst system.

  报道了一种异质一组分双功能催化剂系统的开发，该系统能够在低温（45°C）下催化二氧化碳和环氧烷的转化为有机环状碳酸酯。该双功能系统可以在需要时轻松回收和再活化。与其他异质有机催化剂相比，该催化剂在更温和的温度下依然活跃，从而强调了这一新催化剂系统的最佳可持续性特征。
• Structure-Based Design of High-Affinity Macrocyclic FKBP51 Inhibitors
  作者：Michael Bauder、Christian Meyners、Patrick L. Purder、Stephanie Merz、Wisely Oki Sugiarto、Andreas M. Voll、Tim Heymann、Felix Hausch

  DOI：10.1021/acs.jmedchem.0c02195

  日期：2021.3.25

  retained full FKBP51 affinity and selectivity over FKBP52 and the incorporation of polar functionalities further enhanced affinity. Six high-resolution crystal structures of macrocyclic inhibitors in complex with FKBP51 confirmed the desired selectivity-enabling binding mode. Our results show that macrocyclization is a viable strategy to target the shallow FKBP51 binding site selectively.

  FK506结合蛋白51（FKBP51）成为与压力有关的疾病，慢性疼痛和肥胖症等几种疾病的关键因素。FK506的线性类似物SAFit被证明对FKBP51具有比其最接近的同源物FKBP52更高的选择性，从而可以在动物模型中进行概念验证研究。在这里，我们设计并合成了第一个大环的FKBP51选择性配体，以稳定活性构象。所有大环保留了完整的FKBP51亲和力和对FKBP52的选择性，极性功能的引入进一步增强了亲和力。与FKBP51配合使用的大环抑制剂的六种高分辨率晶体结构证实了所需的选择性选择性结合模式。我们的结果表明，大环化是一种有针对性的策略，可以选择性地靶向浅FKBP51结合位点。
• Acidity and Stability of 10-Substituted 1,8-Dihydroxy-9(10H)-anthracenones
  作者：Klaus Müller、Ingo Gawlik、Wolfgang Wiegrebe

  DOI：10.1002/ardp.19953280412

  日期：——

  The decomposition of 10‐substituted anthralin derivatives in dimethyl sulfoxide and ethanol was determined. While 10‐ω‐phenylalkylidene derivatives were thoroughly stable, 10‐ω‐phenylacyl‐substituted compounds were slowly degraded to danthron and the corresponding carboxylic acids. However, the stability of these derivatives was markedly improved as compared to that of anthralin. Determination of the

  测定了 10-取代蒽林衍生物在二甲亚砜和乙醇中的分解。虽然 10 - ω - 苯基亚烷基衍生物完全稳定，但 10 - ω - 苯基酰基取代的化合物缓慢降解为丹蒽酮和相应的羧酸。然而，与蒽林相比，这些衍生物的稳定性显着提高。pKa值的测定表明，ω-苯酰基衍生物比地蒽酚具有更强的酸，而ω-苯基亚烷基-取代通常使地蒽酚部分的酸度保持不变。
• 一种稳定同位素标记的盐酸曲托喹酚的合成方法
  申请人：天津阿尔塔科技有限公司

  公开号：CN112358446B

  公开（公告）日：2022-09-20

  本发明涉及一种稳定同位素标记的盐酸曲托喹酚的合成方法，属于有机合成领域。名称为一种稳定同位素标记的盐酸曲托喹酚的合成方法，以化合物(II)为原料，合成得到化合物(III)，进一步与化合物(IV)缩合得到化合物(V)，然后与同位素标记的碘甲烷反应得到同位素标记的化合物(VI)，而后关环生成同位素标记的化合物(VII)，再后还原生成化合物(VIII)，最后经过催化脱苄、成盐得到稳定同位素标记的盐酸曲托喹酚(I)。合成原料和中间体简单易得，目标产物同位素标记的盐酸曲托喹酚的化学纯度及同位素丰度较高，可用于药品质检、运动员药检以及相关代谢机理研究的内标物，具有重要的实际应用价值。
• Photosensitive composition
  申请人：KONICA CORPORATION

  公开号：EP0083971A2

  公开（公告）日：1983-07-20

  The developability of a positive-working photosensitive composition comprising (a) an o-quinonediazide compound is enhanced by incorporating (b) a condensed resin containing a condensation unit composed of an aromatic compound having a carboxylic group and a phenolic ahydroxyl group, and an aldehyde or ketone. Said condensation unit has preferably the formula: wherein n is 1 or 2, R, is hydrogen, hydroxyl, acyloxy, alkyl, alkoxy, halogen, which may be the same or different when n is 2; and R2 and R3, which may be the same or different, are each hydrogen, alkyl having 1 to 4 carbon atoms, phenyl or substituted phenyl.

  通过加入(b)含有缩合单元的缩合树脂，可提高由(a)邻喹酮噻嗪化合物组成的正片工作感光组合物的显影能力，该缩合单元由具有羧基和酚羟基的芳香族化合物以及醛或酮组成。所述缩合单元最好具有如下式子 其中 n 为 1 或 2，R 为氢、羟基、酰氧基、烷基、烷氧基、卤素，当 n 为 2 时可以相同或不同；R2 和 R3 可以相同或不同，各自为氢、具有 1 至 4 个碳原子的烷基、苯基或取代苯基。