4-(3-hydroxy-2-nitrophenyl)-4-oxo-2-butenoic acid | 93367-77-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(3-hydroxy-2-nitrophenyl)-4-oxo-2-butenoic acid
• 英文别名: (E)-4-(3-hydroxy-2-nitrophenyl)-4-oxobut-2-enoic acid；4-(3-hydroxy-2-nitro-phenyl)-4-oxo-trans-crotonic acid；4-(3-Hydroxy-2-nitro-phenyl)-4-oxo-trans-crotonsaeure；(2E)-4-(3-Hydroxy-2-nitrophenyl)-4-oxo-2-butenoic Acid
• CAS: 93367-77-2
• 化学式: C₁₀H₇NO₆
• 分子量: 237.169
• InChiKey: SZTWXYIDDMYRFS-SNAWJCMRSA-N

物化性质

• 熔点：
  158 °C
• 沸点：
  471.5±45.0 °C(Predicted)
• 密度：
  1.555±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(3-hydroxy-2-nitrophenyl)-4-oxo-2-butenoic acid 在 platinum(IV) oxide 氢气 、 氰化汞 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 methyl 4-oxo-4-<2-amino-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxyphenyl>-2-butenoate
  参考文献：
  名称：

  Synthesis of Human Ultraviolet Filter Compounds:  O-β-d-Glucopyranosides of 3-Hydroxykynurenine and 2-Amino-3-hydroxy-γ-oxobenzenebutanoic Acid

  摘要：

  The role of endogenous tryptophan-derived UV filters in aging lenses and in human cataract is becoming increasingly important. The two major UV filters found in the lenses of primates, the O-beta-D-glucopyranosides of 3-hydroxykynurenine and 2-amino-3-hydroxy-gamma-oxobenzenebutanoic acid, 1 and 2, were synthesized from the common benzoyl acrylate precursor 2-amino-3-hydroxybenzoylacrylic acid 10. Synthesis of compound 3, the alpha-N-acetyl derivative of 1, was achieved using coupling of 2-nitro-3-benzyloxyacetophenone 4 with the sodium salt of diethyl acetamidomalonate as a key step. This is the first reported synthesis of the lenticular glucopyranoside 2 and the N-acetyl compound 3.

  DOI：

  10.1021/jo982321n
• 作为产物：
  描述：

  3-羟基苯乙酮 在 盐酸 、 硝酸 、 溶剂黄146 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 20.0h， 生成 4-(3-hydroxy-2-nitrophenyl)-4-oxo-2-butenoic acid
  参考文献：
  名称：

  用LC-MS / MS方法研究冈比亚按蚊3-羟基犬尿氨酸转氨酶的活性和抑制作用。

  摘要：

  在冈比亚按蚊中，疟原虫是恶性疟原虫的最有效载体，3-羟基犬尿氨酸具有潜在的毒性。在成年蚊子中，过量的3-羟基犬尿氨酸被特定的转氨酶（3-羟基犬尿氨酸转氨酶，3-HKT）去除，该酶将化合物转变为更稳定的黄嘌呤酸。干扰冈比亚按蚊中的3-羟基犬尿氨酸代谢是开发阻断传输药物和杀虫剂的潜在方法。因此，这项工作的目的是开发和验证一种新的LC-MS / MS方法，用于评估冈比亚曲霉3-羟基犬尿氨酸转氨酶（Ag-HKT）活性并确定该酶抑制剂的效力。我们建立了一个基于LC-MS / MS的酶法测定方法，用于测定重组Ag-HKT酶的动力学常数值，并通过已知的蛋白质抑制剂（用作参考）和新合成的化合物评估Ag-HKT的抑制作用。色谱分离是在Phenomenex Synergi Polar-RP（150 mm×2.0，4μm）上以含有0.2％甲酸的甲醇和水在梯度模式下进行的。质谱检测是通过配备有ESI源的离子阱在正

  DOI：

  10.1016/j.jpba.2019.05.025

文献信息

• Novel human lens metabolites from normal and cataractous human lenses
  作者：Jasminka Mizdrak、Peter G. Hains、Danuta Kalinowski、Roger J.W. Truscott、Michael J. Davies、Joanne F. Jamie

  DOI：10.1016/j.tet.2007.03.133

  日期：2007.6

  4-(2-Aminophenyl)-4-oxobutanoic acid, 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine have been identified as novel metabolites in normal and cataractous human lenses following total synthesis and comparison with authentic human lens samples. Their structures are consistent with those derived from the major human lens UV filters kynurenine and 3-hydroxykynurenine, and it is proposed that these compounds also play a role as UV filters. These metabolites were isolated in pmol/mg levels (dry mass) in lenses. 4-(2-Amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine were found to be unstable at physiological pH. Other potential metabolites, glutathionyl-3-hydroxykynurenine, kynurenine yellow and 3-hydroxykynurenine yellow, were not detected in either normal or cataractous lenses. (c) 2007 Elsevier Ltd. All rights reserved.
• Butenandt et al., Chemische Berichte, 1957, vol. 90, p. 1120,1124
  作者：Butenandt et al.

  DOI：——

  日期：——
• Synthesis of Human Ultraviolet Filter Compounds:  <i>O</i>-β-<scp>d</scp>-Glucopyranosides of 3-Hydroxykynurenine and 2-Amino-3-hydroxy-γ-oxobenzenebutanoic Acid
  作者：Michael K. Manthey、Joanne F. Jamie、Roger J. W. Truscott

  DOI：10.1021/jo982321n

  日期：1999.5.1

  The role of endogenous tryptophan-derived UV filters in aging lenses and in human cataract is becoming increasingly important. The two major UV filters found in the lenses of primates, the O-beta-D-glucopyranosides of 3-hydroxykynurenine and 2-amino-3-hydroxy-gamma-oxobenzenebutanoic acid, 1 and 2, were synthesized from the common benzoyl acrylate precursor 2-amino-3-hydroxybenzoylacrylic acid 10. Synthesis of compound 3, the alpha-N-acetyl derivative of 1, was achieved using coupling of 2-nitro-3-benzyloxyacetophenone 4 with the sodium salt of diethyl acetamidomalonate as a key step. This is the first reported synthesis of the lenticular glucopyranoside 2 and the N-acetyl compound 3.
• Study of Anopheles gambiae 3-hydroxykynurenine transaminase activity and inhibition by LC-MS/MS method
  作者：Rossana Canavesi、Riccardo Miggiano、Martina Stella、Ubaldina Galli、Franca Rossi、Menico Rizzi、Erika Del Grosso

  DOI：10.1016/j.jpba.2019.05.025

  日期：2019.9

  method for the evaluation of A. gambiae 3-hydroxykynurenine transaminase (Ag-HKT) activity and the determination of the potency of inhibitors of the enzyme. We set up a LC-MS/MS based enzymatic assay for the determination of kinetic constants values of the recombinant Ag-HKT enzyme and for the evaluation of Ag-HKT inhibition by a known protein inhibitor used as reference and a newly synthesized compound

  在冈比亚按蚊中，疟原虫是恶性疟原虫的最有效载体，3-羟基犬尿氨酸具有潜在的毒性。在成年蚊子中，过量的3-羟基犬尿氨酸被特定的转氨酶（3-羟基犬尿氨酸转氨酶，3-HKT）去除，该酶将化合物转变为更稳定的黄嘌呤酸。干扰冈比亚按蚊中的3-羟基犬尿氨酸代谢是开发阻断传输药物和杀虫剂的潜在方法。因此，这项工作的目的是开发和验证一种新的LC-MS / MS方法，用于评估冈比亚曲霉3-羟基犬尿氨酸转氨酶（Ag-HKT）活性并确定该酶抑制剂的效力。我们建立了一个基于LC-MS / MS的酶法测定方法，用于测定重组Ag-HKT酶的动力学常数值，并通过已知的蛋白质抑制剂（用作参考）和新合成的化合物评估Ag-HKT的抑制作用。色谱分离是在Phenomenex Synergi Polar-RP（150 mm×2.0，4μm）上以含有0.2％甲酸的甲醇和水在梯度模式下进行的。质谱检测是通过配备有ESI源的离子阱在正