Chemical Properties
white to slightly yellow crystalline powder or
Uses
2,4-Dihydroxypyrimidine-5-carboxylic acid (Uracil-5-carboxylic acid) has been used for the visual sensing of melamine (at parts-per-billion (ppb) level) by a highly sensitive analytical method based on Au nanoparticles.
Definition
ChEBI: Uracil-5-carboxylic acid is a pyrimidinemonocarboxylic acid that is uracil carrying a carboxy group at position 5. It is functionally related to a uracil. It is a conjugate acid of a uracil-5-carboxylate. It is a tautomer of a 2,4-dihydroxypyrimidine-5-carboxylic acid.
General Description
2,4-Dihydroxypyrimidine-5-carboxylic acid (Uracil-5-carboxylic acid) has been obtained from 5-formyluracil by the action of enzyme, thymine 7-hydroxylase. It has been used to synthesize N1-alkylated uracil derivatives.
Synthesis
The general procedure for synthesizing uracil-5-carboxylic acid from 5-methyluracil was as follows: 100 g of 5-methyluracil and 300 mL of deionized water were added to an autoclave reactor, followed by the addition of 35 mL of a 30% hydrogen peroxide solution. Next, 15 g of 1-hydroxy-1,2,3-benzotriazin-4(3H)-one and 35 g of a pre-prepared catalyst (as described in Example 3) were added. The atmosphere in the autoclave was replaced with oxygen and the reaction system was subsequently heated to 130°C and maintained at this temperature for 3 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature and filtered to remove insoluble material. The filtrate was concentrated under reduced pressure and poured into an ice-water mixture for cooling and crystallization, resulting in 150 g of white solid product. The yield of this step was 96.1%, and the purity of the product was 99.3% as analyzed by high performance liquid chromatography (HPLC).
References
[1] Patent: CN108341785, 2018, A. Location in patent: Paragraph 0014-0020
[2] Nucleic Acids Research, 2015, vol. 43, # 20, p. 10026 - 10038
