23945-44-0

Basic information

• Product Name: 2,4-Dihydroxypyrimidine-5-carboxylic acid
• Synonyms: 1,2,3,4-TETRAHYDRO-2,4-DIOXO-5-PYRIMIDINECARBOXYLIC ACID;2,4-DIHYDROXYPYRIMIDINE-5-CARBOXYLIC ACID;5-CARBOXY-2,4-DIHYDROXYPYRIMIDINE;ISO-OROTIC ACID;URACIL-5-CARBOXYLIC ACID;1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidinecarboxylicaci;5-carboxyuracil;Uracil5-carboxylatehydrate
• CAS NO: 23945-44-0
• Molecular Formula: C₅H₄N₂O₄
• Molecular Weight: 156.1
• EINECS: 245-947-2
• Product Categories: Carboxylic Acids;Pyrazines, Pyrimidines & Pyridazines;Pyridine;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Carboxylic Acids;Pyrazines, Pyrimidines & Pyridazines;Heterocycle-Pyrimidine series
• Mol File: 23945-44-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 283 °C (dec.)(lit.)
• Boiling Point: 280.29°C (rough estimate)
• Flash Point: 295.4 °C
• Appearance: White to slightly yellow/Crystalline Powder
• Density: 1.6814 (rough estimate)
• Refractive Index: 1.4800 (estimate)
• Storage Temp.: Refrigerator
• PKA: 5.08±0.20(Predicted)
• Water Solubility: 1.8g/L(20 oC)
• CAS DataBase Reference: 2,4-Dihydroxypyrimidine-5-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dihydroxypyrimidine-5-carboxylic acid(23945-44-0)
• EPA Substance Registry System: 2,4-Dihydroxypyrimidine-5-carboxylic acid(23945-44-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 23945-44-0(Hazardous Substances Data)

Usage

Description

2,4-Dihydroxypyrimidine-5-carboxylic acid, also known as Uracil-5-carboxylic acid, is a white to slightly yellow crystalline powder derived from 5-formyluracil through the action of the enzyme thymine 7-hydroxylase. It is a significant compound in the field of chemistry and has various applications across different industries.

Uses

Used in Analytical Chemistry:
2,4-Dihydroxypyrimidine-5-carboxylic acid is used as a highly sensitive analytical reagent for the visual sensing of melamine at parts-per-billion (ppb) level. This application utilizes the compound's interaction with gold nanoparticles to create a highly sensitive method for detecting melamine, which is crucial in ensuring the safety and quality of various products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,4-Dihydroxypyrimidine-5-carboxylic acid is used as a key intermediate in the synthesis of N1-alkylated uracil derivatives. These derivatives are important components in the development of new drugs and therapeutic agents, highlighting the compound's significance in drug discovery and medicinal chemistry.
Used in Chemical Synthesis:
2,4-Dihydroxypyrimidine-5-carboxylic acid is also employed as a versatile building block in the synthesis of various organic compounds and materials. Its unique chemical properties and reactivity make it a valuable asset in the development of new chemical entities and materials with potential applications in various fields, including electronics, materials science, and environmental science.

Upstream product

• 65-71-4 thymin 
• 4433-40-3 5-hydroxymethyl uracil 
• 1187-34-4 α-Cyano-β-ethoxy-N-(ethoxycarbonyl)acrylamide 
• 65696-20-0 methyl ureidomethylenemalonate 
• 1195-08-0 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde 
• 3650-93-9 5-carboxylcytosine 
• 4425-56-3 5-cyanouracil 
• 110821-07-3 2,4-dimethoxypyrimidine-5-carboxylic acid 

Downstream Products

• 92264-75-0 2,4-dioxohexahydropyrimidine-5-carboxylic acid 
• 37131-89-8 2,4-dichloropyrimidine-5-carboxylic acid 
• 66-22-8 uracil 
• 56804-96-7 Tris-O-(trimethylsilyl)-5-carboxyuracil 
• 3346-68-7 2,4-dihydroxypyrimidine-5-carboxylic acid chloride 
• 4869-45-8 1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid 
• 88468-97-7 methyl 1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyridine-5-carboxylate 
• 69312-43-2 2,4-dichloropyrimidine-5-carboxylic acid isopropyl ester 
• 3346-68-7 uracil-5-formyl chloride 
• 330784-47-9 avanafil 
• 14599-46-3 5-carboxy-2'-deoxyuridine 

Relevant articles and documents

Preparation method of important intermediate (uracil-5-carboxylic acid) of medicine (avanafil)

The invention discloses a preparation method of an important intermediate (uraciluracil-5-carboxylic acid) of a medicine (avanafil), and belongs to the technical field of drug synthesis. The preparation method is characterized in that the uraciluracil-5-carboxylic acid is prepared by adopting thymine as a starting material and using oxygen for further oxidation under the action of an active-carbon-loaded catalyst. The preparation method disclosed by the invention has the advantages of high yield, low cost, economic and environment-friendly effects and applicability to industrialization and thelike and is a synthesis method with industrial production value.

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

Photochemical deamination and demethylation of 5-methylcytosine

Cytosine methylation is believed to play a pivotal role in eucaryotic cellular development as well as in viral latency. We have been investigating chemical mechanisms for the perturbation of methylation patterns, including the effects of ultraviolet radiation. We observed that, upon exposure to UV light, 5-methylcytosine (5mC) was converted to thymine, cytosine, and a series of 5-substituted cytosine derivatives as analyzed by gas chromatography/mass spectrometry. Deamination of 5mC to thymine proceeds via formation of the intermediate photohydrate. Formation of 5-substituted cytosine derivatives results from oxidation of the 5-methyl group with initial formation of 5-(hydroxymethyl)cytosine (hmC). Upon exposure to UV light, hmC is converted to cytosine. The conversion of hmC to cytosine likely results from photohydration and elimination of formaldehyde. It is proposed that endogenous oxidation and hydrolysis could result in demethylation of 5mC residues in DNA. Whereas hydrolytic deamination of 5mC to thymine has been widely discussed, demethylation of 5mC has not as yet been described.