Uracil

Base Information

• Chemical Name: Uracil
• CAS No.: 66-22-8
• Deprecated CAS: 144104-68-7,42910-77-0,4433-21-0,4433-24-3,766-19-8,138285-60-6,153445-42-2,51953-19-6,138285-60-6,153445-42-2,42910-77-0,4433-24-3,51953-19-6,766-19-8
• Molecular Formula: C4H4N2O2
• Molecular Weight: 114.089
• Hs Code.: 2933.59
• European Community (EC) Number: 200-621-9
• NSC Number: 759649,29742,3970
• UNII: 56HH86ZVCT
• DSSTox Substance ID: DTXSID4021424
• Nikkaji Number: J4.842I
• Wikipedia: Uracil
• Wikidata: Q182990
• NCI Thesaurus Code: C917
• Metabolomics Workbench ID: 37192
• ChEMBL ID: CHEMBL566
• Mol file: 66-22-8.mol

Synonyms:Uracil

Chemical Property of Uracil

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.27E-08mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.501
• Boiling Point: 440.5°C at 760 mmHg
• PKA: 9.45(at 25℃)
• Flash Point: 220.2oC
• PSA: 65.72000
• Density: 1.322 g/cm³
• LogP: -0.93680
• Storage Temp.: +15C to +30C
• Solubility.: Aqueous Acid (Slightly), DMSO (Slightly, Heated, Sonicated), Methanol (Slightly,
• Water Solubility.: SOLUBLE IN HOT WATER
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 112.027277375
• Heavy Atom Count: 8
• Complexity: 161

Purity/Quality:

≥ 99.00% ^*data from raw suppliers

Uracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: C1=CNC(=O)NC1=O
• Recent ClinicalTrials: Study of 0.1% Uracil Topical Cream (UTC) for the Prevention of Hand-Foot Syndrome
• Recent EU Clinical Trials: Onderzoek naar de farmacokinetiek van uracil na orale toediening bij pati?nten met colorectaal carcinoom.
• Recent NIPH Clinical Trials: A phase II trial of uracil ointment for the prevention of capecitabine induced hand-foot syndrome (HFS): .
• Description: Uracil (pyrimidine-2,4(1H,3H)-dione) is a pyrimidine nucleobase that plays a crucial role in biological systems as a component of ribonucleic acid (RNA). It is naturally occurring and characterized by its ability to form hydrogen bonds, which underpins its biological properties. It exists in two tautomeric forms: the amide tautomer called lactam and the imidic acid tautomer called lactim. Despite its non-aromatic structure, uracil exhibits aromatic behavior due to zwitterionic resonance. Uracil serves as a privileged scaffold in drug design, with a diverse range of pharmacological activities attributed to its various substitutions at positions N1, N3, C5, and C6. ^[1]
• Used in Medicinal Chemistry: Uracil and its derivatives are integral components of numerous commercial drugs with therapeutic potential in countering various pathogenic and physiological disorders. These compounds are employed in the treatment of viral infections, cancer, diabetes, thyroid disorders, and autosomal recessive disorders. Uracil-based drugs inhibit RNA viruses like influenza virus and coxsackievirus B4, and they demonstrate antibacterial, antifungal, antimicrobial, antitubercular, and antiprotozoal properties. Additionally, uracil derivatives have shown efficacy against pathogens such as Trichomonas vaginalis, Trypanosoma brucei, Leishmania mexicana, and Trypanosoma cruzi. The pharmacological activities of uracil compounds are attributed to their interactions with specific molecular targets involved in disease pathways, making them valuable candidates for drug discovery and development. ^[1]
• Used in Perovskite Solar Cells: Uracil is utilized in the fabrication of high-performance perovskite solar cells to improve both power conversion efficiency (PCE) and operational stability. When introduced as a "binder" into the perovskite film, uracil efficiently passivates defects and strengthens grain boundaries, enhancing the stability of perovskite films. Additionally, uracil strengthens the interface between the perovskite and the Tin oxide (SnO2) electron transport layer, increasing the binding force. These modifications result in perovskite solar cells with superior operational stability, delivering high PCE and maintaining over 90% of their initial PCE even after extended exposure to continuous light. ^[1]
• Production Methods: Uracil can be synthesized through various methods, including the deamination of cytosine and synthetic routes involving urea, thiourea, maleic acid, and fumaric acid. ^[1]
• References: [1] Therapeutic potential of uracil and its derivatives in countering pathogenic and physiological disorders; DOI 10.1016/j.ejmech.2020.112801; [2] Uracil Induced Simultaneously Strengthening Grain Boundaries and Interfaces Enables High-Performance Perovskite Solar Cells with Superior Operational Stability; DOI 10.1002/adma.202306415

Technology Process of Uracil

There total 295 articles about Uracil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

1,2,4-triazole-3-carboxamide (3641-08-5) + uridine (58-96-8) → uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + ribavirin (36791-04-5,66510-90-5)

Guidance literature:

With aeromonas hydrophila CECT 4226; at 60 ℃; for 26h; pH=7; aq. phosphate buffer; Enzymatic reaction;

DOI:10.3109/10242422.2010.538949

Reference yield: 58.0%

hypoxanthine (68-94-0) + 2',3'-Dideoxyuridine (5983-09-5,153547-98-9) → Dideoxyinosine (69655-05-6) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6)

Guidance literature:

With aeromonas hydrophila CECT 4221; at 45 ℃; for 16h; pH=7; aq. phosphate buffer; Enzymatic reaction;

DOI:10.3109/10242422.2010.538949

Reference yield:

2,6 dichloropurine (5451-40-1) + uridine (58-96-8) → uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + 2,6-dichloropurine riboside (13276-52-3)

Guidance literature:

With potassium phosphate; at 40 ℃; for 6h; pH=7.5; Equilibrium constant; Enzymatic reaction;

DOI:10.3390/molecules25040934

upstream raw materials:

uracil

5'-Desoxy-2',3'-O-isopropylidenuridin-5'-carbonitril

2,4-bis(benzyloxy)pyrimidine

acetic acid methyl ester

Downstream raw materials:

5-chlorouracil

1-acetyl-1H-pyrimidine-2,4-dione

5-fluorouracil

O,O'-bis-(trimethylsilyl)uracil

Refernces

• 1、 Kaspar, Felix,Neubauer, Peter,Kurreck, Anke. "The Peculiar Case of the Hyper-thermostable Pyrimidine Nucleoside Phosphorylase from Thermus thermophilus**". . p. 1385 - 1390. Retrieved 2021/01/29.
• 2、 -. "Green production process of uracil". Paragraph 0046-0048; 0049-0052; 0053-0055; 0056-0086. . Retrieved 2021/04/14.