5-Fluoroorotic acid

Base Information

• Chemical Name: 5-Fluoroorotic acid
• CAS No.: 703-95-7
• Molecular Formula: C5H3FN2O4
• Molecular Weight: 174.088
• Hs Code.: 2933.59
• European Community (EC) Number: 211-876-0
• NSC Number: 31712
• UNII: 7IA9OUC93E
• DSSTox Substance ID: DTXSID90220573
• Nikkaji Number: J13.864I
• Wikipedia: 5-Fluoroorotic_acid
• Wikidata: Q18207160
• ChEMBL ID: CHEMBL1232805
• Mol file: 703-95-7.mol

Synonyms:5-fluoroorotic acid;fluoroorotic acid

Chemical Property of 5-Fluoroorotic acid

Chemical Property:

• Appearance/Colour: white to off-white crystalline solid
• Melting Point: 278 °C (dec.)(lit.)
• Refractive Index: 1.58
• Boiling Point: 143°C (rough estimate)
• PKA: 2.04±0.20(Predicted)
• PSA: 103.02000
• Density: 1.81 g/cm³
• LogP: -1.09950
• Storage Temp.: −20°C
• Solubility.: NH4OH 4 M: 50 mg/mL, clear, faintly yellow
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 174.00768474
• Heavy Atom Count: 12
• Complexity: 309

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Fluoroorotic Acid Monohydrate >95.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36-36/37/39-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1(=C(NC(=O)NC1=O)C(=O)O)F
• Uses: 5-FOA(5-Fluoroorotic acid ) has become a valuable tool for research in the field of molecular genetics. It has been employed in the selection of resistant strains of Saccharomyces cerevisiae that possess a mutant URA3 gene which renders them orotidine-5'-phosphate decarboxylase deficient. 5-FOA is coverted to 5-fluorouridine monophosphate (5-FUMP) in yeast cells, which can become incorporated into RNA or metabolized to the highly toxic 5-fluoro-2’-deoxyuridine monophosphate (5-FdUMP). 5-FdUMP is a potent inhibitor of thymidylate synthase (TS), causing the cessation of DNA synthesis. More recently, 5-FOA has been shown to possess potent antimalarial activity against both chloroquine-susceptible and chloroquine-resistant clones of Plasmodium falciparum. Studies indicate that TS is the primary target of 5-FOA in malarial parasites. The combination of 5-FOA and uracil has been effective in treating mice infected with Plasmodium yoelli. 5-FOA may also have potential in the treatment of human malarial infections when used in combination with other agents. Useful in the selection of orotidine-5′-phosphate decarboxylase mutants of Saccharomyces cerevisiae.

Technology Process of 5-Fluoroorotic acid

There total 6 articles about 5-Fluoroorotic acid 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: 83.0%

C7H7FN2O4 → 5-fluoroorotic acid (703-95-7)

Guidance literature:

With hydrogenchloride; In water; at 50 ℃; for 3h;

Reference yield: 79.0%

C8H9FN2O4 → 5-fluoroorotic acid (703-95-7)

Guidance literature:

With hydrogenchloride; In water; at 60 ℃; for 4h;

Reference yield: 48.4%

ethyl 2-(methylmercapto)-4-hydroxy-5-fluoro-6-pyrimidinecarboxylate (717-48-6) → 5-fluoroorotic acid (703-95-7)

Guidance literature:

With hydrogenchloride; for 4h; Heating;

DOI:10.1021/jm00182a019

upstream raw materials:

2-ethylsulfanyl-5-fluoro-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

ethyl 2-(methylmercapto)-4-hydroxy-5-fluoro-6-pyrimidinecarboxylate

Downstream raw materials:

5-fluorouracil