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| | 5-Fluoroorotic acid Basic information |
| Product Name: | 5-Fluoroorotic acid | | Synonyms: | 1,2,3,6-tetrahydro-2,6-dioxo-5-fluoro-4-pyrimidinecarboxylicaci;1,2,3,6-tetrahydro-2,6-dioxo-5-fluoro-4-pyrimidinecarboxylicacid;5-fluoro-2,4-dioxo-1H-pyrimidine-6-carboxylic acid hydrate;nsc31712;ro2-9945;2,6-Dihydroxy-5-fluoropyrimidine-4-carboxylic acid;5-FLUOROURACIL-4-CARBOXYLIC ACID;5' FOA | | CAS: | 703-95-7 | | MF: | C5H3FN2O4 | | MW: | 174.09 | | EINECS: | 211-876-0 | | Product Categories: | pyrimidine;Fluorine series;Nucleotides and Nucleosides;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Aromatic Halides (substituted);5-FOA;Bases & Related Reagents;Nucleotides | | Mol File: | 703-95-7.mol |  |
| | 5-Fluoroorotic acid Chemical Properties |
| Melting point | 278 °C (dec.)(lit.) | | Boiling point | 143°C (rough estimate) | | density | 1.6154 (estimate) | | storage temp. | Sealed in dry,Store in freezer, under -20°C | | solubility | NH4OH 4 M: 50 mg/mL, clear, faintly yellow | | form | solid | | pka | 2.04±0.20(Predicted) | | color | Pale yellow | | Merck | 14,4176 | | InChIKey | LODRRYMGPWQCTR-UHFFFAOYSA-N | | CAS DataBase Reference | 703-95-7(CAS DataBase Reference) |
| | 5-Fluoroorotic acid Usage And Synthesis |
| Chemical Properties | White to Off-White Crystalline Solid | | 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.
| | Uses | Useful in the selection of orotidine-5′-phosphate decarboxylase mutants of Saccharomyces cerevisiae. |
| | 5-Fluoroorotic acid Preparation Products And Raw materials |
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