5-Fluoroorotic acid
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
- pka
- 2.04±0.20(Predicted)
- form
- solid
- color
- Pale yellow
- Merck
- 14,4176
- InChIKey
- LODRRYMGPWQCTR-UHFFFAOYSA-N
- CAS DataBase Reference
- 703-95-7(CAS DataBase Reference)
Safety Information
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22-36/37/38
- Safety Statements
- 26-36-36/37/39-27
- WGK Germany
- 3
- RTECS
- UV7800000
- F
- 10
- HazardClass
- IRRITANT
- HS Code
- 29335990
MSDS
- Language:English Provider:2,6-Dihydroxy-5-fluoropyrimidine-4-carboxylic acid
5-Fluoroorotic acid Usage And Synthesis
Chemical Properties
White to Off-White Crystalline Solid
Uses
Useful in the selection of orotidine-5′-phosphate decarboxylase mutants of Saccharomyces cerevisiae.
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.
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