5-Fluoroorotic Acid
Title: 5-Fluoroorotic Acid
CAS Registry Number: 703-95-7
CAS Name: 5-Fluoro-1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid
Additional Names: 5-fluoroorotate; 5-fluoro-6-carboxyuracil; 5-FOA
Manufacturers' Codes: ENT-26398; NSC-31712; Ro-2-9945; WR-152520
Molecular Formula: C5H3FN2O4
Molecular Weight: 174.09
Percent Composition: C 34.50%, H 1.74%, F 10.91%, N 16.09%, O 36.76%
Literature References: Pyrimidine precursor; selectively toxic to yeast cells that synthesize the enzyme orotidine-5¢-P decarboxylase. Prepn: R. Duschinsky et al., J. Am. Chem. Soc. 79, 4559 (1957); GB 806584 (1958 to Hoffmann-La Roche); R. Duschinsky, C. Heidelberger, US 2948725 (1960). Improved synthesis: D. H. R. Barton et al., J. Chem. Soc. Perkin Trans. 1 1974, 2095; and mass spectrum: S. N. Alam et al., Acta Pharm. Suec. 12, 375 (1975). Antitumor activity: C. Heidelberger et al., Nature 179, 663 (1957). Inhibition of RNA synthesis: C. T. Garrett et al., Arch. Biochem. Biophys. 155, 342 (1973). Clinical evaluation of antimycotic activity: K. Nikolova et al., Methods Find. Exp. Clin. Pharmacol. 9, 85 (1987). Review of in vitro use in the positive selection of genetically transformed yeast cells: J. D. Boeke et al., Methods Enzymol. 154, 164-175 (1987).
 
Derivative Type: Monohydrate
Properties: Crystals, mp 255° (dec) (Duschinsky, 1957); also reported as 258-259° (Barton). Partially sol in water. uv max (0.1N HCl): 284-285 nm (e 7100). LD50 i.p. in male mice: 300 mg/kg (Nikolova).
Melting point: mp 255° (dec) (Duschinsky, 1957)
Absorption maximum: uv max (0.1N HCl): 284-285 nm (e 7100)
Toxicity data: LD50 i.p. in male mice: 300 mg/kg (Nikolova)
 
Use: Research tool in molecular genetics.

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