Title: Hydroorotic Acid
CAS Registry Number: 155-54-4
CAS Name: Hexahydro-2,6-dioxo-4-pyrimidinecarboxylic acid
Additional Names: 4,5-dihydroorotic acid
Molecular Formula: C5H6N2O4
Molecular Weight: 158.11
Percent Composition: C 37.98%, H 3.82%, N 17.72%, O 40.48%
Literature References: Prepn from carbethoxyasparagine: Miller et al., J. Am. Chem. Soc. 75, 6086 (1953); US 2773872 (1956 to Merck & Co.).
Derivative Type: L-Form
Properties: Crystals, dec 266°. [a]D25.3 +33.23° (c = 1.992 in 1% NaHCO3).
Optical Rotation: [a]D25.3 +33.23° (c = 1.992 in 1% NaHCO3)
Derivative Type: D-Form
Properties: Crystals from water, dec 266°. [a]D25.3 -31.54° (c = 2.01 in 1% NaHCO3).
Optical Rotation: [a]D25.3 -31.54° (c = 2.01 in 1% NaHCO3)
Derivative Type: DL-Form
Properties: Crystals, dec 259°. Forms a water-sol salt.
Use: The L- and DL-dihydroorotic acids are precursors to the biological pyrimidines, such as thymine, uracil, cytosine and hydroxymethylcytosine. When employed in large amounts D-dihydroorotic acid is an antimetabolite of L-dihydroorotic acid in pyrimidine utilization. It has also been found to inhibit the orotic acid utilization of those organisms which have a requirement for it in order to grow. In general it may be said to inhibit bacterial growth. |