6876. Orotic Acid

Nomenclature

CAS number: 65-86-1
1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid; uracil-6-carboxylic acid; whey factor; animal galactose factor; Oropur; Orotyl.
C5H4N2O4; mol wt 156.10.
C 38.47%, H 2.58%, N 17.95%, O 41.00%.

Description and references

A pyrimidine precursor in animal organisms, found in milk: Bachstez, Ber. 64, 2683 (1931); Hilbert, J. Am. Chem. Soc. 54, 2082 (1932); Johnson, Schroeder, ibid. 2942. Synthesis from aspartic acid: Nye, Mitchell, ibid. 69, 1382 (1947). Prepn by condensation of urea with monoethyl ester of oxalacetic acid in methanol: Scriabine, US 2937175 (1960 to Rh^one-Poulenc). Older syntheses from urea and oxalacetic ester: Müller, J. Prakt. Chem. 56, 488 (1897); Behrend, Struve, Ann. 378, 165 (1910). Microbial process by a pyrimidine-requiring Micrococcus glutamicus mutant: Kinoshita et al., US 3086917 (1963 to Kyowa). Classed as a vitamin: Moruzzi et al., Biochem. Z. 333, 318 (1960). Relationship to vitamin B13: Manna, Hauge, J. Biol. Chem. 202, 91 (1953).

Chemical structure

Properties

Crystals from water, mp 345-346°.

Derivative

Monohydrate.

Nomenclature

CAS number: 50887-69-9
Lactinium (Roland); Oroturic.

Properties

Crystals, mp 334°. uv max: 282 nm; min: 255 nm. Sol in water ≈1.7 mg/ml.

Derivative

Methyl ester.

Nomenclature

CAS number: 6153-44-2
C6H6N2O4; mol wt 170.12.
C 42.36%, H 3.55%, N 16.47%, O 37.62%.

Properties

Crystals, mp 249°.

Derivative

Ethyl ester.

Nomenclature

CAS number: 1747-53-1
C7H8N2O4; mol wt 184.15.
C 45.66%, H 4.38%, N 15.21%, O 34.75%.

Properties

Crystals, mp 188-189°.

Derivative

Choline salt.

Nomenclature

CAS number: 24381-49-5
Choline orotate; Cholergol (Giulini).
C5H4N2O4.C5H14NO; mol wt 260.27.
C 46.15%, H 6.97%, N 16.14%, O 30.74%.

Use

Has been proposed as feed supplement in combination with methionine to aid growth of calves.

Therapeutic Category

Uricosuric.

Keywords

Uricosuric