Orotic Acid
Title: Orotic Acid
CAS Registry Number: 65-86-1
CAS Name: 1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid
Additional Names: uracil-6-carboxylic acid; whey factor; animal galactose factor
Trademarks: Oropur; Orotyl
Molecular Formula: C5H4N2O4
Molecular Weight: 156.10
Percent Composition: C 38.47%, H 2.58%, N 17.95%, O 41.00%
Literature 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 Rhône-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).
Properties: Crystals from water, mp 345-346°.
Melting point: mp 345-346°
 
Derivative Type: Monohydrate
CAS Registry Number: 50887-69-9
Trademarks: Lactinium (Roland); Oroturic
Properties: Crystals, mp 334°. uv max: 282 nm; min: 255 nm. Sol in water ~1.7 mg/ml.
Melting point: mp 334°
Absorption maximum: uv max: 282 nm; min: 255 nm
 
Derivative Type: Methyl ester
CAS Registry Number: 6153-44-2
Molecular Formula: C6H6N2O4
Molecular Weight: 170.12
Percent Composition: C 42.36%, H 3.55%, N 16.47%, O 37.62%
Properties: Crystals, mp 249°.
Melting point: mp 249°
 
Derivative Type: Ethyl ester
CAS Registry Number: 1747-53-1
Molecular Formula: C7H8N2O4
Molecular Weight: 184.15
Percent Composition: C 45.66%, H 4.38%, N 15.21%, O 34.75%
Properties: Crystals, mp 188-189°.
Melting point: mp 188-189°
 
Derivative Type: Choline salt
CAS Registry Number: 24381-49-5
Additional Names: Choline orotate
Trademarks: Cholergol (Giulini)
Molecular Formula: C5H4N2O4.C5H14NO
Molecular Weight: 260.27
Percent Composition: 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.
Therap-Cat: Uricosuric.
Keywords: Uricosuric.

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