Title: Cytosine
CAS Registry Number: 71-30-7
CAS Name: 4-Amino-2(1
H)-pyrimidinone
Synonyms: 4-amino-2-oxo-1,2-dihydropyrimidine; 4-amino-2-pyrimidinol; 4-amino-2-hydroxypyrimidine
Molecular Formula: C4H5N3O
Molecular Weight: 111.10
Percent Composition: C 43.24%, H 4.54%, N 37.82%, O 14.40%
Literature References: Widely distributed in nature; constituent of nucleic acids. Isoln by hydrolysis of thymus nucleic acids: Levene, Bass,
Nucleic Acids (New York, 1931) p 57. Syntheses: Hilbert, Johnson,
J. Am. Chem. Soc. 52, 1152 (1930); Hilbert
et al., ibid. 57, 552 (1935);
cf. Hunter, Hlynka,
Biochem. J. 31, 486 (1937); Ballweg,
Tetrahedron Lett. 1968, 2171; David, Lubineau,
Bull. Soc. Chim. Fr. 1969, 816. Synthesis from carbon dioxide and ammonia on kaolinite: G. R. Harvey
et al., Naturwissenschaften 58, 624 (1971). Exists in keto form. Structure: Barker, Marsh,
Acta Crystallogr. 17, 1581 (1964); of monohydrate: Jeffrey, Kinoshita,
ibid. 16, 20 (1963); R. J. McClure, B. M. Craven,
ibid. B29, 1234 (1973). Tautomerism: Y. P. Wong,
J. Am. Chem. Soc. 95, 3511 (1973).
Review: Ts'o, "Bases, Nucleosides and Nucleotides" in
Basic Principles in Nucleic Acid Chemistry vol. 1, P. O. P. Ts'o, Ed. (Academic Press, New York, 1974) pp 453-584.
Derivative Type: Monohydrate
Properties: Lustrous monoclinic or triclinic platelets from water. Anhydr at 100°; brown around 300°; dec 320-325°. uv max (pH 8.8): 196.5, 267 nm (e ′ 10-3 22.5, 6.1). pK1 4.60; pK2 12.16. One gram dissolves in 130 ml water. Slightly sol in alcohol, insol in ether. Gives red color when dissolved in soln of sodium hypochlorite to which a drop of NH4OH is added. Forms salts with acids.
pKa: pK1 4.60; pK2 12.16
Absorption maximum: uv max (pH 8.8): 196.5, 267 nm (e ′ 10-3 22.5, 6.1)
