Adenine
Title: Adenine
CAS Registry Number: 73-24-5
CAS Name: 1H-Purin-6-amine
Additional Names: 6-aminopurine; 6-amino-1H-purine; 6-amino-3H-purine; 6-amino-9H-purine; 1,6-dihydro-6-iminopurine; 3,6-dihydro-6-iminopurine
Trademarks: Leuco-4
Molecular Formula: C5H5N5
Molecular Weight: 135.13
Percent Composition: C 44.44%, H 3.73%, N 51.83%
Literature References: Also referred to as vitamin B4: Lecoq, Int. Z. Vitaminforsch. 27, 291 (1957). Widespread throughout animal and plant tissues combined with niacinamide, D-ribose, and phosphoric acids; a constituent of nucleic acids and coenzymes, such as codehydrase I and II, adenylic acid, coalaninedehydrase. Isoln from bovine pancreas: Kossel, Ber. 18, 79, 1928 (1885). Syntheses: Fischer, ibid. 30, 2226 (1897); Traube, Ann. 331, 64 (1904); Hoffer, Jubilee Vol. Emil Barell 1946, 428-434; Taylor et al., Ciba Found. Symp. Chem. Biol. Purines 1957, 20, C.A. 53, 6238b (1959); Bredereck et al., Angew. Chem. 71, 524 (1959); Morita et al., Chem. Ind. (London) 1968, 1117; Sekiya, Suzuki, Chem. Pharm. Bull. 20, 209 (1972); N. J. Kos et al., J. Org. Chem. 44, 3140 (1979). Toxicity study: Philips et al., J. Pharmacol. Exp. Ther. 104, 20 (1952). 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.
Properties: Trihydrate, orthorhombic needles. Anhydr at 110°, dec 360-365°, subl 220°. uv max (pH 7.0): 207, 260.5 nm (e ´ 10-3 23.2, 13.4). One gram of anhydr compd dissolves in 2000 ml water, 40 ml boiling water; slightly sol in alc. Practically insol in ether, CHCl3. Aq solns are neutral. Combines with acids and bases. LD50 orally in rats: 745 mg/kg (Philips).
Absorption maximum: uv max (pH 7.0): 207, 260.5 nm (e ´ 10-3 23.2, 13.4)
Toxicity data: LD50 orally in rats: 745 mg/kg (Philips)
 
Derivative Type: Hydrochloride hemihydrate
Properties: Monoclinic prisms. One gram dissolves in 42 ml water.
 
Derivative Type: Sulfate dihydrate
Properties: Crystals. One gram dissolves in 150 ml water; slightly sol in alc.
 
Use: In microbial determination of niacin; in research on heredity, virus diseases, and cancer.

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