152. Adenine

Nomenclature

CAS number: 73-24-5
1H-Purin-6-amine; 6-aminopurine; 6-amino-1H-purine; 6-amino-3H-purine; 6-amino-9H-purine; 1,6-dihydro-6-iminopurine; 3,6-dihydro-6-iminopurine; Leuco-4.
C5H5N5; mol wt 135.13.
C 44.44%, H 3.73%, N 51.83%.

Description and 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) DOI. Toxicity study: Philips et al., J. Pharmacol. Exp. Ther. 104, 20 (1952) PubMed. 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.

Chemical structure

Properties

Trihydrate, orthorhombic needles. Anhydr at 110°, dec 360-365°, subl 220°. uv max (pH 7.0): 207, 260.5 nm (ε × 103 23.2, 13.4). Sparingly sol in boiling water. Slightly sol in alcohol. Very slightly sol in water. Practically insol in ether, chloroform. One gram of anhydr compd dissolves in 2000 ml water, 40 ml boiling water. Aq solns are neutral. Combines with acids and bases. LD50 orally in rats: 745 mg/kg (Philips).

Derivative

Hydrochloride hemihydrate.

Properties

Monoclinic prisms. One gram dissolves in 42 ml water.

Derivative

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.