4869. Hypoxanthine

Nomenclature

CAS number: 68-94-0
1,7-Dihydro-6H-purin-6-one; purin-6(1H)-one; sarcine; sarkin.
C5H4N4O; mol wt 136.11.
C 44.12%, H 2.96%, N 41.16%, O 11.75%.

Description and references

Desmotropic forms: purin-6-ol; 1H-purin-6-ol; 3H-purin-6-ol; 9H-purin-6-ol; purin-6(3H)-one; 9H-purin-6(1H)-one. Formed in the animal body during the breakdown of nucleic acids; formation from adenosine continues after death. Also widely distributed in the vegetable kingdom. Numerous syntheses, e.g., from 2,6,8-trichloropurine: Fischer, Ber. 30, 2226 (1897); by oxidation of adenine: Krüger, Z. Physiol. Chem. 18, 445 (1894). By reduction of uric acid: Sundwik, ibid. 76, 486 (1912); by condensing ethyl cyanoacetate and thiourea in the presence of Na-ethoxide: Traube, Ann. 331, 64 (1904); from mercapto-4-hydroxy-6-aminopyrimidine: Taylor, Cheng. J. Org. Chem. 25, 148 (1960). Reviews: Levene, Bass, ACS Monograph Series no. 56, entitled “Nucleic Acids” (New York, 1931); Chargaff, Davidson, Nucleic Acids vols. I & II (Academic Press, New York, 1955).

Chemical structure

Properties

Small octahedra, needles from water, dec 150° without melting. Sol in 1400 parts water, 70 parts boiling water; sol in dil acids, alkalies. Combines with one equivalent of acid or with two equivalents of base. pKb (25°): 8.7. Absorption spectrum: Dhere, Compt. Rend. 141, 720.