2,6-Dihydroxypurine

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 22, p. 1200, 1974 DOI: 10.1248/cpb.22.1200

Biochem/physiol Actions

A high level of xanthine is implicated in metabolic disorders like Lesch-Nyhan syndrome. A xanthine-based biosensor may be useful for detecting xanthine in food and clinical samples. Blood and urine samples of patients with renal failure, gout and xanthinuria show high levels of xanthine.

Purification Methods

The monohydrate separates in a microcrystalline form on slow acidification with acetic acid of a solution of xanthine in dilute NaOH. It is also precipitated by addition of conc NH3 to its solution in hot 2N HCl (charcoal). After washing with H2O and EtOH, it is dehydrated by heating above 125o. Its solubility in H2O is 1 in 14,000parts at 16o and 1 in 1,500parts of boiling H2O, and separates as plates . It has no m, but the perchlorate has m 262-264o [Lister Purines Part II, Fused Pyrimidines Brown Ed, Wiley-Interscience pp252-253 1971, ISBN 0-471-38205-1]. [Beilstein 26 H 447, 26 I 131, 26 II 260, 26 III/IV 2327.]

Definition

A poisonous colorless crystalline organic compound that occurs in blood, coffee beans, potatoes, and urine. It is used as a chemical intermediate.

General Description

Xanthine is a purine that can be produced in the purine metabolic pathway via different precursors:Guanine deamination by guanine deaminaseHypoxanthine conversion by xanthine oxidoreductase