Synthesis of alloxantin (uroxine; alloxantin dihydrate)

Preparation of alloxantin

Preparation of alloxantin (uroxine; alloxantin dihydrate)

Preparation of alloxantin (uroxine; alloxantin dihydrate)

18 ml of conc. hydrochloric acid is mixed with 18 ml of water and obtained solution is treated with 10 g of uric acid in a beaker. The mixture is heated to 35° C and 2.5 g of finely powdered potassium chlorate are added in small quantities at a time with constant shaking. When about 2 g of the potassium chlorate have been added, the uric acid will have nearly dissolved, and the liquid become faint yellow. When all the potassium chlorate has been introduced the mixture is diluted with double its volume of water, left for an hour and filtered. The filtrate is saturated with hydrogen sulfide, and after being left for twelve hours, deposits crystalline crusts often of a reddish tinge consisting of alloxantin mixed with sulfur. It is filtered and washed with cold water, and the alloxantin dissolved in a small quantity of hot water and filtered from sulfur. On cooling the filtered, colorless crystals separate yielding 7-8 g off final product.

A Class-Book of Organic Chemistry, by J. B. Cohen, 63-64, 1919

IUPAC Name

5-hydroxy-5-(5-hydroxy-2,4,6-trioxo-1,3-diazinan-5-yl)-1,3-diazinane-2,4,6-trione

InChI

InChI=1S/C8H6N4O8/c13-1-7(19,2(14)10-5(17)9-1)8(20)3(15)11-6(18)12-4(8)16/h19-20H,(H2,9,10,13,14,17)(H2,11,12,15,16,18)

InChI Key

IWDDXZKCDHOOSF-UHFFFAOYSA-N

Canonical SMILES

C1(=O)C(C(=O)NC(=O)N1)(C2(C(=O)NC(=O)NC2=O)O)O

MeSH Synonyms

alloxantin, uroxin

Depositor-Supplied Synonyms

ALLOXANTIN, Uroxine, ALLOXANTIN, DIHYDRATE, UNII-LTL3CDV62U, 76-24-4, NSC7634, 5,5′-Dihydroxy-5,5′-dibarbituric acid, 5,5′-Bibarbituric acid, 5,5′-dihydroxy-, [5,5′-Bipyrimidine]-2,2′,4,4′,6,6′(1H,1’H,3H,3’H,5H,5’H)-hexone, 5,5′-dihydroxy-, (5,5′-Bipyrimidine)-2,2′,4,4′,6,6′(1H,1’H,3H,3’H,5H,5’H)-hexone, 5,5′-dihydroxy-, 5-hydroxy-5-(5-hydroxy-2,4,6-trioxo-1,3-diazinan-5-yl)-1,3-diazinane-2,4,6-trione, LTL3CDV62U, 5, 5,5′-dihydroxy-, AC1L1MJ0, AC1Q6GF3, AC1Q77VD, SCHEMBL137702, HSDB 2081, IWDDXZKCDHOOSF-UHFFFAOYSA-N, NSC 7634, NSC-7634, EINECS 200-947-1, AR-1H6732, ZINC01683673, AKOS024319143, MCULE-2795569138, VA10223, 5,5′-Dihydroxy-5,5′-bibarbituric acid, 5,5′-Dihydroxy-5,5′-bipyrimidinehexaone, AI3-23206, A0225, 5,5′-Bibarbituric acid, 5,5′-dihydroxy- (8CI), [5,2′,4,4′,6,6′(1H,1’H,3H,3’H,5H,5’H)-hexone, 5,5′-dihydroxy-, (5,5′-Bipyrimidine)-2,2′,4,4′,6,6′(1H,1’H,3H,3’H,5H,5’H)-hexone, 5,5′-dihydroxy, [5,5′-Bipyrimidine]-2,2′,4,4′,6,6′(1H,1’H,3H,3’H,5H,5’H)-hexone,5,5′-dihydroxy-

Removed Synonyms

Uroxin, CID6435, 8027-91-6

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