Synthesis of glucosazone (phenyl glucosazone)

Preparation of glucosazone

Preparation of glucosazone (Phenyl glucosazone)

Preparation of glucosazone (Phenyl glucosazone)

2 ml of glacial acetic acid is mixed with 5 ml of water and 2 ml of phenylhydrazine and solution is shaken until a phenylhydrazine acetate is obtained. To this solution 1 g of glucose dissolved in 5 ml of water is added. The the reaction mixture is gently heated in a boiling water-bath. The yellow glucosazone usually begins to crystallize out after about 15 minutes’ heating. The heating is continued with occasional stirring for 45 minutes, and obtained solutions is filtered, wash with water and then with a few milliliters of methanol. Yield of glucosazone is about 1.5 g. The purification is performed by recrystallization from large amount of methanol or ethanol yielding bright yellow crystals, which melt at 204° C with decomposition.

Practical organic chemistry, by F. G. Mann, 138-139, 1960

IUPAC Name

(5E,6Z)-5,6-bis(phenylhydrazinylidene)hexane-1,2,3,4-tetrol

InChI

InChI=1S/C18H22N4O4/c23-12-16(24)18(26)17(25)15(22-21-14-9-5-2-6-10-14)11-19-20-13-7-3-1-4-8-13/h1-11,16-18,20-21,23-26H,12H2/b19-11-,22-15+

InChI Key

BZVNQJMWJJOFFB-XXUSJLBQSA-N

Canonical SMILES

C1=CC=C(C=C1)NN=CC(=NNC2=CC=CC=C2)C(C(C(CO)O)O)O

Isomeric SMILES

C1=CC=C(C=C1)N/N=C\C(=N/NC2=CC=CC=C2)\C(C(C(CO)O)O)O

Depositor-Supplied Synonyms

Glucosazone, D-Allose phenylosazone, D-Altrose phenylosazone, D-Psicose phenylosazone, NSC-263486, D-ribo-Hexos-2-ulose, bis(phenylhydrazone), AC1O5MOW, BZVNQJMWJJOFFB-XXUSJLBQSA-N, 6164-71-2, NSC263486, D-ribo-Hexosulose, bis(phenylhydrazone), (5E,6Z)-5,6-bis(phenylhydrazinylidene)hexane-1,2,3,4-tetrol

Removed Synonyms

Glucose phenylosazone, CID6436933

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