Synthesis of fructosazone (dextrosazone)

Preparation of fructosazone

Preparation of fructosazone (dextrosazone)

Preparation of fructosazone (dextrosazone)

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 fructose dissolved in 5 ml of water is added. The the reaction mixture is gently heated in a boiling water-bath. The yellow fructosazone usually begins to crystallize out after about 15 minutes’ heating. The heating is continued with occasional stirring for 30 minutes, and obtained solutions is filtered, wash with water and then with a few milliliters of methanol. Yield of fructosazone is about 1.8 g. The purification is performed by recrystallization from large amount of methanol or ethanol yielding bright yellow crystals.

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

IUPAC Name

(5Z,6E)-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-QITQYTSXSA-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

MeSH Synonyms

glucose phenylosazone, glucosephenylosazone

Depositor-Supplied Synonyms

Dextrosazone, D-Fructosazone, D-Glucosazone, D-Mannosazone, D-Glucose phenylosazone, D-Mannose phenylosazone, D-Fructose phenylosazone, D-arabino-Hexos-2-ulose, bis(phenylhydrazone), NSC 2027, 534-97-4, D-arabino-Hexos-2-ulose, 1,2-bis(2-phenylhydrazone), AC1O4R8A, MolPort-004-960-704, EINECS 208-607-4, NSC121358, AKOS022146655, NSC 121358, NSC-121358, D-Arabino-hexosulose bis(phenylhydrazone), 13969P, (5Z,6E)-5,6-bis(phenylhydrazinylidene)hexane-1,2,3,4-tetrol

Removed Synonyms

Glucose phenylosazone, CID6399441, D-Arabino-Hexosulose, bis(phenylhydrazone)

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