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ChemicalBook CAS DataBase List Urocanic acid
104-98-3

Urocanic acid synthesis

1synthesis methods
A method of producing trans-urocanic acid, which involves treating D-glucose with aqueous ammonia and formalin in molar ratio D-glucose: aqueous ammonia: formalin equal to 1:24:2.7, in water in the presence of basic copper carbonate at temperature 85-90°C for 3 hours to form (1S,2S,3S)-1-(1H-imidazol-4-yl)-butane-1,2,3,4-tetrazole, which is extracted in form of a hydrochloride. Through periodate splitting in water, the obtained (1S,2S,3S)-1-(1H-imidazol-4-yl)-butane-1,2,3,4-tetrazole is converted at room temperature to 1H-imidazole-4-carbaldehyde, condensation of which, in acetic anhydride in the presence of anhydrous potassium acetate at temperature 120°C for 2 hours, leads to formation of trans-urocanic acid with subsequent extraction thereof from the reaction mass.
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Yield:-

Reaction Conditions:

with histidase EC 4.3.1.3;Tris buffer in water; pH=9.0 at 37; for 24 h;

References:

Sacks, Gavin L.;Brenna, J. Thomas [Analytical Chemistry,2005,vol. 77,# 4,p. 1013 - 1019]

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