5-hydroxymethylpyridine (pyridoxamine) and 2methyl -3 -hydroxy -4 -formyl -5 -hydroxymethylpyridine (pyridoxal) have been synthesized, and their structures have been proved. These two compounds greatly exceed pyridoxine in growth promoting power for L. casei and S. lactis i?.5•8 Direct oxidation of pyridoxine yielded, in addition to pyridoxal, the lactone of 2-methyl-3-hydroxy-4-carboxy-5-hydroxymethylpyridine.Two other closely related compounds, 2-methyl-3-hydroxy-4-hydroxymethyl-5-aminomethylpyridine and 2-methyl-3-hydroxy-4-hydroxymethyl-5-formylpyridine, have been synthesized and found to be inactive toward lactic acid bacteria.The two amines were converted by nitrous acid to pyridoxine. The two aldehydes were catalytically hydrogenated to yield pyridoxine.Rahway, New Jersey
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