Abstract
It has been shown that treatment of animal diets with ethylene oxide results in severe destruction of thiamine, niacin, pyridoxine, riboflavin, and folic acid (2, 3) and of the essential amino acids, histidine, methionine (4)) and lysine (5). Consequently, studies were undertaken to elucidate the nature of the reactions of ethylene oxide with the above nutrients. The realization that a tertiary nitrogen group was common to six of the labile nutrients prompted the investigation of the reaction of ethylene oxide with pyridine and the closely related nicotinamide and nicotinic acid. Lohmann (6), in 1939, reported that the addition of ethylene oxide to pyridine or quinolme results in the formation of highly colored methanol-water soluble products of undetermined structure. Eastham et al. (7-9) demonstrated that ethylene oxide reacts as readily with tertiary as with primary and secondary amines, and that the reaction with pyridine, in the presence of an acid, yields the Nl-(2-hydroxyethyl)pyridinium salt. The rate of reaction in excess pyridine was shown to be second order, being proportional to the concentration of acid and epoxide. The present paper offers evidence that ethylene oxide reacts with nicotinamide under very mild conditions to yield, after acidification with HCl, the chloride of Nl-(2-hydroxyethyl)nicotinamide, and with nicotinic acid to produce the betaine of N1-(2-hydroxyethyl)nicotinic acid.
Highlights
The present paper offers evidence that ethylene oxide reacts with nicotinamide under very mild conditions to yield, after acidification with HCl, the chloride of Nl-(2-hydroxyethyl)
Biological Activity of Nr-(6-hydroxyethyl)nicotinamide-The data in Table II indicate that N1-(2-hydroxyethyl)nicotinamide has no growth-promoting nor antagonistic action for L. arabinosus when added to a medium containing suboptimal amounts of nicotinic acid
This compound is unstable in alkali and possesses no nicotinic acid activity for L. arabinosus or for the chick; neither does it function as a nicotinic acid antagonist
Summary
The realization that a tertiary nitrogen group was common to six of the labile nutrients prompted the investigation of the reaction of ethylene oxide with pyridine and the closely related nicotinamide and nicotinic acid. Eastham et al [7,8,9] demonstrated that ethylene oxide reacts as readily with tertiary as with primary and secondary amines, and that the reaction with pyridine, in the presence of an acid, yields the Nl-(2-hydroxyethyl)pyridinium salt. The present paper offers evidence that ethylene oxide reacts with nicotinamide under very mild conditions to yield, after acidification with HCl, the chloride of Nl-(2-hydroxyethyl)-. Of Hg. The pressure in the desiccator was restored to ambient by admitting ethylene oxide from a tank of the compressed gas.’. As ethylene oxide dissolved in the solution, additional gas was admitted to maintain ambient pressure. The fluorometric determination of Nl-methylnicotinamide activity was carried out by the method of Huff and Perlzweig [11]
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