N-Nitroso-hydroxyalkyl-alkylamine phosphate esters — a new class of N-nitroso compounds

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Abstract
A new class of phosphate-esterified .alpha.-hydroxyalkyl-alkylnitrosamines is described. Here we report the synthesis of these compounds. The mechanism of their formation from the corresponding .alpha.-acetoxy compounds, and starting from .alpha.-hydroperoxy compounds is studied by monitoring the reactions in the u.v.-spectrophotometer, by reaction with alkaline phosphatase and by determination of aldehydes generated during degradation of the N-nitroacetylesters. Their stability in aqueous solution and their phosphatase-induced degradation was determined. It was found that .alpha.-phosphate-nitrosamines are more stable in aqueous solution than the .alpha.-acetates or the parent .alpha.-hydroxy compounds. Therefore their role as intermediates in nitrosamine metabolism is discussed.