Trapping mechanism of ethanal with deodorant sodium p-aminobenzoate in ambient air: Quinoline ring formation to prevent its release

Article abstract of DOI:10.1515/HC.2006.12.1.11

The trapping experiment of vapor ethanal (1) with solid sodium p-aminobenzoate (2-Na) to prove the effectiveness as a deodorant prompted us to examine their aqueous reaction. After GLC monitoring to show the prerequisite formation of 2-butenal (3), the final product was elucidated as sodium 4-hydroxy-2-methyl-1,2,3,4- tetrahydro-quinoline-6-carboxylate (4-Na), indicating that trapping of 1 with 2-Na proceeded via not simple condensation to a Sniff base but heterocyclization to the quinoline ring, which is a reasonable intermediate in the Doebner-Miller reaction, and irreversible formation of this ring reflects on high deodorant activity of 2-Na.

Full text of DOI:10.1515/HC.2006.12.1.11

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