Premium
Formation of fluorescent substances in reaction of aliphatic aldehydes and methylamine
Author(s) -
Kikugawa Kiyomi,
Sawamura Akiko
Publication year - 1987
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02612993
Subject(s) - methylamine , chemistry , fluorescence , sodium borohydride , photochemistry , aldol condensation , borohydride , salt (chemistry) , aldehyde , organic chemistry , catalysis , physics , quantum mechanics
Treatment of monofunctional aliphatic aldehydes (alkanals, 2‐alkenals and 2,4‐alkadienals) with methylamine at pH 7 produced fluorescence with excitation maxima at 340–360 nm and emission maxima at 410–470 nm. The reaction of 1‐butanal and methylamine gave 2‐ethyl‐2‐hexenal (ii), an aldol condensation product of 1‐butanal, and 3,5‐diethyl‐2‐propyl‐1‐methylpyridinium salt (i). The fluorescence was formed by the reaction of 1‐butanal and/or ii with methylamine in the presence of molecular oxygen. Fluorescent products I, II and III formed by the reaction were partially purified. Fluorescence characteristics of I, II and III were close to those of the fluorophores derived from the reaction of oxidized fatty acids and primary amines, with respect to maximum wavelengths in excitation and emission, and the resistance to sodium borohydride reduction.