Mechanistic Studies of Octahydrophenazine Formation from a 2-Hydroxycyclohexanone/Ammonium Acetate Model System in Ethanol.
Synopsis Model systems composed of 2-hydroxycyclohexanone and ammonium acetate in a mole ratio of 1 to 3 were set up to study the formation of octahydrophenazine (OHP). Octahydrophenazine and an intermediate were isolated and characterized by GC/MS (El and Cl). This intermediate was the condensation product between a molecule of 2-hydroxycyclohexanone and 2-amino-cyclohexanone via the SchifT base formation mechanism. A larger amount of the intermediate than of OHP was found in the solvent system containing less than 20% ethanol, the relative proportion of the intermediate decreasing as the percentage of ethanol was increased. The formation mechanism for OHP is proposed.
a Department of Food Science and Technology , National Pingtung Polytechnic Institute , Pingtung 912 , Taiwan.
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a Department of Food Science and Technology , National Pingtung Polytechnic Institute , Pingtung 912 , Taiwan.|b Department of Food Science , Rutgers University , New Brunswick, New Jersey 08903 , U.S.A.
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a Department of Food Science and Technology , National Pingtung Polytechnic Institute , Pingtung 912 , Taiwan.|b Department of Food Science , Rutgers University , New Brunswick, New Jersey 08903 , U.S.A.
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Schiff base; octahydrophenazine; solvent effect; tricyclic pyrazine