Pyrolysis/GC/MS Analysis of N-(1-Deoxy-d-fructos-1-yl)-l-phenylalanine:  Identification of Novel Pyridine and Naphthalene Derivatives

Abstract

Pyrolysis/GC/MS has been employed to analyze phenylalanine specific products formed during Maillard reaction. Phenylalanine Amadori product and different model systems containing phenylalanine and glucose, ribose, or glycerladehyde were studied. Ribbon pyrolysis was used to study the effect of temperature (150, 200, 250 °C) on the efficiency of formation of initial pyrolysis products from phenylalanine and Amadori phenylalanine. Quartz tube pyrolysis was used at 250 °C to enhance the secondary reactions. To address specific mechanistic questions, [1-13 C]glucose was used. These studies revealed the formation of pyridine and naphthalene derivatives such as 3,5-diphenylpyridine, 1(2)-naphthaleneamine, N-methyl-1(2)-aminonaphthalene, 1-aminoanthracene, 2′-phenylpyrrolo[4,5-a]dihydronaphthalene, 1(2)-(N-phenethyl)naphthaleneamine, and 1( 2)-(N-phenethyl-N-methyl)naphthaleneamine. The precursors for pyridine and naphthalene derivatives were verified by GC/MS identification of the target compounds in the reaction mixtures of the postulated precursors.

Fatty acid composition and volatile compounds of selected marine oils and meals

“…16 Ethyl, dimethyl and trimethyl benzenes and toluene can also arise from the thermal degradation of sugars or amino cids. 4,49 The latter gives a possible explanation for their higher contents in fish meals than in fish oils, since part of them could be a result of thermal processing of fish amino acids during meal manufacture. A distinct increase in aromatic hydrocarbons on heating fish powders has been reported.…”

NO and N2O precursors (NH3 and HCN) from biomass pyrolysis: Co-pyrolysis of amino acids and cellulose, hemicellulose and lignin

“…The pyrolysis of amino acids has also been extensively studied in last two decades [12][13][14][15][16][17][18][19], which mainly concerned thermal decomposition mechanism of amino acids. Few literatures were focused on nitrogen species release during pyrolysis of amino acid.…”

Evaluation of Volatile Compounds of “Tiger Nut Beverage” (Orxata de Xufla) Headspace by Optimized Solid-Phase Micro-Extraction

“…Among them, isomers of dimethylethylbenzene and trimethylbenzenes were detected. Trimethylbenzenes, ethylbenzene and toluene could be derived from the thermal degradation of sugar or amino acid [24].…”