Nonvolatile Compounds Formed on the Thermal Degradation of Phenylalanine

Papadopoulou, Kiriaki; Ames, Jennifer M.

doi:10.1021/jf00041a011

Cited by 5 publications

(3 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The corresponding benzaldehyde adduct [N-(phenylmethylene)phenethylamine] was detected in the heated (10 min) methanolic solution of ARPP in 10% water (Table 2). If the above enamine reacts with another mole of phenylacetaldehyde as an N-nucleophile, it eventually leads to the formation of N-(2-phenethyl)-2,4-diphenylpyrrole (Papadopoulou and Ames, 1994). However, enamines can act as C-nucleophiles and undergo condensation reactions with other carbonyls such as phenylacetaldehyde or acetaldehyde to produce 1 (Figure 2).…”

Section: Resultsmentioning

confidence: 99%

“…Kato et al (1971) identified, in the volatiles generated from heating of phenylalanine at 300 °C, several alkylsubstituted benzene derivatives, aromatic amines, bibenzyl, stilbene, acetaldehyde, and aromatic aldehydes. Papadopoulou and Ames (1994) extracted and identified two nonvolatile products, N-(2-phenethyl)-3,4-diphenylpyrrole and N-(2-phenethyl)-3,4-diphenyl-3-pyrroline-2,5-dione, from phenylalanine heated at 210 °C in paraffin oil. According to Baltes and Mevissen (1988), under roasting conditions phenylalanine with a 6-fold excess of glucose produces 155 volatile components including furans, pyrones, pyrazines, pyrroles, aromatic compounds, and, in addition to parent pyridine, 4-me-thylpyridine and 3-phenylpyridine.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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

Keyhani

Yaylayan

1996

J. Agric. Food Chem.

View full text Add to dashboard Cite

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.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Keyhani

Yaylayan

1996

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…In recent years, phenylalanine alone (Papadopoulou and Ames, 1994) and sugar/phenylalanine systems (Kunert-Kirchhoff and Baltes, 1990;Keyhani and Yay-layan, 1996;Yaylayan and Matni, 1997) have been studied. Well-known sugar degradation products and nitrogen-containing compounds, some of them specific reaction products of phenylalanine, have been identified.…”

Section: Introductionmentioning

confidence: 99%

Effect of Hexanal and Iron on Color Development in a Glucose/Phenylalanine Model System

Fallico

Ames

1999

J. Agric. Food Chem.

Self Cite

View full text Add to dashboard Cite

Aqueous glucose/phenylalanine (0.1 M with respect to each reactant) systems were heated in an autoclave for 30 min at 140 degrees C, in the presence of hexanal (0.04, 0.1, and 0.2 M) or FeCl(2) (0.01 M). Results show that hexanal significantly inhibited color development at pH 5 and 6 and led to an increase of 5-(hydroxymethyl)furfural. Iron addition had similar effects at pH 5, but only small effects at pH 6. The reaction routes proposed give key roles to the alpha-dicarbonyl compounds, to the Strecker aldehyde, and to the Schiff base formed by the reaction between hexanal and phenylalanine.

show abstract

Proposal of a mechanism for the inhibition of all-trans-β-carotene autoxidation at elevated temperature by N-(2-phenylethyl)-3,4-diphenylpyrrole

Papadopoulou

Ames

1995

Food Chemistry

View full text Add to dashboard Cite

Nonvolatile Compounds Formed on the Thermal Degradation of Phenylalanine

Cited by 5 publications

References 3 publications

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

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

Effect of Hexanal and Iron on Color Development in a Glucose/Phenylalanine Model System

Proposal of a mechanism for the inhibition of all-trans-β-carotene autoxidation at elevated temperature by N-(2-phenylethyl)-3,4-diphenylpyrrole

Contact Info

Product

Resources

About