Identifizierung und Quantifizierung von Reaktionsprodukten aus Chinasäure Säure, Chinasäurelacton und Chlorogensäure mit Strecker Aldehyde in geröstetem Kaffee

2021 ◽  
Vol 75 (S1) ◽  
Author(s):  
Michael Gigl ◽  
Oliver Frank ◽  
Johanna Barz ◽  
Anna Gabler ◽  
Christian Hegmanns ◽  
...  
Keyword(s):  
Strecker Aldehyde

scholarly journals Acrylamide Formation in Food: A Mechanistic Perspective

2005 ◽  
Vol 88 (1) ◽  
pp. 262-267 ◽  
Author(s):  
Varoujan A Yaylayan ◽  
Richard H Stadler
Keyword(s):  
Amino Acid ◽  
Carbonyl Compounds ◽  
Azomethine Ylide ◽  
Significant Progress ◽  
Acid Moiety ◽  
Sugar Moiety ◽  
Acrylamide Formation ◽  
Amino Acid Moiety ◽  
Strecker Aldehyde

Abstract Earliest reports on the origin of acrylamide in food have confirmed asparagine as the main amino acid responsible for its formation. Available evidence suggests that sugars and other carbonyl compounds play a specific role in the decarboxylation process of asparagine, a necessary step in the generation of acrylamide. It has been proposed that Schiff base intermediate formed between asparagine and the sugar provides a low energy alternative to the decarboxylation from the intact Amadori product through generation and decomposition of oxazolidin-5-one intermediate, leading to the formation of a relatively stable azomethine ylide. Literature data indicate the propensity of such protonated ylides to undergo irreversible 1,2-prototropic shift and produce, in this case, decarboxylated Schiff bases which can easily rearrange into E Decarboxylated Amadori products can either undergo the well known β-elimination process initiated by the sugar moiety to produce 3-aminopropanamide and 1-deoxyglucosone or undergo 1,2-elimination initiated by the amino acid moiety to directly generate acrylamide. On the other hand, the Schiff intermediate can either hydrolyze and release 3-aminopropanamide or similarly undergo amino acid initiated 1,2-elimination to directly form acrylamide. Other thermolytic pathways to acrylamide—considered marginal at this stage—via the Strecker aldehyde, acrolein, and acrylic acid, are also addressed. Despite significant progress in the understanding of the mechanistic aspects of acrylamide formation, concrete evidence for the role of the different proposed intermediates in foods is still lacking.

Strecker Aldehyde Formation in Wine: New Insights into the Role of Gallic Acid, Glucose, and Metals in Phenylacetaldehyde Formation

2017 ◽  
Vol 66 (10) ◽  
pp. 2459-2466 ◽  
Author(s):  
Ana Rita Monforte ◽  
Sara I. F. S. Martins ◽  
Antonio C. Silva Ferreira
Keyword(s):  
Gallic Acid ◽  
Strecker Aldehyde

Evidence of Strecker Aldehyde Excretion by Yeast in Cold Contact Fermentations

2000 ◽  
Vol 48 (6) ◽  
pp. 2384-2386 ◽  
Author(s):  
Philippe Perpète ◽  
Sonia Collin
Keyword(s):  
Strecker Aldehyde

scholarly journals Novel Strecker degradation products of tyrosine and dihydroxyphenylalanine

2013 ◽  
Vol 19 (No. 1) ◽  
pp. 13-18 ◽  
Author(s):  
J. Adamiec ◽  
K. Cejpek ◽  
J. Rössner ◽  
J. Velíšek
Keyword(s):  
Free Radicals ◽  
Benzoic Acid ◽  
Caffeic Acid ◽  
Heterocyclic Compounds ◽  
Degradation Products ◽  
Oxidation Products ◽  
Reaction Products ◽  
Homolytic Cleavage ◽  
Strecker Aldehydes ◽  
Strecker Aldehyde

Tyrosine was oxidised with either potassium peroxodisulphate or glyoxal. Volatile reaction products were isolated and analysed by GC/FID and GC/MS, derivatised with diazomethane and analysed by the same methods. Eight reaction products were identified. The major products were the expected Strecker aldehyde (4-hydroxyphenylacetaldehyde) and its lower homologue 4-hydroxybenzaldehyde. They were followed by 1-(4-hydroxyphenyl)-3-propionaldehyde, phenylacetaldehyde, benzaldehyde, phenol, 4-hydroxybenzoic, and benzoic acid. Analogously, the oxidation of 3,4-dihydroxyphenylalanine yielded the corresponding Strecker aldehyde (3,4-dihydroxyphenylacetaldehyde), its lower homologue 3,4-dihydroxybenzaldehyde, 3,4-dihydroxybenzoic, 3,4-dihydroxyphenylacetic, and caffeic acid. An identification of these oxidation products of tyrosine and 3,4-dihydroxyphenylalanine assumes homolytic cleavage of the Strecker aldehydes and a recombination of free radicals formed by this cleavage. As minor products, six O- and N-heterocyclic compounds arose in systems containing glyoxal (pyrazine, methyl- and ethylpyrazine, 3-furancarbaldehyde, 5-methyl-2-furancarbaldehyde, 2-pyrrolcarbaldehyde).

scholarly journals The Roles of Amino Acids and Sugars in the Production of Volatile Materials in Microwave Heated Tobacco Dust Suspensions

1997 ◽  
Vol 17 (3) ◽  
pp. 75-95 ◽  
Author(s):  
WM Coleman ◽  
TA Perfetti
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Volatile Compounds ◽  
Reaction Pathways ◽  
Low Molecular Weight ◽  
Heat Treated ◽  
Strecker Aldehyde ◽  
Major Reaction ◽  
First Time ◽  
Volatile Materials

AbstractFor the first time, the role(s) of selected amino acids and sugars in the production of volatile compounds in microwave prepared heat treated tobacco suspensions (HTTS) has been unambiguously defined. The role can be expressed in two major reaction pathways:1) Strecker degradation of amino acids and 2) amino acid/sugar Maillard-type reactions. The mechanism of the Strecker degradation was confirmed by the addition of selected13C- labelled amino acids to the reaction suspension. The addition of the amino acid resulted in a dramatic increase in the concentration of the specific, appropriate, low molecular weight Strecker aldehyde in the headspace above the reaction suspension. The mechanism of the amino acid/sugar Maillard-type reactions was substantiated by: 1) adding a wide array of amino acids to the suspension;2) by employing15N-labelled amino acids; and3) employing13C-labelled sugars. Addition of amino acids to the suspension followed by heat treatment resulted in significant increases (2 ×) in the concentration of volatile pyrazines relative to the control. Most amino acids significantly increased the concentration of headspace pyrazines. Reactivity differences, as a function of sugars, was also demonstrated. Analysis of the headspace above suspensions incorporating15N-labelled amino acids and13C-labelled sugars revealed the15N and13C atoms to have been distributed throughout a wide array of volatile pyrazines. The distribution of the15N atoms within the pyrazines was unique to the amino acid and the distribution of the 13C atoms was linked to the type of sugar employed. These results have documented for the first time in a heat treated tobacco formulation the mechanisms of amino acids and sugars in the production of volatile compounds which have documented intense sensory characteristics.

Sign in / Sign up

Export Citation Format

Share Document