Determination of the alkylpyrazine composition of coffee using stable isotope dilution-gas chromatography-mass spectrometry (SIDA-GC-MS). 2013

Stephanie Pickard, and Irina Becker, and Karl-Heinz Merz, and Elke Richling
Food Chemistry and Toxicology, Department of Chemistry, University of Kaiserslautern, Erwin-Schroedinger-Strasse 52, 67663 Kaiserslautern, Germany.

A stable isotope dilution analysis based on gas chromatography-mass spectrometry analysis (SIDA-GC-MS) was developed for the quantitative analysis of 12 alkylpyrazines found in commercially available coffee samples. These compounds contribute to coffee flavor. The accuracy of this method was tested by analyzing model mixtures of alkylpyrazines. Comparisons of alkylpyrazine-concentrations suggested that water as extraction solvent was superior to dichloromethane. The distribution patterns of alkylpyrazines in different roasted coffees were quite similar. The most abundant alkylpyrazine in each coffee sample was 2-methylpyrazine, followed by 2,6-dimethylpyrazine, 2,5-dimethylpyrazine, 2-ethylpyrazine, 2-ethyl-6-methylpyrazine, 2-ethyl-5-methylpyrazine, and 2,3,5-trimethylpyrazine, respectively. Among the alkylpyrazines tested, 2,3-dimethylpyrazine, 2-ethyl-3-methylpyrazine, 2-ethyl-3,6-dimethylpyrazine, and 2-ethyl-3,5-dimethylpyrazine revealed the lowest concentrations in roasted coffee. By the use of isotope dilution analysis, the total concentrations of alkylpyrazines in commercially available ground coffee ranged between 82.1 and 211.6 mg/kg, respectively. Decaffeinated coffee samples were found to contain lower amounts of alkylpyrazines than regular coffee samples by a factor of 0.3-0.7, which might be a result of the decaffeination procedure.

UI MeSH Term Description Entries
D011719 Pyrazines A heterocyclic aromatic organic compound with the chemical formula C4H4N2. Pyrazine
D002110 Caffeine A methylxanthine naturally occurring in some beverages and also used as a pharmacological agent. Caffeine's most notable pharmacological effect is as a central nervous system stimulant, increasing alertness and producing agitation. It also relaxes SMOOTH MUSCLE, stimulates CARDIAC MUSCLE, stimulates DIURESIS, and appears to be useful in the treatment of some types of headache. Several cellular actions of caffeine have been observed, but it is not entirely clear how each contributes to its pharmacological profile. Among the most important are inhibition of cyclic nucleotide PHOSPHODIESTERASES, antagonism of ADENOSINE RECEPTORS, and modulation of intracellular calcium handling. 1,3,7-Trimethylxanthine,Caffedrine,Coffeinum N,Coffeinum Purrum,Dexitac,Durvitan,No Doz,Percoffedrinol N,Percutaféine,Quick-Pep,Vivarin,Quick Pep,QuickPep
D003069 Coffee A beverage made from ground COFFEA beans (SEEDS) infused in hot water. It generally contains CAFFEINE and THEOPHYLLINE unless it is decaffeinated.
D005511 Food Handling Any aspect of the operations in the preparation, processing, transport, storage, packaging, wrapping, exposure for sale, service, or delivery of food. Food Processing,Handling, Food,Processing, Food
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000478 Alkylation The covalent bonding of an alkyl group to an organic compound. It can occur by a simple addition reaction or by substitution of another functional group. Alkylations
D013649 Taste The ability to detect chemicals through gustatory receptors in the mouth, including those on the TONGUE; the PALATE; the PHARYNX; and the EPIGLOTTIS. Gustation,Taste Sense,Gustations,Sense, Taste,Senses, Taste,Taste Senses,Tastes
D015416 Maillard Reaction A group of nonenzymatic reactions in which ALDEHYDES; KETONES; or reducing sugars react with the amino groups of AMINO ACIDS; PEPTIDES; PROTEINS; LIPIDS; or NUCLEIC ACIDS.The reaction with reducing sugars (glycation) results in formation of Schiff bases which undergo Amadori rearrangement and other reactions that result in the irreversible formation of ADVANCED GLYCATION END PRODUCTS (AGEs). Food browning, such as occurs when cooking with high heat (grilling, frying, roasting, etc.) is attributed to the Maillard reaction. Non-enzymatic glycation and subsequent formation of AGEs also occurs in vivo and is accelerated under hyperglycemic and inflammatory conditions, and OXIDATIVE STRESS. Browning Reaction,Food Browning,Fructation,Glucation,Glycation,Lipid Glycation,Non-Enzymatic Glycation,Non-Enzymatic Glycosylation,Nonenzymatic Protein Glycation,Protein Glycation,Ribation,Browning Reactions,Browning, Food,Glycation, Lipid,Glycation, Non-Enzymatic,Glycation, Protein,Glycosylation, Non-Enzymatic,Non Enzymatic Glycation,Non Enzymatic Glycosylation,Protein Glycation, Nonenzymatic,Reaction, Browning,Reaction, Maillard,Reactions, Browning

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