Effects of Reaction Temperature and Time on Generation of Volatile Compounds from Maillard Reaction of Ascorbic Acid and Lysine

Abstract

Abstract: The identification of volatile compounds generated from the Maillard reaction of ascorbic acid and lysine at different reaction temperatures and reaction durations was performed using headspace solid-phase microextraction-gas chromatography-mass spectrometry (HS-SPME-GC-MS). Twenty-eight volatile compounds were identified, including pyrazines, aldehydes, furans, alcohols, benzenamines and quinolines. Sixteen pyrazines were the primary aromatic compounds. The effects of reaction temperature and time on the generation of volatile compounds, especially pyrazines, were investigated. The results showed that increased total amount of pyrazines was observed with increasing reaction temperature and time. Meanwhile, the generation of 2,5-dimethylpyrazine, 2-ethyl-3-methylpyrazine, 2-ethyl-5-methylpyrazine, 3-ethyl-2,5-dimethylpyrazine and 2-methylpyrazine revealed a significant increase during the reaction between ascorbic acid and lysine with increasing reaction temperature, and an obvious high yield of 2,5-dimethylpyrazine was achieved due to increasing reaction time.

Key words: Maillard reaction, ascorbic acid-lysine, reaction temperature, reaction time, pyrazines

CLC Number:

TS201.7

References

[1]Míková K, Davidek J.Formation of alkylimidazoles in a system containing L-ascorbic acid and ammonia[J].Nahrung,1975,19:155-161
[2]Davidek J, Velisek J, Zelinkova Z, Kubelka V.Pyrazine in the reaction of L-dehydroascorbic acid with ammonia and glycine[J].J. Food Sci,1977,42:277-278
[3]Seck S, Crouzet J.Formation of volatile compounds in sugar-phenylalanine and ascorbic acid-phenyllanine model systems during heat treatment[J].J. Food Sci,1981,46:790-793
[4]Hartmann G J, Scheide J D, & Ho C T.Effect of water activity on the major volatiles produced in a model system approximating cooked meat[J].J. Food Sci.,1984,49:607-613
[5]Kennedy J F, Rivera Z S, Warner F P., Lloyd LL., & Jumel K.. .Analysis of carbohydrates and amino acids in aqueous solutions of L-ascirbic acid and correlation of their role in nonenzymic browning of vitamin C[J]..J. Micronutr. Anal,1989,6:1-17
[6]Loscher J, Kroh L, Westphal G., & Vogel J. .L-ascorbic acid – A carbonyl component of nonenzymic browning reactions. Part 2. Amino-carbonyl reactions of L-ascorbic acid[J].,1991,192:323-327
[7]Yin D Z., & Brunk UT... Oxidized ascorbic acid and reaction products between ascorbic and amino acids might constitute part of age pigments[J].,1991,61:99-112
[8]Davies C G. A, & Wedzicha B. L.. Ascorbic acid browning: The incorporation of C1 from ascorbic acid into melanoidins[J].,1994,49:165-167
[9]Rogacheva S, Kuncheva M, Panchev I., & Obretenov C... L-Ascorbic acid in nonenzymatic reactions. Reaction with glycine[J].,1995,200:52-58
[10]Rogacheva S ，Verhe R, Obretenov C. .Aroma compounds formation in the interaction of L-ascorbic acid with α-amino acids[M]. [J].In Flavour Science: Recent Developments; Taylor A, Mottram D, Eds.; The Royal Society of Chemistry: Cambridge, UK,1996,:-
[11]Rogacheva, S, Kuncheva, M,Panchev, I., & Obretenov, C. .Melanoidin formation in L-ascorbic acid-amino acids interaction. A comparotive study[J].,1999,43:105-108
[12]Obretenov, C, Demyttenaere, J, Abbaspour Tehrani, K., Adams, A., Kersiene, M., & DeKimpe, N.. .Flavor release in the presence of melanoidins prepared from L-(+)-ascorbic acid and amino acids[J].,2002,50:4244-4250
[13]Fan, X, Reneker, L, W., Obrenovich, M. E., Cheng, R., & Jarvis, S. M. .Vitamin C mediates chemical aging of lens crystallins by the Maillard reaction in a humanized mouse model[J].,2006,103:16912-16917
[14]Adams A, & De Kimpe N .Formation of pyrazines from ascorbic acid and amino acids under dry-roasting conditions[J].,2009,115:1417-1423
[15]Yu A N., & Deng Q H. .Volatiles from the Maillard reaction of L-ascorbic acid and L-alanine at different pHs[J].. Food Sci. Biotechnol,2009,18:1495-1499
[16]Yu A N., & Zhang A D. .The effect of pH on the formation of aroma compounds produced by heating amodel system containing L-ascorbic acid with L-threonine/L-serine[J].,2010,119:214-219
[17]Yu A N., & Zhang A D.. Aroma compounds generated from thermal reaction of L-ascorbic acid with L-cysteine[J].,2010,121:1060-1065
[18]Jousse, F, Jongen, T, Agterof, W., Russell, S., & Braat, P.. Simplified kinetic scheme of flavor formation by the Maillard reaction[J].,2002,67:2534-2542
[19] Ellis, G P. . The Maillard reaction. In M. L. Wolfrom(Ed.), Advances in carbohydrate chemistry[M] .[J].New York: Academic Press.,1959,,: 63-134
[20]L. Methven, M.Tsoukka, M. J. Oruna-Concha, J. K. Parker, D. S. Mottram. .Influence of sulfur amino acids on the volatile and nonvolatile components of cooked salmon (Salmo salar) [J]. [J].J. Agric. Food Chem,2007,55:1427-1436
[21]A.L. De Oliveira, MN. Eberlin, F. A . Cabral. Prediction of the Solubility of Aromatic Compounds from Brazilian Roasted Coffee (2-Methylpyrazine; 2-Furfurylalcohol; 2,5-Dimethylpyrazine; γ-Butyrolactone and 2-Furfurylacetate) in SC-CO2[J].. J. Chem. Eng. Jpn,2009,42:219-230
[22]G.A. Channell, HYahya, D. J. Cook. Thermal Volatile Generation in Barley Malt: On-line MS Studies[J].. J. Am. Soc. Brew. Chem.,2010,68:175-182
[23]Amrani-Hemaimi, M., Cerny, C, & Fay, L. B.. Mechanisms of formation of alkylpyrazines in the Maillard reaction[J].. J. Agric. Food Chem,1995,43:2818-2822
[24]Vemin G, Chakib S, Rogacheva S, Obretenov T, & Párkányi C.Themal decomposition of ascorbic acid[J].Carbohyd. Res,1998,305:1-15
[25]Abraham F.J., & MdAbul H. S.. Formation of pyrazines in hydroxyacetaldehyde and glycine nonenzymatic browning Maillard reaction: A computational study[J].. Food Chem,2007,103:1208-
[26]Shibamoto T, Akiyama T, Sakaguchi M, Enomoto Y, & Masuda H.. A study of pyrazine formation[J].J. Agric. Food Chem,1979,27:1027-1031
[27]Md.Abul HS.. Formation of pyrazines in dihydroxyacetone and glycine Maillard reaction: A computational study[J].. Food Chem,2006,98:403-415