Volatiles from the Maillard Reaction of L-Ascorbic Acid and L-Alanine at Different pHs

  • Yu, Ai-Nong (Key Laboratory of Biologic Resources Protection and Utilization of Hubei Province, School of Chemistry & Environmental Engineering, Hubei University for Nationalities) ;
  • Deng, Qi-Hui (Key Laboratory of Biologic Resources Protection and Utilization of Hubei Province, School of Chemistry & Environmental Engineering, Hubei University for Nationalities)
  • Published : 2009.12.31

Abstract

The volatiles formed from the reactions of L-ascorbic acid with L-alanine at 5 different pH (5, 6, 7, 8, or 9) and $140{\pm}2^{\circ}C$ for 2 hr was performed using solid-phase microextraction-gas chromatography-mass spectrometry (SPME-GC-MS) analysis were identified to be 25 different kinds. The reaction between L-ascorbic acid and L-alanine led mainly to the formation of pyrazines. Many of these were alkylpyrazines, such as 3-ethyl-2,5-dimethylpyrazine, 2,5-dimethylpyrazine, 2-ethyl-5-methylpyrazine, 3,5-diethyl-2-methylpyrazine, methylpyrazine, 2-ethyl-6-methylpyrazine, and 2,3-diethyl-5-methylpyrazine, other compounds identified were furans, phenols, benzoquinones, 2,4,6-trimethylpyridine, and 2-methylbenzoxazole. The studies showed that furans, such as furfural and benzofuran were formed mainly at acidic pH. In contrast, higher pH values could promote the production of pyrazines.

References

  1. Kennedy JF, Rivera ZS, Warner FP, Lioyd LL, Jumel K. Analysis of carbohydrates and amino acids in aqueous solutions of L-ascorbic acid and correlation of their role in nonenzymic browning of vitamin C. J. Micronutr. Anal. 6: 1-17 (1989)
  2. Mikova K, Davidek J. Formation of alkylimidazoles in a system containing L-ascorbic acid and ammonia. Nahrung 19: 155-161 (1975) https://doi.org/10.1002/food.19750190207
  3. Yu AN, Zhang AD. The effect of pH on the formation of aroma compounds produced by heating a model system containing Lascorbic acid with L-threonine/ L-serine. Food Chem. 119: 214-219 (2010) https://doi.org/10.1016/j.foodchem.2009.06.026
  4. Ellis GP. The Maillard reaction. pp. 63-134. In: Advances in Carbohydrate Chemistry. Wolfrom ML (ed). Academic Press, New York, NY, USA (1959)
  5. Solina M, Baumgartner P, Johnson RL, Whitfield FB. Volatile aroma components of soy protein isolate and acid-hydrolysed vegetable protein. Food Chem. 90: 861-873 (2005) https://doi.org/10.1016/j.foodchem.2004.06.005
  6. Amrani-Hemaimi M, Cerny C, Fay LB. Mechanisms of formation of alkylpyrazines in the maillard reaction. J. Agr. Food Chem. 43: 2818-2822 (1995) https://doi.org/10.1021/jf00059a009
  7. Rogacheva S, Verhe R, Obretenov C. Aroma compounds formation in the interaction of L-ascorbic acid with $\alpha$-amino acids. pp. 250-253. In: Flavour Science: Recent Developments. Taylor A, Mottram D (eds). The Royal Society of Chemistry, Cambridge, UK (1996)
  8. Yin DZ, Brunk UT. Oxidized ascorbic acid and reaction products between ascorbic and amino acids might constitute part of age pigments. Mech. Ageing Dev. 61: 99-112 (1991) https://doi.org/10.1016/0047-6374(91)90009-O
  9. Moon SY, Cliv MA, Li-Chan ECY. Odour-active components of simulated beef Xavour analysed by solid phase microextraction and gas chromatography–ass spectrometry and olfactometry. Food Res. Int. 39: 294-308 (2006) https://doi.org/10.1016/j.foodres.2005.08.002
  10. Obretenov C, Demyttenaere J, Abbaspour Tehrani K, Adams A, Kersiene M, De Kimpe N. Flavor release in the presence of melanoidins prepared from L-(+)-ascorbic acid and amino acids. J. Agr. Food Chem. 50: 4244-4250 (2002) https://doi.org/10.1021/jf0200366
  11. Yano M, Hayashi T, Namiki M. Formation of free radical products by the reaction of dehydroascorbic acid with amino acids. J. Agr. Food Chem. 24: 815-821 (1976) https://doi.org/10.1021/jf60206a046
  12. Shibamoto T, Akiyama T, Sakaguchi M, Enomoto Y, Masuda H. A study of pyrazine formation. J. Agr. Food Chem. 27: 1027-1031 (1979) https://doi.org/10.1021/jf60225a051
  13. Ho CW, Wan Aida WM, Maskat MY, Osman H. Changes in volatile compounds of palm sap (Arenga pinnata) during the heating process for production of palm sugar. Food Chem. 102: 1156-1162 (2007) https://doi.org/10.1016/j.foodchem.2006.07.004
  14. Seck S, Crouzet J. Formation of volatile compounds in sugarphenylalanine and ascorbic acid-phenylalanine model systems during heat treatment. J. Food Sci. 46: 790-793 (1981) https://doi.org/10.1111/j.1365-2621.1981.tb15349.x
  15. Rogacheva S, Kuncheva M, Panchev I, Obretenov C. L-Ascorbic acid in nonenzymatic reactions. Reaction with glycine. Z. Lebensm. Unters. Fors. 200: 52-58 (1995) https://doi.org/10.1007/BF01192908
  16. Koehler PE, Odell GV. Factors affecting the formation of pyrazine compounds in sugar-amine reactions. J. Agr. Food Chem. 18: 895-898 (1970) https://doi.org/10.1021/jf60171a041
  17. Davidek J, Velisek J, Zelinkova Z, Kubelka V. Pyrazine in the reaction of L-dehydroascorbic acid with ammonia and glycine. J. Food Sci. 42: 277-278 (1977) https://doi.org/10.1111/j.1365-2621.1977.tb01272.x
  18. Wang PS, Odell GV. Formation of pyrazines from thermal treatment of some amino-hydroxy compounds. J. Agr. Food Chem. 21: 868-870 (1973) https://doi.org/10.1021/jf60189a032
  19. Davies CGA, Wedzicha BL. Ascorbic acid browning: The incorporation of C1 from ascorbic acid into melanoidins. Food Chem. 49: 165-167 (1994) https://doi.org/10.1016/0308-8146(94)90153-8
  20. Rogacheva S, Kuntcheva M, Panchev I, Obretenov C. Melanoidin formation in L-ascorbic acid-amino acids interaction. A comparative study. Nahrung 43: 105-108 (1999) https://doi.org/10.1002/(SICI)1521-3803(19990301)43:2<105::AID-FOOD105>3.0.CO;2-#
  21. Shephard AB, Nichols SC, Braithwaite A. Moisture induced solid phase degradation of L-ascorbic acid. Part 3. Structural characterisation of the degradation products. Talanta 48: 607-622 (1999) https://doi.org/10.1016/S0039-9140(98)00278-1
  22. Maga JA. Pyrazine update. Food Rev. Int. 8: 479-558 (1992) https://doi.org/10.1080/87559129209540951
  23. 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. Z. Lebensm. Unters. Fors. 192: 323-327 (1991) https://doi.org/10.1007/BF01202762
  24. Adams A, De Kimpe N. Formation of pyrazines from ascorbic acid and amino acids under dry-roasting conditions. Food Chem. 115: 1417-1423 (2009) https://doi.org/10.1016/j.foodchem.2009.01.071
  25. Hartmann GJ, Scheide JD, Ho CT. Effect of water activity on the major volatiles produced in a model system approximating cooked meat. J. Food Sci. 49: 607-613 (1984) https://doi.org/10.1111/j.1365-2621.1984.tb12480.x
  26. Jousse F, Jongen T, Agterof W, Russell S, Braat P. Simplified kinetic scheme of flavor formation by the Maillard reaction. J. Food Sci. 67: 2534-2542 (2002) https://doi.org/10.1111/j.1365-2621.2002.tb08772.x
  27. Beal AD, Mottram DS. Compounds contributing to the characteristic aroma of malted barley. J. Agr. Food Chem. 42: 2880-2884 (1994) https://doi.org/10.1021/jf00048a043
  28. Fan X, Reneker LW, Obrenovich ME, Strauch C, Cheng R, Jarvis SM. Vitamin C mediates chemical aging of lens crystallins by the Maillard reaction in a humanized mouse model. P. Natl. Acad. Sci. USA 103: 16912-16917 (2006) https://doi.org/10.1073/pnas.0605101103
  29. Vernin G, Chakib S, Rogacheva S, Obretenov T, Parkanyi C. Thermal decomposition of ascorbic acid. Carbohyd. Res. 305: 1-15 (1998) https://doi.org/10.1016/S0008-6215(97)00234-6