Factors affecting thermally induced furan formation

Furan, a potential carcinogen, can be induced by heat from sugars, ascorbic acid, and fatty acids. The objective of this research was to investigate the effect of pH, phosphate, temperature, and heating time on furan formation. Heat-induced furan formation from free sugars, ascorbic acid, and linoleic acid was profoundly affected by pH and the presence of phosphate. In general, the presence of phosphate increased furan formation in solutions of sugars and ascorbic acid. In a linoleic acid emulsion, phosphate increased the formation of furan at pH 6 but not at pH 3. When an ascorbic acid solution was heated, higher amounts of furan were produced at pH 3 than at pH 6 regardless of phosphate's presence. However, in linoleic acid emulsion, more furan was produced at pH 6 than at pH 3. The highest amount of furan was formed from the linoleic acid emulsion at pH 6. In fresh apple cider, a product with free sugars as the major components (besides water) and little fatty acids, ascorbic acid, or phosphate, small or very low amounts of furan was formed by heating at 90-120 degrees C for up to 10 min. The results indicated that free sugars may not lead to significant amounts of furan formation under conditions for pasteurization and sterilization. Importantly, this is the first report demonstrating that phosphate (in addition to pH) plays a significant role in thermally induced furan formation.     

Formation of odorants in Maillard model systems based on l-proline as affected by pH

Formation of the odorants acetic acid, 4-hydroxy-2,5-dimethyl-3-(2H)-furanone (HDMF), 6-acetyl-1,2,3,4-tetrahydropyridine (ATHP), and 2-acetyl-1-pyrroline (AP) was monitored by isotope dilution assays at pH 6, 7, and 8 in Maillard model reactions containing glucose and proline (Glc/Pro) or the corresponding Amadori compound fructosyl-proline (Fru-Pro). In general, higher yields were obtained at pH 7 and 8. Acetic acid was the major odorant with up to 40 mg/mmol precursor followed by HDMF (up to 0.25 mg/mmol), the formation of which was favored in the Fru-Pro reaction systems. On the contrary, ATHP (up to 50 microg/mmol) and AP (up to 5 microg/mmol) were more abundant in Glc/Pro. However, the sensory relevance of the two N-heterocycles was more pronounced on the basis of odor activity values, confirming their contribution to the overall roasty note of the reaction samples. It was also found that formation and decomposition of Fru-Pro were faster at pH 7 as compared to pH 6, explaining in part the preferred formation of the four odorants studied under neutral and slightly alkaline conditions. After 4 h of reaction at pH 7 in the presence of proline, about one-fourth of the glucose was consumed leading to acetic acid with a transformation yield of almost 40 mol %.     

3-deoxypentosulose: an alpha-dicarbonyl compound predominating in nonenzymatic browning of oligosaccharides in aqueous solution

The thermal degradation of D-glucose, maltose, and maltotriose in aqueous solution was investigated under caramelization (no glycine) and Maillard (with glycine) conditions. Degradation of the sugar and alpha-dicarbonyls product was monitored. Under both caramelization and Maillard reaction conditions, 3-deoxypentosulose was the predominating alpha-dicarbonyl compound formed from maltose and maltotriose. In the absence of an amino compound, however, 3-deoxypentosulose is formed in much lower concentration. It was concluded that 3-deoxypentosulose is formed by a pathway specific for oligo- and polysaccharides since this alpha-dicarbonyl is formed from the alpha-1-->4 glucans such as maltose and maltotriose but not from glucose. For its formation, a retro Claisen reaction of an enolization product of 1-amino-1,4-dideoxyhexosulose is proposed as the route to its formation. 1-Amino-1,4-dideoxyhexosulose could be formed by vinylogous alpha-elimination from the 2,3-enediol structure after Amadori rearrangement, favored by planar alignment of the bonds between C1 and C4. Subsequent rearrangement by keto-enoltautomerization leads to a 1-imino-3-keto structure. In this structure, attack of a hydroxyl anion, provided by water at neutral pH, could cause a splitting off of the C1. This reaction gives rise to formic acid or formamide and a pentose derivative, which reacts further to give 3-deoxypentosulose.     

High-pressure effects on Maillard reaction between glucose and lysine

Glucose-lysine model systems prepared over a range of pH values (5-10) in unbuffered and buffered media were incubated at 60 degrees C either under atmospheric pressure or at 400 MPa. The results obtained showed that high pressure affected in different ways the different stages of the Maillard reaction and that such effects were strongly influenced by pressure-induced changes in the pH of the systems. In unbuffered media, at an initial pH < or =8.0, the formation of Amadori rearrangement products (ARP) was not considerably affected by pressure, whereas the intermediate and advanced stages of the Maillard reaction were suppressed, suggesting a retardation of the degradation of the ARP. In buffered media, at pH values < or =8.0, pressure slowed the Maillard reaction from the initial stages. These effects are attributed to the pH drop caused by the pressure-induced dissociation of the acid groups. In unbuffered and buffered media at initial pH = 10.2, high pressure accelerated the formation and subsequent degradation of ARP, leading to increased levels of intermediate and advanced reaction products.     

Role of phosphate and carboxylate ions in maillard browning

The Maillard reaction of carbohydrates and amino acids is the underlying chemical basis for flavor and color formation in many processed foods. Phosphate and other polyatomic anions will accelerate the rate of Maillard browning, and this effect has been explained by invoking enhanced proton abstraction from intermediate Amadori compounds. In this work, the effect of phosphate and carboxylate ions on browning was measured for a series of reducing sugars with and without the presence of beta-alanine. Significant browning was observed for sugars alone suggesting that polyatomic anions contribute to Maillard browning by providing reactive intermediates directly from sugars. A mechanism is proposed for decomposition of sugars by polyatomic anions and efforts to trap reactive species using o-phenylenediamine (OPD) are described. The results of this study suggest how complications may arise from the popular usage of phosphate buffers in the study of Maillard reaction kinetics. In addition, the results imply how phosphates may be useful for enhancing browning during food processing.     

Electrochemical study of the Maillard reaction

Electrochemical properties of beta-alanine/carbohydrate Maillard reaction products were measured using a combination platinum/Ag-AgCl (Cl(-)) redox electrode. Changes toward more negative voltages were observed, which were consistent with reductone formation during the course of the Maillard reaction. Using voltage change as a guide, the propensity for reductone formation among various sugars was ribose > xylose approximately arabinose > glucose approximately rhamnose approximately mannose approximately lactose > fructose. Similar electrochemical behavior indicative of reductone formation was observed in the decomposition products of a model Amadori compound, N-(1-deoxyfructos-1-yl)piperidine (1).     

Formation of furan from carbohydrates and ascorbic acid following exposure to ionizing radiation and thermal processing

This study was conducted to investigate the formation of furan from sugars, ascorbic acid, and organic acids as affected by ionizing radiation and thermal treatments. Results showed that both thermal treatments and irradiation induced formation of furan from ascorbic acid, fructose, sucrose, or glucose. Little furan was produced from malic acid or citric acid. The pH and concentration of sugars and ascorbic acid solutions had profound influences on furan formation due to either irradiation or thermal treatment. The rate of irradiation-induced furan formation increased with decreasing pH from 8 to 3. Approximately 1600 times less furan was formed at pH 8 as apposed to pH 3. At the same pHs, the amounts of furan formed from irradiation of ascorbic acid, fructose, and sucrose were always higher than from glucose. As pH decreased from 7 to 3, an increase in thermally induced furan was observed for sucrose and ascorbic acid solutions, but for glucose solution, less furan was formed at pH 3 than at pH 7. The levels of sugars commonly found in fruits and fruit juices, upon irradiation, would be high enough to potentially produce low parts per billion (ppb) levels of furan. The concentration of ascorbic acid at which a maximum of furan was produced upon irradiation was about 0.5 mg/mL, a level commonly found in some foods. Five furan derivatives were tentatively identified in thermally treated ascorbic acid solution, while one furan derivative was tentatively found in both irradiated and thermally treated samples.     

Formation of 2,5-dimethyl-4-hydroxy-3(2H)-furanone through methylglyoxal: a Maillard reaction intermediate

The caramel-like aroma compound, 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) was quantified and verified by HPLC and GC-MS in the Maillard reaction based on methylglyoxal (MG). The reaction was performed in the 0.5 M phosphate buffer by heating MG with or without either glycine or cysteine at 120 degrees C for 1 h. MG alone or MG with cysteine could produce increased level of DMHF with pH increased, whereas MG with glycine had contrary trend. Experiments using a 1:1 mixture of [(13)C6]glucose and [(12)C6]glucose indicate that in the presence of glycine or cysteine, glucose skeleton kept intact during DMHF formation since a 1:1 mixture of [(13)C6]DMHF and [(12)C6]DMHF was formed. Acetylformoin was detected in the glucose with amino acid reaction system as a precursor of DMHF, while in the MG reaction systems, acetylformoin could not be identified. It is suggested different pathways of DMHF formation via MG and glucose.     

Relative quantification of N(epsilon)-(Carboxymethyl)lysine,imidazolone A,and the Amadori product in glycated lysozyme by MALDI-TOF mass spectrometry

The nonenzymatic glycation of proteins by reducing sugars, also known as the Maillard reaction, has received increasing recognition from nutritional science and medical research. In this study, we applied matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) to perform relative and simultaneous quantification of the Amadori product, which is an early glycation product, and of N(epsilon)-(carboxymethyl)lysine and imidazolone A, two important advanced glycation end products. Therefore, native lysozyme was incubated with d-glucose for increasing periods of time (1, 4, 8, and 16 weeks) in phosphate-buffered saline pH 7.8 at 50 degrees C. After enzymatic digestion with endoproteinase Glu-C, the N-terminal peptide fragment (m/z 838; amino acid sequence KVFGRCE) and the C-terminal peptide fragment (m/z 1202; amino acid sequence VQAWIRGCRL) were used for relative quantification of the three Maillard products. Amadori product, N(epsilon)-(carboxymethyl)lysine, and imidazolone A were the main glycation products formed under these conditions. Their formation was dependent on glucose concentration and reaction time. The kinetics were similar to those obtained by competitive ELISA, an established method for quantification of N(epsilon)-(carboxymethyl)lysine and imidazolone A. Inhibition experiments showed that coincubation with N(alpha)-acetylargine suppressed formation of imidazolone A but not of the Amadori product or N(epsilon)-(carboxymethyl)lysine. The presence of N(alpha)-acetyllysine resulted in the inhibition of lysine modifications but in higher concentrations of imidazolone A. o-Phenylenediamine decreased the yield of the Amadori product and completely inhibited the formation of N(epsilon)-(carboxymethyl)lysine and imidazolone A. MALDI-TOF-MS proved to be a new analytical tool for the simultaneous, relative quantification of specific products of the Maillard reaction. For the first time, kinetic data of defined products on specific sites of glycated protein could be measured. This characterizes MALDI-TOF-MS as a valuable method for monitoring the Maillard reaction in the course of food processing.     

On the effect of tetraborate ions in the generation of colored products in thermally processed glycine-carbohydrate solutions

The effect of tetraborate ions on Maillard browning was investigated in a series of monosaccharide-glycine reactions in aqueous bis-tris buffer at pH 7.2. Addition of borax (sodium tetraborate) in catalytic amounts led to enhanced browning measured by absorbance at 420 nm in the order xylose > arabinose > galactose approximately = fructose > ribose > mannose > rhamnose, and the degree of browning with borax was uniformly greater than that produced by phosphate on an equimolar basis. A mechanism is proposed for borax catalysis in which monosaccharide-borate complexation shifts carbohydrate equilibria to favor open-chain (carbonyl) forms, thereby enhancing the rate of the Maillard reaction.     

Why asparagine needs carbohydrates to generate acrylamide

Structural considerations dictate that asparagine alone may be converted thermally into acrylamide through decarboxylation and deamination reactions. However, the main product of the thermal decomposition of asparagine was maleimide, mainly due to the fast intramolecular cyclization reaction that prevents the formation of acrylamide. On the other hand, asparagine, in the presence of reducing sugars, was able to generate acrylamide in addition to maleimide. Model reactions were performed using FTIR analysis, and labeling studies were carried out using pyrolysis-GC/MS as an integrated reaction, separation, and identification system to investigate the role of reducing sugars. The data have indicated that a decarboxylated Amadori product of asparagine with reducing sugars is the key precursor of acrylamide. Furthermore, the decarboxylated Amadori product can be formed under mild conditions through the intramolecular cyclization of the initial Schiff base and formation of oxazolidin-5-one. The low-energy decarboxylation of this intermediate makes it possible to bypass the cyclization reaction, which is in competition with thermally induced decarboxylation, and hence promote the formation of acrylamide in carbohydrate/asparagine mixtures. Although the decarboxylated Amadori compound can be formed under mild conditions, it requires elevated temperatures to cleave the carbon-nitrogen covalent bond and produce acrylamide.     

In-depth mechanistic study on the formation of acrylamide and other vinylogous compounds by the maillard reaction

The formation of acrylamide was studied in low-moisture Maillard model systems (180 degrees C, 5 min) based on asparagine, reducing sugars, Maillard intermediates, and sugar degradation products. We show evidence that certain glycoconjugates play a major role in acrylamide formation. The N-glycosyl of asparagine generated about 2.4 mmol/mol acrylamide, compared to 0.1-0.2 mmol/mol obtained with alpha-dicarbonyls and the Amadori compound of asparagine. 3-Hydroxypropanamide, the Strecker alcohol of asparagine, generated only low amounts of acrylamide ( approximately 0.23 mmol/mol), while hydroxyacetone increased the acrylamide yields to more than 4 mmol/mol, indicating that alpha-hydroxy carbonyls are much more efficient than alpha-dicarbonyls in converting asparagine into acrylamide. The experimental results are consistent with the reaction mechanism based on (i) a Strecker type degradation of the Schiff base leading to azomethine ylides, followed by (ii) a beta-elimination reaction of the decarboxylated Amadori compound to afford acrylamide. The beta-position on both sides of the nitrogen atom is crucial. Rearrangement of the azomethine ylide to the decarboxylated Amadori compound is the key step, which is favored if the carbonyl moiety contains a hydroxyl group in beta-position to the nitrogen atom. The beta-elimination step in the amino acid moiety was demonstrated by reacting under low moisture conditions decarboxylated model Amadori compounds obtained by synthesis. The corresponding vinylogous compounds were only generated if a beta-proton was available, for example, styrene from the decarboxylated Amadori compound of phenylalanine. Therefore, it is suggested that this thermal pathway may be common to other amino acids, resulting under certain conditions in their respective vinylogous reaction products.     

Kinetics of interaction of vanillin with amino acids and peptides in model systems

Model systems were used to study the reaction kinetics of vanillin and pentalysine, lysine, glutathione, cysteine, aspartame, or phenylalanine (molar ratio 1:1) in phosphate buffer. The buffer pH was adjusted to the pK(a)(2) of the available alpha-amino group of each amino acid or peptide. Reductions of vanillin followed first-order kinetics at 55, 65, and 75 degrees C in the presence of each of the amino acids or peptides used. The reaction rates were accelerated as the temperature increased. The rate constants were highest for pentalysine followed by lysine, phenylalanine, glutathione/cysteine, and aspartame. The reduction of phenylalanine followed first-order kinetics, whereas the formation of its reaction product followed zero-order kinetics. The activation energy (E(a)) for the reaction ranged from 5.6 to 14.5 kcal/mol.     

Sugar fragmentation in the maillard reaction cascade: formation of short-chain carboxylic acids by a new oxidative alpha-dicarbonyl cleavage pathway

The formation of short-chain carboxylic acids was studied in Maillard model systems (90 degrees C, pH 6-10) with emphasis on the role of oxygen and water. The total amount of acetic acid formed did not depend on the reaction atmosphere. In the presence of labeled dioxygen or water (18O2, H2 17O), labeled oxygen was partially incorporated into acetic acid. Thermal treatment of 1-deoxy-d-erythro-2,3-hexodiulose (1) and 3-deoxy-d-erythro-hexos-2-ulose in the presence of 17O-enriched water under alkaline conditions led to acetic and formic acid, respectively, as indicated by 17O NMR spectroscopy. The suggested mechanism involves an oxidative alpha-dicarbonyl cleavage leading to an intermediary mixed acid anhydride that releases the acids, e.g., acetic and erythronic acid, from 1. Similarly, glyceric and lactic acids were formed from 1-deoxy-3,4-hexodiuloses, corroborated by complementary analytical techniques. This paper provides for the first time evidence for the direct formation of acids from C6-alpha-dicarbonyls by an oxidative mechanism and incorporation of a 17OH group into the carboxylic moiety. The experimental data obtained support the coexistence of at least two newly described reaction mechanisms leading to carboxylic acids, i.e., (i) a hydrolytic beta-dicarbonyl cleavage as a major pathway and (ii) an alternative minor pathway via oxidative alpha-dicarbonyl cleavage induced by oxidizing species.     

Simultaneous quantitative analysis of maillard reaction precursors and products by high-performance anion exchange chromatography

A new analytical setup allowing the simultaneous analysis of precursors and products of the Maillard reaction is described. It is based on high-performance anion exchange chromatography with electrochemical (ECD) and diode array detectors (DAD) coupled in series. Chromatography and detection were optimized to permit simultaneous monitoring of compounds relevant to the Maillard reaction, such as the sugar, the amino acid, and the corresponding Amadori compound as well as the cyclic intermediates 5-(hydroxymethyl)-2-furaldehyde, maltol, and 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one. Separation was achieved on a CarboPac PA-1 column using a gradient of sodium acetate in aqueous sodium hydroxide. The Amadori compound, glucose, and glycine were monitored by an ECD operating in the integrated amperometry mode. The number of analyzed compounds was further increased by coupling the ECD with a DAD for the analysis of ultraviolet-active constituents. This method was successfully applied to model Maillard reaction mixtures based on glucose and glycine.     

Monitoring carbonyl-amine reaction between pyruvic acid and alpha-amino alcohols by FTIR spectroscopy--a possible route to Amadori products

The carbonyl-amine reaction between pyruvic acid and alpha-amino alcohols was monitored by Fourier transform infrared spectroscopy at a temperature range between 20 and 100 degrees C and under acidic and basic conditions. To avoid interference, the reactions were conducted in the absence of solvent using liquid reactants such as methyl pyruvate, pyruvic acid, ethanolamine, and 1-amino-2,3-propanediol. Analysis of the time- and temperature-dependent spectra indicated that under basic conditions and at room temperature, the initial imine formation and its subsequent isomerization through a 1,3-prototropic shift occur very rapidly and the reaction goes to completion within 12 min. Interestingly, the isomerization product of the initial imine is the so-called Schiff base intermediate formed when the corresponding amino acid and the reducing sugar react during a typical Maillard reaction. Furthermore, the detailed studies also indicated that during the first 30 s, the rate of formation of the initial imine was faster than the rate of its isomerization; however, after 60 s, its rate of isomerization becomes faster than the rate of its formation. The data also indicated that under acidic conditions, this isomerization was prevented from occurring and the reaction was terminated at the initial imine formation stage. In addition, temperature-dependent spectra indicated that the isomerization of the Schiff's base into eneaminol can be achieved at or above 60 degrees C and its subsequent rearrangement into Amadori product can be attained at temperatures above 80 degrees C even under basic conditions, thus providing a novel route to Maillard reaction products starting from a keto acid and an amino alcohol. This observation was also confirmed through identification of the common Amadori product in both keto acid/amino alcohol and sugar/amino acid mixtures, by the application of tandem mass spectrometry and chemical ionization techniques.     

Changes in the pH of Two Different Composts Are Dependent on the Production of Organic Acids

The effects of pH in two different composts were studied. Yamagata compost was made under aerobic conditions, while Shimoduma compost was under semi-aerobic conditions. The change in pH of Yamagata compost was very limited, 7.38–8.97, and it started to increase only after 40-th d of composting. The pH increase from 40 to 70 d coincided with an increase in ammonium content, while a decrease after 70 d was probably as a result of nitrification. The concentration of organic acids (formic, acetic, propionic, iso-butyric and iso-valeric) produced in the first 14 d was high and after that, acetic, propionic and iso-valeric acids decreased quickly. In the Shimoduma compost, however, the range of pH change was wider (3.95–6.65) and increased almost linearly. The quantity of organic acids (citric, lactic, formic and acetic acid) produced depended on the periodic manual stirring. Immediately after stirring the amount of acids decreased, but it increased during the period without stirring.     

Sugar fragmentation in the maillard reaction cascade: isotope labeling studies on the formation of acetic acid by a hydrolytic beta-dicarbonyl cleavage mechanism

The formation of acetic acid was elucidated based on volatile reaction products and related nonvolatile key intermediates. The origin and yield of acetic acid were determined under well-controlled conditions (90-120 degrees C, pH 6-8). Experiments with various 13C-labeled glucose isotopomers in the presence of glycine revealed all six carbon atoms being incorporated into acetic acid: C-1/C-2 ( approximately 70%), C-3/C-4 ( approximately 10%), and C-5/C-6 (approximately 20%). Acetic acid is a good marker of the 2,3-enolization pathway since it is almost exclusively formed from 1-deoxy-2,3-diulose intermediates. Depending on the pH, the acetic acid conversion yield reached 85 mol % when using 1-deoxy-2,3-hexodiulose (1) as a precursor. Hydrolytic beta-dicarbonyl cleavage of 1-deoxy-2,4-hexodiuloses was shown to be the major pathway leading to acetic acid from glucose without the intermediacy of any oxidizing agents. The presence of key intermediates was corroborated for the first time, i.e., tetroses and 2-hydroxy-3-oxobutanal, a tautomer of 1-hydroxy-2,3-butanedione, also referred to as 1-deoxy-2,3-tetrodiulose. The hydrolytic beta-dicarbonyl cleavage represents a general pathway to organic acids, which corresponds to an acyloin cleavage or a retro-Claisen type reaction. Although alternative mechanisms must exist, the frequently reported hydrolytic alpha-dicarbonyl cleavage of 1 can be ruled out as a pathway forming carboxylic acids.     

Monitoring glycation of lysozyme by electrospray ionization mass spectrometry

Electrospray ionization mass spectrometry (ESI-MS) was used to study the glycation of lysozyme by D-glucose (LZM-G) and by D-fructose (LZM-F) under dry heating conditions in the presence and in the absence of oxygen. ESI-MS proved to be a precise method for monitoring protein glycation with respect to following the extent of glycation and changes in the glycoconjugate profile with time. The ESI-MS spectrum of glycated LZM revealed a heterogeneous distribution of glycoforms of LZM at different reaction stages. D-Glucose showed a higher level of reactivity with the amino groups of LZM than D-fructose, both in the presence and in the absence of oxygen. The presence of oxygen in the reaction system induced oxidative side reactions, which competed with and slowed the initial rate of formation of Amadori or Heyns products. The more reactive glycoxidation products formed during the initial stages of incubation in the presence of oxygen accelerated the rate of glycation during the later stages of incubation and increased the involvement of arginine residues of LZM in the glycation reaction. The interaction between the initial glycoxidation product(s) of the reducing sugars and intact lysozyme during the later stages of incubation was observed by the appearance of a different cluster of glycoconjugates in the mass spectrum during the latter stages of incubation. The molecular weight differences between the molecular ions of the new cluster of glycoconjugates are consistent with the formation of D-glucosone from the autoxidation of D-glucose or from the oxidative cleavage of the glucose-lysozyme imine adduct in the lysozyme-glucose system. The effect of oxygen-induced glycoxidation on the glycation reaction was also more pronounced in the LZM-G system compared with that in the LZM-F system.     

Ionizing radiation induces formation of malondialdehyde, formaldehyde, and acetaldehyde from carbohydrates and organic acid

A study was conducted to investigate irradiation-induced formation of malondialdehyde (MDA), formaldehyde (FA), and acetaldehyde (ACT) from fructose, sucrose, glucose, and malic acid solutions. MDA and FA were generated from the carbohydrate solutions upon irradiation while little was formed from malic acid solution. On the other hand, a much higher amount of ACT was formed from malic acid than from the carbohydrate solutions. The G values (number of molecules formed per 100 eV radiation) for MDA were 0.042, 0.0066, and 0.0026 from 0.9 mg mL(-1) fructose, sucrose, and glucose solutions at pH 3.5, respectively. The G values for FA formation were 0.134, 0.233, and 0.0081 from the fructose, sucrose, and glucose solutions, respectively. As concentration of sugars in solutions increased from 0 to 90 mg mL(-1), the formation of these compounds increased rapidly. A further increase in sugar concentration from 90 to 900 mg mL(-1) resulted in a lower rate of increase in MDA and FA formation. pH had a profound effect on the irradiation-induced formation of these compounds from carbohydrates, especially on MDA formation. The minimum amount of MDA from fructose and glucose solutions was observed at pH 5 while formation of MDA from sucrose solution decreased as pH decreased from 7 to 2. The results can be used by the food industry to optimize food formulation in order to minimize formation of these compounds.