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1.
The influence of ingredients, additives, and process conditions on acrylamide formation in gingerbread was investigated. The sources for reducing sugars and free asparagine were identified, and the effect of different baking agents on acrylamide formation was evaluated. Ammonium hydrogencarbonate strongly enhanced acrylamide formation, but its N atom was not incorporated into acrylamide, nor did acrylic acid form acrylamide in gingerbread. Acrylamide concentration and browning intensity both increased with baking time and correlated with each other. The use of sodium hydrogencarbonate as baking agent reduced the acrylamide concentration by >60%. Free asparagine was a limiting factor for acrylamide formation, but the acrylamide content could also be lowered by replacing reducing sugars with sucrose or by adding organic acids. It is concluded that a significant reduction of acrylamide in gingerbread can be achieved by using sodium hydrogencarbonate as baking agent, minimizing free asparagine, and avoiding prolonged baking.  相似文献   

2.
The relationship between acrylamide and its precursors, namely, free asparagine and reducing sugars, was studied in cakes made from potato flake, wholemeal wheat, and wholemeal rye, cooked at 180 degrees C, from 5 to 60 min. Between 5 and 20 min, major losses of asparagine, water, and total reducing sugars were accompanied by large increases in acrylamide, which maximized in all three products between 25 and 30 min, followed by a slow linear reduction. Acrylamide formation did not occur to a large degree until the moisture contents of the cakes fell below 5%. Linear relationships were observed for acrylamide formation with the residual levels of asparagine and reducing sugars for all three food materials.  相似文献   

3.
In this study different Arabica and Robusta coffee beans from different regions of the world were analyzed for acrylamide after roasting in a laboratory roaster. Due to the complex matrix and the comparably low selectivity of the LC-MS at m/ z 72, acrylamide was analyzed after derivatization with 2-mercaptobenzoic acid at m/ z 226. Additionally, the potential precursors of acrylamide (3-aminopropionamide, carbohydrates, and amino acids) were studied. The highest amounts of acrylamide formed in coffee were found during the first minutes of the roasting process [3800 ng/g in Robusta ( Coffea canephora robusta) and 500 ng/g in Arabica ( Coffea arabica)]. When the roasting time was increased, the concentration of acrylamide decreased. It was shown that especially the roasting time and temperature, species of coffee, and amount of precursors in raw material had an influence on acrylamide formation. Robusta coffee contained significantly larger amounts of acrylamide (mean = 708 ng/g) than Arabica coffee (mean = 374 ng/g). Asparagine is the limiting factor for acrylamide formation in coffee. 3-Aminopropionamide formation was observed in a dry model system with mixtures of asparagine with sugars (sucrose, glucose). Thermal decarboxylation and elimination of the alpha-amino group of asparagine at high temperatures (>220 degrees C) led to a measurable but low formation of acrylamide.  相似文献   

4.
Acrylamide in French fries: influence of free amino acids and sugars   总被引：8，自引：0，他引：8  
The free amino acid profile and sugar (fructose, glucose, and sucrose) composition were determined in potato samples selected to give a large range of variation (a total of 66 samples). From these samples French fries were produced in a laboratory-scale simulation of an industrial process followed by a finish fry at 180 degrees C for 3.5 min using a restaurant fryer. The final product was blast frozen and analyzed for acrylamide. Acrylamide was detected in all samples, but its concentration varied significantly from 50 to 1800 ng/g. For isotope dilution (13C3) acrylamide analysis, samples were extracted with water, cleaned up on HLB Oasis polymeric and Accucat mixed mode anion and cation exchange SPE columns, and analyzed by LC-MS/MS. Statistical analysis of the data indicates that the effect of sugars and asparagine on the concentration of acrylamide in French fries is positive and significant (p < 0.001). It appears that one of the ways acrylamide formation in French fries can be effectively controlled is by the use of raw products with low sugar (and to a lesser degree, asparagine) content.  相似文献   

5.
Consistent evidence suggests that the probable human carcinogen acrylamide is formed in starch-rich foodstuffs through heat-induced interaction of asparagine and reducing sugars during Maillard browning. However, information regarding the influence of processing parameters on acrylamide formation is scarce. We investigated the impact of temperature, heating time, browning level, and surface-to-volume ratio (SVR) on acrylamide generation in fried potatoes. Acrylamide content was determined by liquid chromatography (LC) and electrospray ionization tandem mass spectrometry (ESI-MS/MS). In potato shapes with low SVR, acrylamide content consistently increased with increasing temperature and processing times. By contrast, in shapes with intermediate to high SVR, maximal acrylamide formation occurred at 160-180 degrees C, while higher temperatures or prolonged processing times caused a decrease of acrylamide levels. Moreover, browning levels were not a reliable measure of acrylamide content in large-surface products.  相似文献   

6.
Glucose, fructose, sucrose, free asparagine, and free glutamine were analyzed in 74 potato samples from 17 potato cultivars grown in 2002 at various locations in Switzerland and different farming systems. The potential of these potatoes for acrylamide formation was measured with a standardized heat treatment. These potentials correlated well with the product of the concentrations of reducing sugars and asparagine. Glucose and fructose were found to determine acrylamide formation. The cultivars showed large differences in their potential of acrylamide formation which was primarily related to their sugar contents. Agricultural practice neither influenced sugars and free asparagine nor the potential of acrylamide formation. It is concluded that acrylamide contents in potato products can be substantially reduced primarily by selecting cultivars with low concentrations of reducing sugars.  相似文献   

7.
Acrylamide is formed via the Maillard reaction between reducing sugars and asparagine in a number of carbohydrate-rich foods during heat treatment. High acrylamide levels have been found in potato products processed at high temperatures. To examine the impact of harvest year, information on weather conditions during growth, that is, temperature, precipitation, and light, was collected, together with analytical data on the concentrations of free amino acids and sugars in five potato clones and acrylamide contents in potato chips (commonly known as crisps in Europe). The study was conducted for 3 years (2004-2006). The contents of acrylamide precursors differed between the clones and the three harvest years; the levels of glucose were up to 4.2 times higher in 2006 than in 2004 and 2005, and the levels of fructose were 5.6 times higher, whereas the levels of asparagine varied to different extents. The high levels of sugars in 2006 were probably due to the extreme weather conditions during the growing season, and this was also reflected in acrylamide content that was approximately twice as high as in preceding years. The results indicate that acrylamide formation is dependent not only on the content and relative amounts of sugars and amino acids but also on other factors, for example, the food matrix, which may influence the availability of the reactants to participate in the Maillard reaction.  相似文献   

8.
Why asparagine needs carbohydrates to generate acrylamide   总被引：15，自引：0，他引：15  
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.  相似文献   

9.
Acrylamide formed in browning model systems was analyzed using a gas chromatograph with a nitrogen-phosphorus detector. Asparagine alone produced acrylamide via thermal degradation at the level of 0.99 microgram/g of asparagine. When asparagine was heated with triolein-which produced acrolein at the level of 1.82 +/- 0.31 (n = 5) mg/L of headspace by heat treatment-acrylamide was formed at the level of 88.6 microgram/g of asparagine. When acrolein gas was sprayed onto asparagine heated at 180 degrees C, a significant amount of acrylamide was formed (114 microgram/g of asparagine). On the other hand, when acrolein gas was sprayed onto glutamine under the same conditions, only a trace amount of acrylamide was formed (0.18 microgram/g of glutamine). Relatively high levels of acrylamide (753 microgram/g of ammonia) were formed from ammonia and acrolein heated at 180 degrees C in the vapor phase. The reaction of acrylic acid, which is an oxidation product of acrolein and ammonia, produced a high level of acrylamide (190 000 microgram/g of ammonia), suggesting that ammonia and acrolein play an important role in acrylamide formation in lipid-rich foods. Acrylamide can be formed from asparagine alone via thermal degradation, but carbonyl compounds, such as acrolein, promote its formation via a browning reaction.  相似文献   

10.
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.  相似文献   

11.
Acrylamide is formed from reducing sugars and asparagine during the preparation of French fries. The commercial preparation of French fries is a multistage process involving the preparation of frozen, par-fried potato strips for distribution to catering outlets, where they are finish-fried. The initial blanching, treatment in glucose solution, and par-frying steps are crucial because they determine the levels of precursors present at the beginning of the finish-frying process. To minimize the quantities of acrylamide in cooked fries, it is important to understand the impact of each stage on the formation of acrylamide. Acrylamide, amino acids, sugars, moisture, fat, and color were monitored at time intervals during the frying of potato strips that had been dipped in various concentrations of glucose and fructose during a typical pretreatment. A mathematical model based on the fundamental chemical reaction pathways of the finish-frying was developed, incorporating moisture and temperature gradients in the fries. This showed the contribution of both glucose and fructose to the generation of acrylamide and accurately predicted the acrylamide content of the final fries.  相似文献   

12.
A review of agronomic and genetic approaches as strategies for the mitigation of acrylamide risk in wheat and potato is presented. Acrylamide is formed through the Maillard reaction during high-temperature cooking, such as frying, roasting, or baking, and the main precursors are free asparagine and reducing sugars. In wheat flour, acrylamide formation is determined by asparagine levels and asparagine accumulation increases dramatically in response to sulfur deprivation and, to a much lesser extent, with nitrogen feeding. In potatoes, in which sugar concentrations are much lower, the relationships between acrylamide and its precursors are more complex. Much attention has been focused on reducing the levels of sugars in potatoes as a means of reducing acrylamide risk. However, the level of asparagine as a proportion of the total free amino acid pool has been shown to be a key parameter, indicating that when sugar levels are limiting, competition between asparagine and the other amino acids for participation in the Maillard reaction determines acrylamide formation. Genetic approaches to reducing acrylamide risk include the identification of cultivars and other germplasm in which free asparagine and/or sugar levels are low and the manipulation of genes involved in sugar and amino acid metabolism and signaling. These approaches are made more difficult by genotype/environment interactions that can result in a genotype being "good" in one environment but "poor" in another. Another important consideration is the effect that any change could have on flavor in the cooked product. Nevertheless, as both wheat and potato are regarded as of relatively high acrylamide risk compared with, for example, maize and rice, it is essential that changes are achieved that mitigate the problem.  相似文献   

13.
The influences of composition and roasting conditions on acrylamide formation in almonds and hazelnuts were investigated. Eighteen samples of almonds originating from the U.S. and Europe were analyzed for sugars and free amino acids, and acrylamide formed during roasting was determined. Asparagine was the main free amino acid in raw almonds and correlated with the acrylamide content of dark roasted almonds. Roasting temperature was another key factor and had a very strong influence on acrylamide formation. Almonds of European origin contained significantly less free asparagine and formed significantly less acrylamide during roasting as compared to the almonds from the U.S. Roasted hazelnuts contained very little acrylamide because of the low content of free asparagine in the raw nut. Reducing sugars, although being consumed much faster than free amino acids in both types of nuts, were not decisive for the extent of acrylamide formation during roasting.  相似文献   

14.
To examine how sulfur deprivation may affect acrylamide formation in cooked potatoes, three varieties of potato were grown under conditions of either severe sulfur deprivation or an adequate supply of sulfur. In all three varieties sulfur deprivation led to a decrease in acrylamide formation, even though the levels of sugars, which are acrylamide precursors, were higher in tubers of the sulfur-deprived plants. In one variety the concentration of free asparagine, the other precursor for acrylamide, was also higher. There was a very close correlation between the concentration of asparagine in the tubers expressed as a proportion of the total free amino acid pool and the formation of acrylamide upon cooking, whereas sugars were poorly correlated with acrylamide. In potatoes, where concentrations of sugars are usually limiting, competition between asparagine and other amino acids participating in the Maillard reaction may be a key determinant of the amount of acrylamide that is formed during processing.  相似文献   

15.
Acrylamide in foods: occurrence,sources, and modeling   总被引：24，自引：0，他引：24  
Acrylamide in food products-chiefly in commercially available potato chips, potato fries, cereals, and bread-was determined by liquid chromatography-tandem mass spectrometry (LC-MS/MS). Samples were homogenized with water/dichloromethane, centrifuged, and filtered through a 5 kDa filter. The filtrate was cleaned up on mixed mode, anion and cation exchange (Oasis MAX and MCX) and carbon (Envirocarb) cartridges. Analysis was done by isotope dilution ([D(3)]- or [(13)C(3)]acrylamide) electrospray LC-MS/MS using a 2 x 150 mm (or 2 x 100 mm) Thermo HyperCarb column eluted with 1 mM ammonium formate in 15% (or 10% for the 2 x 100 mm column) methanol. Thirty samples of foods were analyzed. Concentrations of acrylamide varied from 14 ng/g (bread) to 3700 ng/g (potato chips). Acrylamide was formed during model reactions involving heating of mixtures of amino acids and glucose in ratios similar to those found in potatoes. In model reactions between amino acids and glucose, asparagine was found to be the main precursor of acrylamide. Thus, in the reaction between nitrogen-15 (amido)-labeled asparagine and glucose, corresponding (15)N-labeled acrylamide was formed. The yield of the model reaction is approximately 0.1%.  相似文献   

16.
A number of parameters linked to storage of potatoes were evaluated with regard to their potential to influence the acrylamide formation in French fries. Acrylamide, which is a potential human carcinogen, is reported to be formed during the frying of potatoes as a result of the reactions between asparagine and reducing sugars. This study was conducted using three potato varieties (Bintje, Ramos, and Saturna) typically used in Belgium, The Netherlands, and the northern part of France for French fry and crisp production. Saturna, mainly used in crisp production, appeared to be the least susceptible for acrylamide formation during frying. Especially storage at low temperatures (4 degrees C) compared to storage at 8 degrees C seemed to enhance acrylamide formation due to a strong increase in reducing sugars caused by low-temperature storage. Because of the reversible nature of this physiological reaction, it was possible to achieve a significant reduction of the reducing sugars after a reconditioning of the cold-stored potatoes for 3 weeks at 15 degrees C. All changes in acrylamide concentrations could mainly be explained by the reducing sugar content of the potato (R2 = 0.84, n = 160). This means that, by ensuring a low reducing sugar content of the potato tuber, the risk for acrylamide formation will largely be reduced. Finally the use of a sprout inhibitor did not influence the composition of the potato, and thus acrylamide formation was not susceptible to this treatment.  相似文献   

17.
The effect of different sugars and glyoxal on the formation of acrylamide in low-moisture starch-based model systems was studied, and kinetic data were obtained. Glucose was more effective than fructose, tagatose, or maltose in acrylamide formation, whereas the importance of glyoxal as a key sugar fragmentation intermediate was confirmed. Glyoxal formation was greater in model systems containing asparagine and glucose rather than fructose. A solid phase microextraction GC-MS method was employed to determine quantitatively the formation of pyrazines in model reaction systems. Substituted pyrazine formation was more evident in model systems containing fructose; however, the unsubstituted homologue, which was the only pyrazine identified in the headspace of glyoxal-asparagine systems, was formed at higher yields when aldoses were used as the reducing sugar. Highly significant correlations were obtained for the relationship between pyrazine and acrylamide formation. The importance of the tautomerization of the asparagine-carbonyl decarboxylated Schiff base in the relative yields of pyrazines and acrylamide is discussed.  相似文献   

18.
In this paper the relationship between virgin olive oil (VOO) phenol compounds and the formation of acrylamide in potato crisps was investigated. The phenol compositions of 20 VOO samples were screened by LC-MS, and 4 oils, characterized by different phenol compound patterns, were selected for frying experiments. Slices of potatoes were fried at 180 degrees C for 5, 10, and 15 min, and acrylamide content was determined by LC-MS. Results demonstrated that VOO phenolic compounds are not degraded during frying, and crisp color was not significantly different among the four VOOs. Acrylamide concentration in crisps increased during frying time, but the formation was faster in the oil having the lowest concentration of phenolic compounds. Moreover, the VOO having the highest concentration of ortho-diphenolic compounds is able to efficiently inhibit acrylamide formation in crisps from mild to moderate frying conditions. It was concluded that the use of ortho-diphenolic-rich VOOs can be proposed as a reliable mitigation strategy to reduce acrylamide formation in domestic deep-frying.  相似文献   

19.
The relations between the formation of acrylamide and color, pyrazines, or antioxidants in an asparagine/d-glucose browning model system under various conditions were investigated. The highest level of acrylamide was produced in the asparagine/glucose (1:3) system heated at 170 degrees C for 30 min (2629 microg/g asparagine). Color intensity increased with temperature and heating time. The formation of pyrazines increased steadily with an increase of temperature (140-170 degrees C) and heating time (15-60 min). Antioxidant formation varied among the samples heated under different conditions. A clear correlation between formation of acrylamide and browning color was obtained. The formation of acrylamide was linearly correlated with the formation of total pyrazines during the initial stages of the Maillard reaction. No obvious correlation between formation of acrylamide and antioxidants was observed. However, excess amounts of asparagine increased the formation of antioxidants, whereas excess amounts of glucose reduced its formation.  相似文献   

20.
The presence of acrylamide was investigated in different presentations of commercial black ripe olives, a well-known sterilized alkali-treated product. The analysis was performed by gas chromatography-mass spectrometry (GC-MS) after bromination of acrylamide, using (13C3)acrylamide as internal standard. In-house validation data for commercial ripe olives showed good precision and accuracy of the method, with repeatability below 3% and recoveries between 94 and 105%. Acrylamide was detected in all samples, but its concentration varied significantly from 176 to 1578 microg/kg of pulp. The effects of different processing conditions (two preservation methods and three darkening methods), cultivar (Hojiblanca or Manzanilla), and presentation form (pitted or sliced olives) on acrylamide content were evaluated in experiments performed in an olive-processing plant. All canned samples were sterilized at 121 degrees C for 30 min. Statistical analysis of the data indicated that the effects of darkening method and olive cultivar were the most pronounced. Acrylamide contents did not significantly differ after 6 months of storage. The small amounts of free amino acids and reducing sugars found in olives before sterilization did not significantly correlate with the acrylamide formed.  相似文献   

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