Reports of the presence of acrylamide in a range of fried and oven-cooked foods have caused worldwide concern because this compound has been classified as probably carcinogenic in humans. Here we show how acrylamide can be generated from food components during heat treatment as a result of the Maillard reaction between amino acids and reducing sugars. We find that asparagine, a major amino acid in potatoes and cereals, is a crucial participant in the production of acrylamide by this pathway.

Acrylamide is formed in the Maillard reaction

Reaction products (adducts) of acrylamide with N termini of hemoglobin (Hb) are regularly observed in persons without known exposure. The average Hb adduct level measured in Swedish adults is preliminarily estimated to correspond to a daily intake approaching 100 μg of acrylamide. Because this uptake rate could be associated with a considerable cancer risk, it was considered important to identify its origin. It was hypothesized that acrylamide was formed at elevated temperatures in cooking, which was indicated in earlier studies of rats fed fried animal feed. This paper reports the analysis of acrylamide formed during heating of different human foodstuffs. Acrylamide levels in foodstuffs were analyzed by an improved gas chromatographic−mass spectrometric (GC-MS) method after bromination of acrylamide and by a new method for measurement of the underivatized acrylamide by liquid chromatography−mass spectrometry (LC-MS), using the MS/MS mode. For both methods the reproducibility, given as coefficient of vari...

Analysis of Acrylamide, a Carcinogen Formed in Heated Foodstuffs

Acrylamide (CH2CHCONH2), an industrially produced α,β-unsaturated (conjugated) reactive molecule, is used worldwide to synthesize polyacrylamide. Polyacrylamide has found numerous applications as a soil conditioner, in wastewater treatment, in the cosmetic, paper, and textile industries, and in the laboratory as a solid support for the separation of proteins by electrophoresis. Because of the potential of exposure to acrylamide, effects of acrylamide in cells, tissues, animals, and humans have been extensively studied. Reports that acrylamide is present in foods formed during their processing under conditions that also induce the formation of Maillard browning products heightened interest in the chemistry, biochemistry, and safety of this vinyl compound. Because exposure of humans to acrylamide can come from both external sources and the diet, a need exists to develop a better understanding of its formation and distribution in food and its role in human health. To contribute to this effort, this integrate...

https://pubag.nal.usda.gov/pubag/downloadPDF.xhtml?id=25505&content=PDF

Chemistry, biochemistry, and safety of acrylamide. A review.

Deep-fat frying produces desirable or undesirable flavor compounds and changes the flavor stability and quality of the oil by hydrolysis, oxidation, and polymerization. Tocopherols, essential amino acids, and fatty acids in foods are degraded during deep-fat frying. The reactions in deep-fat frying depend on factors such as replenishment of fresh oil, frying conditions, original quality of frying oil, food materials, type of fryer, antioxidants, and oxygen concentration. High frying temperature, the number of fryings, the contents of free fatty acids, polyvalent metals, and unsaturated fatty acids of oil decrease the oxidative stability and flavor quality of oil. Antioxidant decreases the frying oil oxidation, but the effectiveness of antioxidant decreases with high frying temperature. Lignan compounds in sesame oil are effective antioxidants in deep-fat frying.

https://onlinelibrary.wiley.com:443/doi/pdf/10.1111/j.1750-3841.2007.00352.x

Chemistry of deep-fat frying oils

Recent findings of a potential human carcinogen, acrylamide, in foods have focused research on the possible mechanisms of formation. We present a mechanism for the formation of acrylamide from the reaction of the amino acid asparagine and a carbonyl-containing compound at typical cooking temperatures. The mechanism involves formation of a Schiff base followed by decarboxylation and elimination of either ammonia or a substituted imine under heat to yield acrylamide. Isotope substitution studies and mass spectrometric analysis of heated model systems confirm the presence of key reaction intermediates. Further confirmation of this mechanism is accomplished through selective removal of asparagine with asparaginase that results in a reduced level of acrylamide in a selected heated food.

https://www.courses.psu.edu/fd_sc/fd_sc400_jnc3/FDSC500/4-acrylamide%20-%20heated.pdf

Acrylamide formation mechanism in heated foods.

Exposure to acrylamide (AA) has been monitored by mass spectrometric detection of the adduct, N-(2-carbamoylethyl)valine (CEV), to the N-termini of hemoglobin (Hb), according to the N-alkyl Edman method In these studies, a conspicuous background level, about 40 pmol/g of globin, of apparently the same adduct was regularly observed in Hb from persons without known exposure to AA For testing of the hypothesis that this adduct originates from AA formed in cooking, rats were fed fried animal standard diet for 1 or 2 months These animals exhibited a strong increase of the level of the studied Hb adduct, compared to control rats fed unfried diet By gas chromatography/tandem mass spectrometry, the identity with CEV was confirmed by the concordance of the product ion spectrum of the studied adduct with that of a verified standard and by interpretation of the fragment ions Further support of the chemical structure, at the same time pinpointing AA as the causative reactive factor, was obtained through the demo

Acrylamide: A Cooking Carcinogen?

The acrylamide content of heated foodstuffs should be considered to be the net result of complex reactions leading to the formation and elimination/degradation of this compound. The present study, ...

Investigations of factors that influence the acrylamide content of heated foodstuffs.

The state-of-the-art of analysis for acrylamide in food is reviewed. The majority of analytical methods adopts a similar approach: addition of internal standard to the specimen, extraction with water, purification of extract using a solid-phase extraction cartridge, and then determination using either gas chromatography coupled to mass spectroscopy (GC/MS) after bromination, or direct measurement with liquid chromatography coupled to mass spectroscopy (LC/MS). The available methods generally show good agreement and are likely to be accurate. However, improvements in precision (within-laboratory) and repeatability (between-laboratory) are needed by particular data users.

Analytical methods used to measure acrylamide concentrations in foods.

The aim of this thesis was to verify the indicated occurrence of acrylamide formation in heating of food, to identify factors affecting the formation, and to identify important sources of acrylamid ...

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Sune Eriksson

Papers

Analysis of Acrylamide, a Carcinogen Formed in Heated Foodstuffs

Acrylamide: A Cooking Carcinogen?

Investigations of factors that influence the acrylamide content of heated foodstuffs.

Analytical methods used to measure acrylamide concentrations in foods.

Acrylamide in food products : Identification, formation and analytical methodology