ISSN: 1579-4377

ACRYLAMIDE IN FOOD
(Chemical Structure of Acrylamide)
Semih tles1 and Serkan tles2
2

1
Ege University, Food Engineering Department, Izmir, Turkey
Izmir Institute of Technology, Chemical Engineering Department, Izmir, Turkey

KEYWORDS
Acrylamide, food
ABSTRACT
Acrylamide is a versatile organic compound that finds its way into many products in our everyday life.
Acrylamide is a monomer of polyacrylamide. The monomer with form of acrylamide is toxic to the
nervous system, a carcinogen in laboratory animals and a suspected carcinogen in humans. The multiple
unit or polymeric form is not known to be toxic.
The monomeric acrylamide is primarily used in research laboratories for gel preparation. The acrylamide
gel is used for electrophoresis, a technique for protein separation. It is also used to produce grout, dyes,
contact lenses and in the construction of dams, tunnels and sewers. Acrylamide polymers are used as
additives for water treatment, flocculants, paper making aids, thickeners, soil conditioning agents, textiles
(permenant press fabrics), production of organic chemicals and ore and crude oil processing. Although
polyacrylamide is not toxic, a small amount of the acrylamide monomer may leach from the polymer.
Acrylamide and its analogues have been widely used since the last century for various chemical and
environmental applications and can be formed by heating of biological material derived from plant
tissues. This compound, identified previously as a potential industrial hazard, has now been found in
many cooked foods. Reports of the presence of acrylamide in a range of fried and oven-cooked foods
have caused world-wide concern because of its probable carcinogenicity in humans.

INTRODUCTION
Acrylamide and its analogues have been widely used since the last century for various chemical and
environmental applications. Some of the common uses of acrylamide are in the paper, dyes, cosmetics
and toiletry industry. It is produced commercially as an intermediate in the production and synthesis of
polyacrylamides.
Acrylamides have also been used as flocculants for clarifying drinking water and for waste water
treatment. They are also a component of tobacco smoke, which gave the earliest indication that it can be
formed by heating of biological material. Extensive studies have been done on acrylamide on its
mutagenicity and carcinogenicity in bacterial, animal and human systems. Acrylamide has been shown to
be non mutagenic in Salmonella microsome test systems. Acrylamide is known to produce neuropathy
in both human and experimental animals.

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There are some analysis methods to be able to see the levels of acrylamide in food stuff. They are
sampling, extraction, gas chromatography/mass spectrometry, liquid chromatography/tandem mass
spectrometry and identification of acrylamide.
The health impairment caused by acrylamide hinges on its carcinogenic and genotoxic impact.
Acrylamide causes cancer in animals. While there are no scientific reasons to doubt this risk in humans,
in principle, it cannot be reliably estimated, at present, how high the risk of contracting cancer is in
humans after the intake of acrylamide-containing foods (Anon., 2004a-d).
In this report, it is aimed to investigate the analysis methods of acrylamide, acrylamides health damaging
properties and its exposure and also to investigate the what acrylamide consumers can do.

WHAT IS ACRYLAMIDE?
Acrylamide is a versatile organic compound that finds its way into many products in our everyday life.
Acrylamide exists in two forms as a monomer and polyacrylamide as a polymer. The single unit form of
acrylamide is toxic to the nervous system, a carcinogen in laboratory animals, and a suspected carcinogen
in humans. The multiple unit or polymeric form is not known to be toxic (Giese, 2002; Konings et al.,
2003; Richmont and Borrow, 2003; Tyl and Crump, 2002; Vattem and Shetty, 2003).

The Chemical Structure of Acrylamide

Acrylamide is a chemical intermediate (monomer) used in the synthesis of polyacrylamides. This
monomer occurs in a white flowing crystalline form it is odourless, flake like crystals, it is soluble in
water, ethanol, methanol, dimethyl ether and acetone, it is not soluble in heptane and benzene. Figure 1,
shows the chemical structure of acrylamide.

Figure 1. Structure of Acrylamid

It readily polymerises on reaching melting point or exposure to UV light. Solid acrylamide is stable at
room temperature, but may polymerise violently when melted or exposed to oxidating agents. Table 1,
shows the chemical properties of acrylamide.

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Table 1. Chemical Properties of Acrylamide

Synonyms:
CAS No:
Molecular weight:
Chemical Formula:
Boiling Point:
Melting Point:

2-Propenamide; ethylene carboxamide; acrylic amide; vinyl amide

79-06-1
71.09
CH2CHCONH2
125C
87.5C (183F)

Application Areas of Acrylamide

Acrylamide is used in the manufacture of plastics, including some food packaging, and in the production
of synthetic rubber and some copolymers also it is used in water purification. When added to water, it
coagulates and traps suspended solids that can then be easily removed during the treatment of drinking
water. Acrylamide does not bind to soil but is degraded by micro-organisms within a few days in soil and
water. The acrylamide that does not coagulate remains in the water as a contaminant that, under U.S.
Environmental Protection Agency regulations, must be present at less than half a part per billion (0.5
ppb). The monomeric acrylamide is primarily used in research laboratories for gel preparation (Giese,
2002; Simonne and Archer, 2002).
The acrylamide gel is used for electrophoresis, a technique that uses flat gels of polyacrylamide to
separate and isolate DNA and other bio molecules. It is also used to produce grout, dyes, contact lenses,
and in the construction of dams, tunnels, and sewer. Acrylamide polymers are used as flocculants, paper
making aids, thickeners, soil conditioning agents, textiles (permanent-press fabrics), production of
organic chemicals, and ore and crude oil processing. Because of the large application areas of acrylamide,
the annual production of acrylamide in the EU is 80,000 to 100,000 tonnes (Simonne and Archer, 2002).

METHODS OF ANALYSIS
By current standards of analytical science, the recent findings of acrylamide in foodstuffs are reliable.
None of the methods used to measure acrylamide in foodstuffs has yet been fully validated by interlaboratory collaborative trials. However, most methods fulfil the requirements of single laboratory (inhouse) validation and accreditation. (AOAC, 2002; Simonne and Archer, 2002; Tareke et al., 2000)

Sampling
Levels of acrylamide can vary considerably in foods, seemingly due to the processing or cooking
conditions used and the temperature achieved. Consequently, there can be considerable variability from
product to product and even concentration hot-spots within an individual food item. The whole food item
or package should be homogenised before sub sampling and a representative portion taken for analysis.
For the foodstuffs investigated to date, there have been no problems reported of significant losses during
storage and homogenisation of the sample prior to analysis (Tareke et al., 2000).
According to the Swedish Food Administration, fried potato products and bread contributed most to the
exposure of acrylamide. For all foods selected, information on the most used brands sold and on market
shares is obtained from commodity boards and from a commercial market research agency. On the basis
of market shares, the most current brands are selected. For each brand, three different production codes
are sampled. In case of private labels, some different sales locations with the highest market shares are
sampled. If acrylamide concentrations in foods are supposed to be subject to regional variations, like
bread and chips from fish and chips stands, samples are collected from the most important sales-channels
in three regions. All samples are homogenised before analysis. Secondly, to investigate acrylamide levels
in other food sources, single samples are selected from foods, which are exposed to heat during industrial

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processing. If acrylamide appeared to be present in these samples, more brands and production codes are
analysed (Tareke et al., 2000).

Table 2. Acrylamide Levels (g/kg) in Various Foodstuffs (Svensson et al., 2003)

Food/Product Group
Potato crisps
French fries
Fried potato/baked products
Cookies/biscuits/wafers
Crisp bread/thin unleavened bread
Bread
Breakfast cereals
Tortilla crisps
Popcorn
Coffee (medium roast; mixed brands; as ready for consumption)
Wholemeal .our
Rye flour
Oat flakes/rolled
Oat-bran
Oatmeal porridge
Gruel; instant
Gruel; oat based instant
Gruel for adults; instant
Potato (boiled)
Spaghetti (mixed products)
Rice (mixed products)
Rice (boiled + microwave)
Pancake (mixed products)
Waffles (mixed products)
Fish fingers (mixed products)
Chickenbits (restaurant)
Deep fried fish (restaurant)
Meat balls (mixed products)
Bacon (raw)
Eggs; fried
Cauliflower gratin (restaurant)
Vegetarian schnitzel
Taco shells (+ microwave)
Danish pastry
Pistachio garland bun
Soft biscuit
Soft ginger biscuit
Sponge cake
American muffins

N of Samples
11
7
8
11
21
21
14
3
3
2
12

Mean
1360
540
310
300
300
50
220
150
500
25
<30
<30
<30
<30
<30
<30
<30
<230
<30
<30
<30
<30
<30
42
30
39
39
64
<30
<30
<30
<30
<30
<30
<30
<30
<30
<30
<100

Median
980
410
300
230
135
40
100
150
390
25

Min-max
3302300
3001100
34688
<30640
<301900
<30160
<301400
120180
365715
25

Some scientists made an experiment in University of Stockholm in 2002. More than 130 samples were
collected from supermarkets in Uppsala in the spring of 2002. The analytical survey comprised crisp
bread, bread, flour, pasta, rice, fish, chicken, bacon, meatballs, sausages, vegetarian schnitzels, eggs,
biscuits, cookies, Danish pastries, buns, muffins, breakfast cereals, porridge, gruel and coffee and ready
prepared meals such as pizza, pancakes, waffles and products made of potatoes (French fries, potato
crisps and fried potatoes) or corn. Table 2 lists the results of the analytical survey (Svensson et al., 2003).

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Extraction
Free acrylamide is extracted from the sample using cold or hot water. It is demonstrated, by adding
known amounts of acrylamide standard to the sample before extraction, that these extraction procedures
give complete recovery. Many sample extracts can be analyzed directly, however some sample types
benefit from further cleanup and concentration of the extract. It is desirable to add an internal standard to
the food sample at the outset, as an internal standard compensates for any recovery losses in these steps
and helps to ensure that results are reliable (Chakrabarti and Ungeheuer, 2002; Tareke et al., 2000).
In an experiment, samples were homogenised and analysed fresh or stored at 20 C until analysis. To
homogenised samples (4 g), water (40 ml) and an internal standard (deuterium labelled acrylamide) were
added. Samples were extracted by means of a homogeniser, centrifuged and filtered on solid phase
extraction columns. The filtrates were collected and passed through a centrifuge spin filter until a
sufficient volume had been obtained for analysis with LCMSMS (Chakrabarti and Ungeheuer, 2002;
Tareke et al., 2000).

Analysis
Gas chromatography/mass spectrometry (GC-MS)
Although acrylamide can be analysed as such, without derivatization, when using GC-MS, the molecule
is normally brominated to form a derivative that has improved GC properties. The acrylamide derivative
is identified by its retention time and by the ratio of characteristic MS ions. Once the identity of
acrylamide has been established in a particular type of food, it may be possible to use gas
chromatography with electron capture detection (ECD) or other selective detection techniques to
routinely monitor levels, although with this analytical technique the identification rests on the retention
time alone. The lowest level that can be measured when using GC-MS is in the range of 5 to 10 g/kg
(Chakrabarti and Ungeheuer, 2002)
Liquid chromatography/tandem mass spectrometry (LC-MS-MS)
The LCMSMS system consisted of a triple quadrupole. Because there are concerns about possible
artefact formation during the bromination procedure, LC-MS-MS methods are developed for the direct
analysis of acrylamide without the need to derivatize. Identification of the substance is by its retention
time and by the relative ion intensities. The limit of measurement using LC-MS/MS is about 20 to 50
g/kg. (Chakrabarti and Ungeheuer, 2002)
In the experiment they prepared extracts as described before, were analysed according to the method
developed by Rose n and Hellena s, using liquid chromatography tandem mass spectrometry with a
graphitised carbon column, water as mobile phase, and a triple quadrupole. The overall method was
validated for a concentration range of 3010 000 mg kg_1 (accuracy 91102%, relative standard
deviation 321%) (Chakrabarti and Ungeheuer, 2002; Tareke et al., 2000)

Identification of Acrylamide
When the same food sample is extracted and analysed by both methods describe, there is generally
excellent agreement between the results and the putative acrylamide fulfils the identification criteria in
both techniques. This provides adds confidence in the qualitative and quantitative results to date. By
modern standards of analytical evidence, the identification of acrylamide in foodstuffs is highly reliable
(Chakrabarti and Ungeheuer, 2002)

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HEALTH DAMAGING PROPERTIES OF ACRYLAMIDE

The health impairment caused by acrylamide hinges on its carcinogenic and genotoxic impact.
Acrylamide causes cancer in animals. While there are no scientific reasons to doubt this risk in humans,
in principle, it cannot be reliably estimated, at present, how high the risk of contracting cancer is in
humans after the intake of acrylamide-containing foods. In principle, the so-called Alara Principle, i.e. as
low as reasonably achievable, applies to genotoxic and carcinogenic substances. The Scientific
Committee on Food of the European Commission also raised this claim in its opinion on acrylamide in
foods dated 3 July 2002. Due to insufficient data, the fixing of limits is currently neither toxicologically
justifiable nor technically realisable (Chakrabarti and Ungeheuer, 2002; Mottram et al., 2002; Raloff,
2002).
In 2002, The Uppsala Ethical Committee had an animal experiment to be able to see the health
damaging properties of acrylamide. Male CBA-CA mice, aged 78 weeks and weighing approximately
2025 g, were bought from B & K Universal, Sollentuna, Sweden. In the first experiment the mice were
kept in an animal house at EBC, Uppsala University. In the second experiment they were kept at the
locality of the National Food Administration, Sweden. The mice were allowed free access to solid food
and tap water, and were provided with 12 h of light and 12 h darkness. Temperature and humidity were
correctly adjusted to be optimal for the animals (Zetterberg, 2003).
The investigation is divided in two separate experiments. In the first experiment, the studied dose interval
was 0100 mg/kg b.w. In the second experiment, the studied dose interval was 030 mg/kg b.w.
In the first experiment, 49 male CBA mice were involved in this experiment. All animals were
intraperitoneally injected once. The injection volume was 10 l/g of mouse. Three mice constituted the
positive control group and were given a dose of 1 mg/kg b.w. of colchicine dissolved in PBS. The other
46 mice were divided into 22 groups with different doses of AA. AA was dissolved in PBS.

Figure 2. The Frequency of Micronucleated of Male CBA Mice Given 22 Different Doses (single injections) of
Acrylamide (Zetterberg, 2003)

In the second experiment, 35 male CBA mice were treated with different doses of AA. The procedure was
identical to that in Experiment 1, but the doses were 0, 1, 3, 6, 12, 24, and 30 mg/kg b.w., with five
animals in each of the groups. The injection volumes were the same as in Experiment 1.
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After injection, blood samples were collected under light anaesthesia with fluothane from the orbital
plexus of each animal at 42 h after the injections (the same procedure in both experiments). Directly after
the collection of blood, the animals were killed by cervical dislocation. The results from the analysis in
peripheral blood (fMPCE) are shown in figure 2.
In Experiment 1, each value represents the mean of two animals, except for the control group: 0 and 75
mg/kg b.w. group (three animals each). From each AA-treated animal, in general 280,000 PCE were
analysed. Due to the production of cell doublets, some of the parallel samples were excluded from the
analysis, resulting in less than four parallel samples from some of the mice. In Experiment 2, each mean
value represents five animals treated with the same AA dose. From each animal, in general 350,000 PCE
were analysed. In both experiments, the frequency of PCE in peripheral blood was found to be almost the
same for all AA dose groups which indicated that no depression of the cell proliferation occurred at these
doses. No sign of sickness or decreased activity of the mice was noticed during the experiments.

DISCUSSION
Acrylamide concentrations for different food items or food groups were determined by various authors. In
some cases the foodstuffs analysed are well characterized, but in other cases the results were assigned to a
product group and no further details regarding the specific food item were provided. Therefore additional
studies on the acrylamide levels in specific foods on the country base are necessary.

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