Acrylamide

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Acrylamide
200px
IUPAC name 2-propenamide
Identifiers
CAS number 79-06-1
SMILES C=CC(=O)N
Properties
Molecular formula C3H5NO
Molar mass 71.08 g/mol
Density 1.13 g/cm³
Melting point

84.5 °C

Boiling point

- (polymerization)

Solubility in water 204 g/100 ml (25 °C)
Hazards
EU classification Toxic (T)
Template:Carc2
Template:Muta2
Template:Repr3
EU Index 616-003-00-0
NFPA 704

NFPA 704.svg

2
3
2
 
S-phrases S53, S45
Flash point 138 °C
Autoignition
temperature
424 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

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Overview

The chemical compound acrylamide (acrylic amide) has the chemical formula C3H5NO. Its IUPAC name is 2-propenamide. It is a white odourless crystalline solid, soluble in water, ethanol, ether and chloroform. Acrylamide is incompatible with acids, bases, oxidizing agents, iron and iron salts. It decomposes non thermally to form ammonia and thermal decomposition produces carbon monoxide, carbon dioxide and oxides of nitrogen.

Most acrylamide is used to synthesize polyacrylamides which find many uses as water-soluble thickeners. These include use in wastewater treatment, gel electrophoresis (SDS-PAGE), papermaking, ore processing, and the manufacture of permanent press fabrics. Some acrylamide is used in the manufacture of dyes and the manufacture of other monomers.

Acrylamide was accidentally discovered in foods in April 2002 by scientists in Sweden when they found large amounts of the chemical in starchy foods, such as potato chips, French fries, and bread. It is not found in food which has been boiled.[1]

Occurrence in daily life

Acrylamide in fried or baked goods is produced by the reaction between asparagine and reducing sugars (fructose, glucose, etc.) or reactive carbonyls. Acrylamide in olives and prune juice comes through another process. It has been suggested that environmental pathways, such as the breakdown of the herbicide glyphosate (Roundup), are sources too. Smoking is also a major acrylamide producer. Estimates for the proportion in the diet coming from the consumption of coffee range from twenty to forty percent. Acrylamide cannot be created by boiling, and very few uncooked foods contain any detectable amounts. Browning during baking, frying or deep-frying will produce acrylamide and over-cooking of foods will produce large amounts of acrylamide. Acrylamides can also be created during microwaving.

Reduction of acrylamide formation

Storage

In the case of potatoes for instance the storage temperature should not drop below 8°C. When the temperature is as low as 4°C the fructose content rises sharply, so that the acrylamide formation during baking or deep-frying will be higher.

Raw Material

New varieties of potatoes are being bred that produce less or no acrylamide.

Production methods

In many cases it is advisable to lower the maximum temperature during baking. Also new production methods such as vacuum frying may lower the acrylamide formation. When silicone is used as a foam inhibitor in deep-frying fats in the food industry the acrylamide content is doubled.

Recipe Formulation

Asparaginase, a naturally-occurring enzyme, can be added to bread or potato mixtures to reduce formation of acrylamide during cooking [2]

Potential health risk

There is evidence that exposure to large doses can cause damage to the male reproductive glands. Direct exposure to pure acrylamide by inhalation, skin absorption, or eye contact irritates the exposed mucous membranes, e.g. the nose, and can also cause sweating, urinary incontinence, nausea, myalgia, speech disorders, numbness, paresthesia, and weakened legs and hands. In addition, the acrylamide monomer is a potent neurotoxin, causing the disassembly or rearrangement of intermediate filaments[3]. Ingested acrylamide is metabolised to a chemically reactive epoxide, glycidamide.[1]

Cancer

According to a 2005 review[4], acrylamide reliably produces various types of cancer in experimental mice and rats. However, studies in human populations have failed to produce consistent results, and it remains unclear whether this is due to a reduced risk in a natural setting or the methodological difficulties inherent in such studies. For example, it might be difficult to isolate the effects of acrylamide because it is so ubiquitous in western diets.

Public awareness

In 2002-04-24 the Swedish National Food Administration (Livsmedelsverket) announced that acrylamide can be found in baked and fried starchy foods, such as potato chips, breads and cookies. Concern was raised mainly because of the carcinogenic effects of acrylamide. This was followed by a strong but short-lived interest from the press. On 2005-08-26, California attorney general Bill Lockyer filed a lawsuit against top makers of french fries and potato chips to warn consumers of the potential risk from consuming acrylamide. [2]

See also

References

  1. Food Standards Agency, www.food.gov.uk
  2. KORNBRUST, B. A.; Stringer, M. A., Hendriksen, H. V. (September 17-20, 2006). "Enzymatic reduction of acrylamide formation using asparaginase from Aspergillus oryzae". World Grains Summit: Foods and Beverages. 
  3. Alberts, Lewis, Johnson, Raff, Roberts, and Walter ,Molecular Biology of the Cell, 4th Edition, Routledge, March, 2002, ISBN 0-8153-3218-1
  4. Rice, Jerry M (2005). "The carcinogenicity of acrylamide". Mutation Research/Genetic Toxicology and Environmental Mutagenesis 580 (1-2): 3-20. PMID 15668103.

External links

'Acrylamide and Food'

de:Acrylamidit:Acrilammide nl:Acrylamideno:Akrylamidsv:Akrylamid th:อะคริลาไมด์


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