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Acrylamide
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) Carc. Cat. 2 Muta. Cat. 2 Repr. Cat. 3
EU Index	616-003-00-0
NFPA 704	2 3 2
R-phrases	R45, R46, R20/21, R25, R36/38, R43, R48/23/24/25, R62
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) Infobox disclaimer and references

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 dimethylamine 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.

Contents 1 Occurrence in daily life 2 Reduction of acrylamide formation 2.1 Storage 2.2 Raw Material 2.3 Production methods 3 Potential health risk 3.1 Cancer 3.2 Public awareness 4 See also 5 References 6 External links

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 nearly all uncooked foods do not 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.

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.

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

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.

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.

According to a 2005 review^[1], 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.

In 2002-04-24, Swedish Livsmedelsverket (National Food Administration) announced that acrylamide can be found in baked and fried starchy foods, such as potato chips and breads, and concern was raised mainly as it may be a carcinogen. This was followed by a strong but short-lived interest of 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 of consuming acrylamide. [1]

• Acrydite- research on this compound casts light on Acrylamide
• Deep-frying
• Deep fryer
• Vacuum fryer

1. ^ Rice, Jerry M (2005). "The carcinogenicity of acrylamide". Mutation Research/Genetic Toxicology and Environmental Mutagenesis 580 (1-2): 3-20. PMID 15668103. 

• International Chemical Safety Card 0091
• NIOSH Pocket Guide to Chemical Hazards 0012
• Institut national de recherche et de sécurité (1992). "Acrylamide." Fiche toxicologique n° 119. Paris:INRS. (PDF file, in French)

• IARC Monograph "Acrylamide."
• Chemical information
• National Pollutant Inventory - Acrylamide
• World Health Organization
• Environmental Protection Agency

'Acrylamide and Food'

• Harvard School of Public Health press release; baked and fried food does not increase risk of certain cancers in humans
• Harvard School of Public Health press release; no breast cancer risks from acrylamide via food
• Acrylamide Infonet
• Girls who eat chips more likely to get breast cancer
• California Wants to Serve a Warning With Fries
• Prospective study of dietary acrylamide and risk of colorectal cancer among women
• Report about acrylamide in food and cancer risks
• www.foodrisk.org/acrylamide
• Court case about a suspected acrylamide poisoning
• Center for Food Safety and Nutrition (cfsan.fda.gov) FAQ

• Links to external chemical sources