Acrylamide
IUPAC name	prop-2-enamide
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 Image File history File links Download high-resolution version (1100x693, 23 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Acrylamide ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...
Boiling point	- (polymerization) Italic text This article is about the boiling point of liquids. ... An example of alkene polymerisation, in which each Styrene monomer units double bond reforms as a single bond with another styrene monomer and forms polystyrene. ...
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	Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main European Union law concerning chemical safety. ... The hazard symbol for carcinogenic chemicals in the Globally Harmonized System. ... In biology, a mutagen (Latin, literally origin of change) is a physical or chemical agent that changes the genetic information (usually DNA) of an organism and thus increases the number of mutations above the natural background level. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links 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 ammonia and thermal decomposition produces carbon monoxide, carbon dioxide and oxides of nitrogen.
R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... For other uses, see Flash point (disambiguation). ... The autoignition temperature, or the ignition temperature of a substance is the lowest temperature at which a chemical will spontaneously ignite in a normal atmosphere, without an external source of ignition, such as a flame or spark. ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... Amide functional group Amides possess a conjugated system spread over the O, C and N atoms, consisting of molecular orbitals occupied by delocalized electrons. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... The International Union of Pure and Applied Chemistry (IUPAC) is an international non-governmental organization devoted to the advancement of chemistry. ... Crystal (disambiguation) Insulin crystals A crystal is a solid in which the constituent atoms, molecules, or ions are packed in a regularly ordered, repeating pattern extending in all three spatial dimensions. ... H2O and HOH redirect here. ... Grain alcohol redirects here. ... This article is about the chemical compound. ... R-phrases , , , S-phrases , Flash point Non-flammable U.S. Permissible exposure limit (PEL) 50 ppm (240 mg/m3) (OSHA) Supplementary data page Structure and properties n, εr, etc. ... For other uses, see Ammonia (disambiguation). ... Carbon monoxide, with the chemical formula CO, is a colorless, odorless, and tasteless gas. ... Carbon dioxide is a chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ...

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. Polyacrylamide is an acrylate polymer formed from acrylamide subunits that is readily cross-linked. ... Thickening agents, or thickeners, are substances which, when added to the mixture, increase its viscosity without substantially modifying its other properties, like eg. ... Wastewater is any water that has been adversely affected in quality by anthropogenic influence. ... Gel electrophoresis is a technique used for the separation of deoxyribonucleic acid, ribonucleic acid, or protein molecules through an electric charge. ... Picture of an SDS-PAGE. The molecular marker is in the left lane SDS-PAGE stands for Sodium Dodecyl Sulfate Polyacrylamide Gel Electrophoresis. ... The Diamond Sutra of the Chinese Tang Dynasty, the oldest dated printed book in the world, found at Dunhuang, from 868 AD. Papermaking is the process of making paper, a material which is ubiquitous today for writing and packaging. ... Iron ore (Banded iron formation) Manganese ore Lead ore Gold ore An ore is a volume of rock containing components or minerals in a mode of occurrence which renders it valuable for mining. ... A permanent press is a fabric that has been chemically processed with methanol to resist wrinkles and hold its shape. ... Look up dye in Wiktionary, the free dictionary. ... In chemistry, a monomer (from Greek mono one and meros part) is a small molecule that may become chemically bonded to other monomers to form a polymer. ...

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] For the other potato product referred to as chips see French fried potatoes. ... French fries (North America; sometimes also uncapitalized as french fries[1] or simply fries[2]), or chips (United Kingdom, Republic of Ireland, and most Commonwealth nations), are pieces of potato that have been cut into batons and deep-fried. ...

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. Plantains frying in vegetable oil. ... Wikibooks Cookbook has an article on Baking Baking is the technique of prolonged cooking of food by dry heat acting by conduction, and not by radiation, normally in an oven, but also in hot ashes, or on hot stones. ... For other articles using the abbreviation or acronym asn see ASN. Asparagine is one of the 20 most common natural amino acids on Earth. ... A reducing sugar is any sugar that, in basic solution, forms some aldehyde or ketone. ... Fructose (or levulose) is a simple sugar (monosaccharide) found in many foods and is one of the three most important blood sugars along with glucose and galactose. ... Glucose (Glc), a monosaccharide (or simple sugar), is an important carbohydrate in biology. ... Carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e. ... Binomial name L. 19th century illustration The Olive (Olea europaea) is a species of small tree in the family Oleaceae, native to coastal areas of the eastern Mediterranean region, from Lebanon and the maritime parts of Asia Minor and northern Iran at the south end of the Caspian Sea. ... Species See text. ... A herbicide is a pesticide used to kill unwanted plants. ... It has been suggested that Roundup be merged into this article or section. ... The cigarette is the most common method of smoking tobacco. ... For the several U.S. counties named Coffee, see Coffee County. ... The Maillard reaction is a chemical reaction between an amino acid and a reducing sugar, usually requiring the addition of heat. ... Wikibooks Cookbook has an article on Baking Baking is the technique of prolonged cooking of food by dry heat acting by conduction, and not by radiation, normally in an oven, but also in hot ashes, or on hot stones. ... Plantains frying in vegetable oil. ... A Deep fried Twinkie Breaded, deep-fried squid Deep frying is a cooking method whereby food is submerged in hot oil or fat. ... It has been suggested that this article or section be merged with microwave oven. ...

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. Fructose (or levulose) is a simple sugar (monosaccharide) found in many foods and is one of the three most important blood sugars along with glucose and galactose. ...

Raw Material

New varieties of potatoes are being bred that produce less or no acrylamide. Binomial name Solanum tuberosum L. The potato (Solanum tuberosum) is a perennial plant of the Solanaceae, or nightshade, family, grown for its starchy tuber. ...

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. Vacuum fryers were originally developed for the potato chip production as they are fit to process low-quality potatoes that contain higher reducing sugar levels than normal, as they frequently have to be processed in spring and early summer before the potatoes from the new harvest become available. ... Silicones (more accurately called polymerized siloxanes or polysiloxanes) are inorganic-organic polymers with the chemical formula [R2SiO]n, where R = organic groups such as methyl, ethyl, and phenyl. ... For other uses, see FAT. Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water. ... The food industry is the complex, global collective of diverse businesses that together supply much of the food energy consumed by the world population. ...

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] Reproduction is the creation of one thing as a copy of, product of, or replacement for a similar thing, e. ... Human submaxillary gland. ... The mucous membranes (or mucosa) are linings of ectodermic origin, covered in epithelium, that line various body cavities and internal organs. ... For other uses, see Nose (disambiguation). ... Perspiration (also called sweating or sometimes transpiration) is the production and evaporation of a fluid, consisting primarily of water as well as a smaller amount of sodium chloride (the main constituent of table salt), that is excreted by the sweat glands in the skin of mammals. ... The tone or style of this article or section may not be appropriate for Wikipedia. ... For other uses, see Nausea (disambiguation). ... Myalgia means muscle pain and is a symptom of many diseases and disorders. ... Speech disorders or speech impediments, as they are also called, are a type of communication disorders where normal speech is disrupted. ... Paresthesia (paraesthesia in British) is a sensation of tingling, pricking, or numbness of the skin with no apparent physical cause, more generally known as the feeling of pins and needles. ... Paresthesia or paraesthesia (in British English) is a sensation of tingling, pricking, or numbness of a persons skin with no apparent long-term physical effect, more generally known as the feeling of pins and needles or of a limb being asleep (but not directly related to the phenomenon of... A neurotoxin is a toxin that acts specifically on nerve cells – neurons – usually by interacting with membrane proteins such as ion channels. ... // Intermediate filaments (IFs) are important structural proteins which are located both in the cytoplasm and the nucleus. ...

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] Also see: 2002 (number). ... is the 114th day of the year (115th in leap years) in the Gregorian calendar. ... Wikibooks Cookbook has an article on Baking Baking is the technique of prolonged cooking of food by dry heat acting by conduction, and not by radiation, normally in an oven, but also in hot ashes, or on hot stones. ... Plantains frying in vegetable oil. ... Saratoga chips Potato chips (British English or Hiberno-English: crisps) are slim slices of potatoes deep fried or baked until crisp. ... For other uses, see Bread (disambiguation). ... This article is about the food. ... The hazard symbol for carcinogenic chemicals in the Globally Harmonized System. ... Year 2005 (MMV) was a common year starting on Saturday (link displays full calendar) of the Gregorian calendar. ... is the 238th day of the year (239th in leap years) in the Gregorian calendar. ... Official language(s) English Capital Sacramento Largest city Los Angeles Largest metro area Greater Los Angeles Area  Ranked 3rd  - Total 158,302 sq mi (410,000 km²)  - Width 250 miles (400 km)  - Length 770 miles (1,240 km)  - % water 4. ... In most common law jurisdictions, the Attorney General is the main legal adviser to the government, and in some jurisdictions may in addition have executive responsibility for law enforcement or responsibility for public prosecutions. ... William Westwood Bill Lockyer (born May 8, 1941) is the current State Treasurer of California. ... French fried potatoes, commonly known as French fries or fries (North America) or chips (United Kingdom, Republic of Ireland and Commonwealth) are pieces of potato that have been chopped into batons and deep fried. ... Saratoga chips Potato chips (British English or Hiberno-English: crisps) are slim slices of potatoes deep fried or baked until crisp. ...

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

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

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

'Acrylamide and Food' The National Institute for Occupational Safety and Health (NIOSH) is the United States federal agency responsible for conducting research and making recommendations for the prevention of work-related injury and illness. ... “PDF” redirects here. ... IARC could mean: International Agency for Research on Cancer is part of the World Health Organization. ...

• 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