Citizendia

Acrylamide
IUPAC nameprop-2-enamide
Identifiers
CAS number[79-06-1]
SMILESC=CC(=O)N
Properties
Molecular formulaC3H5NO
Molar mass71. 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 They are also referred to A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 08 g/mol
Density1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 13 g/cm³
Melting point

84. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 5 °C

Boiling point

- (polymerization)

Solubility in water204 g/100 ml (25 °C)
Hazards
EU classificationToxic (T)
Carc. Cat. 2
Muta. Cat. 2
Repr. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid In Polymer chemistry, polymerization is a process of reacting Monomer Molecules together in a Chemical reaction to form three-dimensional networks Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. 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 The term carcinogen refers to any substance Radionuclide or radiation that is an agent directly involved in the promotion of Cancer or in the fatation of its propagation In Biology, a mutagen ( Latin, literally origin of change) is a physical or chemical agent that changes the genetic information (usually DNA) Cat. 3
EU Index616-003-00-0
NFPA 704
2
3
2
 
R-phrasesR45, R46, R20/21,
R25, R36/38, R43,
R48/23/24/25, R62
S-phrasesS53, S45
Flash point138 °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. Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning 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. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air The autoignition temperature or kindling point of a substance is the lowest temperature at which it will spontaneously ignite in a normal atmosphere without an external In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. In Chemistry, an amide is one of three kinds of Compounds (sometimes called acid amide the organic Functional group characterized A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Its IUPAC name is 2-propenamide. The International Union of Pure and Applied Chemistry ( IUPAC) (aɪjuːpæk or ay-yoo-pec) is an international Non-governmental organization It is a white odourless crystalline solid, soluble in water, ethanol, ether and chloroform. In Materials science, a crystal is a Solid in which the constituent Atoms Molecules or Ions are packed in a regularly ordered repeating Water ( H2[[oxygen O]] H OH) is the most abundant Molecule on Earth 's surface composing of about 70% of the Earth's surface as Diethyl ether, also known as ether and ethoxyethane, is a clear colorless and highly Flammable liquid with a low Boiling point and a Chloroform, also known as trichloromethane and methyl trichloride, is a Chemical compound with formula C[[Hydrogen H]] Cl 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. Ammonia is a compound with the formula N[[hydrogen H3]] It is normally encountered as a Gas with a characteristic pungent Odor Carbon monoxide, with the chemical formula CO is a colorless odorless tasteless yet highly toxic Gas. Carbon dioxide ( Chemical formula:) is a Chemical compound composed of two Oxygen Atoms covalently bonded to a single Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14

Most acrylamide is used to synthesize polyacrylamides which find many uses as water-soluble thickeners. Polyacrylamide ( IUPAC poly(2-propenamide or poly(1-carbamoylethylene) is a polymer (-CH2CHCONH2- formed from Acrylamide Thickening agents, or thickeners, are substances which when added to an aqueous mixture increase its Viscosity without substantially modifying its other properties These include use in wastewater treatment, gel electrophoresis (SDS-PAGE), papermaking, ore processing, and the manufacture of permanent press fabrics. Distinguish from Wastwater (a lake in the Lake District in northwest England SDS-PAGE, Sodium dodecyl sulfate Polyacrylamide gel Electrophoresis, is a technique widely used in Biochemistry, forensics Papermaking is the process of making Paper, a material which is used ubiquitously today for writing and packaging An ore is a volume of rock containing components or Minerals in a mode of occurrence that renders it valuable for mining A permanent press is a fabric that has been chemically processed to resist Wrinkles and hold its shape Some acrylamide is used in the manufacture of dyes and the manufacture of other monomers. A dye can generally be described as a Colored substance that has an affinity to the substrate to which it is being applied A monomer (from Greek mono "one" and meros "part" is a small Molecule that may become chemically bonded to other

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 that had been heated (production of acrylamide in the heating process was shown to be temperature-dependent). Starch, CAS # 9005-25-8 Chemical formula (C6H10O5n is a Polysaccharide A potato chip or crisp is a thin slice of Potato, deep fried or baked until Crisp. French fries ( North American English; sometimes not capitalized chips ( British English) fries or French-fried potatoes (formal [1] It was not found in food which had been boiled[1][2] nor in foods that were not heated. [1]

Contents

Laboratory Use

Polyacrylamide was first used in a laboratory setting in the early 1950s. The 1950s Decade refers to the years of 1950 to 1959 inclusive In 1959 two independent groups published papers; Davis and Ornstein, and Raymond and Weintraub) on the use of polyacrylamide gel electrophoresis to separate charged molecules[3]. SDS-PAGE, Sodium dodecyl sulfate Polyacrylamide gel Electrophoresis, is a technique widely used in Biochemistry, forensics In Chemistry, a molecule is defined as a sufficiently stable electrically neutral group of at least two Atoms in a definite arrangement held together by Unfortunately, the Davis publication is no longer available online, although references to it can be found in numerous successive papers. The technique is widely accepted today, and is still an extremely common protocol in molecular biology labs. In the Natural sciences a protocol is a predefined written procedural method in the design and implementation of Experiments. Molecular biology is the study of Biology at a molecular level

Acrylamide also has many other uses in the modern molecular biology laboratory, including the use of linear polyacrylamide (LPA) as a carrier which aids in the precipitation of small amounts of DNA. Deoxyribonucleic acid ( DNA) is a Nucleic acid that contains the genetic instructions used in the development and functioning of all known Many laboratory supply companies sell LPA as a commercial product for just this use. [4]

Occurrence in daily lifestyle

Acrylamide in fried or baked goods is produced by the reaction between asparagine and reducing sugars (fructose, glucose, etc. Frying is the Cooking of food in Oil or Fat, a technique that originated in ancient Egypt around 2500BC Baking is the technique of prolonged Cooking of Food by dry heat acting by conduction, and not by radiation, normally in an Oven, Asparagine (abbreviated as Asn or N; Asx or B represent either asparagine or Aspartic acid) is one of the 20 most common natural A reducing sugar is any sugar that in basic solution forms some Aldehyde or Ketone. Fructose (also levulose or laevulose) is a simple reducing Sugar ( Monosaccharide) found in many foods and is one of the three Glucose (Glc a Monosaccharide (or simple Sugar) also known as grape sugar, is an important Carbohydrate in Biology. ) or reactive carbonyls at temperatures above 120oC. In Organic chemistry, a carbonyl group is a Functional group composed of a Carbon Atom double-bonded to an Oxygen [5][6] Acrylamide in olives and prune juice comes through another process. The Olive ( Olea europaea) is a Species of small Tree in the family Oleaceae, native to the coastal areas of the eastern A plum or gage is a stone fruit Tree in the genus Prunus, subgenus Prunus. It has been suggested that environmental pathways, such as the breakdown of the herbicide glyphosate (Roundup), are sources too. A herbicide is used to kill unwanted Plants Selective herbicides kill specific targets while leaving the desired Crop relatively unharmed Glyphosate (N-(phosphonomethyl glycine is a non-selective Systemic Herbicide, absorbed through the leaves injected into the bole or applied to the stump of Smoking is also a major acrylamide producer. Tobacco Smoking is the inhalation of smoke from burned dried or cured leaves of the Tobacco plant most often in the form of a Cigarette. Estimates for the proportion in the diet coming from the consumption of coffee range from twenty to forty percent. CoFFEE is an Open source Software for computer supported collaborative learning (CSCL in a digital classroom 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. The Maillard reaction is a Chemical reaction between an Amino acid and a Reducing sugar, usually requiring Heat. Baking is the technique of prolonged Cooking of Food by dry heat acting by conduction, and not by radiation, normally in an Oven, Frying is the Cooking of food in Oil or Fat, a technique that originated in ancient Egypt around 2500BC Deep frying is a Cooking method in which food is submerged in hot oil or Fat. Acrylamides can also be created during microwaving. A microwave oven, or a microwave, is a Kitchen appliance that cooks or heats Food by Dielectric heating.

The FDA has analyzed a variety of U. S. food products for levels of acrylamide since 2002, these results can be found here.

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 (also levulose or laevulose) is a simple reducing Sugar ( Monosaccharide) found in many foods and is one of the three

Raw Material

New varieties of potatoes are being bred that produce less or no acrylamide. The potato is a Starchy Tuberous crop Vegetable from the perennial Solanum tuberosum of the Solanaceae

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. A Vacuum fryer is a Deep-frying device originally developed for Potato chip production When silicone is used as a foam inhibitor in deep-frying fats in the food industry the acrylamide content is doubled. Silicones are largely inert compounds with a wide variety of forms and uses 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. Asparaginase ( is an Enzyme that catalyzes the Hydrolysis of Asparagine to Aspartic acid. [7]

Potential health risk

There is evidence that exposure to large doses can cause damage to the male reproductive glands. Reproduction is the Biological process by which new individual Organisms are produced A gland is an organ in an animal's body that synthesizes a substance for release such as Hormones or Breast milk, often into the Bloodstream Direct exposure to pure acrylamide by inhalation, skin absorption, or eye contact irritates the exposed mucous membranes, e. The mucous membranes (or mucosae; singular mucosa) are linings of mostly endodermal origin covered in Epithelium, which are involved in g. the nose, and can also cause sweating, urinary incontinence, nausea, myalgia, speech disorders, numbness, paresthesia, and weakened legs and hands. Anatomically a nose is a protuberance in Vertebrates that houses the Nostrils or nares which admit and expel air for respiration in conjunction with the Urinary incontinence ( UI) is any involuntary leakage of Urine. Nausea ( Latin: Nausea, Greek:, " Sea-sickness " also called wamble) is the sensation of unease and discomfort 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 (pron /ˌpɛɹɪsˈθiʒə/ paraesthesia in British English, pron Paresthesia (pron /ˌpɛɹɪsˈθiʒə/ paraesthesia in British English, pron In addition, the acrylamide monomer is a potent neurotoxin, causing the disassembly or rearrangement of intermediate filaments. 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 cytoskeletal structures formed by members of a family of related proteins called Keratin. [8][9] Ingested acrylamide is metabolised to a chemically reactive epoxide, glycidamide. An epoxide is a cyclic Ether with only three ring atoms This ring approximately is an Equilateral triangle, i [10]

Cancer

Acrylamide reliably produces various types of cancer in experimental mice and rats. Cancer (medical term Malignant Neoplasm) is a class of Diseases in which a group of cells display uncontrolled [11][12][13] 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. A Dutch study on 62000 women over an 11 year period has recently concluded that those who ingest more acrylamide in their regular diet are twice as likely to develop endometrial or ovarian cancer. Endometrial cancer refers to several types of malignancy which arise from the Endometrium, or lining of the Uterus. Ovarian cancer is a cancerous growth arising from an Ovary. The cancer most commonly forms in the lining of the ovary (resulting in epithelial [14]

Public awareness

On April 24, 2002, 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. Events 1479 BC - Thutmose III ascends to the throne of Egypt, although power effectively shifts to Hatshepsut (according to See also 2002 (disambiguation Year 2002 ( MMII) was a Common year starting on Tuesday of the Gregorian calendar. Baking is the technique of prolonged Cooking of Food by dry heat acting by conduction, and not by radiation, normally in an Oven, Frying is the Cooking of food in Oil or Fat, a technique that originated in ancient Egypt around 2500BC Food is any substance usually composed primarily of Carbohydrates Fats water and/or Proteins that can be eaten or drunk by an A potato chip or crisp is a thin slice of Potato, deep fried or baked until Crisp. Bread is a Staple food prepared by Baking a Dough of Flour and Water. In the United States and Canada, a cookie is a small flat-baked treat usually round containing milk flour eggs and sugar etc Concern was raised mainly because of the carcinogenic effects of acrylamide. The term carcinogen refers to any substance Radionuclide or radiation that is an agent directly involved in the promotion of Cancer or in the fatation of its propagation 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. Year 2005 ( MMV) was a Common year starting on Saturday (link displays full calendar of the Gregorian calendar. Events 1071 - Battle of Manzikert: The Seljuk Turks defeat the Byzantine Army at Manzikert. California ( is a US state on the West Coast of the United States, along the Pacific Ocean. In most Common law jurisdictions the Attorney General, or Attorney-General, is the main legal advisor to the government and in some jurisdictions may in addition William Westwood Lockyer (born May 8 1941) is the current State Treasurer of California. French fries ( North American English; sometimes not capitalized chips ( British English) fries or French-fried potatoes (formal A potato chip or crisp is a thin slice of Potato, deep fried or baked until Crisp. [15]

See also

References

  1. ^ a b c Tareke E, Rydberg P. Acrydite is a Phosphoramidite that allows the synthesis of Oligonucleotides with a methacryl group at the 5' end (less commonly 3' or internal Deep frying is a Cooking method in which food is submerged in hot oil or Fat. A deep fryer (or frier) is a Kitchen appliance used for Deep-frying. A Vacuum fryer is a Deep-frying device originally developed for Potato chip production et al. (2002). "Analysis of acrylamide, a carcinogen formed in heated foodstuffs". J. Agric. Food. Chem. 50 (17): 4998-5006. doi:10.1021/jf020302f. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 12166997.  
  2. ^ Food Standards Agency, Acrylamide: your questions answered [1] Retrieved on 2008-01-01
  3. ^ Reynolds S, Weintraub L. 2008 ( MMVIII) is the current year in accordance with the Gregorian calendar, a Leap year that started on Tuesday of the Common New Year See also New Year The Ancient Romans began their consular year on January 1st since 153 BC (1959). "Acrylamide Gel as a Supporting Medium for Zone Electrophoresis". Science 130 (3377): 711. PMID 14436634.  
  4. ^ Linear Polyacrylamide as a commercially sold DNA carrier. [2]
  5. ^ Mottram DS, Wedzicha BL. and Dodson AT. (2002). "Acrylamide is formed in the Maillard reaction". Nature 419 (6906): 448-449. doi:10.1038/419448a. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 12368844.  
  6. ^ Chemistry World, Acrylamide cancer link confirmed [3] Retrieved on 2008-01-01
  7. ^ KORNBRUST, B. 2008 ( MMVIII) is the current year in accordance with the Gregorian calendar, a Leap year that started on Tuesday of the Common New Year See also New Year The Ancient Romans began their consular year on January 1st since 153 BC 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.  
  8. ^ Kuperman AS. (1958). "Effects of acrylamide on the central nervous system of the cat". J. Pharmacol. Exp. Ther. 123 (3): 182-192. PMID 13564393.  
  9. ^ Alberts, Lewis, Johnson, Raff, Roberts, and Walter ,Molecular Biology of the Cell, 4th Edition, Routledge, March, 2002, ISBN 0-8153-3218-1
  10. ^ Joint FAO/WHO expert committee on food additives, Sixty-fourth meeting, Rome, 8-17 February 2005, Summary and conclusions. [4] Retrieved on 2008-01-01
  11. ^ Rice, Jerry M (2005). 2008 ( MMVIII) is the current year in accordance with the Gregorian calendar, a Leap year that started on Tuesday of the Common New Year See also New Year The Ancient Romans began their consular year on January 1st since 153 BC "The carcinogenicity of acrylamide". Mutation Research/Genetic Toxicology and Environmental Mutagenesis 580 (1-2): 3-20. doi:10.1016/j.mrgentox.2004.09.008. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 15668103.  
  12. ^ Bull RJ, Robinson M, et al. (1984). "Carcinogenic effects of acrylamide in Sencar and A/J mice". Cancer. Res. 44 (1): 107-111. PMID 6360343.  
  13. ^ Johnson KA, Gorzinski SJ, et al. (1986). "Chronic toxicity and oncogenicity study on acrylamide incorporated in the drinking water of Fischer 344 rats". Toxicol. Appl. Pharmacol. 85 (2): 154-168. doi:10.1016/0041-008X(86)90109-2. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 3764902.  
  14. ^ Hogervorst JG, Schouten LJ, et al. (2007). "A prospective study of dietary acrylamide intake and the risk of endometrial, ovarian, and breast cancer". Cancer. Epidemiol. Biomarkers. Prev. 16 (11): 2304-2313. doi:10.1158/1055-9965.EPI-07-0581. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 18006919.  
  15. ^ Office of the attorney general, State of California, Department of justice [5] Retrieved on 2008-01-01

External links

iArc is internationally awarded Architects practice based in Seoul, South Korea, led by four partners Kerl Yoo AIA Insoo Park KIRA Jeongim Kim and

Dictionary

acrylamide

-noun

  1. (organic chemistry) The amide of acrylic acid, CH2=CH.CONH2; used in the manufacture of polyacrylamides.
© 2009 citizendia.org; parts available under the terms of GNU Free Documentation License, from http://en.wikipedia.org
 Dapyx Software network: MP3 Explorer | Ebook Manager | Zenithic