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News About Acrylamide

14-September-2008 18:38:37 - Acrylamide Acrylamide IUPAC name prop-2-enamide Identifiers CAS number 79-06-1 SMILES C=CC=ON Properties Molecular formula C3H5NO Isomers 71.078061 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 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. 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 that had been heated production of acrylamide in the heating process was shown to be temperature-dependent.1 It was not found in food that had been boiled12 nor in foods that were not heated.1 Contents 1 Laboratory Use 2 Prepared Foods 2.1 Raw, Dried, and Pickled Foods 2.2 Tobacco 2.3 Beverages 2.4 Cooking Methods that Affect Acrylamide Production 3 Reduction of acrylamide formation 3.1 Storage 3.2 Raw Material 3.3 Production methods 3.4 Recipe formulation 4 Published articles on the potential health risks to humans 4.1 Inhaled, absorbed or ingested acrylamide 4.2 British Journal of Cancer 4.3 Cancer, Epidemiology, Biomarkers Prevention 4.4 Heat-generated Food Toxicants HEATOX 4.5 International Journal of Cancer 4.6 Journal of the American Medical Association 4.7 World Health Organization 5 Safe levels of Acrylamide 6 Public awareness 7 See also 8 References 9 External links Laboratory Use Polyacrylamide was first used in a laboratory setting in the early 1950s. In 1959 two independent groups published papers; Davis and Ornstein, and Raymond and Weintraub on the use of polyacrylamide gel electrophoresis to separate charged molecules3. 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. 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. Many laboratory supply companies sell LPA as a commercial product for just this use. 4 Prepared Foods Acrylamide levels appear to rise as food is heated for longer periods of time. Though researchers are still unsure of the precise mechanisms by which acrylamide forms in foods, many believe it is a byproduct of the Maillard reaction. In fried or baked goods, acrylamide may be produced by the reaction between asparagine and reducing sugars fructose, glucose, etc. or reactive carbonyls at temperatures above 120 °C 248 °F.56 A study by the USFDA proposed a mechanism that involves asparagine which, when heated in the presence of glucose, forms acrylamide. Based on current stage of knowledge, acrylamide is a natural byproduct that forms when certain carbohydrate-rich foods are fried, baked, or roasted at high temperatures above 120 °C. Acrylamide can cause cancer in laboratory animals at high doses, although it is not clear whether it causes cancer in humans at the much lower levels found in food. 7 Raw, Dried, and Pickled Foods Acrylamide in olives, prunes, and dried pears8 develops through another process. Genetics professor Joe Cummins suggests a link between acrylamide and herbicides such as glyphosate Roundup, citing studies which show that heat and light can decompose polyacrylamide, the thickening agent used in commercial herbicides, into acrylamide.9 Tobacco Cigarette smoking is also a major acrylamide source.10 Beverages Estimates for the proportion of acrylamide in adults' diet coming from the consumption of coffee range from twenty to forty percent; prune juice has a high concentration of acrylamide, though adults consume it in far smaller quantities.11 Cooking Methods that Affect Acrylamide Production 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 foods may produce large amounts of acrylamide. Acrylamides can also be created during microwaving. 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 The Confederation of the Food and Drink Industries in the EU CIAA has published a number of brochures to help people reduce the amount of acrylamide formed in their food. They offer a general acrylamide toolbox as well as publications specific to reducing the acrylamide in biscuits, crackers crispbreads, bread products, breakfast cereals, potato crisps chips, and French fries. Storage In the case of potatoes for instance the storage temperature should not drop below 8 °C 46 °F. When the temperature is as low as 4 °C 39 °F 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. 12 Published articles on the potential health risks to humans Inhaled, absorbed or ingested acrylamide 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.1314 Ingested acrylamide is metabolised to a chemically reactive epoxide, glycidamide.15 British Journal of Cancer In 2003, the British Journal of Cancer published an article titled Dietary acrylamide and cancer of the large bowel, kidney, and bladder: Absence of an association in a population-based study in Sweden. The article was based on a study led by L A Mucci that reanalysed a population-based Swedish case-control study encompassing cases with cancer of the large bowel, bladder and kidney, and 538 healthy controls. Researchers assessed the impact of dietary acrylamide by linking extensive food frequency data with acrylamide levels in certain food items recorded by the Swedish National Food Administration. Unconditional logistic regression was used to estimate odds ratios, adjusting for potential confounders. Dr. Mucci's group found consistently a lack of an excess risk, or any convincing trend, of cancer of the bowel, bladder, or kidney in high consumers of 14 different food items with a high range 300-1200 mug kg-1 or moderate range 30-299 mug kg-1 acrylamide content. Dr. Mucci's group was surprised by one finding, writing Unexpectedly, an inverse trend was found for large bowel cancer P for trend 0.01 with a 40% reduced risk in the highest compared to lowest quartile. Sounding a note of cautious optimism, the article concludes We found reassuring evidence that dietary exposure to acrylamide in amounts typically ingested by Swedish adults in certain foods has no measurable impact on risk of three major types of cancer. It should be noted, however, that relation of risk to the acrylamide content of all foods could not be studied. 16 Cancer, Epidemiology, Biomarkers Prevention A number of studies pertaining to acrylamide have appeared in various issues of Cancer, Epidemiology, Biomarkers Prevention. Two of the more germane are Prospective Study of Dietary Acrylamide Intake and the Risk of Endometrial, Ovarian, and Breast Cancer and Toxicokinetics of Acrylamide in Humans after Ingestion of a Defined Dose in a Test Meal to Improve Risk Assessment for Acrylamide Carcinogenicity. The first study was led by Dr. Janneke G. Hogervorst and included 62,573 women, aged 55-69 years. The acrylamide intake of subcohort members and cases was assessed with a food frequency questionnaire and was based on chemical analysis of all relevant Dutch foods. Subgroup analyses were done for never-smokers to eliminate the influence of smoking; an important source of acrylamide. After 11.3 years of follow-up, the researchers observed 327, 300, and 1,835 cases of endometrial, ovarian, and breast cancer, respectively. Hogervorst's group concluded that his subjects faced increased risks of postmenopausal endometrial and ovarian cancer with increasing dietary acrylamide intake, particularly among never-smokers. Risk of breast cancer was not associated with acrylamide intake. 17 The second study was led by Dr. Uwe Fuhr and sought to evaluate the how much of the acrylamide humans eat is absorbed into the body. The study consisted of six young healthy volunteers consuming a meal containing 0.94 mg of acrylamide and then providing urine was for up to 72 hours thereafter. Fuhr's group concluded that most of the acrylamide ingested with food is absorbed in humans. 18 Heat-generated Food Toxicants HEATOX The Heat-generated Food Toxicants HEATOX Project was a multidisciplinary research project involving 24 partners in 14 countries. It ran from late 2003 to early 2007. Its objectives were to estimate health risks that may be associated with hazardous compounds in heat-treated food ; and find cooking/processing methods which minimise the amounts of these compounds, thereby providing safe, nutritious and high-quality food-stuffs.19 Its final report is located here. Unlike more academic studies, HEATOX sought also to provide consumers with advice on how to lower their intake of acrylamide. The group recommends that National authorities highlight the following: Potatoes low in sugar Low sugar potato varieties Maintenance of suitable storage temperature during the supply chain Low sugar levels in prefabricated potato products for domestic frying. Best frying temperature Frying temperature in the range 145 to 170 °C 293 to 338 °F for deep frying potatoes. Clear and accurate cooking instruction on the package of pre-fried products. Clear and accurate instruction for fryers for domestic use. Golden, not brown! French fries and roast potatoes cooked to a golden-yellow rather than golden-brown colour. Bread toasted to the lightest colour acceptable. 19 International Journal of Cancer In March, 2003, the International Journal of Cancer published an article with the forthright title Fried potatoes and human cancer. The article reported on a study conducted between 1991 - 2000 in Italy and Switzerland that analyzed the risk of cancer of the oral cavity and pharynx, esophagus, larynx, large bowel, breast and ovaries. It was led by Claudio Pelucchi whose team found reassuring evidence for the lack of an important association between consumption of fried/baked potatoes and cancer risk.20 More recently, in January, 2008, one of the HEATOX members published Acrylamide exposure and incidence of breast cancer among postmenopausal women in the Danish Diet, Cancer and Health Study. The article addresses a study led by Dr. PT Olesen of the National Food Institute, Technical University of Denmark. The abstract to the study states So far, epidemiological studies have not shown any association between human cancer risk and dietary exposure to acrylamide. The purpose of this study was to conduct a nested case control study within a prospective cohort study on the association between breast cancer and exposure to acrylamide using biomarkers. The study found that after adjustment for smoking behavior. . . a positive association was seen between acrylamide-hemoglobin levels and estrogen receptor positive breast cancer. . . . A weak association between glycidamide hemoglobin levels and incidence of estrogen receptor positive breast cancer was also found, this association, however, entirely disappeared when acrylamide and glycidamide hemoglobin levels were mutually adjusted. 21 Journal of the American Medical Association The March 15, 2005 issue of the Journal of the American Medical Association JAMA contained an article titled Acrylamide Intake and Breast Cancer Risk in Swedish Women, written by Lorelei A. Mucci, ScD, MPH. The study cohort consisted of 43,404 Swedish women in the Women's Lifestyle and Health Cohort. The women's greatest single source of acrylamide was from coffee 54% of intake, fried potatoes 12% of intake, and crisp bread 9% of intake. The study concluded Compared with the lowest quintile of acrylamide intake, there was no significantly increased risk of breast cancer in the higher quintiles and no evidence of a linear dose response. For quintile 5 compared with quintile 1, the relative risk was 1.19 95% confidence interval, 0.91-1.55. Furthermore, there was no association between breast cancer risk and higher intake of any specific foods including coffee, fried potatoes, and crisp bread. 22 World Health Organization The World Health Organization WHO has set up a clearinghouse for information about acrylamide that includes database of researchers/data providers; References for research published elsewhere; Information updates about the current status of research efforts; and updates on information relevant to the health risk of acrylamide in food. One question the site's FAQ addresses is whether there can be an acceptable level of acrylamide in food. The WHO states that Acrylamide belongs to the group of chemicals thought to have no reliably identifiable 'threshold' of effects, meaning that very low concentrations will also result in very low risks, but not in zero risk: some risk is always present when the chemical is ingested. However, for these carcinogens, risk is thought to increase with increasing exposure. Very low risks even of cancer, such as those that are less than one in one million, are considered to be acceptable to some consumers. To others this is unacceptable. The important pre-requisite for any decision is, however a clear picture of the nature and level of the risk, as well as the potential for lowering this level. This clear picture does not exist for acrylamide at present. 23 Safe levels of Acrylamide In June of 2002, the Food and Agriculture Organization of the United Nations FAO and the World Health Organization WHO issued a report about the health implications of acrylamide in food. After study, the Consultation concluded that the no observed adverse effect level NOAEL for acrylamide neuropathy is 0.5 mg/kg body weight/day and the NOAEL for fertility changes is four times higher than for peripheral neuropathy. The study continued, On the basis of current knowledge, controlling for peripheral neuropathy is expected to control for effects on fertility. The estimated average chronic human dietary intake is in the order of 1 μg/kg body weight/day. This provides a margin between exposure and the NOAEL of 500. 24 Hence, a woman weighing 132 pounds about 60 kg could safely consume 30mg of acrylamide daily; a man weighing 180 pounds about 82 kg, about 41 mg; a child weighing 40 pounds about 18 kg, 9 mg. 25 Referring to the chart below for the amount of acrylamide in foods, in a single day, the child can eat 13 KG 28 pounds of French fried potatoes, the woman can drink 86 KG 23 gallons of prune juice, and the man can eat 29 KG 63 pounds of oven baked potatoes and each of them will have ingested less than 50 percent of the NOAEL of acrylamide. Food AA Concentration μg/kg Portion Size g AA μg per Portion French Fries OB 697.8 70 48.8 Prune Juice 174 140 24.4 French Fries RF 333.7 70 23.3 Postum 93 240 22.3 Potato Chips 545.9 30 16.4 Canned Black Olives 550 15 8.2 Breakfast Cereal 131 55 7.3 Brewed Coffee 8.5 240 3.2 adapted from Table: Top Eight Foods by Acrylamide Per Portion, page 17 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. 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.26 The lawsuit was settled on 2008-08-01 with the food producers agreeing to cut acrylamide levels in half.27 In 2007, more than 100 articles were written about acrylamide, according to Nexis and Factiva, including pieces in the LA Times28, the Boston Globe 29, the Guardian30, and the Wall Street Journal, among others. Of these articles, nearly half appeared in November and December, when people were frying potatoes for latkes, and roasting pigs and turkeys. On August 1, 2008, four food manufacturers - H.J. Heinz Co., Frito-Lay, Kettle Foods Inc., and Lance Inc. - agreed to reduce levels of Acrylamide in their products such as potato chips and French fries over a three-year period and pay a combined $3 million in fines as a settlement with the California attorney general's office. California had sued these four companies in 2005, alleging they violated a state requirement that companies post warning labels on products with carcinogens.31 See also Acrydite- research on this compound casts light on Acrylamide Deep-frying Deep fryer Vacuum fryer References ^ a b c Tareke E, Rydberg P. et al. 2002. Analysis of acrylamide, a carcinogen formed in heated foodstuffs. J. Agric. Food. Chem. 50 17: 4998-5006. PMID 12166997. ^ Food Standards Agency, Acrylamide: your questions answered 1 Retrieved on 2008-01-01 ^ Reynolds S, Weintraub L. 1959. Acrylamide Gel as a Supporting Medium for Zone Electrophoresis. Science 130 3377: 711. PMID 14436634. ^ Linear Polyacrylamide as a commercially sold DNA carrier.2 ^ Mottram DS, Wedzicha BL. and Dodson AT. 2002. Acrylamide is formed in the Maillard reaction. Nature 419 6906: 448-449. PMID 12368844. ^ Chemistry World, Acrylamide cancer link confirmed 3 Retrieved on 2008-01-01 ^ Acrylamide in Foods: A Review and Update ^ Acrylamide in dried Fruits ^ Cummins, Joe 2002-08-01. Acrylamide In Cooked Foods: The Glyphosate Connection. Institute of Science in Society. Retrieved on 2008-08-20. ^ http://cebp.aacrjournals.org/cgi/content/abstract/16/11/2471 Assessment of the Relation between Biomarkers for Smoking and Biomarkers for Acrylamide Exposure in Humans ^ page 17 Top Eight Foods by Acrylamide Per Portion ^ 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. ^ Kuperman AS. 1958. Effects of acrylamide on the central nervous system of the cat. J. Pharmacol. Exp. Ther. 123 3: 182-192. PMID 13564393. ^ Alberts, Lewis, Johnson, Raff, Roberts, and Walter ,Molecular Biology of the Cell, 4th ion, Routledge, March, 2002, ISBN 0-8153-3218-1 ^ 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 ^ Dietary acrylamide and cancer of the large bowel, kidney, and bladder: Absence of an association in a population-based study in Sweden. ^ A Prospective Study of Dietary Acrylamide Intake and the Risk of Endometrial, Ovarian, and Breast Cancer ^ Toxicokinetics of Acrylamide in Humans after Ingestion of a Defined Dose in a Test Meal to Improve Risk Assessment for Acrylamide Carcinogenicity ^ a b http://www.slv.se/upload/heatox/documents/D62_final_project_leaflet_.pdf ^ Fried potatoes and human cancer ^ Acrylamide exposure and incidence of breast cancer among postmenopausal women in the Danish Diet, Cancer and Health Study. ^ Acrylamide Intake and Breast Cancer Risk in Swedish Women, ^ WHO | Frequently asked questions - acrylamide in food ^ FAO/WHO Consultation on the Health Implications of Acrylamide in Food; Geneva, 25-27 June 2002, Summary Report ^ for these and all other unit conversions, see this ^ Office of the attorney general, State of California, Department of justice 5 Retrieved on 2008-01-01 ^ Lawsuit over potato chip ingredients settled 6 Retrieved on 2008-08-02 ^ KFC to tell diners of chemical in potatoes - Los Angeles Times ^ Does a chemical formed in cooking french fries really cause cancer? - The Boston Globe ^ The question: Is cooked food dangerous? | Science | The Guardian ^ Settlement will reduce carcinogens in potato chips. Associated Press. Retrieved on 2008-08-02. External links Acrylamide Infonet California Wants to Serve a Warning With Fries Center for Food Safety and Nutrition cfsan.fda.gov FAQ Court case about a suspected acrylamide poisoning Environmental Protection Agency Acrylamide and Food EPA releases a Toxicological Review of Acrylamide External Review Draft for public comment - 01/2008 Girls who eat chips more likely to get breast cancer 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 IARC Monograph Acrylamide. Information about Acrylamide from www.foodrisk.org International Chemical Safety Card 0091 Institut national de recherche et de sécurité 1992. Acrylamide.PDF Fiche toxicologique n° 119. Paris:INRS. French National Pollutant Inventory - Acrylamide NIOSH Pocket Guide to Chemical Hazards 0012 Prospective study of dietary acrylamide and risk of colorectal cancer among women Report about acrylamide in food and cancer risks World Health Organization Retrieved from http://en..org/wiki/Acrylamide Categories: Amides | Hazardous air pollutants | IARC Group 2A carcinogens | Monomers Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية Dansk Deutsch Español Français Italiano Nederlands 日本語 ‪Norsk bokmål‬ Polski Português Svenska ไทย 中文 This page was last modified on 4 September 2008, at 18:43

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