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Acrylamide information


Acrylamide
Names
Preferred IUPAC name
Prop-2-enamide[2]
Other names
Acrylamide
Acrylic amide[1]
Identifiers
CAS Number
  • 79-06-1 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:28619 checkY
ChEMBL
  • ChEMBL348107 checkY
ChemSpider
  • 6331 checkY
ECHA InfoCard 100.001.067 Edit this at Wikidata
IUPHAR/BPS
  • 4553
KEGG
  • C01659 checkY
PubChem CID
  • 6579
UNII
  • 20R035KLCI checkY
CompTox Dashboard (EPA)
  • DTXSID5020027 Edit this at Wikidata
InChI
  • InChI=1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5) checkY
    Key: HRPVXLWXLXDGHG-UHFFFAOYSA-N checkY
  • InChI=1/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
    Key: HRPVXLWXLXDGHG-UHFFFAOYAS
SMILES
  • O=C(C=C)N
  • C=CC(=O)N
Properties
Chemical formula
C3H5NO
Molar mass 71.079 g·mol−1
Appearance white crystalline solid, no odor[1]
Density 1.322 g/cm3
Melting point 84.5 °C (184.1 °F; 357.6 K)
Boiling point None (polymerization); decomposes at 175-300°C[1]
Solubility in water
390 g/L (25 °C)[3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
potential occupational carcinogen[1]
GHS labelling:
Pictograms
GHS06: ToxicGHS08: Health hazard[4]
Hazard statements
H301, H312, H315, H317, H319, H332, H340, H350, H361, H372[4]
Precautionary statements
P201, P280, P301+P310, P305+P351+P338, P308+P313[4]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
2
2
2
Flash point 138 °C (280 °F; 411 K)
Autoignition
temperature
424 °C (795 °F; 697 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
100-200 mg/kg (mammal, oral)
107 mg/kg (mouse, oral)
150 mg/kg (rabbit, oral)
150 mg/kg (guinea pig, oral)
124 mg/kg (rat, oral)[5]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 0.3 mg/m3 [skin][1]
REL (Recommended)
Ca TWA 0.03 mg/m3 [skin][1]
IDLH (Immediate danger)
60 mg/m3[1]
Safety data sheet (SDS) ICSC 0091
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Acrylamide (or acrylic amide) is an organic compound with the chemical formula CH2=CHC(O)NH2. It is a white odorless solid, soluble in water and several organic solvents. From the chemistry perspective, acrylamide is a vinyl-substituted primary amide (CONH2). It is produced industrially mainly as a precursor to polyacrylamides, which find many uses as water-soluble thickeners and flocculation agents.[6]

Acrylamide forms in burnt areas of food, particularly starchy foods like potatoes, when cooked with high heat, above 120 °C (248 °F).[7] Despite health scares following its discovery in 2002, and its possible classification as a carcinogen, acrylamide from diet is thought unlikely to cause cancer in humans; Cancer Research UK categorized the idea that burnt food causes cancer as a "myth".[8][9]

  1. ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0012". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 842. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  3. ^ "Human Metabolome Database: Showing metabocard for Acrylamide (HMDB0004296)".
  4. ^ a b c Sigma-Aldrich Co., Acrylamide. Retrieved on 2022-02-15.
  5. ^ Cite error: The named reference idlh was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Ull was invoked but never defined (see the help page).
  7. ^ "Does burnt food give you cancer?". University of Birmingham. Retrieved 2022-09-30.
  8. ^ Cite error: The named reference acs was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference cruk was invoked but never defined (see the help page).

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Acrylamide (or acrylic amide) is an organic compound with the chemical formula CH2=CHC(O)NH2. It is a white odorless solid, soluble in water and several...

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formation of acrylamide molecules (C3H5NO) by nitrile hydratase. Acrylamide monomer is in a powder state before addition of water. Acrylamide is toxic to...

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industry's recipes. At high temperatures, a probable carcinogen called acrylamide can form. This can be discouraged by heating at a lower temperature, adding...

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Postum

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versions have been introduced. When tested by the FDA, Postum had more acrylamide than any other product, by dry weight. Lost Eyesight through Coffee Drinking...

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Shallow frying

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highly increased the acrylamide content in foods like potatoes and grains to a similar degree. Roasting the same potatoes kept acrylamide production comparatively...

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Potato chip

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levels of acrylamide, which is listed by California since the 1990s as a carcinogen. These companies paid fines and agreed to reduce acrylamide levels to...

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Gel electrophoresis

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concentrations of acrylamide and bis-acrylamide powder used in creating a gel. Care must be used when creating this type of gel, as acrylamide is a potent neurotoxin...

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Polyacrylamide

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precursor acrylamide is a neurotoxin and carcinogen. Thus, concerns naturally center on the possibility that polyacrylamide is contaminated with acrylamide. Considerable...

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French fries

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some of the highest levels of acrylamides of any foodstuff, and experts have raised concerns about the effects of acrylamides on human health. According...

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Polyquaternium

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chloride-hydroxyethyl cellulose copolymer Polyquaternium-5 Copolymer of acrylamide and quaternized dimethylammoniumethyl methacrylate Polyquaternium-6...

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(approximately 130 °C (266 °F)), the formation of suspected carcinogen acrylamide is significantly lower than in standard atmospheric fryers, where the...

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Bread

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leavening, bread can be defined as a foam, or a gas-in-solid solution. Acrylamide, like in other starchy foods that have been heated higher than 120 °C...

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value of food. One example of a toxic product of the Maillard reaction is acrylamide, a neurotoxin and possible carcinogen that is formed from free asparagine...

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List of cooking appliances

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stoves C. Granda; R. G. Moreira; S. E. Tichy (October 2004). "Reduction of Acrylamide Formation in Potato Chips by Low-temperature Vacuum Frying". Journal of...

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Ontbijtkoek

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Netherlands. It has been found that ontbijtkoek can contain high levels of acrylamide, which was once regarded as a potential carcinogen. Gingerbread Coffee...

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Acrylonitrile

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manufacture of acrylamide and acrylic acid. Hydrogenation of acrylonitrile is one route to propionitrile. Hydrolysis with sulfuric acid gives acrylamide sulfate...

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Asparagine

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carbonyls produces acrylamide in food. These products occur in baked goods such as French fries, potato chips, and toasted bread. Acrylamide is converted in...

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Potato

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qualities and leads to higher acrylamide levels in the cooked product, especially in deep-fried dishes. The discovery of acrylamides in starchy foods in 2002...

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Furylfuramide isomerase

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(E)-2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide ⇌ {\displaystyle \rightleftharpoons } (Z)-2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide Hence, this enzyme has one substrate...

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Glycidamide

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glycidamide forms from acrylamide. The acrylamide is generated by pyrolysis of proteins rich in asparagine. Oxidation of acrylamide, catalyzed by the enzyme...

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Kettle Foods

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levels of acrylamide, a carcinogen. Kettle Foods paid $350,000 in civil penalties and costs and agreed to cut their potato chips' levels of acrylamide to 275...

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Cooking

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until a toasted crust is formed generates significant concentrations of acrylamide. This discovery in 2002 led to international health concerns. Subsequent...

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Soil conditioner

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polyacrylamide is as a chemical intermediate in the production of N-methylol acrylamide and N-butoxyacrylamide. The most common use of soil conditioners is to...

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Microwave oven

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acrylamide in potatoes, however unlike deep-frying, it is of only limited effectiveness in reducing glycoalkaloid (i.e., solanine) levels. Acrylamide...

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Biotransformation

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and water as substrates, nitrile hydratase enzymes are used to produce acrylamide, a valued monomer.[citation needed] Many kinds of fuels and lubricants...

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UN number

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transport. Some hazardous substances have their own UN numbers (e.g. acrylamide has UN 2074), while sometimes groups of chemicals or products with similar...

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Food browning

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amino acid (asparagine here) and the carbonyl carbon of the sugar (glucose). The end product is acrylamide. For more information, visit Maillard reaction....

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