File:Acrylamide-2D-skeletal.png · Wikimedia Commons · See Wikimedia Commons
acrylamide
Sign in to saveAlso known as ethylenecarboxamide, prop-2-enamide
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.
OverviewAI-generated
Acrylamide is a chemical compound with the formula C₃H₅NO and an IUPAC name of prop-2-enamide. It has a molecular mass of 71.037 and a density of 1.12. The substance melts at 184 and decomposes at 572. Its vapor pressure is 0.007, and it has a flash point of 280 and an autoignition temperature of 424. Acrylamide is soluble at a level of 216.
Safety data for acrylamide includes an immediately dangerous to life or health level of 60. The median lethal dose (LD50) is 1150. Exposure limits are set at a time-weighted average of 0.3 and a short-term limit of 0.9. The compound has an ionization energy of 9.5.
In computational chemistry, acrylamide has a canonical SMILES notation of C=CC(=O)N. It possesses one hydrogen bond donor and one hydrogen bond acceptor, with a topological polar surface area of 43.1 and an xlogp of -0.7. The compound carries a charge of 0.
Synthesized by Vinony from 32 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C3H5NO
- Molecular weight
- 71.08 g/mol
- IUPAC name
- prop-2-enamide
- SMILES
- C=CC(=O)N
- InChIKey
- HRPVXLWXLXDGHG-UHFFFAOYSA-N
- XLogP
- -0.7
- Polar surface area
- 43.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
23,188 papers- Acrylamide.IARC monographs on the evaluation of carcinogenic risks to humans · 1994
- Acrylamide in food products and the role of electrochemical biosensors in its detection: a comprehensive review.Analytical methods : advancing methods and applications · 2024
- Acrylamide: its metabolism, developmental and reproductive effects, genotoxicity, and carcinogenicity.Mutation research · 1988
- Acrylamide neurotoxicity: neurological, morhological and molecular endpoints in animal models.Advances in experimental medicine and biology · 2005
- Acrylamide formation in food: a mechanistic perspective.Journal of AOAC International · 2005
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 71.037
- Image
- Acrylamid.jpg
- Autonomy
- 424
Show 16 more facts
- Commons category
- Acrylamide
- chemical formula
- C₃H₅NO
- immediately dangerous to life or health
- 60
- NIOSH Pocket Guide ID
- 0012
- density
- 1.12
- melting point
- 84.5
- decomposition point
- 347
- vapor pressure
- 0.007
- flash point
- 280
- solubility
- 216
- ionization energy
- 9.5
- time-weighted average exposure limit
- 0.05
- median lethal dose (LD50)
- 280
- short-term exposure limit
- 0.1
- canonical SMILES
- C=CC(=O)N
- MCN code
- 2924.19.31
Sources (9)
via Wikidata · CC0
~8 min read
Encyclopedic overview
14 sectionsContents
- Production
- Uses
- Toxicity and carcinogenicity
- Europe
- United States
- Opinions of health organizations
- Hazards
- Mechanism of action
- Occurrence in food
- Occurrence in cigarettes
- See also
- References
- Further reading
- External links
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.
Acrylamide forms in burnt areas of food, particularly starchy foods like potatoes, when cooked with high heat, above . Despite health scares following this discovery in 2002, and its classification as a probable carcinogen, there is ongoing debate as to whether acrylamide consumed through diet is likely to cause cancer in humans; Cancer Research UK categorized the idea that eating burnt food causes cancer as a myth.
Excerpted from Wikipedia’s “acrylamide” article, available under the CC BY-SA 4.0 licence.