Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120082
Identification
Name: acrylamide
Description:A member of the class of acrylamides that results from the formal condensation of acrylic acid with ammonia.
Structure
Thumb
Synonyms:
  • 2-Propenamide
  • Acrylamide
  • acrylamide
  • Akrylamid
  • ethylenecarboxamide
Chemical Formula: C3H5NO
Average Molecular Weight: 71.079
Monoisotopic Molecular Weight: 71.03712
InChI Key: HRPVXLWXLXDGHG-UHFFFAOYSA-N
InChI:InChI=1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
CAS number: 79-06-1
IUPAC Name:prop-2-enamide
Traditional IUPAC Name: acrylamide
SMILES:C=CC(=O)N
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboximidic acids and derivatives
Direct Parent Carboximidic acids
Alternative Parents
Substituents
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 84.5 °C
Experimental Properties:
PropertyValueReference
Melting Point84.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility390 mg/mL at 25 °CNot Available
LogP-0.67HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility120.0 mg/mLALOGPS
logP-0.65ALOGPS
logP-0.27ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)16.7ChemAxon
pKa (Strongest Basic)0.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity19.11 m3·mol-1ChemAxon
Polarizability6.88 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-9000000000-7b30073e15256ba58af1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-9000000000-26ca703d558096e73e80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0kfx-9000000000-da086ba0e1b4f10d534fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-05dl-9000000000-2c812f3ba789fd949662View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0fbc-9000000000-133d475aa82b7785e9d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-05dl-9000000000-1a51b235c01925474be9View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Tareke E, Rydberg P, Karlsson P, Eriksson S, Törnqvist M (2002)Analysis of acrylamide, a carcinogen formed in heated foodstuffs. Journal of agricultural and food chemistry 50, Pubmed: 12166997
  • Adler ID, Baumgartner A, Gonda H, Friedman MA, Skerhut M (2000)1-Aminobenzotriazole inhibits acrylamide-induced dominant lethal effects in spermatids of male mice. Mutagenesis 15, Pubmed: 10719038
  • Lopachin RM, Decaprio AP (2005)Protein adduct formation as a molecular mechanism in neurotoxicity. Toxicological sciences : an official journal of the Society of Toxicology 86, Pubmed: 15901921
  • Besaratinia A, Pfeifer GP (2004)Genotoxicity of acrylamide and glycidamide. Journal of the National Cancer Institute 96, Pubmed: 15240786
  • Fan X, Mastovska K (2006)Effectiveness of ionizing radiation in reducing furan and acrylamide levels in foods. Journal of agricultural and food chemistry 54, Pubmed: 17032038
  • Turko IV, Sechi S (2007)Acrylamide--a cysteine alkylating reagent for quantitative proteomics. Methods in molecular biology (Clifton, N.J.) 359, Pubmed: 17484107
  • Besaratinia A, Pfeifer GP (2007)A review of mechanisms of acrylamide carcinogenicity. Carcinogenesis 28, Pubmed: 17234719
  • Zhang Y, Zhang Y (2007)Formation and reduction of acrylamide in Maillard reaction: a review based on the current state of knowledge. Critical reviews in food science and nutrition 47, Pubmed: 17558658
  • Hogervorst JG, Schouten LJ, Konings EJ, Goldbohm RA, van den Brandt PA (2008)Dietary acrylamide intake and the risk of renal cell, bladder, and prostate cancer. The American journal of clinical nutrition 87, Pubmed: 18469268
  • Ghanayem BI, Bai R, Burka LT (2009)Effect of dose volume on the toxicokinetics of acrylamide and its metabolites and 2-deoxy-D-glucose. Drug metabolism and disposition: the biological fate of chemicals 37, Pubmed: 19022940
  • Lineback DR, Coughlin JR, Stadler RH (2012)Acrylamide in foods: a review of the science and future considerations. Annual review of food science and technology 3, Pubmed: 22136129
  • Garey J, Paule MG (2010)Effects of chronic oral acrylamide exposure on incremental repeated acquisition (learning) task performance in Fischer 344 rats. Neurotoxicology and teratology 32, Pubmed: 19846048
  • Haase NU, Grothe KH, Matthäus B, Vosmann K, Lindhauer MG (2012)Acrylamide formation and antioxidant level in biscuits related to recipe and baking. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 29, Pubmed: 22784192
  • Segerbäck D, Calleman CJ, Schroeder JL, Costa LG, Faustman EM (1995)Formation of N-7-(2-carbamoyl-2-hydroxyethyl)guanine in DNA of the mouse and the rat following intraperitoneal administration of [14C]acrylamide. Carcinogenesis 16, Pubmed: 7767980
  • Garey J, Paule MG (2007)Effects of chronic low-dose acrylamide exposure on progressive ratio performance in adolescent rats. Neurotoxicology 28, Pubmed: 17720246
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
HMDBHMDB04296
CHEMSPIDER6331
CHEBI28619
PUBCHEM6579
LIGAND-CPDC01659
NCI7785