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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:44:37 UTC
Update Date2017-12-20 20:30:55 UTC
HMDB IDHMDB0031647
Secondary Accession Numbers
  • HMDB31647
Metabolite Identification
Common NameAcrylic acid
DescriptionAcrylic acid, also known as acrylate or propenoic acid, is a member of the class of compounds known as acrylic acids. Acrylic acids are organic compounds containing acrylic acid CH2=CHCO2H. Thus, acrylic acid is considered to be a fatty acid lipid molecule. Acrylic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Acrylic acid can be found in pineapple, which makes acrylic acid a potential biomarker for the consumption of this food product. Acrylic acid can be found primarily in saliva. In humans, acrylic acid is involved in few metabolic pathways, which include cyclophosphamide metabolism pathway, cyclophosphamide pathway, ifosfamide metabolism pathway, and ifosfamide pathway. Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually (Wikipedia). Polyacrylic acid, sodium salt is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]").
Structure
Thumb
Synonyms
ValueSource
2-Propenoic acidChEBI
Acroleic acidChEBI
AcrylateChEBI
Ethylenecarboxylic acidChEBI
PropenoateChEBI
Propenoic acidChEBI
Vinylformic acidChEBI
2-PropenoateGenerator
AcroleateGenerator
EthylenecarboxylateGenerator
VinylformateGenerator
Prop-2-enoic acidHMDB
Propene acidHMDB
Acrylic acid, magnesium saltMeSH
Acrylic acid, ca (2:1) saltMeSH
Acrylic acid, ca (2:1) salt, dihydrateMeSH
HystoacrilMeSH
Acrylic acid, fe (3+) saltMeSH
Acrylic acid, aluminum saltMeSH
Acrylic acid, ammonium saltMeSH
Acrylic acid, sodium saltMeSH
Acrylic acid, cobalt (2+) saltMeSH
Acrylic acid, potassium saltMeSH
Acrylic acid, silver saltMeSH
Acrylic acid, zinc saltMeSH
Chemical FormulaC3H4O2
Average Molecular Weight72.0627
Monoisotopic Molecular Weight72.021129372
IUPAC Nameprop-2-enoic acid
Traditional Nameacrylic acid
CAS Registry Number79-10-7
SMILES
OC(=O)C=C
InChI Identifier
InChI=1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5)
InChI KeyNIXOWILDQLNWCW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acrylic acids. These are organic compounds containing acrylic acid CH2=CHCO2H.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAcrylic acids and derivatives
Direct ParentAcrylic acids
Alternative Parents
Substituents
  • Acrylic acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Environmental role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point13 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP0.35Not Available
Predicted Properties
PropertyValueSource
Water Solubility123 g/LALOGPS
logP0.46ALOGPS
logP0.53ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)4.72ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.29 m³·mol⁻¹ChemAxon
Polarizability6.38 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00b9-9000000000-ebdb7274700971cd6f14View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-0699bc1a72211c124b60View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05di-9100000000-9bb15bc91b0dbc41366eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-cc4e478e1301778cd785View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-e516a2a0fc66993edc39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-9000000000-03ea2b65243048d48e73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adi-9000000000-930c69d5a821060550f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-325d5750ffad7fd1e4dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-1692fe79b4f0bd127e1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-145a2180b79b5fc678c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9000000000-8ef27af021e3e37a326dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Saliva
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Cyclophosphamide Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Cyclophosphamide Metabolism PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Ifosfamide Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Ifosfamide Metabolism PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02579
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010091
KNApSAcK IDNot Available
Chemspider ID6333
KEGG Compound IDC19501
BioCyc IDMY149879
BiGG IDNot Available
Wikipedia LinkAcrylic_acid
METLIN IDNot Available
PubChem Compound6581
PDB IDAKR
ChEBI ID18308
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). EAFUS: Everything Added to Food in the United States.. .