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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:44:37 UTC
Update Date2023-02-21 17:21:06 UTC
HMDB IDHMDB0031647
Secondary Accession Numbers
  • HMDB31647
Metabolite Identification
Common NameAcrylic acid
DescriptionAcrylic acid, also known as 2-propenoic acid or acrylate, belongs to the class of organic compounds known as acrylic acids. These are organic compounds containing acrylic acid CH2=CHCO2H. Acrylic acid exists in all living organisms, ranging from bacteria to humans. Acrylic acid has been detected, but not quantified in, pineapples (Ananas comosus). This could make acrylic acid a potential biomarker for the consumption of these foods. Acrylic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Acrylic acid.
Structure
Data?1677000066
Synonyms
ValueSource
2-Propenoic acidChEBI
Acroleic acidChEBI
AcrylateChEBI
Ethylenecarboxylic acidChEBI
PropenoateChEBI
Propenoic acidChEBI
Vinylformic acidChEBI
Polyacrylic acidKegg
Carbopol 1342Kegg
2-PropenoateGenerator
AcroleateGenerator
EthylenecarboxylateGenerator
VinylformateGenerator
PolyacrylateGenerator
HystoacrilMeSH
Acrylic acid, ca (2:1) saltMeSH
Acrylic acid, ca (2:1) salt, dihydrateMeSH
Acrylic acid, fe (3+) saltMeSH
Acrylic acid, aluminum saltMeSH
Acrylic acid, ammonium saltMeSH
Acrylic acid, cobalt (2+) saltMeSH
Acrylic acid, magnesium saltMeSH
Acrylic acid, potassium saltMeSH
Acrylic acid, silver saltMeSH
Acrylic acid, sodium saltMeSH
Acrylic acid, zinc saltMeSH
Magnesium acrylateMeSH
Prop-2-enoic acidHMDB
Propene acidHMDB
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
Description 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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point13 °CNot Available
Boiling Point141.20 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mLNot Available
LogP0.35Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+112.09331661259
DarkChem[M-H]-104.15231661259
DeepCCS[M+H]+119.89930932474
DeepCCS[M-H]-117.46330932474
DeepCCS[M-2H]-153.48130932474
DeepCCS[M+Na]+128.03830932474
AllCCS[M+H]+121.532859911
AllCCS[M+H-H2O]+116.932859911
AllCCS[M+NH4]+125.832859911
AllCCS[M+Na]+127.032859911
AllCCS[M-H]-127.932859911
AllCCS[M+Na-2H]-133.532859911
AllCCS[M+HCOO]-139.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.43 minutes32390414
Predicted by Siyang on May 30, 202210.1302 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.49 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid163.5 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1104.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid402.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid136.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid299.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid109.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid317.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid403.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)335.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid753.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid218.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid924.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid261.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid333.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate671.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA338.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water192.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Acrylic acidOC(=O)C=C1704.4Standard polar33892256
Acrylic acidOC(=O)C=C778.7Standard non polar33892256
Acrylic acidOC(=O)C=C710.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acrylic acid,1TMS,isomer #1C=CC(=O)O[Si](C)(C)C814.3Semi standard non polar33892256
Acrylic acid,1TBDMS,isomer #1C=CC(=O)O[Si](C)(C)C(C)(C)C1049.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Acrylic acid EI-B (Non-derivatized)splash10-00b9-9000000000-ebdb7274700971cd6f142017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acrylic acid EI-B (Non-derivatized)splash10-00b9-9000000000-ebdb7274700971cd6f142018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acrylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-0699bc1a72211c124b602017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acrylic acid GC-MS (1 TMS) - 70eV, Positivesplash10-05di-9100000000-9bb15bc91b0dbc41366e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acrylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Acrylic acid LC-ESI-QQ , negative-QTOFsplash10-00di-9000000000-cc4e478e1301778cd7852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acrylic acid LC-ESI-QQ , negative-QTOFsplash10-00di-9000000000-e516a2a0fc66993edc392017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylic acid 10V, Positive-QTOFsplash10-05fr-9000000000-03ea2b65243048d48e732016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylic acid 20V, Positive-QTOFsplash10-0adi-9000000000-930c69d5a821060550f72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylic acid 40V, Positive-QTOFsplash10-004i-9000000000-325d5750ffad7fd1e4db2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylic acid 10V, Negative-QTOFsplash10-00di-9000000000-1692fe79b4f0bd127e1a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylic acid 20V, Negative-QTOFsplash10-00di-9000000000-145a2180b79b5fc678c82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylic acid 40V, Negative-QTOFsplash10-0udi-9000000000-8ef27af021e3e37a326d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylic acid 10V, Negative-QTOFsplash10-00di-9000000000-85ee1d7f8db31720e3cf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylic acid 20V, Negative-QTOFsplash10-00di-9000000000-85ee1d7f8db31720e3cf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylic acid 40V, Negative-QTOFsplash10-00di-9000000000-4e32b50451337c7993fb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylic acid 10V, Positive-QTOFsplash10-0a4i-9000000000-03b32f0d2a31bee0e6172021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylic acid 20V, Positive-QTOFsplash10-0a4i-9000000000-03b32f0d2a31bee0e6172021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-03b32f0d2a31bee0e6172021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB008302
KNApSAcK IDC00034423
Chemspider ID6333
KEGG Compound IDC19501
BioCyc IDMY149879
BiGG IDNot Available
Wikipedia LinkAcrylic_acid
METLIN IDNot Available
PubChem Compound6581
PDB IDNot Available
ChEBI ID18308
Food Biomarker OntologyNot Available
VMH IDACRYL
MarkerDB IDNot Available
Good Scents IDrw1216141
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
  2. (). EAFUS: Everything Added to Food in the United States.. .