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Record Information
Version3.6
Creation Date2012-09-13 11:41:02 UTC
Update Date2017-03-02 21:45:47 UTC
HMDB IDHMDB41822
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcrolein
DescriptionAcrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colourless liquid with a piercing, disagreeable, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat breaking down into acrolein. It is produced industrially from propylene and mainly used as a biocide and a building block to other chemical compounds, such as the amino acid methionine. Acrolein is used as an etherification agent in the preparation of modified food starches. Acrolein is an herbicide and algicide used in water treatment. It is produced by microorganisms, e.g. Clostridium perfringens. Acrolein is a relatively electrophilic compound and a reactive one, hence its high toxicity. It is a good Michael acceptor, hence its useful reaction with thiols. It forms acetals readily, a prominent one being the spirocycle derived from pentaerythritol, diallylidene pentaerythritol. Acrolein participates in many Diels-Alder reactions, even with itself. Via Diels-Alder reactions, it is a precursor to some commercial fragrances, including lyral, norbornene-2-carboxaldehyde, and myrac aldehyde. Acrolein is toxic and is a strong irritant for the skin, eyes, and nasal passages. The main metabolic pathway for acrolein is the alkylation of glutathione. The WHO suggests a 'tolerable oral acrolein intake' of 7.5 mg/day per kilogram of body weight. Although acrolein occurs in French fries, the levels are only a few micrograms per kilogram.
Structure
Thumb
Synonyms
ValueSource
AcrylaldehydeChEBI
Acrylic aldehydeChEBI
PropenalChEBI
2-Propen-1-oneHMDB
2-PropenalHMDB
2-PropenaldehydeHMDB
AcquiniteHMDB
AcraldehydeHMDB
AcroleinaHMDB
Aldehyde, acrylicHMDB
Aldehyde, allylHMDB
Aldehyde, ethyleneHMDB
Allyl aldehydeHMDB
AqualinHMDB
AqualineHMDB
BiocideHMDB
CH2=chchoHMDB
CroleanHMDB
Ethylene aldehydeHMDB
MagnacideHMDB
Magnacide HHMDB
Magnacide H and bHMDB
PapiteHMDB
Prop-2-en-1-alHMDB
Prop-2-enalHMDB
PropenaldehydeHMDB
Propylene aldehydeHMDB
SlimicideHMDB
trans-Acrolein formylethyleneHMDB
2 PropenalMeSH
Chemical FormulaC3H4O
Average Molecular Weight56.0633
Monoisotopic Molecular Weight56.02621475
IUPAC Nameprop-2-enal
Traditional Nameacrolein
CAS Registry Number107-02-8
SMILES
C=CC=O
InChI Identifier
InChI=1S/C3H4O/c1-2-3-4/h2-3H,1H2
InChI KeyHGINCPLSRVDWNT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentEnals
Alternative Parents
Substituents
  • Enal
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Toxin/Pollutant
Biofunction
  • Waste products
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-87.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility212 mg/mL at 25 °CNot Available
LogP-0.01Not Available
Predicted Properties
PropertyValueSource
Water Solubility107.0 mg/mLALOGPS
logP0.18ALOGPS
logP0.37ChemAxon
logS0.28ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16.37 m3·mol-1ChemAxon
Polarizability5.58 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-0a4i-9000000000-f6aba25388da7855f3ebView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-004i-9000000000-a667e77a9d666459b411View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-cf50f66835baacbc5db4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-abefe6f7a672744326c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-32a4911454ef635f19edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-4740fe3b45257adba96aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-e578c9fb2097eb472d12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-c28d7e42ec75bd010f50View in MoNA
MSMass Spectrum (Electron Ionization)splash10-056r-9000000000-34c0891db414206d2b40View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Cyclophosphamide Metabolism PathwaySMP00604Not Available
Cyclophosphamide PathwaySMP00447Not Available
Ifosfamide Metabolism PathwaySMP00605Not Available
Ifosfamide PathwaySMP00448Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    BloodDetected and Quantified30.32 +/- 8.92 uMAdult (>18 years old)BothNormal details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Newborn (0-30 days old)Both
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      BiofluidStatusValueAgeSexConditionReferenceDetails
      BloodDetected and Quantified180.15 uMAdult (>18 years old)Bothuremia details
      FecesDetected but not Quantified Adult (>18 years old)Both
      Campylobacter jejuni infection
      details
      FecesDetected but not Quantified Adult (>18 years old)Both
      Clostridium difficile infection
      details
      FecesDetected but not Quantified Adult (>18 years old)Both
      Nonalcoholic fatty liver disease (NAFLD)
      details
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDNot Available
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDFDB008307
      KNApSAcK IDNot Available
      Chemspider ID7559
      KEGG Compound IDC01471
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia Linkacrolein
      NuGOwiki LinkHMDB41822
      Metagene LinkHMDB41822
      METLIN IDNot Available
      PubChem Compound7847
      PDB IDNot Available
      ChEBI ID15368
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Download (PDF)
      General ReferencesNot Available