Showing Compound Card for Acrolein (CDB000549)

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Record Information
Version1.0
Created at2020-03-19 00:43:08 UTC
Updated at2020-12-07 19:07:31 UTC
CannabisDB IDCDB000549
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAcrolein
DescriptionAcrolein, also known as propenal or acrylic aldehyde, belongs to the class of organic compounds known as enals. These are alpha, beta unsaturated aldehydes, with the general chemical formula RC=C-CH=O in which the aldehydic C=O function is conjugated to the C=C double bond located at the alpha beta position. Acrolein 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. Acrolein 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. It is also used as an herbicide and algicide in water treatment. It can be produced by microorganisms, e.g. Clostridium perfringens. Acrolein is a relatively electrophilic compound and, due to its reactivity it shows high toxicity. It is a good Michael acceptor, making it a useful reaction tool 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 to 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. Acrolein has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Acrolein is found in fruit aromas, black tea, carrot, cooked potato, cheeses, white wine, hydrolyzed soy protein, turkey, pork, beef fat and other foods. Acrolein has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AcrylaldehydeChEBI
Acrylic aldehydeChEBI
PropenalChEBI
2-Propen-1-oneHMDB
2-PropenalHMDB, MeSH
2-PropenaldehydeHMDB
AcquiniteHMDB
AcraldehydeHMDB, MeSH
AcroleinaHMDB
Aldehyde, acrylicHMDB, MeSH
Aldehyde, allylHMDB, MeSH
Aldehyde, ethyleneHMDB, MeSH
Allyl aldehydeHMDB, MeSH
AqualinHMDB, MeSH
AqualineHMDB
BiocideHMDB
CH2=chchoHMDB
CroleanHMDB
Ethylene aldehydeHMDB, MeSH
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, HMDB
Chemical FormulaC3H4O
Average Molecular Weight56.06
Monoisotopic Molecular Weight56.0262
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
Description Belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Environmental role:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-87.7 °CNot Available
Boiling Point53 °CWikipedia
Water Solubility212 mg/mL at 25 °CNot Available
logP-0.01Not Available
Predicted Properties
PropertyValueSource
logP0.18ALOGPS
logP0.37ChemAxon
logS0.28ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16.37 m³·mol⁻¹ChemAxon
Polarizability5.58 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-056r-9000000000-34c0891db414206d2b402014-09-20View Spectrum
GC-MSAcrolein, non-derivatized, GC-MS Spectrumsplash10-0a4i-9000000000-f6aba25388da7855f3ebSpectrum
GC-MSAcrolein, non-derivatized, GC-MS Spectrumsplash10-004i-9000000000-a667e77a9d666459b411Spectrum
GC-MSAcrolein, non-derivatized, GC-MS Spectrumsplash10-0a4i-9000000000-f6aba25388da7855f3ebSpectrum
GC-MSAcrolein, non-derivatized, GC-MS Spectrumsplash10-004i-9000000000-a667e77a9d666459b411Spectrum
Predicted GC-MSAcrolein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a6r-9000000000-4a086c1c9c7836b7b307Spectrum
Predicted GC-MSAcrolein, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-cf50f66835baacbc5db42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-abefe6f7a672744326c12015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-32a4911454ef635f19ed2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-4740fe3b45257adba96a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-e578c9fb2097eb472d122015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-c28d7e42ec75bd010f502015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-af8a08e40e7604e1b1052021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-a0d6dd919aed0acdb7152021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-f12145ad941c7b169c502021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-23a60e5f52ca732e0f562021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-23a60e5f52ca732e0f562021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-23a60e5f52ca732e0f562021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0041822
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008307
KNApSAcK IDC00052796
Chemspider ID7559
KEGG Compound IDC01471
BioCyc IDACROLEIN
BiGG IDNot Available
Wikipedia LinkAcrolein
METLIN IDNot Available
PubChem Compound7847
PDB IDNot Available
ChEBI ID15368
References
General References
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  2. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]