Showing Compound Card for Methacrolein (CDB000632)

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Record Information
Version1.0
Created at2020-03-19 00:47:42 UTC
Updated at2020-11-18 16:35:21 UTC
CannabisDB IDCDB000632
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMethacrolein
DescriptionMethacrolein, also known as methacrylaldehyde, 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 a C=C double bond. It is a clear, colorless, flammable liquid. Methacrolein a major product from the reaction of isoprene with atmospheric OH, methyl vinyl ketone (MVK) being the other mayor product from that reaction ( Ref:DOI ). Both are important components of the atmospheric oxidation chemistry of biogenic chemicals. Methacrolein is highly irritating to the eyes, nose, throat and lungs. The primary industrial use of methacrolein is for the manufacture of synthetic resins and polymers. Methacrolein can naturally be found in the essential oil of the plant Big Sagebrush (Artemisia tridentata), which contains approximately 5% of methacrolein. Methacrolein has also been reported to be present in cigarette smoke. Furthermore, it has been reported to be a volatile component of cannabis samples (PMID: 26657499 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-MethylacroleinHMDB
MethacrylaldehydeHMDB
Chemical FormulaC4H6O
Average Molecular Weight70.09
Monoisotopic Molecular Weight70.0419
IUPAC Name2-methylprop-2-enal
Traditional Namemethacrolein
CAS Registry NumberNot Available
SMILES
CC(=C)C=O
InChI Identifier
InChI=1S/C4H6O/c1-4(2)3-5/h3H,1H2,2H3
InChI KeySTNJBCKSHOAVAJ-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 DescriptorsNot Available
Ontology
Disposition

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point−81 °CWikipedia
Boiling Point69 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.59ALOGPS
logP0.77ChemAxon
logS-0.06ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.72 m³·mol⁻¹ChemAxon
Polarizability7.48 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMethacrolein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9000000000-e9fce90afc0d563bb754Spectrum
Predicted GC-MSMethacrolein, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethacrolein, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-b09f171e7339d27f8a142016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-5fec8f83e1aea1a554092016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9000000000-1aaf49c3682bc4feff102016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-66bbd6afc3250c768fa92016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-9de313b3b845cb249c262016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-9000000000-6d875ba145f8c281d4222016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-1fe3e74f4451b5653b932021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-11b89cb85a2481163c362021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbc-9000000000-bc4b995c8394ef6a29172021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-2c321e49c0a9728673ee2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-7aa8a05bade372ff883d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-1104d40a7596119610cf2021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0061874
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethacrolein
METLIN IDNot Available
PubChem Compound6562
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. 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 ]