Record Information
Version1.0
Creation date2010-04-08 22:07:56 UTC
Update date2020-09-17 15:39:32 UTC
Primary IDFDB008134
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Methyl-2-butenal
Description3-Methyl-2-butenal, also known as senecialdehyde or 3,3-dimethylacrolein, 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. 3-Methyl-2-butenal is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Methyl-2-butenal exists in all living organisms, ranging from bacteria to humans. 3-Methyl-2-butenal is a sweet, almond, and brown tasting compound. Outside of the human body, 3-Methyl-2-butenal has been detected, but not quantified in, several different foods, such as wild celeries, chinese cinnamons, persimmons, cereals and cereal products, and beans. This could make 3-methyl-2-butenal a potential biomarker for the consumption of these foods. An enal consisting of but-2-ene with a methyl substituent at position 3 and an oxo group at position 1.
CAS Number107-86-8
Structure
Thumb
Synonyms
SynonymSource
3,3-Dimethyl-acrylaldehydeChEBI
3,3-DimethylacroleinChEBI
3-MethylcrotonaldehydeChEBI
beta,beta-DimethylacroleinChEBI
beta-MethylcrotonaldehydeChEBI
PrenalChEBI
SenecialdehydeChEBI
SenecioaldehydeChEBI
b,b-DimethylacroleinGenerator
Β,β-dimethylacroleinGenerator
b-MethylcrotonaldehydeGenerator
Β-methylcrotonaldehydeGenerator
3-Methylbut-2-enalHMDB
beta,beta-Dimethylacrylic aldehydeHMDB
2-Methyl-2-buten-4-alHMDB
3,3-DimethylacrylaldehydeHMDB
3-Methyl-2-buten-1-alHMDB
3-Methyl-2-butenalHMDB
3-Methyl-2-butenaldehydeHMDB
β,β-Dimethylacrylic aldehydeHMDB
β-methylcrotonaldehydebiospider
β,β-dimethylacroleinbiospider
2-Butenal, 3-methyl-biospider
3-methyl-2-butenal (prenal)biospider
3-Methylcrotonaldehyde, 8CIdb_source
Beta-methylcrotonaldehydebiospider
Beta,beta-dimethylacroleinbiospider
Beta,beta-dimethylacrylic aldehydebiospider
Crotonaldehyde, 3-methyl-biospider
Crotonaldehyde, 3-methyl- (8CI)biospider
FEMA 3646db_source
β-methylcrotonaldehydeGenerator
β,β-dimethylacroleinGenerator
Predicted Properties
PropertyValueSource
Water Solubility63.6 g/LALOGPS
logP0.97ALOGPS
logP1ChemAxon
logS-0.12ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.32 m³·mol⁻¹ChemAxon
Polarizability9.51 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H8O
IUPAC name3-methylbut-2-enal
InChI IdentifierInChI=1S/C5H8O/c1-5(2)3-4-6/h3-4H,1-2H3
InChI KeySEPQTYODOKLVSB-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CC=O
Average Molecular Weight84.1164
Monoisotopic Molecular Weight84.057514878
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 71.39%; H 9.59%; O 19.02%DFC
Melting PointNot Available
Boiling PointBp 132-133°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 0.87DFC
Refractive Indexn20D 1.4526DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a5c-9000000000-1ec92de58f3b78822176JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a5c-9000000000-1ec92de58f3b78822176JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-9000000000-5092b9dfda47020345edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-de8a6eec89362bfff45aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9000000000-0865f5d08c1ce95bdd58JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9000000000-32ba84192db5d33a736cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-392e24493caefed8d41dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-2568b7ba82ce5430fe4bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-1cc850ae9a5dbeac5dc7JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-003r-9000000000-259c3199037e112aa7efJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID54980
ChEMBL IDCHEMBL453815
KEGG Compound IDC15604
Pubchem Compound ID61020
Pubchem Substance IDNot Available
ChEBI ID15825
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12157
CRC / DFC (Dictionary of Food Compounds) IDDCL51-L:DCL51-L
EAFUS ID2270
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1037231
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pungent
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
brown
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
nutty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
almond
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cherry
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference