Record Information
Version1.0
Creation date2010-04-08 22:07:56 UTC
Update date2018-01-23 19:01:35 UTC
Primary IDFDB008134
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Methyl-2-butenal
DescriptionPresent in blackberry, grape brandy, cocoa, currants, baked potato, tea, costmary and white bread. Flavouring ingredient 3-Methyl-2-butenal is derivative of acrolein that is an alpha, beta unsaturated carbonyl metabolite. It can be formed endogenously during lipid peroxidation or after oxidative stress, and is considered to play an important role in human carcinogenesis. The endogenously formed acroleins are a constant source of DNA damage, can lead to mutation and can also induce tumors in humans. (PMID: 8319634); 3-methyl-2-butenal, which is an unsaturated aldehyde bearing substitution at the alkene terminus, is a poor inactivator of the enzymes protein tyrosine phosphatases (PTPs). The inactivation of PTPs can yield profound biological consequences arising from the disruption of cellular signaling pathways (PMID: 17655273). 3-Methyl-2-butenal is found in many foods, some of which are macadamia nut, sweet bay, annual wild rice, and calabash.
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
β-methylcrotonaldehydebiospider
β,β-dimethylacroleinbiospider
2-Butenal, 3-methyl-biospider
3-methyl-2-butenal (prenal)biospider
3-Methylcrotonaldehyde, 8CIdb_source
3,3-Dimethylacrylaldehydebiospider
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
Bioavailability1ChemAxon
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
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 Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a5c-9000000000-1ec92de58f3b78822176View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a5c-9000000000-1ec92de58f3b78822176View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-9000000000-5092b9dfda47020345edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-de8a6eec89362bfff45aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9000000000-0865f5d08c1ce95bdd58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9000000000-32ba84192db5d33a736cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-392e24493caefed8d41dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-2568b7ba82ce5430fe4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-1cc850ae9a5dbeac5dc7View in MoNA
MSMass Spectrum (Electron Ionization)splash10-003r-9000000000-259c3199037e112aa7efView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
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
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