3-METHYL-2-BUTENAL (CED0012179)

Record Information
Version1.0
Creation Date2016-05-19 02:14:48 UTC
Update Date2026-04-16 21:12:20 UTC
Accession NumberCHEM006522
Identification
Common Name3-METHYL-2-BUTENAL
ClassSmall Molecule
Description
3-METHYL-2-BUTENAL belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds. This organic oxygen compound has the chemical formula C5H8O and an average molecular weight of 84.12 g/mol. Industrially, it is utilized as a fragrance, as well as a flavouring and nutrient. The compound is recorded in six different sources. It is found in household cleaning and consumer products, specifically bleaching agents and cigar cigarettes, and is present in drinking water and water supply systems. It is also detected in indoor air, dust, and atmospheric transport, as well as in auxiliary devices within electrical and electronic equipment. Additionally, it is associated with food, cookware, and food processing, specifically within fermentation processes for beer. Recorded routes of exposure include inhalation and oral ingestion. Regarding plastics, 3-METHYL-2-BUTENAL has been detected in polyethylene terephthalate, although it was not detected in low-density polyethylene.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC5H8O
Average Molecular Mass84.116 g/mol
Monoisotopic Mass84.058 g/mol
CAS Registry Number107-86-8
IUPAC Name3-methylbut-2-enal
Traditional Nameprenal
SMILESCC(C)=CC=O
InChI IdentifierInChI=1S/C5H8O/c1-5(2)3-4-6/h3-4H,1-2H3
InChI KeySEPQTYODOKLVSB-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0a5c-9000000000-1ec92de58f3b78822176Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a5c-9000000000-1ec92de58f3b78822176Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-053u-9000000000-5092b9dfda47020345edNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9000000000-de8a6eec89362bfff45aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-9000000000-0865f5d08c1ce95bdd58Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gbc-9000000000-32ba84192db5d33a736cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-392e24493caefed8d41dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-2568b7ba82ce5430fe4bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-9000000000-1cc850ae9a5dbeac5dc7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-bb5ff4f4247f9b92d7b4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-c6adf8b427f15f31188aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-44aeba383c0994cb6326Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-1fe8bbf8f6ab17ae0b2bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-6b3dd865845396e5b217Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-9000000000-9b4ce98aee0a57ea1914Not AvailableView Spectrum
MSMS Spectrumsplash10-003r-9000000000-259c3199037e112aa7efNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1072.0Log mg/kg[600:1900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
19Indoor airAir, dust & atmospheric transportNot Available
115Drinking waterDrinking water & water supplyNot Available
490Personal care & cosmeticsNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
604Pest AttractantsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureProtein-S-isoprenylcysteine O-methyltransferaseQ9WVM4Rattus norvegicusPredicted (SEA)6.61718
Click to view 3D structureProtein-S-isoprenylcysteine O-methyltransferaseP32584Saccharomyces cerevisiae S288cPredicted (SEA)9.6533
Alpha-synuclein structureClick to view 3D structureAlpha-synucleinP37840HumansPredicted (SEA)2216.76
Amyloid-beta precursor protein structureClick to view 3D structureAmyloid-beta precursor proteinP05067HumansPredicted (SEA)6458.53
All-trans-retinol dehydrogenase [NAD(+)] ADH7 structureClick to view 3D structureAll-trans-retinol dehydrogenase [NAD(+)] ADH7P40394HumansPredicted (SEA)82.6759
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)7724.9
Macrophage scavenger receptor types I and II structureClick to view 3D structureMacrophage scavenger receptor types I and IIP21757HumansPredicted (SEA)42.2721
Transient receptor potential cation channel subfamily A member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily A member 1O75762HumansPredicted (SEA)6920.95
Click to view 3D structureSqualene epoxidaseA7L861Sus scrofaPredicted (SEA)7.70707
Nuclear factor erythroid 2-related factor 2 structureClick to view 3D structureNuclear factor erythroid 2-related factor 2Q16236HumansPredicted (SEA)1848.61
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)7406.57
Click to view 3D structureSqualene synthase ERG9P29704Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast)Predicted (SEA)12.1445
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abP0DTD1SARS-CoV-2Predicted (SEA)7658.73
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)7648.76
Click to view 3D structureGlutamate receptor ionotropic, kainate 4Q01812Rattus norvegicusPredicted (SEA)33.0081
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)7426.97
Pyruvate kinase PKM structureClick to view 3D structurePyruvate kinase PKMP14618HumansPredicted (SEA)4105.53
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)7564.84
Tissue factor structureClick to view 3D structureTissue factorP13726HumansPredicted (SEA)4370.07
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)7628.37
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)7642.07
Aldo-keto reductase family 1 member B1 structureClick to view 3D structureAldo-keto reductase family 1 member B1P15121HumansPredicted (SEA)6577.79
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)7630.47
Click to view 3D structureTransient receptor potential cation channel subfamily A member 1Q6RI86Rattus norvegicusPredicted (SEA)6844.11
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)7628.29
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0012157
FooDB IDFDB008134
Phenol Explorer IDNot Available
KNApSAcK IDC00052688
BiGG IDNot Available
BioCyc IDPRENAL
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID54980
ChEBI ID15825
PubChem Compound ID61020
Kegg Compound IDC15604
YMDB IDNot Available
ECMDB IDM2MDB005795
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1120289
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24254865
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=8319634
4. Eder E, Hoffman C, Sporer S, Scheckenbach S: Biomonitoring studies and susceptibility markers for acrolein congeners and allylic and benzyl compounds. Environ Health Perspect. 1993 Mar;99:245-7.
5. Seiner DR, LaButti JN, Gates KS: Kinetics and mechanism of protein tyrosine phosphatase 1B inactivation by acrolein. Chem Res Toxicol. 2007 Sep;20(9):1315-20. Epub 2007 Jul 27.