Record Information
Version1.0
Creation date2010-04-08 22:07:57 UTC
Update date2019-11-26 03:02:14 UTC
Primary IDFDB008178
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Methyl-3-penten-2-one, 9CI
Description4-Methyl-3-penten-2-one, 9CI, also known as isopropylidene acetone or (CH3)2C=chc(=o)CH3, belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. Thus, 4-methyl-3-penten-2-one, 9CI is considered to be an oxygenated hydrocarbon lipid molecule. 4-Methyl-3-penten-2-one, 9CI is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Methyl-3-penten-2-one, 9CI is a sweet, acrylic, and chemical tasting compound. 4-Methyl-3-penten-2-one, 9CI has been detected, but not quantified in, several different foods, such as yellow bell peppers, red bell peppers, green bell peppers, pepper (c. frutescens), and herbs and spices. This could make 4-methyl-3-penten-2-one, 9CI a potential biomarker for the consumption of these foods. 4-Methyl-3-penten-2-one, 9CI is a potentially toxic compound. 4-Methyl-3-penten-2-one, 9CI, with regard to humans, has been linked to the inborn metabolic disorder celiac disease.
CAS Number141-79-7
Structure
Thumb
Synonyms
SynonymSource
(CH3)2C=chc(=o)CH3HMDB
1-Methylpent-2-en-4-oneHMDB
2,2-Dimethylvinyl methyl ketoneHMDB
2-Methyl-2-penten-4-oneHMDB
2-Methyl-2-pentenone-4HMDB
2-Methyl-4-oxo-2-penteneHMDB
3-Isohexen-2-oneHMDB
3-PENTEN,2-one,4-methyl mesityloxideHMDB
4-Methyl-3-penten-2-ONHMDB
4-Methyl-3-penten-2-oneHMDB
4-Methyl-3-penten-2-one (mesityl oxide)HMDB
4-Methyl-3-pentene-2-oneHMDB
4-Methylpent-3-en-2-oneHMDB
4-Metil-3-penten-2-oneHMDB
FEMA 3368HMDB
Isobutenyl methyl ketoneHMDB
Isopropylidene acetoneHMDB
Isopropylidene-acetoneHMDB
IsopropylideneacetoneHMDB
Mesityl oxideHMDB
MesityloxidHMDB
MesityloxydeHMDB
Methyl 2,2-dimethylvinyl ketoneHMDB
Methyl 2-methyl-1-propenyl ketoneHMDB
Methyl isobutenyl ketoneHMDB
Ossido di mesitileHMDB
Oxyde de mesityleHMDB
(CH3)2C=CHC(=O)CH3biospider
3-Penten-2-one, 4-methyl-biospider
3-PENTEN,2-ONE,4-METHYL MESITYLOXIDEbiospider
4-Methyl-3-penten-2-onbiospider
4-methyl-3-penten-2-one (mesityl oxide)biospider
Acetone, isopropylidene-biospider
Mesityl oxide [UN1229] [Flammable liquid]biospider
Mesityloxid(german)biospider
Predicted Properties
PropertyValueSource
Water Solubility20.5 g/LALOGPS
logP1.01ALOGPS
logP1.49ChemAxon
logS-0.68ALOGPS
pKa (Strongest Acidic)19.78ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity30.8 m³·mol⁻¹ChemAxon
Polarizability11.52 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H10O
IUPAC name4-methylpent-3-en-2-one
InChI IdentifierInChI=1S/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3
InChI KeySHOJXDKTYKFBRD-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CC(C)=O
Average Molecular Weight98.143
Monoisotopic Molecular Weight98.073164942
Classification
Description belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentEnones
Alternative Parents
Substituents
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.43%; H 10.27%; O 16.30%DFC
Melting PointMp -41.5° (-59°)DFC
Boiling PointBp37 50°DFC
Experimental Water Solubility28.9 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKapKa 0.25 (25°, 0.2M HClO4)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd254 0.85DFC
Refractive Indexn13D 1.4484DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a7i-9000000000-3661666f8de0c561e186JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a7l-9000000000-3abe2bd4b3b37c4ed2ccJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a7i-9000000000-3661666f8de0c561e186JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a7l-9000000000-3abe2bd4b3b37c4ed2ccJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0536-9000000000-2812ff25d24931b41744JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-9000000000-1cada987a9858a217a77JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-9000000000-e609ed7c7875fbd22551JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-9000000000-fe1499144a8401242c76JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-623d2802baf709699403JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-9000000000-16572bb315d857e26b9bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-9000000000-59b1a0eada94cc3c451eJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-053s-9000000000-6fe7e7a277af44176ff4JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID8526
ChEMBL IDCHEMBL3185916
KEGG Compound IDNot Available
Pubchem Compound ID8858
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31563
CRC / DFC (Dictionary of Food Compounds) IDDDF86-C:DDF86-C
EAFUS ID2452
Dr. Duke ID4-METHYL-3-PENTEN-2-ONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID141-79-7
GoodScent IDrw1035971
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. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
chemical
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
pungent
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
earthy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vegetable
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
acrylic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).