3-Oxo-beta-ionone (YMDB01609)

Identification
YMDB IDYMDB01609
Name3-Oxo-beta-ionone
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description3-Oxo-beta-ionone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 3-Oxo-beta-ionone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2,4,4-trimethyl-3-(3-oxo-1-butenyl)cyclohex-2-en-1-one
  • 2,4,4-Trimethyl-3-[(1E)-3-oxo-1-butenyl]-2-cyclohexen-1-one
  • 3-Keto-beta-ionone
  • 4-Oxo-beta-ionone
  • 3-oxo-b-Ionone
  • 3-oxo-Β-ionone
CAS number27185-77-9
WeightAverage: 206.2808
Monoisotopic: 206.13067982
InChI KeyOBHGOXFSRVNKBS-UHFFFAOYSA-N
InChIInChI=1S/C13H18O2/c1-9(14)5-6-11-10(2)12(15)7-8-13(11,3)4/h5-6H,7-8H2,1-4H3
IUPAC Name2,4,4-trimethyl-3-(3-oxobut-1-en-1-yl)cyclohex-2-en-1-one
Traditional IUPAC Name2,4,4-trimethyl-3-(3-oxobut-1-en-1-yl)cyclohex-2-en-1-one
Chemical FormulaC13H18O2
SMILESCC(=O)C=CC1=C(C)C(=O)CCC1(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Megastigmane sesquiterpenoid
  • Cyclofarsesane sesquiterpenoid
  • Ionone derivative
  • Cyclohexenone
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Cyclic ketone
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.26 g/LALOGPS
logP2.88ALOGPS
logP2.61ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.52 m³·mol⁻¹ChemAxon
Polarizability23.46 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-3900000000-e07e3214c50514fd81dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0950000000-82de7bcbf5ca14d2b2f6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052s-4910000000-b21c4dd1243c6c09c767JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-9500000000-00b17b7c231e59c0d0a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0290000000-d6b8b009d962e9f08f75JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1790000000-5ebe9812818cbf1efc41JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3900000000-e353efc723f307e518f3JSpectraViewer
References
References:
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID5363876
Kegg IDNot Available
ChemSpider ID21173162
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available