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Identification
YMDB IDYMDB01634
Namealpha-Isomethyl-ionone
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, also known as alpha-isomethyl ionone or 3-methyl-a-ionone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one is a potentially toxic compound.
Structure
Thumb
Synonyms
  • .alpha. Isomethyl ionone
  • 8-Methyl-alpha-ionone
  • alpha Isomethyl ionone
  • alpha-Cetone
  • alpha-Ionone, isomethyl-
  • Cetone alpha
  • iso-alpha-methyl ionone
  • Isomethyl-alpha-ionone
  • Methyl-alpha-isoionone
  • 3-Methyl-a-ionone
  • FEMA 2714
  • Isomethyl-a-ionone
  • alpha-Isomethyl ionone
  • alpha-Isomethylionone
  • Methyl ionone gamma
CAS number127-51-5
WeightAverage: 206.3239
Monoisotopic: 206.167065326
InChI KeyJRJBVWJSTHECJK-PKNBQFBNSA-N
InChIInChI=1S/C14H22O/c1-10-7-6-8-14(4,5)13(10)9-11(2)12(3)15/h7,9,13H,6,8H2,1-5H3/b11-9+
IUPAC Name(3E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
Traditional IUPAC Name(3E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
Chemical FormulaC14H22O
SMILESCC(=O)C(\C)=C\C1C(C)=CCCC1(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
  • Cyclofarsesane sesquiterpenoid
  • Megastigmane sesquiterpenoid
  • Sesquiterpenoid
  • Ionone derivative
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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 Solubility0.064 g/LALOGPS
logP4.69ALOGPS
logP3.71ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)19.7ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity66.45 m³·mol⁻¹ChemAxon
Polarizability24.96 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-4900000000-188a75ba35cc10a457d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3980000000-aecfe987633b1b3253c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-5910000000-d30c3fd0fb817411950bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9100000000-9b4de8add50fbadeab2bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-832ea298f97bab583ddcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-3890000000-f8b94bab666cc1f09e7cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02ga-4900000000-aab4a14210d641ae936fJSpectraViewer
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 IDHMDB0031738
Pubchem Compound ID5372174
Kegg IDNot Available
ChemSpider ID4522510
FOODB IDFDB008407
Wikipedia IDNot Available
BioCyc IDNot Available