3-Oxo-alpha-ionol (YMDB01608)

Identification
YMDB IDYMDB01608
Name3-Oxo-alpha-ionol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description3-Oxo-alpha-ionol, also known as 3-oxo-α-ionol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on 3-Oxo-alpha-ionol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (4S)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one
  • (6S,9R)-6-Hydroxy-3-oxo-alpha-ionol
  • (6S,9R)-Vomifoliol
  • Blumenol A
  • Vomifoliol
  • 3-oxo-a-Ionol
  • 3-oxo-Α-ionol
CAS number23526-45-6
WeightAverage: 208.2967
Monoisotopic: 208.146329884
InChI KeyMDCGEAGEQVMWPE-UHFFFAOYSA-N
InChIInChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-7,10,12,14H,8H2,1-4H3
IUPAC Name4-[(1E)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one
Traditional IUPAC Name4-[(1E)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one
Chemical FormulaC13H20O2
SMILESCC(O)C=CC1C(C)=CC(=O)CC1(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
  • Cyclohexenone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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 Solubility0.71 g/LALOGPS
logP2.14ALOGPS
logP2.27ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)16.91ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.71 m³·mol⁻¹ChemAxon
Polarizability23.87 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
SpiceFDB021721
SpicyFDB021721
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, Positivesplash10-014l-6900000000-175ed8e8e900e68622a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0920000000-e28db426c476498cb016JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-2910000000-f6f0342c3271b58e2297JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-5900000000-d9246d5b91f9921a98adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-2bb483ac3840a1da1c87JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-1980000000-49bfac00968f2c20a928JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05g3-3900000000-2dc31331233702d75f51JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05bf-0920000000-8d8e372877b113a5e4e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-4900000000-9239880d66792714b68aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-6900000000-47292d29c4724121a75bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-43a9bdbf7663e467c30dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0910000000-4d272d0d821e030fd7baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p2-1900000000-cca33764e7d01a23d9d8JSpectraViewer
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 ID49164
HMDB IDHMDB0303805
Pubchem Compound ID5370052
Kegg IDC01760
ChemSpider ID4520951
FOODB IDFDB021721
Wikipedia IDNot Available
BioCyc IDNot Available