trans-beta-damascenone (YMDB01468)

Identification
YMDB IDYMDB01468
Nametrans-beta-damascenone
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Descriptionbeta-Damascenone, also known as damascenone, 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, beta-damascenone is considered to be an isoprenoid. beta-Damascenone exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on beta-Damascenone.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one
  • (2E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one
  • (e)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one
  • (e)-beta-Damascenone
  • beta-(e)-Damascenone
  • Damascenone
  • trans-beta-Damascenone
  • trans-Damascenone
  • (e)-b-Damascenone
  • (e)-Β-damascenone
  • b-(e)-Damascenone
  • Β-(e)-damascenone
  • trans-b-Damascenone
  • trans-Β-damascenone
  • b-Damascenone
  • Β-damascenone
CAS number23696-85-7
WeightAverage: 190.2814
Monoisotopic: 190.135765198
InChI KeyPOIARNZEYGURDG-FNORWQNLSA-N
InChIInChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+
IUPAC Name(2E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
Traditional IUPAC Namedamascenone
Chemical FormulaC13H18O
SMILES[H]\C(=C(\[H])C([H])([H])[H])C(=O)C1=C(C([H])=C([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]
Chemical Taxonomy
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 homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP4.02ALOGPS
logP3.68ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.02 m³·mol⁻¹ChemAxon
Polarizability22.61 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic Properties
Flavour/OdourSource
AppleFDB015480
HoneyFDB015480
RoseFDB015480
SmokyFDB015480
SweetFDB015480
TobaccoFDB015480
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, Positivesplash10-01dm-5900000000-4bcd624fdf9c5e42b887JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-8da6e151fea92abe412aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kg-6900000000-2069d91b82e6511da0aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9200000000-6695f41d1b443f4da598JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-3f94da9b260ed91041b8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2900000000-7afc8b9366085d67da73JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007n-4900000000-d38de494cceadf7b6a17JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-797743ba698bddb677b1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-d9210597b39735810ebfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-2900000000-4ac82453126eb07d119fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-022c-0900000000-3c6a17c1864038197fc5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-2900000000-7fc87120284ef620e86aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ac0-7900000000-3e0424c46a79abc4667dJSpectraViewer
References
References:
  • Gallardo-Chacon, J. J., Vichi, S., Lopez-Tamames, E., Buxaderas, S. (2010). "Changes in the Sorption of Diverse Volatiles by Saccharomyces cerevisiae Lees during Sparkling Wine Aging." J Agric Food Chem :.21073195
  • Mahadevan, K., Farmer, L. (2006). "Key odor impact compounds in three yeast extract pastes." J Agric Food Chem 54:7242-7250.16968089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID67251
HMDB IDHMDB0013804
Pubchem Compound ID5366074
Kegg IDNot Available
ChemSpider ID24590142
FOODB IDFDB015480
WikipediaDamascenone
BioCyc IDNot Available