1-[2,6,6-Trimethyl-1,3-cyclohexadien-1-yl]-2-buten-1-one (YMDB01375)

Identification
YMDB IDYMDB01375
Name1-[2,6,6-Trimethyl-1,3-cyclohexadien-1-yl]-2-buten-1-one
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionDamascenones are a series of closely related chemical compounds that are components of a variety of essential oils. The damascenones belong to a family of chemicals known as rose ketones, which also includes damascones and ionones. beta-Damascenone is a major contributor to the aroma of roses, despite its very low concentration, and is an important fragrance chemical used in perfumery. The damascenones are derived from the degradation of carotenoids. [Wikipedia]
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
SMILESCC=CC(=O)C1=C(C)C=CCC1(C)C
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 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, Positivesplash10-01dm-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:
  • Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). "A new process for wine production by penetration of yeast in uncrushed frozen grapes." Appl Biochem Biotechnol 162:1109-1121.20151225
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