4-HYDROXY-4-(3-HYDROXY-1-BUTENYL)-3,5,5-TRIMETHYL-2-CYCLOHEXEN-1-ONE (CHEM006062)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:09:35 UTC
Update Date2016-11-09 01:09:40 UTC
Accession NumberCHEM006062
Identification
Common Name4-HYDROXY-4-(3-HYDROXY-1-BUTENYL)-3,5,5-TRIMETHYL-2-CYCLOHEXEN-1-ONE
ClassSmall Molecule
DescriptionA (6S)-vomifoliol with a R configuration for the hydroxy group at position 9.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(4S)-4-Hydroxy-4-[(1E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-oneChEBI
(6S,9R)-6-Hydroxy-3-oxo-alpha-ionolChEBI
Blumenol aChEBI
VomifoliolChEBI
(6S,9R)-6-Hydroxy-3-oxo-a-ionolGenerator
(6S,9R)-6-Hydroxy-3-oxo-α-ionolGenerator
Chemical FormulaC13H20O3
Average Molecular Mass224.300 g/mol
Monoisotopic Mass224.141 g/mol
CAS Registry Number23526-45-6
IUPAC Name(4S)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one
Traditional Name(6S,9R)-vomifoliol
SMILESC[C@@H](O)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C
InChI IdentifierInChI=1S/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+/t10-,13-/m1/s1
InChI KeyKPQMCAKZRXOZLB-KOIHBYQTSA-N
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
  • Cyclofarsesane sesquiterpenoid
  • Megastigmane sesquiterpenoid
  • Ionone derivative
  • Cyclohexenone
  • Tertiary alcohol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.43 g/LALOGPS
logP1.24ALOGPS
logP1.42ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)13.4ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.93 m³·mol⁻¹ChemAxon
Polarizability24.63 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1290000000-6503dbe714326635d7c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-5960000000-160023ee9b53b92fd109Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-9400000000-effb33726aac710baa8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1390000000-3283e5c97745e2da7575Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-3390000000-6e989e8d0cd753ed3d08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbi-9710000000-e39dfca2324d645f4627Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00029834
BiGG IDNot Available
BioCyc ID--6-HYDROXY-3-OXO-ALPHA-IONOL
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID49164
PubChem Compound ID5280462
Kegg Compound IDC01760
YMDB IDNot Available
ECMDB IDM2MDB005640
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19336938
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22364828