Record Information
Version1.0
Creation date2010-04-08 22:07:07 UTC
Update date2019-11-26 03:01:07 UTC
Primary IDFDB006379
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(+)-Dehydrovomifoliol
Description(+)-dehydrovomifoliol, also known as (6s)-6-hydroxy-3-oxo-alpha-ionone, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thus, (+)-dehydrovomifoliol is considered to be an isoprenoid lipid molecule (+)-dehydrovomifoliol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-dehydrovomifoliol can be found in rice, which makes (+)-dehydrovomifoliol a potential biomarker for the consumption of this food product.
CAS Number15764-81-5
Structure
Thumb
Synonyms
SynonymSource
(4S)-4-Hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-enyl]cyclohex-2-en-1-oneChEBI
(6R)-6-Hydroxy-3-oxo-alpha-iononeChEBI
(6S)-6-Hydroxy-3-oxo-alpha-iononeChEBI
DehydrovomifoliolChEBI
(6R)-6-Hydroxy-3-oxo-a-iononeGenerator
(6R)-6-Hydroxy-3-oxo-α-iononeGenerator
(6S)-6-Hydroxy-3-oxo-a-iononeGenerator
(6S)-6-Hydroxy-3-oxo-α-iononeGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.55 g/LALOGPS
logP1.41ALOGPS
logP1.65ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)13.37ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.93 m³·mol⁻¹ChemAxon
Polarizability24.15 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H18O3
IUPAC name(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one
InChI IdentifierInChI=1S/C13H18O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,16H,8H2,1-4H3/b6-5+/t13-/m1/s1
InChI KeyJJRYPZMXNLLZFH-URWSZGRFSA-N
Isomeric SMILES[H]\C(=C(\[H])[C@@]1(O)C(C)=CC(=O)CC1(C)C)C(C)=O
Average Molecular Weight222.284
Monoisotopic Molecular Weight222.12559444
Classification
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
  • Megastigmane sesquiterpenoid
  • Cyclofarsesane sesquiterpenoid
  • Ionone derivative
  • Cyclohexenone
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Tertiary alcohol
  • Ketone
  • Cyclic ketone
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-1390000000-4e60e0949700e5a7866cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-6960000000-13f3c7a12fb342f032baSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-9400000000-e6f96a4aba3f87be5d0fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1290000000-532cf596c2cdb0015193Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-3590000000-de4cf83db1750d791a7aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-9720000000-35064bd3d2f1d6e41fb0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0490000000-654708f6f22dc249fdd8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052u-7930000000-c75cc836c4e99d9cb5b8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-386e524a1645cf2f1b7aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0690000000-ed548d7a227093275795Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-5a5f74386d1c4a0f34f0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-3930000000-6051e849c6c0c241b22fSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke ID(+)-DEHYDROVOMIFOLIOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).