Record Information
Version1.0
Creation date2010-04-08 22:12:02 UTC
Update date2019-11-26 03:12:11 UTC
Primary IDFDB015766
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameVomifoliol
DescriptionVomifoliol, also known as (+/-)-6-hydroxy-3-oxo-alpha-ionol, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Vomifoliol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Vomifoliol is a fruity tasting compound found in common grape, which makes vomifoliol a potential biomarker for the consumption of this food product.
CAS Number23526-45-6
Structure
Thumb
Synonyms
SynonymSource
(+/-)-6-hydroxy-3-oxo-alpha-ionolChEBI
(+/-)-6-hydroxy-3-oxo-a-ionolGenerator
(+/-)-6-hydroxy-3-oxo-α-ionolGenerator
(6S,9R)-6-Hydroxy-3-oxo-alpha-ionolbiospider
Blumenol Adb_source
Vomifolioldb_source
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
Polarizability24.79 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H20O3
IUPAC name4-hydroxy-4-[(1E)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one
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+
InChI KeyKPQMCAKZRXOZLB-AATRIKPKSA-N
Isomeric SMILESCC(O)\C=C\C1(O)C(C)=CC(=O)CC1(C)C
Average Molecular Weight224.2961
Monoisotopic Molecular Weight224.141244506
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
  • 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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.61%; H 8.99%; O 21.40%DFC
Melting PointMp 113-114°DFC
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, Positivesplash10-0a4i-1290000000-7605c7a6e9c95681e7e02019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-6940000000-4afb0a1b0e2f552a476e2019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9300000000-a3e23e3aa33fc7dc28e62019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-d66ee0a3b03f94ba960f2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-2290000000-76c959bbc2d98521ffe12019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k9i-9810000000-27d3420b9d1cc7ea64af2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a70-0980000000-2ebd3ec8948a8222407e2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-7930000000-a3c1df3373d362cc523d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059x-9200000000-447bb5645c4c98e1baab2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fmi-0970000000-4a92efd55a33f5edca8b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-2951434f9e08e5e0e8012021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0m0i-1920000000-fe2aae318254611b3e622021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC01760
Pubchem Compound ID5280462
Pubchem Substance IDNot Available
ChEBI ID49164
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJFD65-N:KHN15-V
EAFUS ID1749
Dr. Duke IDVOMIFOLIOL
BIGG IDNot Available
KNApSAcK IDC00029834
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1618341
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
Flavours
FlavorCitations
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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).