You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2013-03-07 21:34:48 UTC
Update Date2019-07-23 07:13:06 UTC
HMDB IDHMDB0059883
Secondary Accession Numbers
  • HMDB59883
Metabolite Identification
Common Namealpha-Ionone
Descriptionalpha-Ionone, also known as (e)-α-ionone or trans-a-ionone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. alpha-Ionone is an extremely weak basic (essentially neutral) compound (based on its pKa). alpha-Ionone is a potentially toxic compound.
Structure
Data?1563865986
Synonyms
ValueSource
(e)-alpha-IononeChEBI
alpha-(e)-IononeChEBI
alpha-CyclocitrylideneacetoneChEBI
alpha-IononChEBI
trans-alpha-IononeChEBI
(e)-a-IononeGenerator
(e)-Α-iononeGenerator
a-(e)-IononeGenerator
Α-(e)-iononeGenerator
a-CyclocitrylideneacetoneGenerator
Α-cyclocitrylideneacetoneGenerator
a-IononGenerator
Α-iononGenerator
trans-a-IononeGenerator
trans-Α-iononeGenerator
a-IononeGenerator
Α-iononeGenerator
(3E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-ONHMDB
alpha-Ionone, (e)-isomerMeSH
alpha-Ionone, (e)-(+-)-isomerMeSH
alpha-Ionone, (+)-iosmerMeSH
Chemical FormulaC13H20O
Average Molecular Weight192.2973
Monoisotopic Molecular Weight192.151415262
IUPAC Name(3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
Traditional Nameα-ionone
CAS Registry NumberNot Available
SMILES
CC(=O)\C=C\C1C(C)=CCCC1(C)C
InChI Identifier
InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+
InChI KeyUZFLPKAIBPNNCA-BQYQJAHWSA-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
  • Cyclofarsesane sesquiterpenoid
  • Megastigmane sesquiterpenoid
  • Sesquiterpenoid
  • Ionone derivative
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.05 g/LALOGPS
logP4.14ALOGPS
logP3.32ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)19.83ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.09 m³·mol⁻¹ChemAxon
Polarizability23.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-4900000000-acff00e4fe614e1e5bc8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0900000000-0d1ee7a07c25e0eb379aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004u-3900000000-122599cd5a3606da3858Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9400000000-5525adff7c75947a3830Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-86ad4191ecec06d667ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-81ca79f706995e1f2313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aed-2900000000-e754146e5b21f942f91eSpectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9800000000-d19fa6227b12fe21dbc3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)BothNormal details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014484
KNApSAcK IDNot Available
Chemspider ID4445317
KEGG Compound IDC12286
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIonone
METLIN IDNot Available
PubChem Compound5282108
PDB IDNot Available
ChEBI ID32319
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.