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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-03-07 21:34:48 UTC
Update Date2022-03-07 03:17:37 UTC
HMDB IDHMDB0059883
Secondary Accession Numbers
  • HMDB59883
Metabolite Identification
Common Namealpha-Ionone
Descriptionalpha-Ionone, also known as (e)-alpha-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 a potentially toxic compound. Alpha-ionone is a neutral compound. Alpha-ionone has a dry, floral, and flower taste with a cedar wood-like scent. It is a naturally occurring organic compound found in a variety of essential oils, including rose oil, flowers from Boronia megastigma (brown boronia; doi: 10.21273/hortsci.30.4.876d) and coml oil. Alpha-ionone is found in highest concentrations in corns, tea, and carrots and in lower concentrations in hyssops, peppermints, and safflowers. Alpha-ionone has also been detected in common grapes, sour cherries, common wheats, garden tomato, and wakames making beta-ionone a potential biomarker for the consumption of these foods. Alpha-ionone is used as to make Vitamins A, E and K1. It is used as a fragrance in perfumes, cosmetics and personal care products, and household cleaners and detergents. Alpha-ionone is used as a food flavoring in beverages, ice cream, baked goods and candies.
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
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+148.69730932474
DeepCCS[M-H]-146.30130932474
DeepCCS[M-2H]-180.48230932474
DeepCCS[M+Na]+155.10230932474
AllCCS[M+H]+143.032859911
AllCCS[M+H-H2O]+138.932859911
AllCCS[M+NH4]+146.832859911
AllCCS[M+Na]+147.932859911
AllCCS[M-H]-149.732859911
AllCCS[M+Na-2H]-150.732859911
AllCCS[M+HCOO]-151.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-IononeCC(=O)\C=C\C1C(C)=CCCC1(C)C1841.1Standard polar33892256
alpha-IononeCC(=O)\C=C\C1C(C)=CCCC1(C)C1402.6Standard non polar33892256
alpha-IononeCC(=O)\C=C\C1C(C)=CCCC1(C)C1426.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Ionone,1TMS,isomer #1C=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C1603.3Semi standard non polar33892256
alpha-Ionone,1TMS,isomer #1C=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C1627.6Standard non polar33892256
alpha-Ionone,1TMS,isomer #1C=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C1744.1Standard polar33892256
alpha-Ionone,1TBDMS,isomer #1C=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C(C)(C)C1839.7Semi standard non polar33892256
alpha-Ionone,1TBDMS,isomer #1C=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C(C)(C)C1864.7Standard non polar33892256
alpha-Ionone,1TBDMS,isomer #1C=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C(C)(C)C1896.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Ionone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-4900000000-acff00e4fe614e1e5bc82016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Ionone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9800000000-d19fa6227b12fe21dbc32014-10-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Ionone 10V, Positive-QTOFsplash10-002f-0900000000-0d1ee7a07c25e0eb379a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Ionone 20V, Positive-QTOFsplash10-004u-3900000000-122599cd5a3606da38582016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Ionone 40V, Positive-QTOFsplash10-014i-9400000000-5525adff7c75947a38302016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Ionone 10V, Negative-QTOFsplash10-0006-0900000000-86ad4191ecec06d667eb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Ionone 20V, Negative-QTOFsplash10-0006-0900000000-81ca79f706995e1f23132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Ionone 40V, Negative-QTOFsplash10-0aed-2900000000-e754146e5b21f942f91e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Ionone 10V, Positive-QTOFsplash10-006x-0900000000-dca766c12d151f3d74b12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Ionone 20V, Positive-QTOFsplash10-05fu-8900000000-26ead371c8e940e8859e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Ionone 40V, Positive-QTOFsplash10-05mo-9600000000-ad142c26c199a3741a022021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Ionone 10V, Negative-QTOFsplash10-0006-0900000000-14436e4d9ff8d032db542021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Ionone 20V, Negative-QTOFsplash10-00di-0900000000-7cd7cf4235cb00fbc0b52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Ionone 40V, Negative-QTOFsplash10-0kmj-3900000000-b5da866d6db21994e86c2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>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
MarkerDB IDNot Available
Good Scents 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.