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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:43:17 UTC
Update Date2021-10-13 06:57:19 UTC
HMDB IDHMDB0036565
Secondary Accession Numbers
  • HMDB36565
Metabolite Identification
Common Namebeta-Ionone
Descriptionbeta-Ionone, also known as (e)-b-ionone or trans-beta-ionone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on beta-Ionone.
Structure
Data?1587133588
Synonyms
ValueSource
(e)-beta-IononeChEBI
beta-e-IononeChEBI
beta-IononChEBI
trans-beta-IononeChEBI
(e)-b-IononeGenerator
(e)-Β-iononeGenerator
b-e-IononeGenerator
Β-e-iononeGenerator
b-IononGenerator
Β-iononGenerator
trans-b-IononeGenerator
trans-Β-iononeGenerator
b-IononeGenerator
Β-iononeGenerator
(3E)-4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-oneHMDB
(3E)-4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-oneHMDB
(e)-beta -IononeHMDB
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-(e)-3-buten-2-oneHMDB
beta -e-IononeHMDB
FEMA 2595HMDB
Ionone, betaHMDB
trans-beta -IononeHMDB
[e]-4-[2,6,6-Trimethyl-1-cyclohexen-1-yl]-3-buten-2-oneHMDB
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-oneMeSH, HMDB
beta-Ionone, (trans)-isomerMeSH, HMDB
Chemical FormulaC13H20O
Average Molecular Weight192.2973
Monoisotopic Molecular Weight192.151415262
IUPAC Name(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one
Traditional Nameβ-ionone
CAS Registry Number79-77-6
SMILES
CC(=O)\C=C\C1=C(C)CCCC1(C)C
InChI Identifier
InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8H,5-6,9H2,1-4H3/b8-7+
InChI KeyPSQYTAPXSHCGMF-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

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point266.00 to 269.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility25.16 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.710 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP10(4.11) g/LALOGPS
logP10(3.28) g/LChemAxon
logS10(-3.3) g/LALOGPS
pKa (Strongest Acidic)19.71ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.82 m³·mol⁻¹ChemAxon
Polarizability23.36 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-IononeCC(=O)\C=C\C1=C(C)CCCC1(C)C1898.1Standard polar33892256
beta-IononeCC(=O)\C=C\C1=C(C)CCCC1(C)C1446.8Standard non polar33892256
beta-IononeCC(=O)\C=C\C1=C(C)CCCC1(C)C1451.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
beta-Ionone,1TMS,isomer #1C=C(/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C1658.3Semi standard non polar33892256
beta-Ionone,1TMS,isomer #1C=C(/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C1703.4Standard non polar33892256
beta-Ionone,1TBDMS,isomer #1C=C(/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C1896.1Semi standard non polar33892256
beta-Ionone,1TBDMS,isomer #1C=C(/C=C/C1=C(C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C1945.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - beta-Ionone EI-B (Non-derivatized)splash10-002f-8900000000-c13b694647d1f5e201bf2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Ionone EI-B (Non-derivatized)splash10-004i-3900000000-b2fd6907056260485dd22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Ionone EI-B (Non-derivatized)splash10-004l-9800000000-3e2f914b8442dedd62d92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Ionone EI-B (Non-derivatized)splash10-004l-6900000000-a0ed0929b7cb7526955d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Ionone EI-B (Non-derivatized)splash10-004l-4900000000-3169016f24891f9035d62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Ionone EI-B (Non-derivatized)splash10-002f-8900000000-c13b694647d1f5e201bf2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Ionone EI-B (Non-derivatized)splash10-004i-3900000000-b2fd6907056260485dd22018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Ionone EI-B (Non-derivatized)splash10-004l-9800000000-3e2f914b8442dedd62d92018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Ionone EI-B (Non-derivatized)splash10-004l-6900000000-a0ed0929b7cb7526955d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Ionone EI-B (Non-derivatized)splash10-004l-4900000000-3169016f24891f9035d62018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Ionone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-2900000000-00c10c6b19261d08ffea2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Ionone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004l-6900000000-9288b23b92d86ede53362014-10-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Ionone 10V, Positive-QTOFsplash10-002f-0900000000-0f7a122ff9743bcbf0772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Ionone 20V, Positive-QTOFsplash10-004u-4900000000-9dad39944d71a20a0f872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Ionone 40V, Positive-QTOFsplash10-0gbc-9400000000-77a4b4a15731ccc833162016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Ionone 10V, Negative-QTOFsplash10-0006-0900000000-b62117da7fb50997c0272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Ionone 20V, Negative-QTOFsplash10-0006-0900000000-e7133a7253517651678a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Ionone 40V, Negative-QTOFsplash10-05ed-3900000000-c1d86be9896bad6ad97e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Ionone 10V, Positive-QTOFsplash10-0006-1900000000-2dfc2141d793c1b81afc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Ionone 20V, Positive-QTOFsplash10-05gl-7900000000-4e2d786c5425c33577a52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Ionone 40V, Positive-QTOFsplash10-052f-9500000000-66ef449f7e5f912217042021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Ionone 10V, Negative-QTOFsplash10-0006-0900000000-14436e4d9ff8d032db542021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Ionone 20V, Negative-QTOFsplash10-0007-0900000000-85f77f47306d558369112021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Ionone 40V, Negative-QTOFsplash10-0002-1900000000-5f53d8abc51bbf1e4e992021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB015469
KNApSAcK IDC00029816
Chemspider ID553581
KEGG Compound IDC12287
BioCyc IDCPD-7204
BiGG IDNot Available
Wikipedia LinkIonone
METLIN IDNot Available
PubChem Compound638014
PDB IDID3
ChEBI ID32325
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1131301
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Duncan RE, Lau D, El-Sohemy A, Archer MC: Geraniol and beta-ionone inhibit proliferation, cell cycle progression, and cyclin-dependent kinase 2 activity in MCF-7 breast cancer cells independent of effects on HMG-CoA reductase activity. Biochem Pharmacol. 2004 Nov 1;68(9):1739-47. [PubMed:15450939 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Asymmetrically cleaves beta-carotene at the 9',10' double bond resulting in the formation of beta-apo-10'-carotenal and beta-ionone. Besides beta-carotene, lycopene is also oxidatively cleaved. The apocarotenals formed by this enzyme may be the precursors for the biosynthesis of retinoic acid or exert unknown physiological effects.
Gene Name:
BCO2
Uniprot ID:
Q9BYV7
Molecular weight:
61509.65
Reactions
beta-Carotene + Oxygen → all-trans-10'-apo-beta-carotenal + beta-Iononedetails