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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:43:17 UTC
Update Date2017-12-07 03:45:48 UTC
HMDB IDHMDB0036565
Secondary Accession Numbers
  • HMDB36565
Metabolite Identification
Common Namebeta-Ionone
DescriptionBeta-ionone, also known as trans-beta-ionone or (E)-B-ionone, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Beta-ionone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Beta-ionone is a dry, floral, and flower tasting compound and can be found in a number of food items such as guava, wild carrot, spearmint, and common wheat, which makes beta-ionone a potential biomarker for the consumption of these food products. Beta-ionone can be found primarily in saliva. The ionones are a series of closely related chemical substances that are part of a group of compounds known as rose ketones, which also includes damascones and damascenones. Ionones are aroma compounds found in a variety of essential oils, including rose oil. β-Ionone is a significant contributor to the aroma of roses, despite its relatively low concentration, and is an important fragrance chemical used in perfumery. The ionones are derived from the degradation of carotenoids (Wikipedia). beta-Ionone is found in carrot. beta-Ionone is found in many essential oils including oil of Boronia megastigma (brown boronia) and commercial ionone. beta-Ionone is a flavouring agent.
Structure
Thumb
Synonyms
ValueSource
(e)-beta-IononeChEBI
beta-e-IononeChEBI
beta-IononChEBI
trans-beta-IononeChEBI
(e)-b-IononeGenerator
(e)-β-iononeGenerator
b-IononeGenerator
β-iononeGenerator
b-e-IononeGenerator
β-e-iononeGenerator
b-IononGenerator
β-iononGenerator
trans-b-IononeGenerator
trans-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
beta-Ionone, (trans)-isomerMeSH
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
DescriptionThis compound 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

Industrial application:

Biological role:

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 Solubility0.1 g/LALOGPS
logP4.11ALOGPS
logP3.28ChemAxon
logS-3.3ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-8900000000-c13b694647d1f5e201bfView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-3900000000-b2fd6907056260485dd2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004l-9800000000-3e2f914b8442dedd62d9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004l-6900000000-a0ed0929b7cb7526955dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004l-4900000000-3169016f24891f9035d6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-2900000000-00c10c6b19261d08ffeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0900000000-0f7a122ff9743bcbf077View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004u-4900000000-9dad39944d71a20a0f87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9400000000-77a4b4a15731ccc83316View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-b62117da7fb50997c027View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-e7133a7253517651678aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ed-3900000000-c1d86be9896bad6ad97eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-004l-6900000000-9288b23b92d86ede5336View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
FoodDB 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
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
B-Carotene + Oxygen → all-trans-10'-apo-beta-carotenal + beta-Iononedetails