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Record Information
Version3.6
Creation Date2012-09-11 21:43:17 UTC
Update Date2016-02-11 02:44:27 UTC
HMDB IDHMDB36565
Secondary Accession NumbersNone
Metabolite Identification
Common Namebeta-Ionone
Descriptionbeta-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. Beta-ionone has been shown to exhibit anti-proliferative function (PMID 15450939 ).
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
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 KeyInChIKey=PSQYTAPXSHCGMF-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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrient
  • anti-proliferative
Application
  • Flavoring Agent
  • Nutrient
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.82 m3·mol-1ChemAxon
Polarizability23.36 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-004l-6900000000-9288b23b92d86ede5336View in MoNA
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB015469
KNApSAcK IDC00029816
Chemspider ID553581
KEGG Compound IDC12287
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIonone
NuGOwiki LinkHMDB36565
Metagene LinkHMDB36565
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. [15450939 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

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