Beta-Ionone

Basic Info

Common NameBeta-Ionone(F09046)
2D Structure
FRCD IDF09046
CAS Number14901-07-6
PubChem CID638014
FormulaC13H20O
IUPAC Name

(E)-4-(2,6,6-trimethylcyclohexen-1-yl)but-3-en-2-one

InChI Key

PSQYTAPXSHCGMF-BQYQJAHWSA-N

InChI

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+

Canonical SMILES

CC1=C(C(CCC1)(C)C)C=CC(=O)C

Isomeric SMILES

CC1=C(C(CCC1)(C)C)/C=C/C(=O)C

WikipediaBeta-Ionone
Synonyms
        
            BETA-IONONE
        
            79-77-6
        
            14901-07-6
        
            trans-beta-Ionone
        
            (E)-beta-Ionone
        
            .beta.-Ionone
        
            (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one
        
            4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one
        
            UNII-A7NRR1HLH6
        
            4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-one
Classifies
                

                  
                    Food Additive
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassSesquiterpenoids
Intermediate Tree NodesNot available
Direct ParentSesquiterpenoids
Alternative Parents
Molecular FrameworkAliphatic homomonocyclic compounds
SubstituentsCyclofarsesane 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
DescriptionThis compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Properties

Property NameProperty Value
Molecular Weight192.302
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count2
Complexity292
Monoisotopic Mass192.151
Exact Mass192.151
XLogP2.9
Formal Charge0
Heavy Atom Count14
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9667
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7833
P-glycoprotein SubstrateNon-substrate0.5587
P-glycoprotein InhibitorNon-inhibitor0.5853
Non-inhibitor0.5401
Renal Organic Cation TransporterNon-inhibitor0.7848
Distribution
Subcellular localizationLysosome0.4058
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8506
CYP450 2D6 SubstrateNon-substrate0.8609
CYP450 3A4 SubstrateSubstrate0.6196
CYP450 1A2 InhibitorNon-inhibitor0.7697
CYP450 2C9 InhibitorNon-inhibitor0.8616
CYP450 2D6 InhibitorNon-inhibitor0.9513
CYP450 2C19 InhibitorNon-inhibitor0.8316
CYP450 3A4 InhibitorNon-inhibitor0.9491
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6895
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8862
Non-inhibitor0.8869
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.6926
Fish ToxicityHigh FHMT0.8766
Tetrahymena Pyriformis ToxicityHigh TPT0.8403
Honey Bee ToxicityHigh HBT0.8298
BiodegradationReady biodegradable0.6605
Acute Oral ToxicityIII0.7883
Carcinogenicity (Three-class)Non-required0.5366
Model Value Unit
Absorption
Aqueous solubility-2.2407LogS
Caco-2 Permeability1.9848LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.6532LD50, mol/kg
Fish Toxicity0.5815pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1648pIGC50, ug/L

References

TitleJournalDatePubmed ID
Sensory and Flavor Characteristics of Tomato Juice from Garden Gem and RomaTomatoes with Comparison to Commercial Tomato Juice.J Food Sci2018 Jan29135026
Study on the developmental toxicity of β-ionone in the rat.Regul Toxicol Pharmacol2018 Aug29928934
Characterization of the Key Aroma Compounds in Five Varieties of Mandarins by GasChromatography-Olfactometry, Odor Activity Values, Aroma Recombination, andOmission Analysis.J Agric Food Chem2017 Sep 2728885016
Polyunsaturated lipids and vitamin A oxidation during cod liver oil in vitro gastrointestinal digestion. Antioxidant effect of added BHT.Food Chem2017 Oct 128490135
Effect of Raw Material, Pressing and Glycosidase on the Volatile CompoundComposition of Wine Made From Goji Berries.Molecules2016 Oct 227706098
Characterization of the Key Aroma Volatile Compounds in Cranberry (Vacciniummacrocarpon Ait.) Using Gas Chromatography-Olfactometry (GC-O) and Odor Activity Value (OAV).J Agric Food Chem2016 Jun 2227265519
Green tea flavour determinants and their changes over manufacturing processes.Food Chem2016 Dec 127374591
Influence of the use of fungicides on the volatile composition of Monastrell red wines obtained from inoculated fermentation.Food Chem2015 Mar 125306363
Identification of geosmin and 2-methylisoborneol in cyanobacteria and moleculardetection methods for the producers of these compounds.Water Res2015 Jan 125462716
Environmental and seasonal influences on red raspberry flavour volatiles andidentification of quantitative trait loci (QTL) and candidate genes.Theor Appl Genet2013 Jan22890807
Formation of norisoprenoid flavor compounds in carrot (Daucus carota L.) roots:characterization of a cyclic-specific carotenoid cleavage dioxygenase 1 gene.J Agric Food Chem2013 Dec 1824289159
Enzymatic production and in situ separation of natural β-ionone from β-carotene.J Ind Microbiol Biotechnol2012 Dec22911237
Study on the mutagenicity and antimutagenicity of beta-ionone in the Salmonella/microsome assay.Food Chem Toxicol2006 Apr16223554