Methylionone (CHEM009975)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 03:14:15 UTC
Update Date2016-11-09 01:14:06 UTC
Accession NumberCHEM009975
Identification
Common NameMethylionone
ClassSmall Molecule
Description1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one is a flavouring ingredient.
Contaminant Sources
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1E)-1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-oneHMDB
(e)-1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)pent-1-en-3-oneHMDB
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)pent-1-en-3-oneHMDB
1-(2,6,6-Trimethyl-2-cyclohexene-1-yl)-1-penten-3-oneHMDB
1-2,6,6-Trimethylcyclohex-2-en-1-ylHMDB
1-Methyl-a-iononeHMDB
5-(2,6,6-Trimethyl-2-cyclohexenyl)-4-penten-3-oneHMDB
6-MethyliononeHMDB
alpha-CetoneHMDB
alpha-MethyliononeHMDB
FEMA 2711HMDB
Methyl-iononeHMDB
MethyliononeHMDB, MeSH
N-Methyl-a-iononeHMDB
Pent-1-en-3-oneHMDB
Chemical FormulaC14H22O
Average Molecular Mass206.324 g/mol
Monoisotopic Mass206.167 g/mol
CAS Registry Number1335-46-2
IUPAC Name(1E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)pent-1-en-3-one
Traditional Nameirone
SMILESCCC(=O)\C=C\C1C(C)=CCCC1(C)C
InChI IdentifierInChI=1S/C14H22O/c1-5-12(15)8-9-13-11(2)7-6-10-14(13,3)4/h7-9,13H,5-6,10H2,1-4H3/b9-8+
InChI KeyVPKMGDRERYMTJX-CMDGGOBGSA-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 DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.029 g/LALOGPS
logP4.57ALOGPS
logP4.02ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity66.72 m³·mol⁻¹ChemAxon
Polarizability25.05 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054w-4900000000-b045f61f4b940110d85eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1790000000-09686e5ff6b3a58b4acfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053j-6910000000-fecd50f9bb9d5c4c3c91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ktu-9200000000-785074f4dff70d3ce57bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-bad4fe272ecf0676b0f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3690000000-4c790dd84825b7f4dda3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ts-4900000000-a18d770da8832df84b3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-2d8ac504a1490d38e7adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dj-1910000000-5813a9f1a635d1587838Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0q2a-8910000000-94c9ddb49918998223f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1910000000-52aca7acb363bd0c28c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-4900000000-0d6be0132d5d641de6d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-9500000000-9bdb96bba0f00804a71eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0035245
FooDB IDFDB013905
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4521710
ChEBI IDNot Available
PubChem Compound ID5371084
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yamazaki Y, Hayashi Y, Arita M, Hieda T, Mikami Y: Microbial Conversion of alpha-Ionone, alpha-Methylionone, and alpha-Isomethylionone. Appl Environ Microbiol. 1988 Oct;54(10):2354-60.
2. Politano VT, Lewis EM, Hoberman AM, Christian MS, Diener RM, Api AM: Evaluation of the developmental toxicity of alpha-iso-methylionone in rats. Int J Toxicol. 2007 May-Jun;26(3):271-6.
3. Lapczynski A, Lalko J, Politano VT, McGinty D, Bhatia S, Letizia CS, Api AM: Fragrance material review on alpha-iso-methylionone. Food Chem Toxicol. 2007;45 Suppl 1:S280-9. Epub 2007 Sep 14.
4. Politano VT, Lapczynski AA, Ritacco G, Api AM: Ninety-day toxicity study of alpha-iso-methylionone in rats. Int J Toxicol. 2012 Nov-Dec;31(6):595-601. doi: 10.1177/1091581812466116.
5. Bernaola G, Escayol P, Fernandez E, Fernandez de Corres L: Contact dermatitis from methylionone fragrance. Contact Dermatitis. 1989 Jan;20(1):71-2.
6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
7. 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.
8. 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.
9. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
10. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
11. The lipid handbook with CD-ROM