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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:11:48 UTC
Update Date2019-07-23 06:18:08 UTC
HMDB IDHMDB0035245
Secondary Accession Numbers
  • HMDB35245
Metabolite Identification
Common Name1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one
Description1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one, also known as 6-methylionone or 1-2,6,6-trimethylcyclohex-2-en-1-yl, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862688
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
N-Methyl-a-iononeHMDB
Pent-1-en-3-oneHMDB
Chemical FormulaC14H22O
Average Molecular Weight206.3239
Monoisotopic Molecular Weight206.167065326
IUPAC Name(1E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)pent-1-en-3-one
Traditional Nameirone
CAS Registry Number127-42-4
SMILES
CCC(=O)\C=C\C1C(C)=CCCC1(C)C
InChI Identifier
InChI=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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 Solubility0.029 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054w-4900000000-b045f61f4b940110d85eSpectrum
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
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013905
KNApSAcK IDNot Available
Chemspider ID4521710
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5371084
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:16347747 ]
  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. [PubMed:17564909 ]
  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. [PubMed:18037210 ]
  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. [PubMed:23283689 ]
  5. Bernaola G, Escayol P, Fernandez E, Fernandez de Corres L: Contact dermatitis from methylionone fragrance. Contact Dermatitis. 1989 Jan;20(1):71-2. [PubMed:2914440 ]
  6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  10. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  11. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.