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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:38:32 UTC
Update Date2022-03-07 02:54:34 UTC
HMDB IDHMDB0035631
Secondary Accession Numbers
  • HMDB35631
Metabolite Identification
Common Namealpha-Irone
Descriptionalpha-Irone, also known as 6-methyl-a-ionone or α-iron, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on alpha-Irone.
Structure
Data?1563862748
Synonyms
ValueSource
6-Methyl-alpha-iononeChEBI
alpha-IronChEBI
Methyl alpha-iononeChEBI
Methyl-alpha-iononeChEBI
6-Methyl-a-iononeGenerator
6-Methyl-α-iononeGenerator
a-IronGenerator
Α-ironGenerator
Methyl a-iononeGenerator
Methyl α-iononeGenerator
Methyl-a-iononeGenerator
Methyl-α-iononeGenerator
a-IroneGenerator
Α-ironeGenerator
4-(2,5,6,6-Tetramethyl-2-cyclo-hexen-1-yl)-3-buten-2-oneHMDB
4-(2,5,6,6-Tetramethyl-2-cyclohexen-1-yl)-3-buten-2-oneHMDB
4-(2,5,6,6-Tetramethyl-2-cyclohexen-1-yl)-3-buten-2-one, 9ciHMDB
4-(2,5,6,6-Tetramethylcyclohex-2-enyl)but-3-en-2-oneHMDB
6-Methyl iononeHMDB
6-Methyl-alpha -iononeHMDB
alpha -IroneHMDB
alpha -Methyl-iononeHMDB
alpha 6-Methyl--iononeHMDB
alpha-CyclocitrylidenebutanoneHMDB
alpha-Cyclocitrylidenemethyl ethyl ketoneHMDB
alpha-Inone, methyl- (6ci)HMDB
cis-2,6-cis-(2(1),2(2))-alpha-IononeHMDB
FEMA 2597HMDB
Ionone 6-methyl, alphaHMDB
IroneHMDB
Methyl-alpha -iononeHMDB
Methyl-alpha-inoneHMDB
Chemical FormulaC14H22O
Average Molecular Weight206.3239
Monoisotopic Molecular Weight206.167065326
IUPAC Name(3E)-4-(2,5,6,6-tetramethylcyclohex-2-en-1-yl)but-3-en-2-one
Traditional Nameα-iron
CAS Registry Number79-69-6
SMILES
CC1CC=C(C)C(\C=C\C(C)=O)C1(C)C
InChI Identifier
InChI=1S/C14H22O/c1-10-6-7-11(2)14(4,5)13(10)9-8-12(3)15/h6,8-9,11,13H,7H2,1-5H3/b9-8+
InChI KeyJZQOJFLIJNRDHK-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 Descriptors
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point110.00 to 112.00 °C. @ 3.00 mm HgThe Good Scents Company Information System
Water Solubility110 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP4.354 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP4.37ALOGPS
logP3.61ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)19.83ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity66.64 m³·mol⁻¹ChemAxon
Polarizability25.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+160.44430932474
DeepCCS[M-H]-158.08630932474
DeepCCS[M-2H]-191.00230932474
DeepCCS[M+Na]+166.53730932474
AllCCS[M+H]+146.632859911
AllCCS[M+H-H2O]+142.632859911
AllCCS[M+NH4]+150.232859911
AllCCS[M+Na]+151.332859911
AllCCS[M-H]-154.932859911
AllCCS[M+Na-2H]-155.832859911
AllCCS[M+HCOO]-156.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-IroneCC1CC=C(C)C(\C=C\C(C)=O)C1(C)C1893.6Standard polar33892256
alpha-IroneCC1CC=C(C)C(\C=C\C(C)=O)C1(C)C1483.9Standard non polar33892256
alpha-IroneCC1CC=C(C)C(\C=C\C(C)=O)C1(C)C1530.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Irone,1TMS,isomer #1C=C(/C=C/C1C(C)=CCC(C)C1(C)C)O[Si](C)(C)C1697.2Semi standard non polar33892256
alpha-Irone,1TMS,isomer #1C=C(/C=C/C1C(C)=CCC(C)C1(C)C)O[Si](C)(C)C1689.2Standard non polar33892256
alpha-Irone,1TBDMS,isomer #1C=C(/C=C/C1C(C)=CCC(C)C1(C)C)O[Si](C)(C)C(C)(C)C1942.2Semi standard non polar33892256
alpha-Irone,1TBDMS,isomer #1C=C(/C=C/C1C(C)=CCC(C)C1(C)C)O[Si](C)(C)C(C)(C)C1930.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Irone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-3900000000-b4a715b98f10ee9cec482017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Irone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Irone 10V, Positive-QTOFsplash10-0a4r-0950000000-70fd0f0822b39f0c81432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Irone 20V, Positive-QTOFsplash10-000b-4910000000-e34040151d7830394e0a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Irone 40V, Positive-QTOFsplash10-014i-9500000000-39043a12d53e0892753b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Irone 10V, Negative-QTOFsplash10-0a4i-0290000000-8c80db8fb62c557031462016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Irone 20V, Negative-QTOFsplash10-0a4i-1790000000-2fbdf8062ade1ea9e56b2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Irone 40V, Negative-QTOFsplash10-000i-2900000000-69279f9e831387c30def2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Irone 10V, Negative-QTOFsplash10-0a4i-0090000000-3601d41603fac89c511d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Irone 20V, Negative-QTOFsplash10-08g1-0930000000-65aa652057f35fd0bd342021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Irone 40V, Negative-QTOFsplash10-0apj-2910000000-9d2cfc1547118383cb262021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Irone 10V, Positive-QTOFsplash10-053i-1920000000-ea38e53cb8217c61eb1a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Irone 20V, Positive-QTOFsplash10-05o9-3900000000-ab74961732052d20ebb82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Irone 40V, Positive-QTOFsplash10-052f-9400000000-6dc44e6945fdbed5ed982021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB014339
KNApSAcK IDC00003153
Chemspider ID4521669
KEGG Compound IDC09690
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIrone
METLIN IDNot Available
PubChem Compound5371002
PDB IDNot Available
ChEBI ID10284
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1006691
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.