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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 22:23:05 UTC
Update Date2023-02-21 17:25:36 UTC
HMDB IDHMDB0037139
Secondary Accession Numbers
  • HMDB37139
Metabolite Identification
Common Name4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone
Description4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone, also known as 3,4-didehydro-7,8-dihydro-beta-ionone or dehydrodihydroionone, 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 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone.
Structure
Data?1677000336
Synonyms
ValueSource
3,4-Didehydro-7,8-dihydro-beta-iononeChEBI
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)butan-2-oneChEBI
4-(2,6,6-Trimethyl-1,3-cyclohexadienyl)-2-butanoneChEBI
4-(2,6,6-Trimethylcyclohexa-1,3-dien-1-yl)butan-2-oneChEBI
4-(2,6,6-Trimethylcyclohexa-1,3-dienyl)butan-2-oneChEBI
7,8-Dihydro-3,4-dehydro-beta-iononeChEBI
DehydrodihydroiononeChEBI
FEMA 3447ChEBI
3,4-Didehydro-7,8-dihydro-b-iononeGenerator
3,4-Didehydro-7,8-dihydro-β-iononeGenerator
7,8-Dihydro-3,4-dehydro-b-iononeGenerator
7,8-Dihydro-3,4-dehydro-β-iononeGenerator
4-(2,6,6-Trimethyl cyclohexa-1,3-dienyl) butane-2-oneHMDB
dihydrodehydro-beta-IononeHMDB
Chemical FormulaC13H20O
Average Molecular Weight192.2973
Monoisotopic Molecular Weight192.151415262
IUPAC Name4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-2-one
Traditional Name4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-2-one
CAS Registry Number20483-36-7
SMILES
CC(=O)CCC1=C(C)C=CCC1(C)C
InChI Identifier
InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h5-6H,7-9H2,1-4H3
InChI KeySQFRYZPEWOZAKJ-UHFFFAOYSA-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
  • Megastigmane sesquiterpenoid
  • Sesquiterpenoid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point126.00 to 128.00 °C. @ 12.00 mm HgThe Good Scents Company Information System
Water Solubility14.09 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.681 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP4.15ALOGPS
logP2.92ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)19.6ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity61.85 m³·mol⁻¹ChemAxon
Polarizability23.14 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
DarkChem[M+H]+147.05131661259
DarkChem[M-H]-143.56931661259
DeepCCS[M+H]+147.68230932474
DeepCCS[M-H]-145.32430932474
DeepCCS[M-2H]-180.54930932474
DeepCCS[M+Na]+155.14930932474
AllCCS[M+H]+143.532859911
AllCCS[M+H-H2O]+139.532859911
AllCCS[M+NH4]+147.332859911
AllCCS[M+Na]+148.432859911
AllCCS[M-H]-149.832859911
AllCCS[M+Na-2H]-150.832859911
AllCCS[M+HCOO]-151.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanoneCC(=O)CCC1=C(C)C=CCC1(C)C1879.0Standard polar33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanoneCC(=O)CCC1=C(C)C=CCC1(C)C1395.9Standard non polar33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanoneCC(=O)CCC1=C(C)C=CCC1(C)C1413.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TMS,isomer #1CC(=CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C1661.8Semi standard non polar33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TMS,isomer #1CC(=CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C1606.2Standard non polar33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TMS,isomer #2C=C(CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C1640.2Semi standard non polar33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TMS,isomer #2C=C(CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C1590.3Standard non polar33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TBDMS,isomer #1CC(=CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C(C)(C)C1905.7Semi standard non polar33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TBDMS,isomer #1CC(=CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C(C)(C)C1867.1Standard non polar33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TBDMS,isomer #2C=C(CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C(C)(C)C1878.4Semi standard non polar33892256
4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone,1TBDMS,isomer #2C=C(CCC1=C(C)C=CCC1(C)C)O[Si](C)(C)C(C)(C)C1843.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-5900000000-5736fe8e960c46e93ba32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 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 - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 10V, Positive-QTOFsplash10-002f-1900000000-0e04520fc1c4c99c54262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 20V, Positive-QTOFsplash10-00p3-4900000000-95189d759958da4cd7db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 40V, Positive-QTOFsplash10-0gb9-9400000000-a0c1a282f3fe2da241442016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 10V, Negative-QTOFsplash10-0006-0900000000-88505512782936b3ed7e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 20V, Negative-QTOFsplash10-0006-2900000000-d9772c13d17a491dc87d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 40V, Negative-QTOFsplash10-0a4i-9600000000-d83f781d2e263e20e0072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 10V, Positive-QTOFsplash10-0019-0900000000-25eb405119b32dd9570a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 20V, Positive-QTOFsplash10-05g3-5900000000-f9568278d81f5d6dc1b32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 40V, Positive-QTOFsplash10-05mo-9400000000-cdeeb27239a996dcb3ab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 10V, Negative-QTOFsplash10-0006-0900000000-14436e4d9ff8d032db542021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 20V, Negative-QTOFsplash10-00dl-2900000000-4fc59527a3e46530a6312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-butanone 40V, Negative-QTOFsplash10-052e-5900000000-68b6ab45c521a59d612e2021-09-23Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016134
KNApSAcK IDNot Available
Chemspider ID501713
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound577126
PDB IDNot Available
ChEBI ID88549
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1042201
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.