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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:33 UTC
Update Date2022-03-07 02:52:52 UTC
HMDB IDHMDB0031195
Secondary Accession Numbers
  • HMDB31195
Metabolite Identification
Common Name3,5,5-Trimethyl-2-cyclohexen-1-one
Description3,5,5-Trimethyl-2-cyclohexen-1-one, also known as isoacetophorone or isoforone, belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 3,5,5-Trimethyl-2-cyclohexen-1-one is a sweet, camphor, and camphoraceous tasting compound. 3,5,5-Trimethyl-2-cyclohexen-1-one is found, on average, in the highest concentration within kohlrabis (Brassica oleracea var. gongylodes). 3,5,5-Trimethyl-2-cyclohexen-1-one has also been detected, but not quantified in, several different foods, such as cherry tomatoes (Solanum lycopersicum var. cerasiforme), white mustards (Sinapis alba), garden tomato (var.), herbs and spices, and saffrons (Crocus sativus). This could make 3,5,5-trimethyl-2-cyclohexen-1-one a potential biomarker for the consumption of these foods. 3,5,5-Trimethyl-2-cyclohexen-1-one is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 3,5,5-Trimethyl-2-cyclohexen-1-one.
Structure
Data?1563862094
Synonyms
ValueSource
1,1,3-Trimethyl-3-cyclohexene-5-oneChEBI
3,5,5-Trimethyl-2-cyclohexen-1-ONChEBI
IsoacetophoroneChEBI
IsoforoneChEBI
IsooctopheroneChEBI
IzoforonChEBI
DiisophoroneMeSH
1,1, 3-Trimethyl-3-cyclohexene-5-oneHMDB
1,5,5-Trimethyl-1-cyclohexen-3-oneHMDB
3,3,5-Trimethyl-2-cyclohexen-1-oneHMDB
3,5, 5-Trimethyl-2-cyclohexene-1-oneHMDB
3,5,5-Trimethyl-2-cyclohexene-1-oneHMDB
3,5,5-Trimethyl-2-cyclohexenoneHMDB
3,5,5-Trimethylcyclohex-2-enoneHMDB
3,5,5-Trimethylcyclohexen oneHMDB
3,5,5-Trimethylcyclohexen-2-one-1HMDB
3,5,5-TrimethylcyclohexenoneHMDB
3,5,5-Trimetil-2-cicloesen-1-oneHMDB
a-IsophoroneHMDB
alpha -IsophoronHMDB
alpha -IsophoroneHMDB
alpha-IsophoroneHMDB
FEMA 3553HMDB
IsoforonHMDB
IsophoronHMDB
IsophoroneHMDB
Isophorone, reagHMDB
Nchem.180-comp3HMDB
Chemical FormulaC9H14O
Average Molecular Weight138.2069
Monoisotopic Molecular Weight138.10446507
IUPAC Name3,5,5-trimethylcyclohex-2-en-1-one
Traditional Nameisophorone
CAS Registry Number78-59-1
SMILES
CC1=CC(=O)CC(C)(C)C1
InChI Identifier
InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3
InChI KeyHJOVHMDZYOCNQW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclohexenones
Alternative Parents
Substituents
  • Cyclohexenone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-8.1 °CNot Available
Boiling Point213.00 to 215.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility12 mg/mL at 25 °CNot Available
LogP1.70Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.89 g/LALOGPS
logP1.9ALOGPS
logP2.32ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.65 m³·mol⁻¹ChemAxon
Polarizability16.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.73631661259
DarkChem[M-H]-129.86931661259
DeepCCS[M+H]+137.79230932474
DeepCCS[M-H]-135.19430932474
DeepCCS[M-2H]-170.97330932474
DeepCCS[M+Na]+146.40430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,5,5-Trimethyl-2-cyclohexen-1-oneCC1=CC(=O)CC(C)(C)C11561.8Standard polar33892256
3,5,5-Trimethyl-2-cyclohexen-1-oneCC1=CC(=O)CC(C)(C)C11059.8Standard non polar33892256
3,5,5-Trimethyl-2-cyclohexen-1-oneCC1=CC(=O)CC(C)(C)C11108.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,5,5-Trimethyl-2-cyclohexen-1-one,1TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(C)(C)C11256.1Semi standard non polar33892256
3,5,5-Trimethyl-2-cyclohexen-1-one,1TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(C)(C)C11228.3Standard non polar33892256
3,5,5-Trimethyl-2-cyclohexen-1-one,1TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C11486.0Semi standard non polar33892256
3,5,5-Trimethyl-2-cyclohexen-1-one,1TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C11442.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one EI-B (Non-derivatized)splash10-001i-9000000000-8ed7b012531653c3a41e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one EI-B (Non-derivatized)splash10-001i-9200000000-e8bfe4751592e28e4c9e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one CI-B (Non-derivatized)splash10-000i-2900000000-44ee32aafc71c88ceb862017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one EI-B (Non-derivatized)splash10-001i-9000000000-35f5f51e1d1c8b9f41eb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one EI-B (Non-derivatized)splash10-001i-9000000000-8ed7b012531653c3a41e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one EI-B (Non-derivatized)splash10-001i-9200000000-e8bfe4751592e28e4c9e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one CI-B (Non-derivatized)splash10-000i-2900000000-44ee32aafc71c88ceb862018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one EI-B (Non-derivatized)splash10-001i-9000000000-35f5f51e1d1c8b9f41eb2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-008i-9300000000-2b6a3c30cc2cb9b7c81d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 10V, Positive-QTOFsplash10-000i-0900000000-c0e6d09278faa8f9f6422021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 10V, Positive-QTOFsplash10-000i-0900000000-dccd82444801bb71001a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 20V, Positive-QTOFsplash10-000i-4900000000-5268782d409da6b9a25a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 40V, Positive-QTOFsplash10-053u-9100000000-6b6035d03526824e4f4a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 10V, Negative-QTOFsplash10-000i-0900000000-10c654c5b0e1c7d814282015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 20V, Negative-QTOFsplash10-000i-0900000000-f5ce7cb3d1f20b415ad92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 40V, Negative-QTOFsplash10-007c-9600000000-8b2034251abbccebb7392015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 10V, Positive-QTOFsplash10-000i-9700000000-eaf3d45b160fad9677282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 20V, Positive-QTOFsplash10-0560-9100000000-d0446ecf5f19dbc3eeae2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 40V, Positive-QTOFsplash10-0a7i-9000000000-49bfbbf2837b17d788982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 10V, Negative-QTOFsplash10-000i-0900000000-928b413704490084a3032021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 20V, Negative-QTOFsplash10-000i-0900000000-928b413704490084a3032021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 40V, Negative-QTOFsplash10-00xr-4900000000-88d428c6a2e6fff994aa2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB003216
KNApSAcK IDC00030540
Chemspider ID6296
KEGG Compound IDC14743
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsophorone
METLIN IDNot Available
PubChem Compound6544
PDB IDNot Available
ChEBI ID34800
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1036811
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .