Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:45:13 UTC
Update Date2021-10-13 08:25:27 UTC
HMDB IDHMDB0040216
Secondary Accession Numbers
  • HMDB40216
Metabolite Identification
Common Name2,6,6-Trimethyl-2-cyclohexene-1,4-dione
Description2,6,6-Trimethyl-2-cyclohexene-1,4-dione, also known as 4-ketoisophorone or 2-cyclohexen-1,4-dione, 2,6,6-trimethyl, 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. 2,6,6-Trimethyl-2-cyclohexene-1,4-dione has been detected, but not quantified in, several different foods, such as black tea, green tea, herbal tea, red tea, and teas (Camellia sinensis). This could make 2,6,6-trimethyl-2-cyclohexene-1,4-dione a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2,6,6-Trimethyl-2-cyclohexene-1,4-dione.
Structure
Data?1563863507
Synonyms
ValueSource
2,2,6-Trimethyl-2-cyclohexene-1,4-dione (cetoisophorone)HMDB
2,2,6-Trimethylcyclohex-2-en-1,4-dione (4-oxo-isophorone)HMDB
2,6,6-Trimethy-2-cyclohexene-1,4-dione (4-oxoisophorone)HMDB
2,6,6-Trimethyl-2-cyclohexen-1,4-dioneHMDB
2,6,6-Trimethylcyclohex-2-ene-1,4-dioneHMDB
2-Cyclohexen-1,4-dione, 2,6,6-trimethylHMDB
3,5,5-Trimethyl-2-cyclohexene-1,4-dioneHMDB
3,5,5-Trimethylcyclohex-2-en-1,4-dioneHMDB
3,5,5-Trimethylcyclohex-2-ene-1,4-dioneHMDB
4-KetoisophoroneHMDB
4-oxo-alpha-IsophoroneHMDB
4-OxoisophoroneHMDB
6-OxoisophoroneHMDB
FEMA 3421HMDB
Keto-isophoroneHMDB
KetoisophoroneHMDB
OxoisophoroneHMDB
OxopholoneHMDB
OxophoroneHMDB
Chemical FormulaC9H12O2
Average Molecular Weight152.1904
Monoisotopic Molecular Weight152.083729628
IUPAC Name2,6,6-trimethylcyclohex-2-ene-1,4-dione
Traditional Name2,6,6-trimethylcyclohex-2-ene-1,4-dione
CAS Registry Number1125-21-9
SMILES
CC1=CC(=O)CC(C)(C)C1=O
InChI Identifier
InChI=1S/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H3
InChI KeyAYJXHIDNNLJQDT-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 DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point21 °CNot Available
Boiling Point92.00 to 94.00 °C. @ 11.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP0.994 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.73 g/LALOGPS
logP10(1.51) g/LALOGPS
logP10(2.16) g/LChemAxon
logS10(-1.2) g/LALOGPS
pKa (Strongest Acidic)18.85ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.39 m³·mol⁻¹ChemAxon
Polarizability16.33 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]+133.93631661259
DarkChem[M-H]-130.28831661259
DeepCCS[M+H]+134.99330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,6,6-Trimethyl-2-cyclohexene-1,4-dioneCC1=CC(=O)CC(C)(C)C1=O1704.0Standard polar33892256
2,6,6-Trimethyl-2-cyclohexene-1,4-dioneCC1=CC(=O)CC(C)(C)C1=O1084.2Standard non polar33892256
2,6,6-Trimethyl-2-cyclohexene-1,4-dioneCC1=CC(=O)CC(C)(C)C1=O1123.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,6,6-Trimethyl-2-cyclohexene-1,4-dione,1TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1=O1463.1Semi standard non polar33892256
2,6,6-Trimethyl-2-cyclohexene-1,4-dione,1TMS,isomer #1CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1=O1353.3Standard non polar33892256
2,6,6-Trimethyl-2-cyclohexene-1,4-dione,1TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1=O1673.4Semi standard non polar33892256
2,6,6-Trimethyl-2-cyclohexene-1,4-dione,1TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1=O1584.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pbc-9400000000-ac4a8e5a500a122e89612016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 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 - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 10V, Positive-QTOFsplash10-0udi-1900000000-a2ede87c0b92081444bf2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 20V, Positive-QTOFsplash10-0udi-5900000000-43128d887aa49e04c9962015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 40V, Positive-QTOFsplash10-052f-9000000000-8359b62696f36de8253d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 10V, Negative-QTOFsplash10-0udi-0900000000-4d79e09516d33207e3522015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 20V, Negative-QTOFsplash10-0udi-1900000000-ebd44ede68a343ed2c8c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 40V, Negative-QTOFsplash10-052r-9300000000-edfbab726fbefc90241c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 10V, Negative-QTOFsplash10-0udi-0900000000-3cd265ceef2fb5f5db202021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 20V, Negative-QTOFsplash10-0udi-2900000000-031e7bfb242b17e4a4952021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 40V, Negative-QTOFsplash10-0uyl-9200000000-9950f21d73347619ba592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 10V, Positive-QTOFsplash10-0udi-1900000000-bde85b5db3f5d24f0db42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 20V, Positive-QTOFsplash10-053g-9300000000-e49845f95178fde26c7e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 40V, Positive-QTOFsplash10-0006-9000000000-506b290021f45d0865df2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB004389
KNApSAcK IDC00035002
Chemspider ID56162
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62374
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1029401
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jerkovic I, Mastelic J, Marijanovic Z: A variety of volatile compounds as markers in unifloral honey from dalmatian sage (Salvia officinalis L.). Chem Biodivers. 2006 Dec;3(12):1307-16. [PubMed:17193245 ]
  2. Lechtenberg M, Schepmann D, Niehues M, Hellenbrand N, Wunsch B, Hensel A: Quality and functionality of saffron: quality control, species assortment and affinity of extract and isolated saffron compounds to NMDA and sigma1 (sigma-1) receptors. Planta Med. 2008 Jun;74(7):764-72. doi: 10.1055/s-2008-1074535. Epub 2008 May 21. [PubMed:18496783 ]
  3. Raimondi S, Roncaglia L, Amaretti A, Leonardi A, Buzzini P, Forti L, Rossi M: Rapid method for screening enoate reductase activity in yeasts. J Microbiol Methods. 2010 Nov;83(2):106-10. doi: 10.1016/j.mimet.2010.09.007. Epub 2010 Sep 16. [PubMed:20849886 ]
  4. Goretti M, Ponzoni C, Caselli E, Marchegiani E, Cramarossa MR, Turchetti B, Forti L, Buzzini P: Bioreduction of alpha,beta-unsaturated ketones and aldehydes by non-conventional yeast (NCY) whole-cells. Bioresour Technol. 2011 Mar;102(5):3993-8. doi: 10.1016/j.biortech.2010.12.062. Epub 2010 Dec 22. [PubMed:21232941 ]
  5. Zhuang X, Klingeman WE, Hu J, Chen F: Emission of volatile chemicals from flowering dogwood (cornus Florida L.) flowers. J Agric Food Chem. 2008 Oct 22;56(20):9570-4. doi: 10.1021/jf801651v. Epub 2008 Sep 24. [PubMed:18811168 ]
  6. Jerkovic I, Tuberoso CI, Gugic M, Bubalo D: Composition of sulla (Hedysarum coronarium L.) honey solvent extractives determined by GC/MS: norisoprenoids and other volatile organic compounds. Molecules. 2010 Sep 9;15(9):6375-85. doi: 10.3390/molecules15096375. [PubMed:20877229 ]
  7. Kataoka M, Kotaka A, Hasegawa A, Wada M, Yoshizumi A, Nakamori S, Shimizu S: Old Yellow Enzyme from Candida macedoniensis catalyzes the stereospecific reduction of the C=C bond of ketoisophorone. Biosci Biotechnol Biochem. 2002 Dec;66(12):2651-7. [PubMed:12596862 ]
  8. Chen K, Sun Y, Wang C, Yao J, Chen Z, Li H: Aerobic oxidation of beta-isophorone catalyzed by N-hydroxyphthalimide: the key features and mechanism elucidated. Phys Chem Chem Phys. 2012 Sep 21;14(35):12141-6. doi: 10.1039/c2cp41617d. Epub 2012 Jul 31. [PubMed:22850899 ]
  9. Kataoka M, Kotaka A, Thiwthong R, Wada M, Nakamori S, Shimizu S: Cloning and overexpression of the old yellow enzyme gene of Candida macedoniensis, and its application to the production of a chiral compound. J Biotechnol. 2004 Oct 19;114(1-2):1-9. [PubMed:15464593 ]
  10. Raimondi S, Romano D, Amaretti A, Molinari F, Rossi M: Enoate reductases from non conventional yeasts: bioconversion, cloning, and functional expression in Saccharomyces cerevisiae. J Biotechnol. 2011 Dec 20;156(4):279-85. doi: 10.1016/j.jbiotec.2011.08.033. Epub 2011 Sep 16. [PubMed:21933690 ]
  11. Hegazy ME, Hirata T, Abdel-Lateff A, el-Razek MH, Mohamed Ael-H, Hassan NM, Pare PW, Mahmoud AA: Ketoisophorone transformation by Marchantia polymorpha and Nicotiana tabacum cultured cells. Z Naturforsch C. 2008 May-Jun;63(5-6):403-8. [PubMed:18669027 ]
  12. Mohr S, Fisher K, Scrutton NS, Goddard NJ, Fielden PR: Continuous two-phase flow miniaturised bioreactor for monitoring anaerobic biocatalysis by pentaerythritol tetranitrate reductase. Lab Chip. 2010 Aug 7;10(15):1929-36. doi: 10.1039/c003561k. Epub 2010 Jun 7. [PubMed:20526519 ]
  13. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .