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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:45:13 UTC

Update Date

2023-02-21 17:27:56 UTC

HMDB ID

HMDB0040216

Secondary Accession Numbers

HMDB40216

Metabolite Identification

Common Name

2,6,6-Trimethyl-2-cyclohexene-1,4-dione

Description

2,6,6-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
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-dione	HMDB
2,6,6-Trimethylcyclohex-2-ene-1,4-dione	HMDB
2-Cyclohexen-1,4-dione, 2,6,6-trimethyl	HMDB
3,5,5-Trimethyl-2-cyclohexene-1,4-dione	HMDB
3,5,5-Trimethylcyclohex-2-en-1,4-dione	HMDB
3,5,5-Trimethylcyclohex-2-ene-1,4-dione	HMDB
4-Ketoisophorone	HMDB
4-oxo-alpha-Isophorone	HMDB
4-Oxoisophorone	HMDB
6-Oxoisophorone	HMDB
FEMA 3421	HMDB
Keto-isophorone	HMDB
Ketoisophorone	HMDB
Oxoisophorone	HMDB
Oxopholone	HMDB
Oxophorone	HMDB

Chemical Formula

C₉H₁₂O₂

Average Molecular Weight

152.1904

Monoisotopic Molecular Weight

152.083729628

IUPAC Name

2,6,6-trimethylcyclohex-2-ene-1,4-dione

Traditional Name

2,6,6-trimethylcyclohex-2-ene-1,4-dione

CAS Registry Number

1125-21-9

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 Key

AYJXHIDNNLJQDT-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040216)

Source

Endogenous

Endogenous (HMDB: HMDB0040216)

Plant

Plant (HMDB: HMDB0040216)

Exogenous

Food

Food (HMDB: HMDB0040216)

Tea

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0040216)

Role

Biological role

Energy source (HMDB: HMDB0040216)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040216)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040216)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	21 °C	Not Available
Boiling Point	92.00 to 94.00 °C. @ 11.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	0.994 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.73 g/L	ALOGPS
logP	1.51	ALOGPS
logP	2.16	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	18.85	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	43.39 m³·mol⁻¹	ChemAxon
Polarizability	16.33 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.936	31661259
DarkChem	[M-H]-	130.288	31661259
DeepCCS	[M+H]+	134.993	30932474
DeepCCS	[M-H]-	131.165	30932474
DeepCCS	[M-2H]-	168.619	30932474
DeepCCS	[M+Na]+	144.158	30932474
AllCCS	[M+H]+	130.8	32859911
AllCCS	[M+H-H2O]+	126.4	32859911
AllCCS	[M+NH4]+	135.0	32859911
AllCCS	[M+Na]+	136.1	32859911
AllCCS	[M-H]-	132.7	32859911
AllCCS	[M+Na-2H]-	134.3	32859911
AllCCS	[M+HCOO]-	136.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6,6-Trimethyl-2-cyclohexene-1,4-dione	CC1=CC(=O)CC(C)(C)C1=O	1704.0	Standard polar	33892256
2,6,6-Trimethyl-2-cyclohexene-1,4-dione	CC1=CC(=O)CC(C)(C)C1=O	1084.2	Standard non polar	33892256
2,6,6-Trimethyl-2-cyclohexene-1,4-dione	CC1=CC(=O)CC(C)(C)C1=O	1123.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,6,6-Trimethyl-2-cyclohexene-1,4-dione,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1=O	1463.1	Semi standard non polar	33892256
2,6,6-Trimethyl-2-cyclohexene-1,4-dione,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1=O	1353.3	Standard non polar	33892256
2,6,6-Trimethyl-2-cyclohexene-1,4-dione,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1=O	1673.4	Semi standard non polar	33892256
2,6,6-Trimethyl-2-cyclohexene-1,4-dione,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1=O	1584.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pbc-9400000000-ac4a8e5a500a122e8961	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 10V, Positive-QTOF	splash10-0udi-1900000000-a2ede87c0b92081444bf	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 20V, Positive-QTOF	splash10-0udi-5900000000-43128d887aa49e04c996	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 40V, Positive-QTOF	splash10-052f-9000000000-8359b62696f36de8253d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 10V, Negative-QTOF	splash10-0udi-0900000000-4d79e09516d33207e352	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 20V, Negative-QTOF	splash10-0udi-1900000000-ebd44ede68a343ed2c8c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 40V, Negative-QTOF	splash10-052r-9300000000-edfbab726fbefc90241c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 10V, Negative-QTOF	splash10-0udi-0900000000-3cd265ceef2fb5f5db20	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 20V, Negative-QTOF	splash10-0udi-2900000000-031e7bfb242b17e4a495	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 40V, Negative-QTOF	splash10-0uyl-9200000000-9950f21d73347619ba59	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 10V, Positive-QTOF	splash10-0udi-1900000000-bde85b5db3f5d24f0db4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 20V, Positive-QTOF	splash10-053g-9300000000-e49845f95178fde26c7e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-2-cyclohexene-1,4-dione 40V, Positive-QTOF	splash10-0006-9000000000-506b290021f45d0865df	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004389

KNApSAcK ID

C00035002

Chemspider ID

56162

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62374

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1029401

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2,6,6-Trimethyl-2-cyclohexene-1,4-dione (HMDB0040216)

MOL for HMDB0040216 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)

3D MOL for HMDB0040216 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)

3D SDF for HMDB0040216 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)

3D-SDF for HMDB0040216 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)

PDB for HMDB0040216 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)

3D PDB for HMDB0040216 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)

SMILES for HMDB0040216 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)

INCHI for HMDB0040216 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)

Structure for HMDB0040216 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)

3D Structure for HMDB0040216 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra