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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:33 UTC

Update Date

2023-02-21 17:20:01 UTC

HMDB ID

HMDB0031195

Secondary Accession Numbers

HMDB31195

Metabolite Identification

Common Name

3,5,5-Trimethyl-2-cyclohexen-1-one

Description

3,5,5-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

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,1,3-Trimethyl-3-cyclohexene-5-one	ChEBI
3,5,5-Trimethyl-2-cyclohexen-1-ON	ChEBI
Isoacetophorone	ChEBI
Isoforone	ChEBI
Isooctopherone	ChEBI
Izoforon	ChEBI
Diisophorone	MeSH
1,1, 3-Trimethyl-3-cyclohexene-5-one	HMDB
1,5,5-Trimethyl-1-cyclohexen-3-one	HMDB
3,3,5-Trimethyl-2-cyclohexen-1-one	HMDB
3,5, 5-Trimethyl-2-cyclohexene-1-one	HMDB
3,5,5-Trimethyl-2-cyclohexene-1-one	HMDB
3,5,5-Trimethyl-2-cyclohexenone	HMDB
3,5,5-Trimethylcyclohex-2-enone	HMDB
3,5,5-Trimethylcyclohexen one	HMDB
3,5,5-Trimethylcyclohexen-2-one-1	HMDB
3,5,5-Trimethylcyclohexenone	HMDB
3,5,5-Trimetil-2-cicloesen-1-one	HMDB
a-Isophorone	HMDB
alpha -Isophoron	HMDB
alpha -Isophorone	HMDB
alpha-Isophorone	HMDB
FEMA 3553	HMDB
Isoforon	HMDB
Isophoron	HMDB
Isophorone	HMDB
Isophorone, reag	HMDB
Nchem.180-comp3	HMDB

Chemical Formula

C₉H₁₄O

Average Molecular Weight

138.2069

Monoisotopic Molecular Weight

138.10446507

IUPAC Name

3,5,5-trimethylcyclohex-2-en-1-one

Traditional Name

isophorone

CAS Registry Number

78-59-1

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 Key

HJOVHMDZYOCNQW-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

cyclic ketone (CHEBI:34800 )
enone (CHEBI:34800 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031195)
Cytoplasm (HMDB: HMDB0031195)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031195)

Source

Endogenous

Endogenous (HMDB: HMDB0031195)

Plant

Plant (HMDB: HMDB0031195)

Exogenous

Food

Food (HMDB: HMDB0031195)

Vegetable

Root vegetable

Kohlrabi (FooDB: FOOD00033)

Fruit vegetable

Herb and spice

Spice

White mustard (FooDB: FOOD00413)
Saffron (FooDB: FOOD00063)

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0031195)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031195)

Environmental role

Hazardous air pollutant (HMDB: HMDB0031195)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-8.1 °C	Not Available
Boiling Point	213.00 to 215.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	12 mg/mL at 25 °C	Not Available
LogP	1.70	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.89 g/L	ALOGPS
logP	1.9	ALOGPS
logP	2.32	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	42.65 m³·mol⁻¹	ChemAxon
Polarizability	16.22 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]+	132.736	31661259
DarkChem	[M-H]-	129.869	31661259
DeepCCS	[M+H]+	137.792	30932474
DeepCCS	[M-H]-	135.194	30932474
DeepCCS	[M-2H]-	170.973	30932474
DeepCCS	[M+Na]+	146.404	30932474
AllCCS	[M+H]+	126.3	32859911
AllCCS	[M+H-H2O]+	121.8	32859911
AllCCS	[M+NH4]+	130.6	32859911
AllCCS	[M+Na]+	131.8	32859911
AllCCS	[M-H]-	129.4	32859911
AllCCS	[M+Na-2H]-	131.3	32859911
AllCCS	[M+HCOO]-	133.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5,5-Trimethyl-2-cyclohexen-1-one	CC1=CC(=O)CC(C)(C)C1	1561.8	Standard polar	33892256
3,5,5-Trimethyl-2-cyclohexen-1-one	CC1=CC(=O)CC(C)(C)C1	1059.8	Standard non polar	33892256
3,5,5-Trimethyl-2-cyclohexen-1-one	CC1=CC(=O)CC(C)(C)C1	1108.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,5,5-Trimethyl-2-cyclohexen-1-one,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1	1256.1	Semi standard non polar	33892256
3,5,5-Trimethyl-2-cyclohexen-1-one,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1	1228.3	Standard non polar	33892256
3,5,5-Trimethyl-2-cyclohexen-1-one,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1	1486.0	Semi standard non polar	33892256
3,5,5-Trimethyl-2-cyclohexen-1-one,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1	1442.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one EI-B (Non-derivatized)	splash10-001i-9000000000-8ed7b012531653c3a41e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one EI-B (Non-derivatized)	splash10-001i-9200000000-e8bfe4751592e28e4c9e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one CI-B (Non-derivatized)	splash10-000i-2900000000-44ee32aafc71c88ceb86	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one EI-B (Non-derivatized)	splash10-001i-9000000000-35f5f51e1d1c8b9f41eb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one EI-B (Non-derivatized)	splash10-001i-9000000000-8ed7b012531653c3a41e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one EI-B (Non-derivatized)	splash10-001i-9200000000-e8bfe4751592e28e4c9e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one CI-B (Non-derivatized)	splash10-000i-2900000000-44ee32aafc71c88ceb86	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one EI-B (Non-derivatized)	splash10-001i-9000000000-35f5f51e1d1c8b9f41eb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-008i-9300000000-2b6a3c30cc2cb9b7c81d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 10V, Positive-QTOF	splash10-000i-0900000000-c0e6d09278faa8f9f642	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 10V, Positive-QTOF	splash10-000i-0900000000-dccd82444801bb71001a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 20V, Positive-QTOF	splash10-000i-4900000000-5268782d409da6b9a25a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 40V, Positive-QTOF	splash10-053u-9100000000-6b6035d03526824e4f4a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 10V, Negative-QTOF	splash10-000i-0900000000-10c654c5b0e1c7d81428	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 20V, Negative-QTOF	splash10-000i-0900000000-f5ce7cb3d1f20b415ad9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 40V, Negative-QTOF	splash10-007c-9600000000-8b2034251abbccebb739	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 10V, Positive-QTOF	splash10-000i-9700000000-eaf3d45b160fad967728	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 20V, Positive-QTOF	splash10-0560-9100000000-d0446ecf5f19dbc3eeae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 40V, Positive-QTOF	splash10-0a7i-9000000000-49bfbbf2837b17d78898	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 10V, Negative-QTOF	splash10-000i-0900000000-928b413704490084a303	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 20V, Negative-QTOF	splash10-000i-0900000000-928b413704490084a303	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclohexen-1-one 40V, Negative-QTOF	splash10-00xr-4900000000-88d428c6a2e6fff994aa	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isophorone

METLIN ID

Not Available

PubChem Compound

6544

PDB ID

Not Available

ChEBI ID

34800

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036811

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 3,5,5-Trimethyl-2-cyclohexen-1-one (HMDB0031195)

MOL for HMDB0031195 (3,5,5-Trimethyl-2-cyclohexen-1-one)

3D MOL for HMDB0031195 (3,5,5-Trimethyl-2-cyclohexen-1-one)

3D SDF for HMDB0031195 (3,5,5-Trimethyl-2-cyclohexen-1-one)

3D-SDF for HMDB0031195 (3,5,5-Trimethyl-2-cyclohexen-1-one)

PDB for HMDB0031195 (3,5,5-Trimethyl-2-cyclohexen-1-one)

3D PDB for HMDB0031195 (3,5,5-Trimethyl-2-cyclohexen-1-one)

SMILES for HMDB0031195 (3,5,5-Trimethyl-2-cyclohexen-1-one)

INCHI for HMDB0031195 (3,5,5-Trimethyl-2-cyclohexen-1-one)

Structure for HMDB0031195 (3,5,5-Trimethyl-2-cyclohexen-1-one)

3D Structure for HMDB0031195 (3,5,5-Trimethyl-2-cyclohexen-1-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra