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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:51:57 UTC

Update Date

2023-02-21 17:23:52 UTC

HMDB ID

HMDB0034080

Secondary Accession Numbers

HMDB34080

Metabolite Identification

Common Name

3-Methyl-1,2-cyclohexanedione

Description

3-Methyl-1,2-cyclohexanedione belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. 3-Methyl-1,2-cyclohexanedione is a burnt, coffee, and sugar tasting compound. 3-Methyl-1,2-cyclohexanedione has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 3-methyl-1,2-cyclohexanedione a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Methyl-1,2-cyclohexanedione.

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-Hydroxy-3-methyl-2-cyclohexen-1-one	HMDB
FEMA 3305	HMDB

Chemical Formula

C₇H₁₀O₂

Average Molecular Weight

126.1531

Monoisotopic Molecular Weight

126.068079564

IUPAC Name

3-methylcyclohexane-1,2-dione

Traditional Name

3-methylcyclohexane-1,2-dione

CAS Registry Number

3008-43-3

SMILES

CC1CCCC(=O)C1=O

InChI Identifier

InChI=1S/C7H10O2/c1-5-3-2-4-6(8)7(5)9/h5H,2-4H2,1H3

InChI Key

JDXJKLGWPNXSHL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Ingestion (HMDB: HMDB0034080)

Source

Exogenous

Food

Food (HMDB: HMDB0034080)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0034080)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034080)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0034080)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	64 - 65 °C	Not Available
Boiling Point	69.00 to 72.00 °C. @ 1.00 mm Hg	The Good Scents Company Information System
Water Solubility	104800 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.787 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	17.4 g/L	ALOGPS
logP	1.03	ALOGPS
logP	1.88	ChemAxon
logS	-0.86	ALOGPS
pKa (Strongest Acidic)	17.05	ChemAxon
pKa (Strongest Basic)	-8.6	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	33.57 m³·mol⁻¹	ChemAxon
Polarizability	13.25 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]+	125.938	31661259
DarkChem	[M-H]-	121.774	31661259
DeepCCS	[M+H]+	132.803	30932474
DeepCCS	[M-H]-	130.04	30932474
DeepCCS	[M-2H]-	166.562	30932474
DeepCCS	[M+Na]+	141.325	30932474
AllCCS	[M+H]+	126.3	32859911
AllCCS	[M+H-H2O]+	121.5	32859911
AllCCS	[M+NH4]+	130.7	32859911
AllCCS	[M+Na]+	132.0	32859911
AllCCS	[M-H]-	125.9	32859911
AllCCS	[M+Na-2H]-	128.0	32859911
AllCCS	[M+HCOO]-	130.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-1,2-cyclohexanedione	CC1CCCC(=O)C1=O	1724.2	Standard polar	33892256
3-Methyl-1,2-cyclohexanedione	CC1CCCC(=O)C1=O	1013.2	Standard non polar	33892256
3-Methyl-1,2-cyclohexanedione	CC1CCCC(=O)C1=O	1127.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-1,2-cyclohexanedione,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)CCC1	1271.6	Semi standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)CCC1	1254.9	Standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,1TMS,isomer #2	CC1CCC=C(O[Si](C)(C)C)C1=O	1333.1	Semi standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,1TMS,isomer #2	CC1CCC=C(O[Si](C)(C)C)C1=O	1233.7	Standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CCC1	1417.1	Semi standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CCC1	1475.2	Standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CCC1	1589.5	Semi standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CCC1	1464.0	Standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,1TBDMS,isomer #2	CC1CCC=C(O[Si](C)(C)C(C)(C)C)C1=O	1564.6	Semi standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,1TBDMS,isomer #2	CC1CCC=C(O[Si](C)(C)C(C)(C)C)C1=O	1442.9	Standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CCC1	1926.3	Semi standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CCC1	1784.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-1,2-cyclohexanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9100000000-1f1acecfc19c567d50c7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-1,2-cyclohexanedione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-1,2-cyclohexanedione 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 - 3-Methyl-1,2-cyclohexanedione 10V, Positive-QTOF	splash10-004i-1900000000-7b42029d3aaa9e61ec6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 20V, Positive-QTOF	splash10-056r-8900000000-b799e2f1d5e6ecf4be5c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 40V, Positive-QTOF	splash10-052f-9000000000-c5f5d34c9e18b2dbc78d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 10V, Negative-QTOF	splash10-004i-0900000000-ad62c2519c60710084c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 20V, Negative-QTOF	splash10-004i-1900000000-b13a7946997ff8e3f1cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 40V, Negative-QTOF	splash10-0a4i-9200000000-6f2097c0b3a4722216c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 10V, Negative-QTOF	splash10-004i-0900000000-738068b5fb20db20a035	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 20V, Negative-QTOF	splash10-00ba-9700000000-4a08f9da6bb512b197f5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 40V, Negative-QTOF	splash10-0avl-9200000000-2b7e739c1646124b1583	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 10V, Positive-QTOF	splash10-004i-2900000000-04889c3f3176afdcbec4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 20V, Positive-QTOF	splash10-05mo-9000000000-7c1e484daf53c1b3b36c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 40V, Positive-QTOF	splash10-00kf-9000000000-c97252093fa267aaabdd	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

Not Available

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

FDB012339

KNApSAcK ID

Not Available

Chemspider ID

2568901

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3321360

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1035751

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-Methyl-1,2-cyclohexanedione (HMDB0034080)

MOL for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

3D MOL for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

3D SDF for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

3D-SDF for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

PDB for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

3D PDB for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

SMILES for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

INCHI for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

Structure for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

3D Structure for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra