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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:57 UTC

Update Date

2023-02-21 17:20:46 UTC

HMDB ID

HMDB0031539

Secondary Accession Numbers

HMDB31539

Metabolite Identification

Common Name

2-Methylcyclohexanone

Description

2-Methylcyclohexanone 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. 2-Methylcyclohexanone is a minty and peppermint tasting compound. Based on a literature review very few articles have been published on 2-Methylcyclohexanone.

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-Methyl-1-cyclohexanone	HMDB
alpha-Methylcyclohexanone	HMDB
FEMA 3946	HMDB
O-Methylcyclohexanone	HMDB
tetrahydro-O-Cresol	HMDB
2-Methylcyclohexanone	MeSH

Chemical Formula

C₇H₁₂O

Average Molecular Weight

112.1696

Monoisotopic Molecular Weight

112.088815006

IUPAC Name

2-methylcyclohexan-1-one

Traditional Name

2-methylcyclohexanone

CAS Registry Number

583-60-8

SMILES

CC1CCCCC1=O

InChI Identifier

InChI=1S/C7H12O/c1-6-4-2-3-5-7(6)8/h6H,2-5H2,1H3

InChI Key

LFSAPCRASZRSKS-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

Cellular substructure

Extracellular (HMDB: HMDB0031539)
Cytoplasm (HMDB: HMDB0031539)

Source

Exogenous

Food

Food (HMDB: HMDB0031539)

Exogenous (HMDB: HMDB0031539)

Endogenous

Endogenous (HMDB: HMDB0031539)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031539)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.4 g/L	ALOGPS
logP	1.46	ALOGPS
logP	2.03	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	-7.4	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	32.82 m³·mol⁻¹	ChemAxon
Polarizability	13.11 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]+	123.907	31661259
DarkChem	[M-H]-	117.559	31661259
DeepCCS	[M+H]+	133.611	30932474
DeepCCS	[M-H]-	131.114	30932474
DeepCCS	[M-2H]-	167.475	30932474
DeepCCS	[M+Na]+	142.099	30932474
AllCCS	[M+H]+	123.4	32859911
AllCCS	[M+H-H2O]+	118.5	32859911
AllCCS	[M+NH4]+	127.9	32859911
AllCCS	[M+Na]+	129.3	32859911
AllCCS	[M-H]-	126.1	32859911
AllCCS	[M+Na-2H]-	128.7	32859911
AllCCS	[M+HCOO]-	131.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.16 minutes	32390414
Predicted by Siyang on May 30, 2022	13.872 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.56 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1828.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	505.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	182.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	326.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	305.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	516.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	572.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	121.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1148.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	358.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1158.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	330.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	375.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	499.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	468.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	78.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methylcyclohexanone	CC1CCCCC1=O	1304.0	Standard polar	33892256
2-Methylcyclohexanone	CC1CCCCC1=O	894.9	Standard non polar	33892256
2-Methylcyclohexanone	CC1CCCCC1=O	953.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methylcyclohexanone,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)CCCC1	1155.6	Semi standard non polar	33892256
2-Methylcyclohexanone,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)CCCC1	1165.2	Standard non polar	33892256
2-Methylcyclohexanone,1TMS,isomer #2	CC1CCCC=C1O[Si](C)(C)C	1125.0	Semi standard non polar	33892256
2-Methylcyclohexanone,1TMS,isomer #2	CC1CCCC=C1O[Si](C)(C)C	1165.8	Standard non polar	33892256
2-Methylcyclohexanone,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)CCCC1	1412.8	Semi standard non polar	33892256
2-Methylcyclohexanone,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)CCCC1	1351.9	Standard non polar	33892256
2-Methylcyclohexanone,1TBDMS,isomer #2	CC1CCCC=C1O[Si](C)(C)C(C)(C)C	1359.0	Semi standard non polar	33892256
2-Methylcyclohexanone,1TBDMS,isomer #2	CC1CCCC=C1O[Si](C)(C)C(C)(C)C	1292.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Methylcyclohexanone EI-B (Non-derivatized)	splash10-066r-9000000000-104dcb17b6045eaae29f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylcyclohexanone EI-B (Non-derivatized)	splash10-066r-9100000000-72692ff8e12de3c934c7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylcyclohexanone EI-B (Non-derivatized)	splash10-014l-9000000000-583da36651420dac2bf9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylcyclohexanone EI-B (Non-derivatized)	splash10-066r-9000000000-104dcb17b6045eaae29f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylcyclohexanone EI-B (Non-derivatized)	splash10-066r-9100000000-72692ff8e12de3c934c7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylcyclohexanone EI-B (Non-derivatized)	splash10-014l-9000000000-583da36651420dac2bf9	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcyclohexanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-05x3-9000000000-2584cebf28fa2104c939	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcyclohexanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylcyclohexanone 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-Methylcyclohexanone 10V, Positive-QTOF	splash10-03di-3900000000-2f0f87052a8d12a452c0	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcyclohexanone 20V, Positive-QTOF	splash10-03di-9500000000-220d09454fbca2017479	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcyclohexanone 40V, Positive-QTOF	splash10-1003-9000000000-61b8258c3df2940e8c28	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcyclohexanone 10V, Negative-QTOF	splash10-03di-0900000000-4b26ed68c1b5bbe247ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcyclohexanone 20V, Negative-QTOF	splash10-03di-1900000000-a6ac079a64f346898235	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcyclohexanone 40V, Negative-QTOF	splash10-05ng-9000000000-c8a37d59e8f4d4a4b902	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcyclohexanone 10V, Positive-QTOF	splash10-01ot-9100000000-7739e9aa6c6de0614d8b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcyclohexanone 20V, Positive-QTOF	splash10-05mn-9000000000-0b817ef0aaacc8023c3a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcyclohexanone 40V, Positive-QTOF	splash10-0ar0-9000000000-47b58753289339998292	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcyclohexanone 10V, Negative-QTOF	splash10-03di-0900000000-cc1b76045a872ef7ae94	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcyclohexanone 20V, Negative-QTOF	splash10-03di-1900000000-dd6a94a4dd3cdd83eb99	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylcyclohexanone 40V, Negative-QTOF	splash10-0a4l-9600000000-81dd58c57e289d168d1b	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

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

FDB008147

KNApSAcK ID

Not Available

Chemspider ID

10939

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11419

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 2-Methylcyclohexanone (HMDB0031539)

MOL for HMDB0031539 (2-Methylcyclohexanone)

3D MOL for HMDB0031539 (2-Methylcyclohexanone)

3D SDF for HMDB0031539 (2-Methylcyclohexanone)

3D-SDF for HMDB0031539 (2-Methylcyclohexanone)

PDB for HMDB0031539 (2-Methylcyclohexanone)

3D PDB for HMDB0031539 (2-Methylcyclohexanone)

SMILES for HMDB0031539 (2-Methylcyclohexanone)

INCHI for HMDB0031539 (2-Methylcyclohexanone)

Structure for HMDB0031539 (2-Methylcyclohexanone)

3D Structure for HMDB0031539 (2-Methylcyclohexanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra