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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

HMDB0031540

Secondary Accession Numbers

HMDB31540

Metabolite Identification

Common Name

4-Methylcyclohexanone

Description

4-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. 4-Methylcyclohexanone is an animal and musty tasting compound. Based on a literature review a significant number of articles have been published on 4-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
4-Methyl-1-cyclohexanone	HMDB
4-Methyl-cyclohexanone	HMDB
CYCLOHEXANONE,4-methyl	HMDB
FEMA 3948	HMDB
Methycyclohexanone	HMDB
Methyl-4 cyclohexanone-1	HMDB
Methyl-cyclohexanone	HMDB
Methylcyclohexanone	HMDB
Metylocykloheksanon	HMDB
P-Methyl cyclohexanone	HMDB
tetrahydro-P-Cresol	HMDB

Chemical Formula

C₇H₁₂O

Average Molecular Weight

112.1696

Monoisotopic Molecular Weight

112.088815006

IUPAC Name

4-methylcyclohexan-1-one

Traditional Name

4-methylcyclohexanone

CAS Registry Number

589-92-4

SMILES

CC1CCC(=O)CC1

InChI Identifier

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

InChI Key

VGVHNLRUAMRIEW-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: HMDB0031540)
Cytoplasm (HMDB: HMDB0031540)

Source

Endogenous

Endogenous (HMDB: HMDB0031540)

Exogenous

Food

Food (HMDB: HMDB0031540)

Exogenous (HMDB: HMDB0031540)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031540)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-40.6 °C	Not Available
Boiling Point	169.00 to 171.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	7092 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.38	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.94 g/L	ALOGPS
logP	1.46	ALOGPS
logP	1.78	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	-7.3	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	32.8 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]+	124.388	31661259
DarkChem	[M-H]-	118.422	31661259
DeepCCS	[M+H]+	127.784	30932474
DeepCCS	[M-H]-	124.968	30932474
DeepCCS	[M-2H]-	161.546	30932474
DeepCCS	[M+Na]+	136.334	30932474
AllCCS	[M+H]+	123.7	32859911
AllCCS	[M+H-H2O]+	118.8	32859911
AllCCS	[M+NH4]+	128.2	32859911
AllCCS	[M+Na]+	129.5	32859911
AllCCS	[M-H]-	127.0	32859911
AllCCS	[M+Na-2H]-	129.6	32859911
AllCCS	[M+HCOO]-	132.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methylcyclohexanone	CC1CCC(=O)CC1	1323.0	Standard polar	33892256
4-Methylcyclohexanone	CC1CCC(=O)CC1	922.3	Standard non polar	33892256
4-Methylcyclohexanone	CC1CCC(=O)CC1	961.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Methylcyclohexanone,1TMS,isomer #1	CC1CC=C(O[Si](C)(C)C)CC1	1118.4	Semi standard non polar	33892256
4-Methylcyclohexanone,1TMS,isomer #1	CC1CC=C(O[Si](C)(C)C)CC1	1146.5	Standard non polar	33892256
4-Methylcyclohexanone,1TBDMS,isomer #1	CC1CC=C(O[Si](C)(C)C(C)(C)C)CC1	1338.3	Semi standard non polar	33892256
4-Methylcyclohexanone,1TBDMS,isomer #1	CC1CC=C(O[Si](C)(C)C(C)(C)C)CC1	1297.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Methylcyclohexanone EI-B (Non-derivatized)	splash10-0a4i-9000000000-bd3f17996e8684297021	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methylcyclohexanone EI-B (Non-derivatized)	splash10-0a4i-9000000000-66232bcf6ffeb21e358d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methylcyclohexanone EI-B (Non-derivatized)	splash10-0a4i-9000000000-bd3f17996e8684297021	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methylcyclohexanone EI-B (Non-derivatized)	splash10-0a4i-9000000000-66232bcf6ffeb21e358d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylcyclohexanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-cc2bb41dc7e1d4f6160a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-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 - 4-Methylcyclohexanone 10V, Positive-QTOF	splash10-03di-2900000000-649b3a7e1c82c18444fa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 20V, Positive-QTOF	splash10-03di-9500000000-ae7a1a8b394c67eec1c6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 40V, Positive-QTOF	splash10-0pvl-9000000000-d0355e440438ec45cf53	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 10V, Negative-QTOF	splash10-03di-0900000000-4b26ed68c1b5bbe247ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 20V, Negative-QTOF	splash10-03di-0900000000-4b26ed68c1b5bbe247ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 40V, Negative-QTOF	splash10-01ox-9100000000-3df10b99bc5a4dcd65cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 10V, Negative-QTOF	splash10-03di-0900000000-6e2ef191e20e94bd344c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 20V, Negative-QTOF	splash10-03dl-5900000000-6ea76d503efe22596bdf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 40V, Negative-QTOF	splash10-0006-9000000000-a7c171f744aa225d3694	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 10V, Positive-QTOF	splash10-08fs-9400000000-b64046f59631a4cb3c40	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 20V, Positive-QTOF	splash10-0aor-9000000000-ec17488639ef3688c46c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 40V, Positive-QTOF	splash10-0ap3-9000000000-b91821bd5416732f1c60	2021-09-25	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]+)	2023-02-04	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

FDB008150

KNApSAcK ID

C00050722

Chemspider ID

11041

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11525

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1108151

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Schenkmayerova A, Bucko M, Gemeiner P, Chorvat D Jr, Lacik I: Viability of free and encapsulated Escherichia coli overexpressing cyclopentanone monooxygenase monitored during model Baeyer-Villiger biooxidation by confocal laser scanning microscopy. Biotechnol Lett. 2012 Feb;34(2):309-14. doi: 10.1007/s10529-011-0765-7. Epub 2011 Oct 8. [PubMed:21983971 ]
Chen W, Cheng X, Zhou Z, Liu J, Wang H: Molecular cloning and characterization of a tropinone reductase from Dendrobium nobile Lindl. Mol Biol Rep. 2013 Feb;40(2):1145-54. doi: 10.1007/s11033-012-2156-0. Epub 2012 Oct 27. [PubMed:23104472 ]
Cheong WY, Huang Y, Dangaria N, Gellman AJ: Probing enantioselectivity on chirally modified Cu(110), Cu(100), and Cu(111) surfaces. Langmuir. 2010 Nov 2;26(21):16412-23. doi: 10.1021/la102074a. [PubMed:20973584 ]
Sajjadifar S, Vahedi H, Massoudi A, Louie O: New 3H-indole synthesis by Fischer's method. Part I. Molecules. 2010 Apr 8;15(4):2491-8. doi: 10.3390/molecules15042491. [PubMed:20428058 ]
Kawamoto M, Utsukihara T, Abe C, Sato M, Saito M, Koshimura M, Kato N, Horiuchi CA: Biotransformation of (+/-)-2-methylcyclohexanone by fungi. Biotechnol Lett. 2008 Sep;30(9):1655-60. doi: 10.1007/s10529-008-9729-y. Epub 2008 Apr 22. [PubMed:18427929 ]
Nassimbeni LR, Su H, Curtin TL: Enhanced enantioselectivity of 3-methylcyclohexanone by mixed diol host compounds. Chem Commun (Camb). 2012 Sep 4;48(68):8526-8. doi: 10.1039/c2cc34118b. Epub 2012 Jul 17. [PubMed:22801591 ]
Xin M, Bugg TD: Evidence from mechanistic probes for distinct hydroperoxide rearrangement mechanisms in the intradiol and extradiol catechol dioxygenases. J Am Chem Soc. 2008 Aug 6;130(31):10422-30. doi: 10.1021/ja8029569. Epub 2008 Jul 16. [PubMed:18627158 ]
Jacolot M, Jean M, Levoin N, van de Weghe P: The Prins reaction using ketones: rationalization and application toward the synthesis of the portentol skeleton. Org Lett. 2012 Jan 6;14(1):58-61. doi: 10.1021/ol202829u. Epub 2011 Nov 30. [PubMed:22128826 ]
Tanaka T, Kogure N, Kitajima M, Takayama H: Asymmetric total syntheses of cyclic nitrone-containing phlegmarine-type Lycopodium alkaloids, lycoposerramines-X and -Z. J Org Chem. 2009 Nov 20;74(22):8675-80. doi: 10.1021/jo9018182. [PubMed:19908911 ]
Pena-Lopez M, Martinez MM, Sarandeses LA, Perez Sestelo J: Total synthesis of (+)-neomarinone. Chemistry. 2009;15(4):910-6. doi: 10.1002/chem.200802021. [PubMed:19053110 ]
Pivnenko NS, Turov AV, Abakumov VV, Kutulya LA, Shishkina SV, Shishkin OV: Molecular structures of regioisomeric 7-arylidene hexahydroindazoles from (1)H NMR spectra. Magn Reson Chem. 2009 Jun;47(6):488-96. doi: 10.1002/mrc.2421. [PubMed:19267426 ]
Hsieh MT, Liu HJ, Ly TW, Shia KS: A concise total synthesis of (+/-)-acutifolone A. Org Biomol Chem. 2009 Aug 21;7(16):3285-90. doi: 10.1039/b905910e. Epub 2009 Jun 19. [PubMed:19641787 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-Methylcyclohexanone (HMDB0031540)

MOL for HMDB0031540 (4-Methylcyclohexanone)

3D MOL for HMDB0031540 (4-Methylcyclohexanone)

3D SDF for HMDB0031540 (4-Methylcyclohexanone)

3D-SDF for HMDB0031540 (4-Methylcyclohexanone)

PDB for HMDB0031540 (4-Methylcyclohexanone)

3D PDB for HMDB0031540 (4-Methylcyclohexanone)

SMILES for HMDB0031540 (4-Methylcyclohexanone)

INCHI for HMDB0031540 (4-Methylcyclohexanone)

Structure for HMDB0031540 (4-Methylcyclohexanone)

3D Structure for HMDB0031540 (4-Methylcyclohexanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra