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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:57 UTC
Update Date2023-02-21 17:20:46 UTC
HMDB IDHMDB0031540
Secondary Accession Numbers
  • HMDB31540
Metabolite Identification
Common Name4-Methylcyclohexanone
Description4-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
Data?1677000046
Synonyms
ValueSource
4-Methyl-1-cyclohexanoneHMDB
4-Methyl-cyclohexanoneHMDB
CYCLOHEXANONE,4-methylHMDB
FEMA 3948HMDB
MethycyclohexanoneHMDB
Methyl-4 cyclohexanone-1HMDB
Methyl-cyclohexanoneHMDB
MethylcyclohexanoneHMDB
MetylocykloheksanonHMDB
P-Methyl cyclohexanoneHMDB
tetrahydro-P-CresolHMDB
Chemical FormulaC7H12O
Average Molecular Weight112.1696
Monoisotopic Molecular Weight112.088815006
IUPAC Name4-methylcyclohexan-1-one
Traditional Name4-methylcyclohexanone
CAS Registry Number589-92-4
SMILES
CC1CCC(=O)CC1
InChI Identifier
InChI=1S/C7H12O/c1-6-2-4-7(8)5-3-6/h6H,2-5H2,1H3
InChI KeyVGVHNLRUAMRIEW-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclic ketones
Alternative Parents
Substituents
  • Cyclic ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-40.6 °CNot Available
Boiling Point169.00 to 171.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility7092 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.38Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.94 g/LALOGPS
logP1.46ALOGPS
logP1.78ChemAxon
logS-1.3ALOGPS
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.8 m³·mol⁻¹ChemAxon
Polarizability13.11 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.38831661259
DarkChem[M-H]-118.42231661259
DeepCCS[M+H]+127.78430932474
DeepCCS[M-H]-124.96830932474
DeepCCS[M-2H]-161.54630932474
DeepCCS[M+Na]+136.33430932474
AllCCS[M+H]+123.732859911
AllCCS[M+H-H2O]+118.832859911
AllCCS[M+NH4]+128.232859911
AllCCS[M+Na]+129.532859911
AllCCS[M-H]-127.032859911
AllCCS[M+Na-2H]-129.632859911
AllCCS[M+HCOO]-132.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-MethylcyclohexanoneCC1CCC(=O)CC11323.0Standard polar33892256
4-MethylcyclohexanoneCC1CCC(=O)CC1922.3Standard non polar33892256
4-MethylcyclohexanoneCC1CCC(=O)CC1961.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Methylcyclohexanone,1TMS,isomer #1CC1CC=C(O[Si](C)(C)C)CC11118.4Semi standard non polar33892256
4-Methylcyclohexanone,1TMS,isomer #1CC1CC=C(O[Si](C)(C)C)CC11146.5Standard non polar33892256
4-Methylcyclohexanone,1TBDMS,isomer #1CC1CC=C(O[Si](C)(C)C(C)(C)C)CC11338.3Semi standard non polar33892256
4-Methylcyclohexanone,1TBDMS,isomer #1CC1CC=C(O[Si](C)(C)C(C)(C)C)CC11297.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Methylcyclohexanone EI-B (Non-derivatized)splash10-0a4i-9000000000-bd3f17996e86842970212017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylcyclohexanone EI-B (Non-derivatized)splash10-0a4i-9000000000-66232bcf6ffeb21e358d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylcyclohexanone EI-B (Non-derivatized)splash10-0a4i-9000000000-bd3f17996e86842970212018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylcyclohexanone EI-B (Non-derivatized)splash10-0a4i-9000000000-66232bcf6ffeb21e358d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylcyclohexanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-cc2bb41dc7e1d4f6160a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylcyclohexanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 10V, Positive-QTOFsplash10-03di-2900000000-649b3a7e1c82c18444fa2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 20V, Positive-QTOFsplash10-03di-9500000000-ae7a1a8b394c67eec1c62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 40V, Positive-QTOFsplash10-0pvl-9000000000-d0355e440438ec45cf532016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 10V, Negative-QTOFsplash10-03di-0900000000-4b26ed68c1b5bbe247ca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 20V, Negative-QTOFsplash10-03di-0900000000-4b26ed68c1b5bbe247ca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 40V, Negative-QTOFsplash10-01ox-9100000000-3df10b99bc5a4dcd65cc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 10V, Negative-QTOFsplash10-03di-0900000000-6e2ef191e20e94bd344c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 20V, Negative-QTOFsplash10-03dl-5900000000-6ea76d503efe22596bdf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 40V, Negative-QTOFsplash10-0006-9000000000-a7c171f744aa225d36942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 10V, Positive-QTOFsplash10-08fs-9400000000-b64046f59631a4cb3c402021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 20V, Positive-QTOFsplash10-0aor-9000000000-ec17488639ef3688c46c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcyclohexanone 40V, Positive-QTOFsplash10-0ap3-9000000000-b91821bd5416732f1c602021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008150
KNApSAcK IDC00050722
Chemspider ID11041
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11525
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1108151
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .