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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:15:57 UTC
Update Date2023-02-21 17:25:33 UTC
HMDB IDHMDB0037023
Secondary Accession Numbers
  • HMDB37023
Metabolite Identification
Common Name2-Hydroxy-2,6,6-trimethylcyclohexanone
Description2-Hydroxy-2,6,6-trimethylcyclohexanone belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. 2-Hydroxy-2,6,6-trimethylcyclohexanone is a sweet, herbal, and tobacco tasting compound. 2-Hydroxy-2,6,6-trimethylcyclohexanone has been detected, but not quantified in, several different foods, such as black tea, green tea, herbal tea, red tea, and teas (Camellia sinensis). This could make 2-hydroxy-2,6,6-trimethylcyclohexanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Hydroxy-2,6,6-trimethylcyclohexanone.
Structure
Data?1677000333
Synonyms
ValueSource
2,6,6-Trimethyl-2-hydroxycyclohexanoneHMDB
2-Hydroxy-2,6,6-trimethyl-cyclohexanoneHMDB
Chemical FormulaC9H16O2
Average Molecular Weight156.2221
Monoisotopic Molecular Weight156.115029756
IUPAC Name2-hydroxy-2,6,6-trimethylcyclohexan-1-one
Traditional Name2-hydroxy-2,6,6-trimethylcyclohexan-1-one
CAS Registry Number7500-42-7
SMILES
CC1(C)CCCC(C)(O)C1=O
InChI Identifier
InChI=1S/C9H16O2/c1-8(2)5-4-6-9(3,11)7(8)10/h11H,4-6H2,1-3H3
InChI KeyFWCGLHYHGUHPRY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAcyloins
Alternative Parents
Substituents
  • Acyloin
  • Tertiary alcohol
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point232.00 to 233.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility6304 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.924 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility13 g/LALOGPS
logP1.27ALOGPS
logP2.15ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)13.26ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.53 m³·mol⁻¹ChemAxon
Polarizability17.46 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]+135.02631661259
DarkChem[M-H]-131.87131661259
DeepCCS[M+H]+139.06630932474
DeepCCS[M-H]-135.24830932474
DeepCCS[M-2H]-172.70230932474
DeepCCS[M+Na]+148.18230932474
AllCCS[M+H]+133.132859911
AllCCS[M+H-H2O]+128.732859911
AllCCS[M+NH4]+137.132859911
AllCCS[M+Na]+138.332859911
AllCCS[M-H]-135.632859911
AllCCS[M+Na-2H]-137.332859911
AllCCS[M+HCOO]-139.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-2,6,6-trimethylcyclohexanoneCC1(C)CCCC(C)(O)C1=O1594.4Standard polar33892256
2-Hydroxy-2,6,6-trimethylcyclohexanoneCC1(C)CCCC(C)(O)C1=O1087.0Standard non polar33892256
2-Hydroxy-2,6,6-trimethylcyclohexanoneCC1(C)CCCC(C)(O)C1=O1097.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-2,6,6-trimethylcyclohexanone,1TMS,isomer #1CC1(C)CCCC(C)(O[Si](C)(C)C)C1=O1275.9Semi standard non polar33892256
2-Hydroxy-2,6,6-trimethylcyclohexanone,1TBDMS,isomer #1CC1(C)CCCC(C)(O[Si](C)(C)C(C)(C)C)C1=O1525.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9100000000-188039cffee33a54e5f82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone GC-MS (1 TMS) - 70eV, Positivesplash10-01xx-9320000000-946947ebc74112a75a4c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 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 - 2-Hydroxy-2,6,6-trimethylcyclohexanone 10V, Positive-QTOFsplash10-0a4i-0900000000-f5098fd2747f89a3aa522015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 20V, Positive-QTOFsplash10-0a4i-5900000000-dbe4884f1d7b23faaf8f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 40V, Positive-QTOFsplash10-015c-9000000000-5f4dcf2fb7221b90ead82015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 10V, Negative-QTOFsplash10-0a4i-0900000000-fc3691ad4aaa97d1518d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 20V, Negative-QTOFsplash10-0a4i-1900000000-5d50de549f77bb27a68f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 40V, Negative-QTOFsplash10-00m0-9300000000-45c7e3c65481757e682c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 10V, Negative-QTOFsplash10-0a4i-0900000000-376389ca50b091133eac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 20V, Negative-QTOFsplash10-0a4i-2900000000-5cb0b45f662d9d1535df2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 40V, Negative-QTOFsplash10-0a4i-3900000000-e9a16d8e98a8fb35dc1f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 10V, Positive-QTOFsplash10-0a4i-3900000000-18ebf0f49cd1d539d7b32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 20V, Positive-QTOFsplash10-000x-9100000000-2896f4c14bfcc8b9ff702021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 40V, Positive-QTOFsplash10-00kf-9000000000-e4c4645cd24fd328301d2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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+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
  • Membrane
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 IDFDB016003
KNApSAcK IDNot Available
Chemspider ID91353
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101115
PDB IDNot Available
ChEBI ID171777
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1535881
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .