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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:21 UTC
Update Date2021-10-13 06:24:21 UTC
HMDB IDHMDB0032540
Secondary Accession Numbers
  • HMDB32540
Metabolite Identification
Common Name2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde
Description2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde is a beef, camphor, and cooling tasting compound. 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde has been detected, but not quantified in, cauliflowers (Brassica oleracea var. botrytis). This could make 2,6,6-trimethyl-1-cyclohexen-1-acetaldehyde a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde.
Structure
Data?1563862273
Synonyms
ValueSource
(2,6,6-Trimethyl-1-cyclohexen-1-yl)acetaldehydeHMDB
2,6,6-Trimethyl-1-cyclohexene-1-acetaldehydeHMDB
beta-apo-8-CarotenalHMDB
beta-CyclohomocitralHMDB
beta-HomocyclocitralHMDB
Ghl.PD_Mitscher_leg0.59HMDB
Chemical FormulaC11H18O
Average Molecular Weight166.26
Monoisotopic Molecular Weight166.135765198
IUPAC Name2-(2,6,6-trimethylcyclohex-1-en-1-yl)acetaldehyde
Traditional Name2-(2,6,6-trimethylcyclohex-1-en-1-yl)acetaldehyde
CAS Registry Number472-66-2
SMILES
CC1=C(CC=O)C(C)(C)CCC1
InChI Identifier
InChI=1S/C11H18O/c1-9-5-4-7-11(2,3)10(9)6-8-12/h8H,4-7H2,1-3H3
InChI KeyVHTFHZGAMYUZEP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydrogen aldehydes
Alternative Parents
Substituents
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point58.00 to 59.00 °C. @ 760.40 mm HgThe Good Scents Company Information System
Water Solubility28.31 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.215 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.61 g/LALOGPS
logP10(3.65) g/LALOGPS
logP10(2.34) g/LChemAxon
logS10(-2.4) g/LALOGPS
pKa (Strongest Acidic)15.82ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity51.65 m³·mol⁻¹ChemAxon
Polarizability19.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.49131661259
DarkChem[M-H]-135.4931661259
DeepCCS[M+H]+139.09430932474
DeepCCS[M-H]-136.31430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,6,6-Trimethyl-1-cyclohexen-1-acetaldehydeCC1=C(CC=O)C(C)(C)CCC11574.3Standard polar33892256
2,6,6-Trimethyl-1-cyclohexen-1-acetaldehydeCC1=C(CC=O)C(C)(C)CCC11208.4Standard non polar33892256
2,6,6-Trimethyl-1-cyclohexen-1-acetaldehydeCC1=C(CC=O)C(C)(C)CCC11261.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde,1TMS,isomer #1CC1=C(C=CO[Si](C)(C)C)C(C)(C)CCC11472.5Semi standard non polar33892256
2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde,1TMS,isomer #1CC1=C(C=CO[Si](C)(C)C)C(C)(C)CCC11485.7Standard non polar33892256
2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde,1TBDMS,isomer #1CC1=C(C=CO[Si](C)(C)C(C)(C)C)C(C)(C)CCC11708.9Semi standard non polar33892256
2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde,1TBDMS,isomer #1CC1=C(C=CO[Si](C)(C)C(C)(C)C)C(C)(C)CCC11737.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde EI-B (Non-derivatized)splash10-0pw9-7900000000-2e91ff082564e0fb39dc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde EI-B (Non-derivatized)splash10-0pw9-7900000000-2e91ff082564e0fb39dc2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-3900000000-1a57f1dca626dcca6c7f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde 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 - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde 10V, Positive-QTOFsplash10-014i-1900000000-13130a9d2107a892f3332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde 20V, Positive-QTOFsplash10-014i-7900000000-01a726056dc02a4576c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde 40V, Positive-QTOFsplash10-014l-9100000000-37fa57136f86fd8c933d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde 10V, Negative-QTOFsplash10-014i-0900000000-81a8a3d6f97edabbe3572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde 20V, Negative-QTOFsplash10-014i-1900000000-ce243f44bec9a6d67c142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde 40V, Negative-QTOFsplash10-0006-9800000000-e30136d177fa193a1a1f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde 10V, Negative-QTOFsplash10-00xr-0900000000-f3783199f970a6cc46da2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde 20V, Negative-QTOFsplash10-00di-0900000000-0b49761b8d50c6a2b1672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde 40V, Negative-QTOFsplash10-05al-1900000000-e03b7d1a93523645e4212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde 10V, Positive-QTOFsplash10-00y0-2900000000-193b82758bdabb79d11a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde 20V, Positive-QTOFsplash10-05gr-7900000000-a9f4244bc7ad77d25b942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde 40V, Positive-QTOFsplash10-0ayi-9400000000-a5c068fa7af9f00f326f2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB010415
KNApSAcK IDNot Available
Chemspider ID55072
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61124
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1036391
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). EAFUS: Everything Added to Food in the United States.. .