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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 02:38:34 UTC
Update Date2023-02-21 17:28:32 UTC
HMDB IDHMDB0041011
Secondary Accession Numbers
  • HMDB41011
Metabolite Identification
Common Namebeta-Cyclocitral
Descriptionbeta-Cyclocitral, also known as β-cyclocitral, belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group. beta-Cyclocitral is a sweet, clean, and damascone tasting compound. beta-Cyclocitral is found, on average, in the highest concentration within orange mints (Mentha aquatica) and safflowers (Carthamus tinctorius). beta-Cyclocitral has also been detected, but not quantified in, several different foods, such as garden tomatoes (Solanum lycopersicum), garden tomato (var.), teas (Camellia sinensis), black tea, and cauliflowers (Brassica oleracea var. botrytis). This could make beta-cyclocitral a potential biomarker for the consumption of these foods. beta-Cyclocitral is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on beta-Cyclocitral.
Structure
Data?1677000512
Synonyms
ValueSource
2,6,6-Trimethyl-1-cyclohexene-1-carboxaldehydeChEBI
2,6,6-Trimethyl-1-cyclohexene-1-carbaldehydeKegg
b-CyclocitralGenerator
Β-cyclocitralGenerator
1-Formyl-2,6,6-trimethyl-1-cyclohexeneHMDB
2,6,6-Trimethyl-1-cyclohexen-1-carboxaldehydeHMDB
2,6,6-Trimethyl-cyclohexene-1-carboxaldehydeHMDB
2,6,6-Trimethyl-cyclohexenecarboxaldehydeHMDB
2,6,6-Trimethylcyclohex-1-ene-1-carbaldehydeHMDB
2,6,6-Trimethylcyclohexene-1-carbaldehydeHMDB
2,6,6-TrimethylcyclohexenecarbaldehydeHMDB
alpha(beta)-CyclocitralHMDB
beta -CyclocitralHMDB
beta-CyclocitrolHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde
Traditional Nameβ-cyclocitral
CAS Registry Number432-25-7
SMILES
CC1=C(C=O)C(C)(C)CCC1
InChI Identifier
InChI=1S/C10H16O/c1-8-5-4-6-10(2,3)9(8)7-11/h7H,4-6H2,1-3H3
InChI KeyMOQGCGNUWBPGTQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganic oxides
Sub ClassNot Available
Direct ParentOrganic oxides
Alternative Parents
Substituents
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point62.00 to 63.00 °C. @ 3.00 mm HgThe Good Scents Company Information System
Water Solubility86.14 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.100 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.26 g/LALOGPS
logP2.96ALOGPS
logP2.41ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.1 m³·mol⁻¹ChemAxon
Polarizability18.03 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]+134.20831661259
DarkChem[M-H]-129.39431661259
DeepCCS[M+H]+138.72930932474
DeepCCS[M-H]-135.8430932474
DeepCCS[M-2H]-172.30530932474
DeepCCS[M+Na]+147.84330932474
AllCCS[M+H]+132.532859911
AllCCS[M+H-H2O]+128.132859911
AllCCS[M+NH4]+136.532859911
AllCCS[M+Na]+137.732859911
AllCCS[M-H]-136.132859911
AllCCS[M+Na-2H]-137.732859911
AllCCS[M+HCOO]-139.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-CyclocitralCC1=C(C=O)C(C)(C)CCC11568.5Standard polar33892256
beta-CyclocitralCC1=C(C=O)C(C)(C)CCC11136.2Standard non polar33892256
beta-CyclocitralCC1=C(C=O)C(C)(C)CCC11146.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - beta-Cyclocitral EI-B (Non-derivatized)splash10-0l0i-4900000000-f6c4a4fe93d19741cab02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Cyclocitral EI-B (Non-derivatized)splash10-0l0i-4900000000-f6c4a4fe93d19741cab02018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Cyclocitral GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-3900000000-6391af660fd4d8a215472016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Cyclocitral GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-052o-9300000000-be54b6f8155405712fdf2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cyclocitral 10V, Positive-QTOFsplash10-0udi-1900000000-a06d949d55e95a72b6b72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cyclocitral 20V, Positive-QTOFsplash10-0udi-9800000000-19d87f66741a50d0e6772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cyclocitral 40V, Positive-QTOFsplash10-0gb9-9100000000-9690930ec35bca4593332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cyclocitral 10V, Negative-QTOFsplash10-0udi-0900000000-dcfa64ac0ff4ae18463b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cyclocitral 20V, Negative-QTOFsplash10-0udi-0900000000-6237aac949530326cbf12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cyclocitral 40V, Negative-QTOFsplash10-0kmr-3900000000-5d5d6b808dcc3a96c3e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cyclocitral 10V, Positive-QTOFsplash10-0udi-6900000000-10632e4d0107c6bea6342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cyclocitral 20V, Positive-QTOFsplash10-0arr-9200000000-06e9f20fa2dfd319b3ba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cyclocitral 40V, Positive-QTOFsplash10-067i-9100000000-eec8f7754558ce99427a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cyclocitral 10V, Negative-QTOFsplash10-0uk9-0900000000-242103d291e18a765c212021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cyclocitral 20V, Negative-QTOFsplash10-0fk9-0900000000-64f4832ef5436e56e9ff2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Cyclocitral 40V, Negative-QTOFsplash10-0a4i-0900000000-a4b505d5001ef400c3802021-09-23Wishart 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
  • Membrane
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020874
KNApSAcK IDC00042278
Chemspider ID9511
KEGG Compound IDC20425
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9895
PDB IDNot Available
ChEBI ID53177
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1037211
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.. .