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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-12 02:38:34 UTC
Update Date2019-07-23 06:33:34 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 an extremely weak basic (essentially neutral) compound (based on its pKa). beta-Cyclocitral is a sweet, clean, and damascone. Outside of the human body, beta-cyclocitral is found, on average, in the highest concentration in orange mints and safflowers. beta-cyclocitral has also been detected, but not quantified in, several different foods, such as figs, herbs and spices, oats, and tea. This could make beta-cyclocitral a potential biomarker for the consumption of these foods.
Structure
Data?1563863614
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0l0i-4900000000-f6c4a4fe93d19741cab0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0l0i-4900000000-f6c4a4fe93d19741cab0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-3900000000-6391af660fd4d8a21547Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-a06d949d55e95a72b6b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9800000000-19d87f66741a50d0e677Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-9690930ec35bca459333Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-dcfa64ac0ff4ae18463bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-6237aac949530326cbf1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kmr-3900000000-5d5d6b808dcc3a96c3e3Spectrum
MSMass Spectrum (Electron Ionization)splash10-052o-9300000000-be54b6f8155405712fdfSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>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
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.. .