Showing Compound Card for beta-Cyclocitral (CDB000187)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-18 23:28:01 UTC
Updated at2020-12-07 19:07:14 UTC
CannabisDB IDCDB000187
Secondary Accession NumbersNot Available
Cannabis Compound 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 neutral compound, colorless to pale yellow clear liquid with is a tropical, saffron, herbal, clean, rose, oxide, sweet, tobacco damascene, fruity odor and tropical saffron herbal tobacco medicinal phenolic leathery green flavor ( Ref:DOI ). beta-cyclocitral is found in highest concentrations in orange mints and safflowers and has also been detected in figs, herbs and spices, oats, and tea. This could make beta-cyclocitral a potential biomarker for the consumption of these foods. beta-Cyclocitral is also found in cannabis plants (PMID: 6991645 ). beta-Cyclocitral has been identified endogenously in dozens of plant species, including tomato, rice, parsley, grape, various trees, and moss. In one study, β-Cyclocitral, a small molecule derived from β-carotene, was identified as a regulator of root stem cell behavior in Arabidopsis as well as in rice and tomato (PMID: 31068462 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight152.23
Monoisotopic Molecular Weight152.1201
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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052o-9300000000-be54b6f8155405712fdf2015-03-01View Spectrum
GC-MSbeta-Cyclocitral, non-derivatized, GC-MS Spectrumsplash10-0l0i-4900000000-f6c4a4fe93d19741cab0Spectrum
GC-MSbeta-Cyclocitral, non-derivatized, GC-MS Spectrumsplash10-0l0i-4900000000-f6c4a4fe93d19741cab0Spectrum
Predicted GC-MSbeta-Cyclocitral, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052r-3900000000-6391af660fd4d8a21547Spectrum
Predicted GC-MSbeta-Cyclocitral, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-a06d949d55e95a72b6b72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9800000000-19d87f66741a50d0e6772016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-9690930ec35bca4593332016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-dcfa64ac0ff4ae18463b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-6237aac949530326cbf12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kmr-3900000000-5d5d6b808dcc3a96c3e32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-6900000000-10632e4d0107c6bea6342021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0arr-9200000000-06e9f20fa2dfd319b3ba2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067i-9100000000-eec8f7754558ce99427a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-0900000000-242103d291e18a765c212021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0900000000-64f4832ef5436e56e9ff2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-a4b505d5001ef400c3802021-09-23View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0041011
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Dickinson AJ, Lehner K, Mi J, Jia KP, Mijar M, Dinneny J, Al-Babili S, Benfey PN: beta-Cyclocitral is a conserved root growth regulator. Proc Natl Acad Sci U S A. 2019 May 21;116(21):10563-10567. doi: 10.1073/pnas.1821445116. Epub 2019 May 8. [PubMed:31068462 ]