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Showing Compound beta-Cyclocitral (FDB020874)

Record Information
Version1.0
Creation date2010-04-08 22:15:19 UTC
Update date2020-09-17 15:31:18 UTC
Primary IDFDB020874
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 ( http://www.thegoodscentscompany.com/data/rw1037211.html#toorgano). 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 has been identified endogenously in dozens of plant species, including tomato, rice, parsley, grape, various trees, and moss. In one study, beta-Cyclocitral, a small molecule derived from beta-carotene, was identified as a regulator of root stem cell behavior in Arabidopsis as well as in rice and tomato (PMID: 31068462).
CAS Number432-25-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
β-cyclocitralbiospider
1-Cyclohexene-1-carboxaldehyde, 2,6,6-trimethyl-biospider
2,6,6-trimethyl-cyclohexene-1-carboxaldehydebiospider
2,6,6-trimethylcyclohex-1-ene-1-carbaldehydebiospider
Alpha(beta)-cyclocitralbiospider
Beta-cyclocitralbiospider
Cyclohexenecarboxaldehyde, 2,6,6-trimethyl-biospider
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
Chemical FormulaC10H16O
IUPAC name2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde
InChI IdentifierInChI=1S/C10H16O/c1-8-5-4-6-10(2,3)9(8)7-11/h7H,4-6H2,1-3H3
InChI KeyMOQGCGNUWBPGTQ-UHFFFAOYSA-N
Isomeric SMILESCC1=C(C=O)C(C)(C)CCC1
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting PointNot Available
Boiling PointBp15 94-97°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
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
ChemSpider ID9511
ChEMBL IDCHEMBL1952257
KEGG Compound IDC20425
Pubchem Compound ID9895
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB41011
CRC / DFC (Dictionary of Food Compounds) IDNFQ78-Y:NFQ78-Y
EAFUS IDNot Available
Dr. Duke IDBETA-CYCLOCITRAL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID432-25-7
GoodScent IDrw1037211
SuperScent ID9895
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mint
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
minty
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
tropical
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
saffron
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
clean
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rose oxide
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tobacco
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
damascone
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).