Showing Compound Card for Citronellyl acetate (CDB000585)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:45:07 UTC
Updated at2020-12-07 19:07:32 UTC
CannabisDB IDCDB000585
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCitronellyl acetate
DescriptionCitronellyl acetate, also known as Citronellol acetate or beta-citronellol acetate, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Citronellyl acetate is the acetate ester of citronellol. Citronellyl acetate exists as a clear, transparent liquid. It is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Citronellyl acetate has a floral, rose, fruity, citrus aroma with a fruity, pear and apple-like taste. It is an approved food additive and can be used in apple, pear, banana and berry flavours. Citronellyl acetate is naturally produced by many plants and is found in carrot seeds, celery, citronella, black currants, ginger, grapefruit, lemons, mushrooms, orange, passion fruit, black pepper and wine. It is found in highest concentration in wild carrots, carrots, and lemons and in a lower concentration in mandarin orange (clementine, tangerine). Citronellyl acetate is one of several esters found in cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC12H22O2
Average Molecular Weight198.31
Monoisotopic Molecular Weight198.162
IUPAC Name(3S)-3,7-dimethyloct-6-en-1-yl acetate
Traditional Name(3S)-3,7-dimethyloct-6-en-1-yl acetate
CAS Registry Number67601-05-2
SMILES
C[C@H](CCOC(C)=O)CCC=C(C)C
InChI Identifier
InChI=1S/C12H22O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,11H,5,7-9H2,1-4H3/t11-/m0/s1
InChI KeyJOZKFWLRHCDGJA-NSHDSACASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohol esters
Direct ParentFatty alcohol esters
Alternative Parents
Substituents
  • Fatty alcohol ester
  • Monoterpenoid
  • Acyclic monoterpenoid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.13ALOGPS
logP3.19ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity59.64 m³·mol⁻¹ChemAxon
Polarizability24.41 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5367487
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6999975
PDB IDNot Available
ChEBI IDNot Available
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 ]