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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:18:14 UTC
Update Date2022-03-07 02:56:00 UTC
HMDB IDHMDB0038957
Secondary Accession Numbers
  • HMDB38957
Metabolite Identification
Common NameCitronellyl cinnamate
DescriptionCitronellyl cinnamate belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Based on a literature review a small amount of articles have been published on Citronellyl cinnamate.
Structure
Data?1563863287
Synonyms
ValueSource
Citronellyl cinnamic acidGenerator
2-Propenoic acid, 3-phenyl-, 3,7-dimethyl-6-octenyl esterHMDB
Chemical FormulaC19H26O2
Average Molecular Weight286.4085
Monoisotopic Molecular Weight286.193280076
IUPAC Name3,7-dimethyloct-6-en-1-yl (2E)-3-phenylprop-2-enoate
Traditional Name3,7-dimethyloct-6-en-1-yl (2E)-3-phenylprop-2-enoate
CAS Registry Number10482-79-8
SMILES
CC(CCOC(=O)\C=C\C1=CC=CC=C1)CCC=C(C)C
InChI Identifier
InChI=1S/C19H26O2/c1-16(2)8-7-9-17(3)14-15-21-19(20)13-12-18-10-5-4-6-11-18/h4-6,8,10-13,17H,7,9,14-15H2,1-3H3/b13-12+
InChI KeyKMXKQELDKDGFRN-OUKQBFOZSA-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
  • Cinnamic acid or derivatives
  • Fatty alcohol ester
  • Cinnamic acid ester
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Styrene
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Benzenoid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point380.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.038 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.387 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP5.74ALOGPS
logP5.79ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity90.05 m³·mol⁻¹ChemAxon
Polarizability34.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+173.62431661259
DarkChem[M-H]-170.82531661259
DeepCCS[M+H]+171.35930932474
DeepCCS[M-H]-169.00130932474
DeepCCS[M-2H]-201.88730932474
DeepCCS[M+Na]+177.45330932474
AllCCS[M+H]+173.132859911
AllCCS[M+H-H2O]+170.032859911
AllCCS[M+NH4]+176.032859911
AllCCS[M+Na]+176.832859911
AllCCS[M-H]-177.432859911
AllCCS[M+Na-2H]-177.732859911
AllCCS[M+HCOO]-178.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Citronellyl cinnamateCC(CCOC(=O)\C=C\C1=CC=CC=C1)CCC=C(C)C2766.7Standard polar33892256
Citronellyl cinnamateCC(CCOC(=O)\C=C\C1=CC=CC=C1)CCC=C(C)C2122.8Standard non polar33892256
Citronellyl cinnamateCC(CCOC(=O)\C=C\C1=CC=CC=C1)CCC=C(C)C2214.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citronellyl cinnamate GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-4900000000-76f7f61f5d8383f44f4f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citronellyl cinnamate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl cinnamate 10V, Positive-QTOFsplash10-000i-1790000000-f1e80207f949ca278efa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl cinnamate 20V, Positive-QTOFsplash10-001r-4910000000-da65e0872d1a93042c352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl cinnamate 40V, Positive-QTOFsplash10-0ldl-9400000000-0f4f0594372193d97fb82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl cinnamate 10V, Negative-QTOFsplash10-002r-0960000000-5a09328aafbbf46029b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl cinnamate 20V, Negative-QTOFsplash10-002k-0900000000-ebfaf5ba0364e2bc43672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl cinnamate 40V, Negative-QTOFsplash10-004i-1900000000-9afcacdd72c5a3971b6c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl cinnamate 10V, Positive-QTOFsplash10-0019-3890000000-efb19010187fd305c2882021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl cinnamate 20V, Positive-QTOFsplash10-001i-6910000000-867c0e6fc529edef32da2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl cinnamate 40V, Positive-QTOFsplash10-0ue9-8900000000-b40d6f4e32ea5027cfc52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl cinnamate 10V, Negative-QTOFsplash10-000i-0090000000-0f24c1e7ed8a9b47b39f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl cinnamate 20V, Negative-QTOFsplash10-0udi-2930000000-7c0274468614b4bc53fc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl cinnamate 40V, Negative-QTOFsplash10-0ufr-7900000000-5efa528297e2e857c4382021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB018440
KNApSAcK IDNot Available
Chemspider ID4942248
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6437720
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1015801
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.