CITRONELLAL (CHEM005163)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 01:58:47 UTC
Update Date2016-11-09 01:09:29 UTC
Accession NumberCHEM005163
Identification
Common NameCITRONELLAL
ClassSmall Molecule
DescriptionA monoterpenoid, the main component of citronella oil which gives it its distinctive lemon aroma.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,3-DihydrocitralChEBI
3,7-Dimethyl-6-octen-1-alChEBI
3,7-Dimethyl-6-octenalChEBI
beta-CitronellalChEBI
b-CitronellalGenerator
Β-citronellalGenerator
3,7-Dimethyloct-6-enalHMDB
beta -CitronellalHMDB
FEMA 2307HMDB
RhodinalHMDB
Citronellal, (+-)-isomerMeSH, HMDB
Citronellal, (S)-isomerMeSH, HMDB
Citronellal, (R)-isomerMeSH, HMDB
Chemical FormulaC10H18O
Average Molecular Mass154.253 g/mol
Monoisotopic Mass154.136 g/mol
CAS Registry Number106-23-0
IUPAC Name3,7-dimethyloct-6-enal
Traditional Namecitronella
SMILESCC(CCC=C(C)C)CC=O
InChI IdentifierInChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3
InChI KeyNEHNMFOYXAPHSD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Medium-chain aldehyde
  • Alpha-hydrogen aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP3.25ALOGPS
logP2.71ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)18.32ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity49.3 m³·mol⁻¹ChemAxon
Polarizability19.18 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066v-9200000000-145d8f7001c4ce77fa8cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066u-9100000000-95b49c5f5088a3eddc72Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066v-9200000000-145d8f7001c4ce77fa8cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066u-9100000000-95b49c5f5088a3eddc72Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9400000000-61094362cba6ad2562d7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1900000000-facaeed6253aef58db1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-9700000000-246e147d68730886b936Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldl-9000000000-a497aaf732131b397f9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-804231e21b402460f30fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-e11d5a0124399999066aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-55b14a46099707c2eeb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05o3-9100000000-f88a67993a6d30f736f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lu-9000000000-069ce8d3e8f400ae4384Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a86a178bcdeaecf8351dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-d2363ae8d4dbdcccda80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h90-0900000000-399caab2275c277c7c12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01tc-9000000000-4f5c5668195b4a69808eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0035841
FooDB IDFDB014617
Phenol Explorer IDNot Available
KNApSAcK IDC00035823
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCitronellal
Chemspider ID7506
ChEBI ID47856
PubChem Compound ID7794
Kegg Compound IDC17384
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10771133
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22382815
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22559719
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22972327
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23047114
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23064632
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23065287
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23071142
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=9540973
10. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
11. 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.
12. 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.
13. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
14. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
15. The lipid handbook with CD-ROM