D-Citronellol (CHEM022848)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:56:30 UTC
Update Date2016-11-09 01:17:35 UTC
Accession NumberCHEM022848
Identification
Common NameD-Citronellol
ClassSmall Molecule
DescriptionA citronellol that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7 (the 3R-enantiomer).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(R)-(+)-CitronellolKegg
(+)-beta-CitronellolHMDB
(+)-R-CitronellolHMDB
(3R)-3,7-Dimethyloct-6-en-1-olHMDB
(R)-(+)-beta -CitronellolHMDB
(R)-(+)-beta-CitronellolHMDB
(R)-3,7-Dimethyl-6-octen-1-olHMDB
(R)-3,7-Dimethyloct-6-en-1-olHMDB
3,7-Dimethyl-(3R)-6-octen-1-olHMDB
3,7-Dimethyl-(R)-6-octen-1-olHMDB
Citronellol, (+-)-isomerMeSH, HMDB
CitronellolMeSH, HMDB
Citronellol, (R)-isomerMeSH, HMDB
Citronellol, (S)-isomerMeSH, HMDB
Citronellol, titanium (+4) saltMeSH, HMDB
b-CitronellolGenerator, HMDB
Β-citronellolGenerator, HMDB
(+)-(R)-CitronellolHMDB
(+)-CitronellolHMDB
(+)-β-CitronellolHMDB
(3R)-(+)-beta-CitronellolHMDB
(3R)-(+)-β-CitronellolHMDB
(3R)-3,7-Dimethyl-6-octen-1-olHMDB
(R)-(+)-3,7-Dimethyl-6-octen-1-olHMDB
(R)-(+)-β-CitronellolHMDB
(R)-CitronellolHMDB
(R)-beta-CitronellolHMDB
(R)-β-CitronellolHMDB
D-CitronellolHMDB
d-CitronellolHMDB
Chemical FormulaC10H20O
Average Molecular Mass156.265 g/mol
Monoisotopic Mass156.151 g/mol
CAS Registry Number1117-61-9
IUPAC Name(3R)-3,7-dimethyloct-6-en-1-ol
Traditional Nameβ-citronellol
SMILESC[C@@H](CCO)CCC=C(C)C
InChI IdentifierInChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3/t10-/m1/s1
InChI KeyQMVPMAAFGQKVCJ-SNVBAGLBSA-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
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • 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 Solubility0.85 g/LALOGPS
logP3.48ALOGPS
logP2.75ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)17.11ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity50.49 m³·mol⁻¹ChemAxon
Polarizability20.08 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-9400000000-ba08b011d6d2fa548e82Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ir0-9620000000-5dec8fa14f289a16a8b8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-9f559c6b6bae07c69978Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-8900000000-f8c3d1ff7e6f87d6e43dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-9100000000-8ae7fa4f01b76f1eed16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-82f8313ff8eb7c68242bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0900000000-de94d5335c77bdb5afcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-9800000000-b04acf4b20ad46274796Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-f6034c6a8245c68a37acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-0900000000-4432dcd3f704b4a61b30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9400000000-fe45ce059cb434ed5e0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05o0-9200000000-e66f9e249b523e6771bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-9000000000-6e0012cc1ab177db56c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-97567d47518fef28ec28Spectrum
MSMass Spectrum (Electron Ionization)splash10-015c-9000000000-dfb40ffb3fb172759b4fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDHMDB0035093
FooDB IDFDB013722
Phenol Explorer IDNot Available
KNApSAcK IDC00003038
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCitronellol
Chemspider ID92127
ChEBI ID10360
PubChem Compound ID101977
Kegg Compound IDC09849
YMDB IDNot Available
ECMDB IDM2MDB005688
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM