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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 20:02:11 UTC
Update Date2019-07-23 06:17:44 UTC
HMDB IDHMDB0035093
Secondary Accession Numbers
  • HMDB35093
Metabolite Identification
Common NameD-Citronellol
DescriptionD-Citronellol is found in herbs and spices, as well as bilberry. D-Citronellol is a constituent of black cumin (Nigella sativa) seeds. D-Citronellol is a common constituent of plant oils, especially in the Rutaceae
Structure
Data?1563862664
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, (+-)-isomerHMDB
CitronellolHMDB
Citronellol, (R)-isomerHMDB
Citronellol, (S)-isomerHMDB
Citronellol, titanium (+4) saltHMDB
b-CitronellolGenerator
Β-citronellolGenerator
(+)-(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 Weight156.2652
Monoisotopic Molecular Weight156.151415262
IUPAC Name(3R)-3,7-dimethyloct-6-en-1-ol
Traditional Nameβ-citronellol
CAS Registry Number1117-61-9
SMILES
C[C@@H](CCO)CCC=C(C)C
InChI Identifier
InChI=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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-9400000000-ba08b011d6d2fa548e82JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ir0-9620000000-5dec8fa14f289a16a8b8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-9f559c6b6bae07c69978JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-8900000000-f8c3d1ff7e6f87d6e43dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-9100000000-8ae7fa4f01b76f1eed16JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-82f8313ff8eb7c68242bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0900000000-de94d5335c77bdb5afcfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-9800000000-b04acf4b20ad46274796JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-015c-9000000000-dfb40ffb3fb172759b4fJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0-17960.919 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0-717668.852 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013722
KNApSAcK IDC00003038
Chemspider ID92127
KEGG Compound IDC09849
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCitronellol
METLIN IDNot Available
PubChem Compound101977
PDB IDNot Available
ChEBI ID10360
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.