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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 20:02:11 UTC
Update Date2021-10-13 06:45:50 UTC
HMDB IDHMDB0035093
Secondary Accession Numbers
  • HMDB35093
Metabolite Identification
Common NameD-Citronellol
DescriptionCitronellol is formally classified as alkylalcohol although it is biochemically a monoterpenoid as it is synthesized from isoprene units. Citronellol is a neutral compound. It is a naturally occurring organic compound found in cannabis plants (PMID:6991645 ). Citronellol occurs in many essential oils as either – or + enantiomers. -Citronellol is found in the oils of rose (18-55%) and Pelargonium geraniums while + citronellol is found in citronella oils extracted from the leaves and stems of Cymbopogon nardus or citronella grass. Citronellol has a citrus, floral, and geranium taste with a floral leathery waxy rose citrus odor ( Ref:DOI ). It is used in perfumery to add scents to soaps and incense. It is an insect repellent that repels mosquitos at short distances (PMID:2862274 ). Citronellol is found in highest concentrations in gingers, sweet basils, and winter savories and in lower concentrations in highbush blueberries, bilberries, and cardamoms. Citronellol has also been detected in blackcurrants, fennels, evergreen blackberries, herbs and spices, and nutmegs making citronellol a potential biomarker for the consumption of these foods. Citronellol has promising pharmacological activities (PMID:30453001 ) against human lung cancer (PMID:31280209 ), against induced rat breast cancer (PMID:31313341 ), has antifungal activity against Candida species (PMID:32150884 ) and has anti-hypertensive properties (PMID:26872991 ).
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, (+-)-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 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

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point221.00 to 224.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility105.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.239 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.85 g/LALOGPS
logP10(3.48) g/LALOGPS
logP10(2.75) g/LChemAxon
logS10(-2.3) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.76731661259
DarkChem[M-H]-136.80431661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Citronellol,1TMS,#1CC(C)=CCC[C@@H](C)CCO[Si](C)(C)C1307.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
D-Citronellol,1TBDMS,#1CC(C)=CCC[C@@H](C)CCO[Si](C)(C)C(C)(C)C1521.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - D-Citronellol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-9400000000-ba08b011d6d2fa548e822017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Citronellol GC-MS (1 TMS) - 70eV, Positivesplash10-0ir0-9620000000-5dec8fa14f289a16a8b82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Citronellol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Citronellol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-015c-9000000000-dfb40ffb3fb172759b4f2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Citronellol 10V, Positive-QTOFsplash10-052r-1900000000-9f559c6b6bae07c699782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Citronellol 20V, Positive-QTOFsplash10-052r-8900000000-f8c3d1ff7e6f87d6e43d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Citronellol 40V, Positive-QTOFsplash10-066u-9100000000-8ae7fa4f01b76f1eed162016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Citronellol 10V, Negative-QTOFsplash10-0a4i-0900000000-82f8313ff8eb7c68242b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Citronellol 20V, Negative-QTOFsplash10-056r-0900000000-de94d5335c77bdb5afcf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Citronellol 40V, Negative-QTOFsplash10-0a6u-9800000000-b04acf4b20ad462747962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Citronellol 10V, Negative-QTOFsplash10-0a4i-0900000000-f6034c6a8245c68a37ac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Citronellol 20V, Negative-QTOFsplash10-0ab9-0900000000-4432dcd3f704b4a61b302021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Citronellol 40V, Negative-QTOFsplash10-014i-9400000000-fe45ce059cb434ed5e0c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Citronellol 10V, Positive-QTOFsplash10-05o0-9200000000-e66f9e249b523e6771bb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Citronellol 20V, Positive-QTOFsplash10-053r-9000000000-6e0012cc1ab177db56c02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Citronellol 40V, Positive-QTOFsplash10-0006-9000000000-97567d47518fef28ec282021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1056991
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. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.