Record Information
Version1.0
Created at2020-03-18 23:24:04 UTC
Updated at2020-12-07 19:07:04 UTC
CannabisDB IDCDB000081
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCitronellol
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
Thumb
Synonyms
ValueSource
(-)-3,7-Dimethyloct-6-en-1-olChEBI
(-)-CitronellolChEBI
(S)-3,7-Dimethyl-6-octen-1-olChEBI
L-CitronellolChEBI
(-)-(S)-CitronellolHMDB
(-)-beta-CitronellolHMDB
(-)-β-CitronellolHMDB
(3S)-3,7-Dimethyl-6-octen-1-olHMDB
(S)-(-)-CitronellolHMDB
(S)-(-)-beta-CitronellolHMDB
(S)-(-)-β-CitronellolHMDB
(S)-CitronellolHMDB
(S)-beta-CitronellolHMDB
(S)-β-CitronellolHMDB
l-CitronellolHMDB
(-)-3,7-Dimethyl-6-octen-1-olPhytoBank
3,7-Dimethyl-6-octen-1-olPhytoBank
(±)-3,7-Dimethyl-6-octen-1-olPhytoBank
(±)-CitronellolPhytoBank
(±)-beta-CitronellolPhytoBank
(±)-β-CitronellolPhytoBank
1-Hydroxy-3,7-dimethyl-6-octenePhytoBank
2,3-DihydrogeraniolPhytoBank
2,6-Dimethyl-2-octen-8-olPhytoBank
dl-CitronellolPhytoBank
DihydrogeraniolPhytoBank
beta-CitronellolPhytoBank
β-CitronellolPhytoBank
Chemical FormulaC10H20O
Average Molecular Weight156.27
Monoisotopic Molecular Weight156.1514
IUPAC Name(3S)-3,7-dimethyloct-6-en-1-ol
Traditional Name(-)-citronellol
CAS Registry Number7540-51-4
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-/m0/s1
InChI KeyQMVPMAAFGQKVCJ-JTQLQIEISA-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:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point225 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability20.1 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCitronellol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitronellol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-9f559c6b6bae07c699782016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-8900000000-f8c3d1ff7e6f87d6e43d2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-9100000000-8ae7fa4f01b76f1eed162016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-82f8313ff8eb7c68242b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0900000000-de94d5335c77bdb5afcf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-9800000000-b04acf4b20ad462747962016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05o0-9200000000-e66f9e249b523e6771bb2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-9000000000-6e0012cc1ab177db56c02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-97567d47518fef28ec282021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-f6034c6a8245c68a37ac2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-0900000000-4432dcd3f704b4a61b302021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9400000000-fe45ce059cb434ed5e0c2021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035094
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013723
KNApSAcK IDC00000844
Chemspider ID7505
KEGG Compound IDC11386
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCitronellol
METLIN IDNot Available
PubChem Compound7793
PDB IDNot Available
ChEBI ID88
References
General References
  1. 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 ]
  2. Taylor WG, Schreck CE: Chiral-phase capillary gas chromatography and mosquito repellent activity of some oxazolidine derivatives of (+)- and (-)-citronellol. J Pharm Sci. 1985 May;74(5):534-9. doi: 10.1002/jps.2600740508. [PubMed:2862274 ]
  3. Santos PL, Matos JPSCF, Picot L, Almeida JRGS, Quintans JSS, Quintans-Junior LJ: Citronellol, a monoterpene alcohol with promising pharmacological activities - A systematic review. Food Chem Toxicol. 2019 Jan;123:459-469. doi: 10.1016/j.fct.2018.11.030. Epub 2018 Nov 16. [PubMed:30453001 ]
  4. Yu WN, Lai YJ, Ma JW, Ho CT, Hung SW, Chen YH, Chen CT, Kao JY, Way TD: Citronellol Induces Necroptosis of Human Lung Cancer Cells via TNF-alpha Pathway and Reactive Oxygen Species Accumulation. In Vivo. 2019 Jul-Aug;33(4):1193-1201. doi: 10.21873/invivo.11590. [PubMed:31280209 ]
  5. Rajendran J, Pachaiappan P, Subramaniyan S: Dose-dependent chemopreventive effects of citronellol in DMBA-induced breast cancer among rats. Drug Dev Res. 2019 Sep;80(6):867-876. doi: 10.1002/ddr.21570. Epub 2019 Jul 16. [PubMed:31313341 ]
  6. Silva D, Diniz-Neto H, Cordeiro L, Silva-Neta M, Silva S, Andrade-Junior F, Leite M, Nobrega J, Morais M, Souza J, Rosa L, Melo T, Souza H, Sousa A, Rodrigues G, Oliveira-Filho A, Lima E: (R)-(+)-beta-Citronellol and (S)-(-)-beta-Citronellol in Combination with Amphotericin B against Candida Spp. Int J Mol Sci. 2020 Mar 5;21(5). pii: ijms21051785. doi: 10.3390/ijms21051785. [PubMed:32150884 ]
  7. Ribeiro-Filho HV, de Souza Silva CM, de Siqueira RJ, Lahlou S, dos Santos AA, Magalhaes PJ: Biphasic cardiovascular and respiratory effects induced by beta-citronellol. Eur J Pharmacol. 2016 Mar 15;775:96-105. doi: 10.1016/j.ejphar.2016.02.025. Epub 2016 Feb 9. [PubMed:26872991 ]