Record Information
Version1.0
Creation date2010-04-08 22:11:18 UTC
Update date2018-05-29 01:12:27 UTC
Primary IDFDB014490
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCitronellol
DescriptionOccurs in many essential oils, usually as a partial racemate. obtained mainly from geranium oil or synthetically. Flavour for use in citrus compositions Citronellol, or dihydrogeraniol, is a natural acyclic monoterpenoid. Both enantiomers occur in nature. (+)-Citronellol, which is found in citronella oils, including Cymbopogon nardus (50%), is the more common isomer. (-)-Citronellol is found in the oils of rose (18-55%) and Pelargonium geraniums.
CAS Number106-22-9
Structure
Thumb
Synonyms
SynonymSource
2,3-DihydrogeraniolChEBI
2,6-Dimethyl-2-octen-8-olChEBI
3,7-Dimethyl-6-octen-1-olChEBI
beta-CitronellolChEBI
CephrolChEBI
ElenolChEBI
b-CitronellolGenerator
Β-citronellolGenerator
Citronellol, (S)-isomerMeSH
Citronellol, (R)-isomerMeSH
Citronellol, (+-)-isomerMeSH
Citronellol, titanium (+4) saltMeSH
(±)-3,7-Dimethyl-6-octen-1-olmanual
(±)-beta-Citronellolmanual
(±)-Citronellolmanual
3,7-Dimethyloct-6-en-1-olbiospider
6-Octen-1-ol, 3,7-dimethyl-biospider
Citronelloldb_source
Dihydrogeraniolmanual
DL-Citronellolmanual
Rhodinolmanual
Yacaroldb_source
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
Polarizability20.05 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H20O
IUPAC name3,7-dimethyloct-6-en-1-ol
InChI IdentifierInChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3
InChI KeyQMVPMAAFGQKVCJ-UHFFFAOYSA-N
Isomeric SMILESCC(CCO)CCC=C(C)C
Average Molecular Weight156.269
Monoisotopic Molecular Weight156.151415264
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 76.86%; H 12.90%; O 10.24%DFC
Melting Point< 25 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP3.91GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID8842
Pubchem Substance IDNot Available
ChEBI ID50462
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJRJ33-M:JRJ33-M
EAFUS ID695
Dr. Duke IDCITRONELLOL|BETA-CITRONELLOL
BIGG IDNot Available
KNApSAcK IDC00000844
HET IDNot Available
Flavornet ID106-22-9
GoodScent IDrw1007031
SuperScent ID8842
Wikipedia IDCitronellol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti streptococcic33282 A substance that kills or slows the growth of bacteria.DUKE
candidicideDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
herbicide24527 A substance used to destroy plant pests.DUKE
irritantDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
trichomonicideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
rose
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
geranium
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
leather
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
waxy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rose bud
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
citrus
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).