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Showing Compound Citronellol (FDB014490)

Record Information
Version1.0
Creation date2010-04-08 22:11:18 UTC
Update date2025-11-19 00:47:04 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
MOLSDFPDBSMILESInChI
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCitronellol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02go-9400000000-68f35447a1addaa3c7e9Spectrum
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
NMRNot Available
ChemSpider ID13850135
ChEMBL IDCHEMBL395827
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
Food Biomarker OntologyNot Available
VMH 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 substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
Anti-staphylococcic33282 An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing.DUKE
Anti-streptococcic33282 An agent that targets and combats Streptococcus bacteria, reducing infection and inflammation. Therapeutically, it is used to treat streptococcal infections, such as strep throat and skin infections, and to prevent complications like rheumatic fever.DUKE
CandidicideAn agent that kills Candida species, such as Candida albicans, reducing fungal infections. Therapeutically, it is used to treat candidiasis, with key medical applications in managing oral thrush, vaginal yeast infections, and other fungal diseases.DUKE
Name48318 flavorDUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
Herbicide24527 A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.DUKE
IrritantAn agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.DUKE
Nematicide25491 An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.DUKE
Perfumery48318 The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.DUKE
TrichomonicideAn agent that kills Trichomonas organisms, used to treat Trichomonas vaginalis infections, commonly causing vaginitis, and other related genital tract infections.DUKE
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).