Record Information
Version1.0
Creation date2010-04-08 22:10:54 UTC
Update date2018-05-29 01:07:45 UTC
Primary IDFDB013792
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGeraniol
DescriptionFound in free state and as esters in many essential oils including geranium oil. Most prolific natural source is palmarosa oil. Flavouring agent Geraniol is a monoterpenoid and an alcohol. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type). It also occurs in small quantities in geranium, lemon, and many other essential oils. It has a rose-like odor and is commonly used in perfumes. It is used in flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. It is the isomer of nerol.
CAS Number106-24-1
Structure
Thumb
Synonyms
SynonymSource
(2E)-3,7-Dimethyl-2,6-octadien-1-olChEBI
(e)-3,7-Dimethyl-2,6-octadien-1-olChEBI
(e)-GeraniolChEBI
(e)-NerolChEBI
2-trans-3,7-Dimethyl-2,6-octadien-1-olChEBI
3,7-Dimethyl-trans-2,6-octadien-1-olChEBI
Geranyl alcoholChEBI
LemonolChEBI
t-GeraniolChEBI
trans-3,7-Dimethyl-2,6-octadien-1-olChEBI
trans-GeraniolChEBI
b-GeraniolGenerator
Β-geraniolGenerator
(2E)-3,7-Dimethylocta-2,6-dien-1-olHMDB
2-trans-3,7-Dimethyl-2,6-octadiene-1-olHMDB
2E-GeraniolHMDB
3,7-Dimethyl-(2E)-2,6-octadien-1-olHMDB
3,7-Dimethyl-(e)-2,6-octadien-1-olHMDB
FEMA 2507HMDB
GeraniolHMDB
trans-2,6-Dimethyl-2,6-octadien-8-olHMDB
trans-3,7-Dimethy- octa-2,6-dien-1-olHMDB
Geraniol, (Z)-isomerMeSH
Geraniol, 1-(14)C-labeled, (e)-isomerMeSH
NerolMeSH
Geraniol, 2-(14)C-labeled, (e)-isomerMeSH
Geraniol, titanium (4+) saltMeSH
Geraniol, (e)-isomerMeSH
(E)-3,7-Dimethyl-2,6-octadien-1-olbiospider
(E)-Geraniolbiospider
(E)-Nerolbiospider
2-trans-3,7-dimethyl-2,6-octadiene-1-olbiospider
2,6-Octadien-1-ol, 3,7-dimethyl-, (2E)-biospider
2,6-Octadien-1-ol, 3,7-dimethyl-, (E)-biospider
2,6-Octadien-1-ol, 3,7-dimethyl-, trans-biospider
3,7-Dimethyl-(2e)-2,6-octadien-1-olHMDB
3,7-Dimethyl-2,6-octadien-1-ol, (E)-biospider
beta-Geraniolbiospider
Predicted Properties
PropertyValueSource
Water Solubility1.37 g/LALOGPS
logP2.89ALOGPS
logP2.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.18 m³·mol⁻¹ChemAxon
Polarizability19.67 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H18O
IUPAC name(2E)-3,7-dimethylocta-2,6-dien-1-ol
InChI IdentifierInChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+
InChI KeyGLZPCOQZEFWAFX-JXMROGBWSA-N
Isomeric SMILESCC(C)=CCC\C(C)=C\CO
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 77.87%; H 11.76%; O 10.37%DFC
Melting Point<-15 oC
Boiling PointBp 230°DFC
Experimental Water Solubility0.1 mg/mL at 25 oCCHEMICALS INSPECTION AND TESTING INSTITU (1992)
Experimental logP3.56GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 195 (e 19000) (MeOH) (Berdy)DFC
DensityNot Available
Refractive Indexn30D 1.4777DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-002f-9800000000-16b748da465c428492a4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-25934c23f4bc9ba87142View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9000000000-a4d79e7813b94cf0d54bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-3a5359aae818f9966cbdView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9200000000-4a8a23071f388f446451View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-f24e92e3c3efdc35a606View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-d8e4f64753ef594f6d40View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-2bce8c0905dd12aa5dacView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-002f-9800000000-16b748da465c428492a4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-4900000000-7e43c8601ed65028cae5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014u-9300000000-c85bc4c928fbf7d824e8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-030c-9520000000-69b7fbbb25764f7b612eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1900000000-3d437630e5bec67a7e07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-8900000000-0e505c85cec6344cab5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-c7400df359a9559bd594View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-113756054eed13d33ee4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0900000000-dea43b41c5b791cef9d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-9800000000-c028a2bd655026094251View in MoNA
MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-f59382e51acd0b540204View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID13849989
ChEMBL IDCHEMBL25719
KEGG Compound IDC01500
Pubchem Compound ID637566
Pubchem Substance IDNot Available
ChEBI ID17447
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35155
CRC / DFC (Dictionary of Food Compounds) IDJVC33-F:JHG09-C
EAFUS ID1460
Dr. Duke IDGERANIOL
BIGG IDNot Available
KNApSAcK IDC00000845
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID106-24-1
GoodScent IDrw1006991
SuperScent IDNot Available
Wikipedia IDGeraniol
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 helmintic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti salmonella33282 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 spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti tubercular33282 A substance that kills or slows the growth of bacteria.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
ascaricide33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
candidicideDUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
embryotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
emeticDUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
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
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
Insectiphile24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
mycobactericideDUKE
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. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
geranium
  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
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  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.
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).