Showing Compound Card for 2E-Geraniol (CDB000194)

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Record Information
Version1.0
Created at2020-03-18 23:28:16 UTC
Updated at2020-12-07 19:07:15 UTC
CannabisDB IDCDB000194
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2E-Geraniol
Descriptionbeta-Geraniol, also known as (E)-nerol, the isomer of nerol (or geranyl alcohol, is a monoterpenoid alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. beta-Geraniol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. beta-Geraniol has a sweet, citrus, and floral taste. beta-Geraniol is found in highest concentrations in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. beta-Geraniol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals. This could make beta-geraniol a potential biomarker for the consumption of these foods. It is found in as an alcohol and as its ester in many essential oils including geranium oil. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type) and occurs in small quantities in geranium, lemon, and many other essential oils. Geraniol is a monoterpenoid and an alcohol found in cannabis plants (PMID:6991645 ). Because it has a rose-like odor, it is commonly used in perfumes. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives (http//doi:10.1051/apido:19900403)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2E)-3,7-Dimethyl-2,6-octadien-1-olChEBI
(2E)-GeraniolChEBI
(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-octadienolPhytoBank
trans-1-Hydroxy-3,7-dimethyl-2,6-octadienePhytoBank
beta-GeraniolPhytoBank
Chemical FormulaC10H18O
Average Molecular Weight154.25
Monoisotopic Molecular Weight154.1358
IUPAC Name(2E)-3,7-dimethylocta-2,6-dien-1-ol
Traditional Namegeraniol
CAS Registry Number106-24-1
SMILES
CC(C)=CCC\C(C)=C\CO
InChI Identifier
InChI=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
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

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< -15 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.1 mg/mL at 25 °CNot Available
logP3.56Not Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-f59382e51acd0b5402042014-09-20View Spectrum
GC-MS2E-Geraniol, 1 TMS, GC-MS Spectrumsplash10-002f-9800000000-16b748da465c428492a4Spectrum
GC-MS2E-Geraniol, non-derivatized, GC-MS Spectrumsplash10-014l-9000000000-25934c23f4bc9ba87142Spectrum
GC-MS2E-Geraniol, non-derivatized, GC-MS Spectrumsplash10-014i-9000000000-a4d79e7813b94cf0d54bSpectrum
GC-MS2E-Geraniol, non-derivatized, GC-MS Spectrumsplash10-014i-9100000000-3a5359aae818f9966cbdSpectrum
GC-MS2E-Geraniol, non-derivatized, GC-MS Spectrumsplash10-00kf-9200000000-4a8a23071f388f446451Spectrum
GC-MS2E-Geraniol, non-derivatized, GC-MS Spectrumsplash10-014i-9100000000-f24e92e3c3efdc35a606Spectrum
GC-MS2E-Geraniol, non-derivatized, GC-MS Spectrumsplash10-014i-9100000000-d8e4f64753ef594f6d40Spectrum
GC-MS2E-Geraniol, non-derivatized, GC-MS Spectrumsplash10-014l-9000000000-2bce8c0905dd12aa5dacSpectrum
GC-MS2E-Geraniol, non-derivatized, GC-MS Spectrumsplash10-002f-9800000000-16b748da465c428492a4Spectrum
GC-MS2E-Geraniol, non-derivatized, GC-MS Spectrumsplash10-0006-4900000000-7e43c8601ed65028cae5Spectrum
Predicted GC-MS2E-Geraniol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014u-9300000000-c85bc4c928fbf7d824e8Spectrum
Predicted GC-MS2E-Geraniol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-030c-9520000000-69b7fbbb25764f7b612eSpectrum
Predicted GC-MS2E-Geraniol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2E-Geraniol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0a4i-1900000000-710389d2548f45d605022020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-001r-9500000000-d864036a8f8b4cdb20ae2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-001r-9400000000-e3661fd0b608943d6b6c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-001i-9200000000-d748b4cd92b7c69ffee32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-001i-9100000000-b6abc8d3af3aa99879b42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-001i-9000000000-710e0ba546f9b86b8e402020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-001i-9000000000-4cc179896d05162706592020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-001i-9000000000-7f3a48636d9da2cda8212020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-001i-9000000000-4b196d3d8e84ecd0e9f32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-003r-9000000000-718f1d4e975f4b2446d12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-003u-9000000000-2e43acc8a377504a43292020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-005c-9000000000-fe7ffaf2c7e121c33b7c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-005c-9000000000-467c307d1f0822b86ea02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-005c-9000000000-5939202301ea6107df2c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-002f-9000000000-0e13687577d30f6265cc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-0f96-9000000000-e478c8b2587c1134117d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-1900000000-5f3fc91bdf843e40a2662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-1900000000-ab16b7d86a06d659d4f32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000i-3900000000-4dd10bbea41237cba5352020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1900000000-3d437630e5bec67a7e072016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-8900000000-0e505c85cec6344cab5c2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-c7400df359a9559bd5942016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-113756054eed13d33ee42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0900000000-dea43b41c5b791cef9d22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-9800000000-c028a2bd6550260942512016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
9 Lb HammerDetected and Quantified0.156 mg/g dry wt details
Chemdawg #4Detected and Quantified0.074 mg/g dry wt details
Goji OGDetected and Quantified0.108 mg/g dry wt details
Gorilla Glue #4Detected and Quantified0.27 mg/g dry wt details
Grape StomperDetected and Quantified0.066 mg/g dry wt details
Grizzly KushDetected and Quantified0.114 mg/g dry wt details
Hash PlantDetected and Quantified0.225 mg/g dry wt details
Hash PlantDetected and Quantified0.357 mg/g dry wt details
JabberwockyDetected and Quantified0.114 mg/g dry wt details
JabberwockyDetected and Quantified0.379 mg/g dry wt details
Lemon OGDetected and Quantified0.116 mg/g dry wt details
Liberty HazeDetected and Quantified0.112 mg/g dry wt details
Lucky CharmsDetected and Quantified0.486 mg/g dry wt details
Maui HazeDetected and Quantified0.101 mg/g dry wt details
Purple EclipseDetected and Quantified0.08 mg/g dry wt details
Rocket FuelDetected and Quantified0.4 mg/g dry wt details
Rosetta StoneDetected and Quantified0.072 mg/g dry wt details
Skywalker OGDetected and Quantified0.094 mg/g dry wt details
Strawberry FieldsDetected and Quantified0.291 mg/g dry wt details
Venom OGDetected and Quantified0.321 mg/g dry wt details
HMDB IDHMDB0035155
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013792
KNApSAcK IDC00000845
Chemspider ID13849989
KEGG Compound IDC01500
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGeraniol
METLIN IDNot Available
PubChem Compound637566
PDB IDNot Available
ChEBI ID17447
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. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]