Geraniol

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Geraniol
Accession Number
DB14183
Type
Small Molecule
Groups
Approved, Experimental
Description

Geraniol is a monoterpene that is found within many essential oils of fruits, vegetables, and herbs including rose oil, citronella, lemongrass, lavender, and other aromatic plants. It is emitted from the flowers of many species of plant and is commonly used by the food, fragrance, and cosmetic industry[5]. Geraniol has demonstrated a wide spectrum of pharmacological activities including antimicrobial, anti-inflammatory, antioxidant, anti-cancer, and neuroprotective to name a few [1, 2, 3]. Interestingly, geraniol has also been shown to sensitize tumour cells to commonly used chemotherapies including Fluorouracil and Docetaxel and represents a promising cancer chemopreventive agent [4]. Due to its anticancer effects, geraniol has been found to be effective against a broad range of cancers including breast, lung, colon, prostate, pancreatic, skin, liver, kidney and oral cancers [3].

These pharmacologic effects are clinically important as geraniol is classified as generally-recognized-as-safe (GRAS) by the Flavor and Extract Manufacturers Association (FEMA) and the Food and Drug Administration (FDA) of the United States. Sensitivity to geraniol may be identified with a clinical patch test.

Structure
Thumb
Synonyms
  • (2E)-3,7-dimethylocta-2,6-dien-1-ol
  • (E)-3,7-Dimethyl-2,6-octadien-1-ol
  • (E)-Geraniol
  • (E)-Nerol
  • 2-trans-3,7-Dimethyl-2,6-octadien-1-ol
  • 2,6-Octadien-1-ol, 3,7-dimethyl-, (E)-
  • 2,6-Octadien-1-ol, 3,7-dimethyl-, trans-
  • 3,7-Dimethyl-2,6-octadien-1-ol, (E)-
  • 3,7-Dimethyl-trans-2,6-octadien-1-ol
  • geranyl alcohol
  • Lemonol
  • t-geraniol
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
T.R.U.E. Test Thin-Layer Rapid Use Patch TestGeraniol (81 ug/48h) + 2,2'-Dibenzothiazyl disulfide (20 ug/48h) + 2-mercaptobenzothiazole (61 ug/48h) + 4-(Isopropylamino)diphenylamine (10 ug/48h) + Bacitracin (486 ug/48h) + Balsam of Peru (648 ug/48h) + Benzocaine (378 ug/48h) + Benzylparaben (162 ug/48h) + Bisphenol A diglycidyl ether (32 ug/48h) + Bromothalonil (4 ug/48h) + Bronopol (203 ug/48h) + Budesonide (0.8 ug/48h) + Butylparaben (162 ug/48h) + Chlorquinaldol (77 ug/48h) + Cinchocaine hydrochloride (66 ug/48h) + Cinnamaldehyde (41 ug/48h) + Cinnamyl alcohol (63 ug/48h) + Clioquinol (77 ug/48h) + Cobalt chloride hexahydrate (4 ug/48h) + Diazolidinylurea (446 ug/48h) + Potassium dichromate (15.7 ug/48h) + Dipentamethylenethiuram disulfide (5.5 ug/48h) + Diphenylguanidine (68 ug/48h) + Disperse Blue 106 (41 ug/48h) + Disulfiram (5.5 ug/48h) + Ditiocarb Zinc (68 ug/48h) + Ethyl hydroxybenzoate (162 ug/48h) + Ethylenediamine (18 ug/48h) + Eugenol (41 ug/48h) + Evernia prunastri (81 ug/48h) + Formaldehyde (146 ug/48h) + Hydrocortisone butyrate (16 ug/48h) + Hydroxycitronellal (63 ug/48h) + Imidurea (486 ug/48h) + Isoeugenol (17 ug/48h) + Lanolin alcohols (810 ug/48h) + Methylchloroisothiazolinone (3 ug/48h) + Methylparaben (162 ug/48h) + Morpholinylmercaptobenzothiazole (20 ug/48h) + N,N'-diphenyl-1,4-phenylenediamine (25 ug/48h) + N-Cyclohexyl-N'-phenyl-1,4-phenylenediamine (25 ug/48h) + Neomycin sulfate (486 ug/48h) + Nickel sulfate hexahydrate (36 ug/48h) + P-Tert-Butylphenol-Formaldehyde Resin (Low Molecular Weight) (36 ug/48h) + Parthenolide (2 ug/48h) + Propylparaben (162 ug/48h) + Quaternium-15 (81 ug/48h) + Rosin (972 ug/48h) + Sodium aurotiosulfate (23 ug/48h) + Tetracaine hydrochloride (66 ug/48h) + Tetramethylthiuram monosulfide (5.5 ug/48h) + Thimerosal (6 ug/48h) + Thiohexam (20 ug/48h) + Thiram (5.5 ug/48h) + Tixocortol pivalate (2 ug/48h) + Zinc Dibutyldithiocarbamate (68 ug/48h) + alpha-Amyl cinnamaldehyde (17 ug/48h) + p-Phenylenediamine (65 ug/48h)KitSmartPractice Denmark ApS2012-03-01Not applicableUs
Categories
UNII
L837108USY
CAS number
106-24-1
Weight
Average: 154.253
Monoisotopic: 154.1357652
Chemical Formula
C10H18O
InChI Key
GLZPCOQZEFWAFX-JXMROGBWSA-N
InChI
InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+
IUPAC Name
(2E)-3,7-dimethylocta-2,6-dien-1-ol
SMILES
CC(C)=CCC\C(C)=C\CO

Pharmacology

Indication

Geraniol is approved for use within allergenic epicutaneous patch tests which are indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 6 years of age and older.

Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption

The profile of the geraniol concentrations in rat blood following oral administration of the emulsified formulation was characterized by a peak concentration at 30 min of about 270 μg/mL and an area under concentration (AUC) similar to that obtained by the intravenous administration of the same geraniol dose, indicating an absolute bioavailability of 92% [1]. Geraniol appears able to permeate directly from the bloodstream to the central nervous system following its oral administration to rats, reaching detectable amounts in the CSF; peak concentration in the CSF was found to be about 2.5 μg/mL and was observed 30 min after oral administration [1].

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life

In vitro measurements indicated that geraniol is highly stable in human and rat whole blood, whereas following intravenous administration geraniol is eliminated from the bloodstream with a relatively short half-life (about 12 min), starting from a concentration of about 300 μg/mL [1].

Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Pavan B, Dalpiaz A, Marani L, Beggiato S, Ferraro L, Canistro D, Paolini M, Vivarelli F, Valerii MC, Comparone A, De Fazio L, Spisni E: Geraniol Pharmacokinetics, Bioavailability and Its Multiple Effects on the Liver Antioxidant and Xenobiotic-Metabolizing Enzymes. Front Pharmacol. 2018 Jan 25;9:18. doi: 10.3389/fphar.2018.00018. eCollection 2018. [PubMed:29422862]
  2. Rekha KR, Selvakumar GP, Sethupathy S, Santha K, Sivakamasundari RI: Geraniol ameliorates the motor behavior and neurotrophic factors inadequacy in MPTP-induced mice model of Parkinson's disease. J Mol Neurosci. 2013 Nov;51(3):851-62. doi: 10.1007/s12031-013-0074-9. Epub 2013 Aug 13. [PubMed:23943375]
  3. Cho M, So I, Chun JN, Jeon JH: The antitumor effects of geraniol: Modulation of cancer hallmark pathways (Review). Int J Oncol. 2016 May;48(5):1772-82. doi: 10.3892/ijo.2016.3427. Epub 2016 Mar 9. [PubMed:26983575]
  4. Carnesecchi S, Langley K, Exinger F, Gosse F, Raul F: Geraniol, a component of plant essential oils, sensitizes human colonic cancer cells to 5-Fluorouracil treatment. J Pharmacol Exp Ther. 2002 May;301(2):625-30. [PubMed:11961066]
  5. Geraniol — A review of a commercially important fragrance material; Chen and Viljoen, 2010. [Link]
External Links
Human Metabolome Database
HMDB0035155
KEGG Compound
C01500
ChemSpider
13849989
BindingDB
50037023
ChEBI
17447
ChEMBL
CHEMBL25719
HET
64Z
Wikipedia
Geraniol
PDB Entries
5g1u / 5hss

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Kit
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.37 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.18 m3·mol-1ChemAxon
Polarizability19.67 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-002f-9800000000-16b748da465c428492a4
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-014l-9000000000-25934c23f4bc9ba87142
GC-MS Spectrum - EI-BGC-MSsplash10-014i-9000000000-a4d79e7813b94cf0d54b
GC-MS Spectrum - EI-BGC-MSsplash10-014i-9100000000-3a5359aae818f9966cbd
GC-MS Spectrum - EI-BGC-MSsplash10-00kf-9200000000-4a8a23071f388f446451
GC-MS Spectrum - EI-BGC-MSsplash10-014i-9100000000-f24e92e3c3efdc35a606
GC-MS Spectrum - EI-BGC-MSsplash10-014i-9100000000-d8e4f64753ef594f6d40
GC-MS Spectrum - EI-BGC-MSsplash10-014l-9000000000-2bce8c0905dd12aa5dac
GC-MS Spectrum - GC-MSGC-MSsplash10-002f-9800000000-16b748da465c428492a4
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-4900000000-7e43c8601ed65028cae5
Mass Spectrum (Electron Ionization)MSsplash10-014l-9100000000-f59382e51acd0b540204
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Classification
Not classified

Drug created on July 03, 2018 10:20 / Updated on November 02, 2018 07:51