64Z

Geraniol

Created: 2016-01-26
Last modified:  2016-04-27

Find related ligands:

Chemical Details

Formal Charge0
Atom Count29
Chiral Atom Count0
Bond Count28
Aromatic Bond Count0
2D diagram of 64Z

Chemical Component Summary

NameGeraniol
Systematic Name (OpenEye OEToolkits)(2~{E})-3,7-dimethylocta-2,6-dien-1-ol
FormulaC10 H18 O
Molecular Weight154.249
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01C(=C/CC\C(=C\CO)C)(\C)C
SMILESCACTVS3.385CC(C)=CCCC(C)=CCO
SMILESOpenEye OEToolkits2.0.4CC(=CCCC(=CCO)C)C
Canonical SMILESCACTVS3.385 CC(C)=CCC\C(C)=C\CO
Canonical SMILESOpenEye OEToolkits2.0.4 CC(=CCC/C(=C/CO)/C)C
InChIInChI1.03 InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+
InChIKeyInChI1.03 GLZPCOQZEFWAFX-JXMROGBWSA-N

Drug Info: DrugBank

DrugBank IDDB14183 
NameGeraniol
Groups
  • approved
  • experimental
DescriptionGeraniol 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[L3333]. Geraniol has demonstrated a wide spectrum of pharmacological activities including antimicrobial, anti-inflammatory, antioxidant, anti-cancer, and neuroprotective to name a few [A34260,A34261,A34262]. Interestingly, geraniol has also been shown to sensitize tumour cells to commonly used chemotherapies including [DB00544] and [DB01248] and represents a promising cancer chemopreventive agent [A34263]. 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 [A34262]. 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.
Synonyms
  • t-geraniol
  • (E)-Nerol
  • 2,6-Octadien-1-ol, 3,7-dimethyl-, trans-
  • 3,7-Dimethyl-2,6-octadien-1-ol, (E)-
  • geranyl alcohol
Brand NamesT.R.U.E. Test Thin-Layer Rapid Use Patch Test
IndicationGeraniol 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.
Categories
  • Cell-mediated Immunity
  • Increased Histamine Release
  • Monoterpenes
  • Standardized Chemical Allergen
  • Terpenes
CAS number106-24-1

Related Resource References

Resource NameReference
PubChem 637566
ChEMBL CHEMBL25719
ChEBI CHEBI:17447, CHEBI:24221
CCDC/CSD NEHGOZ, VUYGUT