Structure Database (LMSD)

Common Name
2E-geraniol
Systematic Name
2E-geraniol
Synonyms
LM ID
LMPR0102010016
Formula
Exact Mass
Calculate m/z
154.135765
Status
Curated



Classification

Biological Context

Geraniol is a terpene alcohol found in a variety of plants, including Cannabis, that has diverse biological activities, including insecticide, antioxidant, anti-inflammatory, anticancer, and antimicrobial properties.1,2 Geraniol is an insecticide that induces 100% mortality of C. maculatus, when used at a concentration of 16 µl in an alimentary substrate.3 It has an LD50 value of 0.714 µl in C. maculatus but does not produce adverse effects in rats when administered in the diet at 10,000 ppm for 16 weeks.3,2 Topical administration of geraniol (250 µg) prevents lipid peroxidation, increases glutathione (GSH) levels, and increases the activity of antioxidant enzymes, including catalase, glutathione reductase, glucose-6-phosphate dehydrogenase, and superoxide dismutase in a mouse skin model of oxidative stress and inflammation induced by phorbol 12-myristate 13-acetate (TPA).4 It also decreases the levels of TNF-α, IL-6, and IL-1β in the same model. Geraniol (100 mg/kg) inhibits HMG-CoA reductase and reduces lipogenesis in hamsters fed an atherogenic diet as a model of hyperlipidemia when administered at a dose of 100 mg/kg.5 It also induces apoptosis in and decreases viability of COLO 205 cancer cells (IC50 = 20 µM).6 Formulations containing geraniol have been used as fragrance ingredients and as insecticides in agriculture.

This information has been provided by Cayman Chemical

References

3. Khan, A.Q., Khan, R., Qamar, W., et al. Geraniol attenuates 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced oxidative stress and inflammation in mouse skin: Possible role of p38 MAP Kinase and NF-κB. Exp. Mol. Pathol. 94(3), 419-429 (2013).
5. Elzinga, S., Fischedick, J., Podkolinski, R., et al. Cannabinoids and terpenes as chemotaxonomic markers in Cannabis. Nat. Prod. Chem. Res. 3(4), 181 (2015).

String Representations

InChiKey (Click to copy)
GLZPCOQZEFWAFX-JXMROGBWSA-N
InChi (Click to copy)
InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+
SMILES (Click to copy)
OC/C=C(\C)/CC/C=C(\C)/C

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 11
Rings 0
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 185.07
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 2.96
Molar Refractivity 50.00

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Updated at
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