Structure Database (LMSD)
Common Name
2E-geraniol
Systematic Name
2E-geraniol
Synonyms
3D model of 2E-geraniol
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
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
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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Created at
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Updated at
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