Structure Database (LMSD)
Common Name
2E,6E-farnesol
Systematic Name
2E,6E-farnesol
Synonyms
3D model of 2E,6E-farnesol
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
Farnesyl alcohol is an isoprenoid that has been found in aromatic plants and has diverse biological activities.1,2,3,4 It is an agonist of peroxisome proliferator-activator receptor α (PPARα) and PPARγ (EC50s = 5.5 and 28 µM, respectively, in a reporter assay using CV-1 cells) and increases the expression of mRNA encoding the PPARα targets carnitine palmitoyltransferase 1 (CPT1) and acetyl-CoA synthetase (ACS) in HepG2 cells when used at a concentration of 100 µM.1 Farnesyl alcohol (250 µM) is a fungal quorum-sensing molecule and inhibits the yeast-to-mycelium conversion in C. albicans.2 It decreases the severity of oral candidiasis induced by C. albicans, but does not reduce C. albicans viability or the number of colony forming units (CFUs), in mice immunosuppressed by prednisolone when administered at doses of 1.125, 2.25, and 9 µmol/animal.3 Farnesyl alcohol (0.02-0.1 mg/cm2) repels S. medanensis mites and is toxic to those same mites in a contact assay (LC50 = 0.048 mg/cm2 per vial).4 Formulations containing farnesyl alcohol have been used as pesticides in agriculture.
This information has been provided by Cayman Chemical
References
4. Bakr, A.A., Saad, M.M.G., and Abdelgaleil, A.M. Mite incidence in Egyptian storage facilities and acaricidal activity of selected monoterpenes, phenylpropenes, and sesquiterpenes against Suidasia medanensis Oudemans (Astigmata: Suidasiidae), a formidable storage mite pest. Persian J. Acarol. 11(1), 101–113 (2022).
String Representations
InChiKey (Click to copy)
CRDAMVZIKSXKFV-YFVJMOTDSA-N
InChi (Click to copy)
InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+
SMILES (Click to copy)
OC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/C
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
16
Rings
0
Aromatic Rings
0
Rotatable Bonds
7
Van der Waals Molecular Volume
268.93
Topological Polar Surface Area
20.23
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
1
logP
4.68
Molar Refractivity
72.99
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Updated at
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