Structure Database (LMSD)

Common Name
2E,6E-farnesol
Systematic Name
2E,6E-farnesol
Synonyms
LM ID
LMPR0103010001
Formula
Exact Mass
Calculate m/z
222.198365
Status
Curated



Classification

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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