Structure Database (LMSD)
Common Name
Montanyl alcohol
Systematic Name
1-octacosanol
Synonyms
- octacosan-1-ol
3D model of Montanyl alcohol
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
1-Octacosanol is a very long-chain fatty alcohol that has diverse biological activities, including antibacterial, antifungal, anti-inflammatory, and antioxidative properties.1,2,3 It is active against the bacteria K. pneumoniae, S. flexneri, S. typhi, and E. faecalis (MICs = 4, 8, 2, and 32 µg/ml, respectively), as well as the pathogenic fungi T. ajelloi and T. rubrum (MICs = 4 and 32 µg/ml, respectively), but not the yeast C. albicans, C. lusitaniae, or C. krusei.1 It reduces the expression of TNF-α, inducible nitric oxide synthase (iNOS), IL-1β, and IL-6 in RAW 264.7 cells stimulated with LPS when used at concentrations of 30 and 100 µg/ml.3 1-Octacosanol (100 mg/kg per day) increases body weight, decreases diarrhea and hematochezia, and improves histopathological and morphological changes in the colon in a mouse model of ulcerative colitis induced by dextran sulfate sodium (DSS). 1-Octacosanol (10, 50, or 100 mg/kg) reduces carbon tetrachloride-induced increases in serum transaminase, hepatic myeloperoxidase, and hepatic xanthine oxidase activity, as well as lipid peroxidation, in a rat model of acute liver injury progression.2 It also reverses decreases in hepatic superoxide dismutase and catalase activity, as well as glutathione (GSH) levels, in the same model.
This information has been provided by Cayman Chemical
References
1. Tchakam, P.D., Lunga, P.K., Kowa, T.K., et al. Antimicrobial and antioxidant activities of the extracts and compounds from the leaves of Psorospermum aurantiacum Engl. and Hypericum lanceolatum Lam. BMC Complement. Altern. Med. 12:136, (2012).
3. Guo, T., Lin, Q., Li, X., et al. Octacosanol attenuates inflammation in both RAW264.7 macrophages and a mouse model of colitis. J. Agric. Food Chem. 65(18), 3647-3658 (2017).
String Representations
InChiKey (Click to copy)
CNNRPFQICPFDPO-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C28H58O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29/h29H,2-28H2,1H3
SMILES (Click to copy)
C(CCCCCCCCCCCCCO)CCCCCCCCCCCCCC
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
29
Rings
0
Aromatic Rings
0
Rotatable Bonds
26
Van der Waals Molecular Volume
501.75
Topological Polar Surface Area
20.23
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
1
logP
10.43
Molar Refractivity
133.29
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Updated at
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