Structure Database (LMSD)

Common Name
Oleyl alcohol
Systematic Name
(9E)-octadec-9-en-1-ol
Synonyms
LM ID
LMFA05000684
Formula
C18H36O
Exact Mass
Calculate m/z
268.276615
Sum Composition
FOH 18:1
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty alcohols [FA05]

Biological Context

Elaidyl alcohol is a monounsaturated fatty alcohol produced by the hydrogenation of elaidic acid .1 It is active against herpes simplex virus 2 (HSV-2) and bacteriophage ϕ6, but not Pseudoalteromonas phage PM2, virions in plaque assays (IC50s = 1.9, 0.4, and >75 µM, respectively).2 Elaidyl alcohol has been used in the formation of bimolecular films to study the effect of unsaturation on model lipid membranes.3

This information has been provided by Cayman Chemical

References

1. Legaly, G., Weiss, A., and Stuke, E. Effect of double-bonds on bimolecular films in membrane models. Biochim. Biophys. Acta 470(3), 331-341 (1977).
2. Sands, J., Auperin, D., and Snipes, W. Extreme sensitivity of enveloped viruses, including herpes simplex, to long-chain unsaturated monoglycerides and alcohols. Antimicrob. Agents Chemother. 15(1), 67-73 (1979).
3. Cheah, K.Y., Tang, T.S., Mizukami, F., et al. Selective hydrogenation of oleic acid to 9-octadecen-1-ol: Catalyst preparation and optimum reaction conditions. J. Am. Oil Chem. Soc. 69(5), 410-416 (1992).

Reactions

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Reactions graph legend

String Representations

InChiKey (Click to copy)
ALSTYHKOOCGGFT-MDZDMXLPSA-N
InChi (Click to copy)
InChI=1S/C18H36O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h9-10,19H,2-8,11-18H2,1H3/b10-9+
SMILES (Click to copy)
OCCCCCCCC/C=C/CCCCCCCC

Other Databases

HMDB ID
HMDB29632
PubChem CID
5367665
Cayman ID
30459

Calculated Physicochemical Properties

Heavy Atoms 19
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 326.11
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 6.30
Molar Refractivity 87.03

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Created at
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Updated at
25th Apr 2022