Structure Database (LMSD)

Common Name
(9Z,12Z)-octadecadien-1-ol
Systematic Name
(9Z,12Z)-octadeca-9,12-dien-1-ol
Synonyms
  • (Z,Z)-octadeca-9,12-dien-1-ol
  • 9-cis,12-cis-octadecadien-1-ol
  • cis,cis-9,12-octadecadien-1-ol
  • cis,cis-octadeca-9,12-dien-1-ol
  • linoleyl alcohol
LM ID
LMFA05000557
Formula
C18H34O
Exact Mass
Calculate m/z
266.260965
Sum Composition
FOH 18:2
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

cis,cis-Octadeca-9,12-dienol, known less formally as linoleyl alcohol, is a polyunsaturated fatty alcohol produced by the reduction of linoleic acid . Conversely, it is oxidized in vivo to produce linoleic acid.1 cis,cis-Octadeca-9,12-dienol has been used to coat latex beads for phagocytosis assays and to synthesize a gallic acid ester for weight loss.2,3 This alcohol of linoleic acid is also used in studies centering on the role of the carboxylic group of linoleic acid in enzyme recognition and cell signaling.4,5

This information has been provided by Cayman Chemical

References

1. Shintani, T., Takahashi, N., Fushiki, T., et al. The recognition system of dietary fatty acids by the rat small intestinal cells. Biosci. Biotech. Biochem. 59(3), 479-481 (1995).
2. Totani, N., Tateishi, S., Takimoto, T., et al. Gallic acid glycerol ester promotes weight-loss in rats. J. Oleo Sci. 60(9), 457-462 (2011).
3. Thomas, M.J., Hedrick, C.C., Smith, S., et al. Superoxide generation by the human polymorphonuclear leukocyte in response to latex beads. J. Leukoc. Biol. 51(6), 591-596 (1992).
4. Su, K.L., and Schmid, H.H.O. Metabolism of long-chain polyunsaturated alcohols in myelinating brain. J. Lipid Res. 13(4), 452-457 (1972).
5. Butovich, I.A., Lukyanova, S.M., and Reddy, C.C. Oxidation of linoleyl alcohol by potato tuber lipoxygenase: Possible mechanism and the role of carboxylic group in substrate binding. Biochem. Biophys. Res. Commun. 249(2), 344-349 (1998).

Reactions

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Reactions graph legend

String Representations

InChiKey (Click to copy)
JXNPEDYJTDQORS-HZJYTTRNSA-N
InChi (Click to copy)
InChI=1S/C18H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h6-7,9-10,19H,2-5,8,11-18H2,1H3/b7-6-,10-9-
SMILES (Click to copy)
C(CCCCCCO)C/C=C\C/C=C\CCCCC

Other Databases

CHEBI ID
73534
PubChem CID
5365682
SwissLipids ID
SLM:000000212
Cayman ID
16556

Calculated Physicochemical Properties

Heavy Atoms 19
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 323.47
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 6.08
Molar Refractivity 86.93

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Created at
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Updated at
25th Apr 2022