Structure Database (LMSD)

Common Name
2-Hydroxyoleic acid
Systematic Name
2-Hydroxy-9Z-octadecenoic acid
Synonyms
  • 9-Octadecenoic acid, 2-hydroxy-, (9Z)-
  • 9-Octadecenoic acid, 2-hydroxy-, (Z)-
  • (Z)-2-Hydroxyoctadec-9-enoic acid
  • 2-Hydroxyoleic acid
  • Minerval
  • cis-2-Hydroxy-9-octadecenoic acid
  • -alpha-Hydroxyoleic acid
LM ID
LMFA01050540
Formula
C18H34O3
Exact Mass
Calculate m/z
298.250795
Sum Composition
FA 18:1;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Hydroxy fatty acids [FA0105]
Unsaturated fatty acids [FA0103]

Biological Context

2-hydroxy Oleic acid is a synthetic monounsaturated hydroxylated fatty acid.1 It decreases the lamellar-to-hexagonal transition temperature of bovine liver phosphatidylethanolamine (PE) membranes by approximately 12.5°C when included at a 20:1 molar ratio of PE:2-hydroxy oleic acid. 2-hydroxy Oleic acid increases levels of protein kinase C α (PKCα) in and decreases proliferation of A549 non-small cell lung cancer (NSCLC) cells in a concentration-dependent manner. It reduces tumor growth in an A549 mouse xenograft model when administered at doses of 75 and 200 mg/kg. 2-hydroxy Oleic acid has been used in the generation of liposomes.2

This information has been provided by Cayman Chemical

References

1. Martínez, J., Vögler, O., Casas, J., et al. Membrane structure modulation, protein kinase Cα activation, and anticancer activity of minerval. Mol. Pharmacol. 67(2), 531-540 (2004).
2. Olechowska, K., Mach, M., Hąc-Wydro, K., et al. Studies on the interactions of 2‑hydroxyoleic acid with monolayers and bilayers containing cationic lipid: Searching for the formulations for more efficient drug delivery to cancer cells. Langmuir 35(27), 9084-9092 (2019).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Membrane structure modulation, protein kinase C alpha activation, and anticancer activity of minerval.,
Mol Pharmacol, 2005
Pubmed ID: 15531732

String Representations

InChiKey (Click to copy)
JBSOOFITVPOOSY-KTKRTIGZSA-N
InChi (Click to copy)
InChI=1S/C18H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(19)18(20)21/h9-10,17,19H,2-8,11-16H2,1H3,(H,20,21)/b10-9-
SMILES (Click to copy)
C(C(O)CCCCCC/C=C\CCCCCCCC)(=O)O

Other Databases

CHEBI ID
143096
PubChem CID
9796304
PlantFA ID
10581
Cayman ID
36044

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 341.05
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 5.37
Molar Refractivity 88.99

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Created at
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Updated at
14th Nov 2024