Oleylethanolamide

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Cat.No. 1484 - Oleylethanolamide | C20H39NO2 | CAS No. 111-58-0
Description: Lipid mediator, anorexic actions; also GPR55 and PPARα agonist
Chemical Name: (9Z)-N-(2-Hydroxyethyl)-9-octadecenamide
Purity: ≥99% (HPLC)
Datasheet
Citations (3)
Literature

Biological Activity

Lipid mediator and analog of anandamide (Cat. No. 1339) that is involved in peripheral regulation of feeding. Selective GPR55 agonist (EC50 values are 0.44, >30 and >30 μM at GPR55, CB1 and CB2 respectively) and PPARα agonist (EC50 = 120 nM). Induces satiety through activation of PPARα and is also a ceramidase inhibitor. Also endogenous agonist at the GPR119 receptor.

Technical Data

M. Wt 325.53
Formula C20H39NO2
Storage Store at +4°C
Purity ≥99% (HPLC)
CAS Number 111-58-0
PubChem ID 5283454
InChI Key BOWVQLFMWHZBEF-KTKRTIGZSA-N
Smiles CCCCCCCC\C=C/CCCCCCCC(=O)NCCO

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 32.55 100
ethanol 32.55 100

Preparing Stock Solutions

The following data is based on the product molecular weight 325.53. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3.07 mL 15.36 mL 30.72 mL
5 mM 0.61 mL 3.07 mL 6.14 mL
10 mM 0.31 mL 1.54 mL 3.07 mL
50 mM 0.06 mL 0.31 mL 0.61 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Calignano et al (2001) Antinociceptive activity of the endogenous fatty acid amide, palmitylethanolamide. Eur.J.Pharmacol. 419 191 PMID: 11426841

Coroneos et al (1995) Differential regulation of sphingomyelinase and ceramidase activities by growth factors and cytokines. J.Biol.Chem. 270 23305 PMID: 7559485

de Fonseca et al (2001) An anorexic lipid mediator regulated by feeding. Nature 414 209 PMID: 11700558

Fu et al (2003) Oleylethanolamide regulates feeding and body weight through activation of the nuclear receptor PPAR-α. Nature 425 90 PMID: 12955147

Ryberg et al (2007) The orphan receptor GPR55 is a novel cannabinoid receptor. Br.J.Pharmacol. 152 1092 PMID: 17876302


If you know of a relevant reference for Oleylethanolamide, please let us know.

Keywords: Lipid mediator anorexic actions GPR55 PPARα PPARalpha agonists Ceramidase inhibitors inhibits Endogenous GPR119 receptor Peroxisome Proliferator-activating Receptors PPAR Cannabinoids Other Lipid Metabolism

3 Citations for Oleylethanolamide

Citations are publications that use Tocris products. Selected citations for Oleylethanolamide include:

Suárez et al (2014) Oleoylethanolamide enhances β-adrenergic-mediated thermogenesis and white-to-brown adipocyte phenotype in epididymal white adipose tissue in rat. Dis Model Mech 7 129 PMID: 24159189

Ropero et al (2009) Rapid non-genomic regulation of Ca2+ signals and insulin secretion by PPAR alpha ligands in mouse pancreatic islets of Langerhans. J Endocrinol 200 127 PMID: 19017711

Ho et al (2008) 'Entourage' effects of N-palmitoylethanolamide and N-oleoylethanolamide on vasorelaxation to anandamide occur through TRPV1 receptors. Br J Pharmacol 155 837 PMID: 18695637


Do you know of a great paper that uses Oleylethanolamide from Tocris? If so please let us know.

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Literature in this Area

New Product Guide

New Product Guide (Spring/Summer 2017)

Our new product guide highlights over 130 new products added to the Tocris Bioscience range during the first half of 2017.

  • 7-TM Receptors
  • Enzymes
  • Enzyme-Linked Receptors
  • Ion Channels
  • Nuclear Receptors
  • Transporters
  • Apoptosis
  • Cell Metabolism
  • Epigenetics
  • Fluorescent Imaging
  • Signal Transduction
  • Stem Cells

Pathways for Oleylethanolamide

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