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Details

Stereochemistry ACHIRAL
Molecular Formula C20H39NO2
Molecular Weight 325.5292
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of OLEIC MONOETHANOLAMIDE

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)NCCO

InChI

InChIKey=BOWVQLFMWHZBEF-KTKRTIGZSA-N
InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-

HIDE SMILES / InChI

Molecular Formula C20H39NO2
Molecular Weight 325.5292
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Oleoylethanolamide (oleic monoethanolamide, OEA), the naturally occurring amide of ethanolamine and oleic acid, is an endogenous lipid that modulates feeding, body weight, and lipid metabolism by binding with high affinity to the ligand-activated transcription factor, peroxisome proliferator-activated receptor-alpha (PPAR-alpha). OEA reveals the pharmacological properties in the treatment of obesity, atherosclerosis and other diseases. It was shown, that OEA can be used to control hunger in Prader-Willi syndrome, in addition, it exhibited neuroprotective properties in Parkinson's disease experiments. OEA is an endogenous ligand of the orphan receptor GPR119, a G protein-coupled receptor (GPCR) expressed predominantly in the human and rodent pancreas and gastrointestinal tract and in rodent brain, suggesting that the reported effects of OEA on food intake may be mediated, at least in part, via the GPR119 receptor. Recently was shown, that OEA was an effective inhibitor of hyperpigmentation through activation of ERK, Akt and p38 pathways, inhibition of the CREB pathway, and subsequent down-regulation of MITF, TRP-1 and tyrosinase production. Therefore, OEA could be a useful therapeutic agent for use in the treatment of hyperpigmentation and could be an effective component in whitening and lightening cosmetics.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown
Preventing
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
fasted/refed Magel2 KO mice: intraperitoneal administration of oleoylethanolamine (OEA) (10mg/kg) significantly reduces food intake, pointing to a possible use of this natural compound to control hunger in Prader-Willi syndrome.
Route of Administration: Intraperitoneal
In Vitro Use Guide
It was examined whether oleoylethanolamine (OEA) can influence energy utilization. OEA (1-20 microm) stimulated glycerol and fatty acid release from freshly dissociated rat adipocytes in a concentration-dependent and structurally selective manner. Under the same conditions, OEA had no effect on glucose uptake or oxidation. OEA enhanced fatty acid oxidation in skeletal muscle strips, dissociated hepatocytes, and primary cardiomyocyte cultures.
Substance Class Chemical
Record UNII
1HI5J9N8E6
Record Status Validated (UNII)
Record Version