Oleamide

Names

[ CAS No. ]:
301-02-0

[ Name ]:
Oleamide

[Synonym ]:
(9Z)-9-Octadecenamide
oleicacidamide-heptaglycolether
9-Octadecenamide, (9Z)-
9-Octadecenimidic acid, (9Z)-
Oleic acid amide
9-Octadecenoic acid, amide (cis)
Adogen 73
EINECS 206-103-9
9-Octadecenamide, (Z)- (9CI)
Amide O
OLEAMID
Armid O
MFCD00053638
Slip-eze
(9Z)-9-Octadecenimidic acid
AMD-O
(Z)-9-Octadecenamide
9-Octadecenamide, (Z)-
cis-9,10-Octadecenoamide cis-9-Octadecenamide Oleic acid amide
cis-9,10-Octadecenoamide
cis-9-octadecenamide
Oleamide
9-cis-Oleamide
(9Z)-Octadec-9-enamide
Plastic additive 20

Biological Activity

[Description]:

Oleamide is an endogenous fatty acid amide which can be synthesized de novo in the mammalian nervous system, and has been detected in human plasma.

[Related Catalog]:

Natural Products >> Others

Research Areas >> Others

[Target]

Human Endogenous Metabolite

[In Vitro]

Oleamide accumulates in the cerebrospinal fluid (CSF) of rats after six hours of sleep deprivation and induces sleep in naive rats and mice. Inhibition of the primary catabolic enzyme of oleamide (fatty acid amide hydrolase) by trifluoromethyl-octadecenone reduces sleep latency and increases total sleep time when given centrally to rats and peripherally to mice[1]

[References]

[1]. Mendelson WB, et al. The hypnotic actions of the fatty acid amide, oleamide. Neuropsychopharmacology. 2001 Nov;25(5 Suppl):S36-9.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
433.3±24.0 °C at 760 mmHg

[ Melting Point ]:
70°C

[ Molecular Formula ]:
C₁₈H₃₅NO

[ Molecular Weight ]:
281.477

[ Flash Point ]:
215.9±22.9 °C

[ Exact Mass ]:
281.271851

[ PSA ]:
43.09000

[ LogP ]:
6.75

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.469

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H317-H319-H335

[ Precautionary Statements ]:
P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
1

[ HS Code ]:
2924199090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924199090

[ Summary ]:
2924199090. other acyclic amides (including acyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

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Aquat. Toxicol. 157 , 159-66, (2014)

Bioassay-guided discovery of ichthyotoxic algal compounds using in vivo fish assays is labor intensive, costly, and highly regulated. Since the mode of action of most known algal-mediated fish-killing...

Preventive effects of a fermented dairy product against Alzheimer's disease and identification of a novel oleamide with enhanced microglial phagocytosis and anti-inflammatory activity.

PLoS ONE 10(3) , e0118512, (2015)

Despite the ever-increasing number of patients with dementia worldwide, fundamental therapeutic approaches to this condition have not been established. Epidemiological studies suggest that intake of f...

Connexin 43 expressed in endothelial cells modulates monocyte‑endothelial adhesion by regulating cell adhesion proteins.

Mol. Med. Report. 12 , 7146-52, (2015)

Adhesion between circulating monocytes and vascular endothelial cells is a key initiator of atherosclerosis. In our previous studies, it was demonstrated that the expression of connexin (Cx)43 in mono...