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L1164

Sigma-Aldrich

Linoleyl ethanolamide

≥98%, ethanol solution

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About This Item

CAS Number:
68171-52-8
MDL number:
MFCD00674434
UNSPSC Code:
12352200
PubChem Substance ID:
329817385
NACRES:
NA.77

Quality Level

200

Assay

≥98%

form

ethanol solution

mol wt

apparent mol wt 323.5

shipped in

wet ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C20H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h6-7,9-10,22H,2-5,8,11-19H2,1H3,(H,21,23)/b7-6-,10-9-

InChI key

KQXDGUVSAAQARU-HZJYTTRNSA-N

Biochem/physiol Actions

Linoleoyl ethanolamide (LE), a fatty acid ethanolamide, is present in sake lees. It possesses anti-inflammatory effects by preventing nuclear factor κB (NF-κB) signaling. LE is considered a beneficial therapeutic agent for contact dermatitis.

Preparation Note

To change the solvent, evaporate the ethanol under a gentle stream of nitrogen and immediately add the solvent of choice.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

57.2 °F - closed cup

Flash Point(C)

14 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The endogenous cannabimimetic eicosanoid, anandamide, induces arachidonate release in J774 mouse macrophages.
V Di Marzo et al.
Advances in experimental medicine and biology, 407, 341-346 (1997-01-01)
Thi Ai Diep et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 25(2), 765-774 (2010-10-21)
This study was undertaken to investigate the link between dietary fat content and intestinal levels of anorectic N-acylethanolamines (NAEs), including oleoylethanolamide (OEA), palmitoylethanolamide (PEA), and linoleoylethanolamide (LEA). Male rats were fed high-fat diets (HFDs) with variable percentages of fat [20-45%
Joe Palandra et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 877(22), 2052-2060 (2009-06-19)
A sensitive and selective liquid chromatography tandem mass spectrometry (LC\MS\MS) method has been developed for the simultaneous quantification in human plasma of the endocannabinoid anandamide (AEA) and three other related ethanolamides, linoleoyl ethanolamide (LEA), oleoyl ethanolamide (OEA), and palmitoyl ethanolamide
Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor.
L Hanus et al.
Journal of medicinal chemistry, 36(20), 3032-3034 (1993-10-01)
Harald S Hansen et al.
Biochemical pharmacology, 78(6), 553-560 (2009-05-06)
Anandamide and the other N-acylethanolamines, e.g. oleoylethanolamide (OEA), palmitoylethanolamide (PEA), and linoleoylethanolamide (LEA), may be formed by several enzymatic pathways from their precursors, which are the N-acylated ethanolamine phospholipids. The exact enzymatic pathways involved in their biosynthesis in specific tissues
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