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P0359

Sigma-Aldrich

Palmitoylethanolamide

Synonym(s):

N-(2-Hydroxyethyl)hexadecanamide, PEA, Palmidrol

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About This Item

Empirical Formula (Hill Notation):
C18H37NO2
CAS Number:
544-31-0
Molecular Weight:
299.49
EC Number:
208-867-9
MDL number:
MFCD00020562
UNSPSC Code:
12352200
PubChem Substance ID:
24278619
NACRES:
NA.77

form

powder

Quality Level

200

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCCC(=O)NCCO

InChI

1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h20H,2-17H2,1H3,(H,19,21)

InChI key

HXYVTAGFYLMHSO-UHFFFAOYSA-N

Gene Information

human ... CNR1(1268) , CNR2(1269)
rat ... Faah(29347)

Application

Palmitoylethanolamide has been used as a reference standard in mass spectrometry (MS/MS).

Biochem/physiol Actions

Palmitoylethanolamide (PEA) is a natural fatty acid amide of ethanolamine and palmitic acid. It is found in soybeans, egg yolk, and many other food sources. PEA is an endogenous cannabinoid receptor agonist. It is a peroxisome proliferator-activated receptor α (PPAR-α) ligand. PEA possesses anti-inflammatory, anti-allergic, neuroprotective, and analgesic activities. It belongs to the class of lipid mediators and the N-acylethanolamine family. PEA blocks the release of pro-inflammatory mediators from activated mast cells and prevents the recruitment of activated mast cells at the site of nerve injury.

Linkage

Structural analog of anandamide.

Pictograms

CorrosionEnvironment
GHS05,GHS09

Signal Word

Danger

Hazard Statements

H315 - H318 - H411

Hazard Classifications

Aquatic Chronic 2 - Eye Dam. 1 - Skin Irrit. 2

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Melania Melis et al.
The Laryngoscope, 129(9), E307-E312 (2019-01-25)
Taste sensitivity varies greatly among individuals influencing eating behavior and health, consequently the disorders of this sense can affect the quality of life. The ability to perceive the bitter of thiourea compounds, such as phenylthiocarbamide (PTC), has been largely reported
Didier M Lambert et al.
Current medicinal chemistry, 9(6), 663-674 (2002-04-12)
The discovery of anandamide as an endogenous ligand for the cannabinoid receptors has led to a resurgence of interest in the fatty acid amides. However, N-palmitoylethanolamine (PEA), a shorter and fully saturated analogue of anandamide, has been known since the
Xiao Shi et al.
PloS one, 11(3), e0152581-e0152581 (2016-04-01)
Methamphetamine (MA) and neurotransmitter precursors and metabolites such as tyramine, octopamine, and β-phenethylamine stimulate the G protein-coupled trace amine-associated receptor 1 (TAAR1). TAAR1 has been implicated in human conditions including obesity, schizophrenia, depression, fibromyalgia, migraine, and addiction. Additionally TAAR1 is
Tessa L Crume et al.
American journal of obstetrics and gynecology, 215(5), 609-609 (2016-10-30)
Consistent evidence of an influence of maternal dietary intake during pregnancy on infant body size and composition in human populations is lacking, despite robust evidence in animal models. We sought to evaluate the influence of maternal macronutrient intake and balance
Lili He et al.
Journal of chromatographic science, 54(8), 1428-1434 (2016-05-04)
This article aims to build up a simple, rapid and accurate capillary zone electrophoresis (CZE) method for the separation of biogenic amines (BAs). Here, 10 key BAs (phenethylamine, histamine, tryptamine, tyramine, 5-hydroxytryptamine, octopamine, dopamine, norepinephrine, epinephrine and carnosine) owning significant
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