142128-47-0

Basic information

• Product Name: N-(2-HYDROXY-1R-METHYLETHYL)-HEXADECANAMIDE
• Synonyms: R-1 PMA;R-PALMITOYL-(1-METHYL) ETHANOLAMIDE;N-(2-HYDROXY-1R-METHYLETHYL)-HEXADECANAMIDE;N-[(2R)-1-hydroxypropan-2-yl]hexadecanamide
• CAS NO: 142128-47-0
• Molecular Formula: C19H39NO2
• Molecular Weight: 313.52
• Mol File: 142128-47-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Solubility: ≤10mg/ml in ethanol;25mg/ml in DMSO;3.3mg/ml in dimethyl formamide
• CAS DataBase Reference: N-(2-HYDROXY-1R-METHYLETHYL)-HEXADECANAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-HYDROXY-1R-METHYLETHYL)-HEXADECANAMIDE(142128-47-0)
• EPA Substance Registry System: N-(2-HYDROXY-1R-METHYLETHYL)-HEXADECANAMIDE(142128-47-0)

Safety Data

• Hazardous Substances Data: 142128-47-0(Hazardous Substances Data)

Usage

Biological Activity

r-palmitoyl-(1-methyl) ethanolamide, a synthetic analog of palmitoyl ethanolamide (pea), incorporates the (r)-methyl group vicinal to the alcohol on the ethanolamine moiety. the analogous modification to arachidonoyl ethanolamide (aea) protects the molecule from hydrolysis by fatty acid amide hydrolase, prolongs duration of action and enhances potency in vivo [1].pea is an endogenous cannabinoid existed in mammalian tissues, such as liver and brain. pea has also been isolated from egg yolk [2, 3]. pea is a compound with documented anti-nociceptive and anti-inflammatory effects. during inflammation, pea is accumulated and exihibits anti-inflammatory effects, including beneficial effects in clinically relevant animal models of inflammatory pain [4].

references

[1] abadji v, lin s, taha g, et al. (r)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability[j]. journal of medicinal chemistry, 1994, 37(12): 1889-1893.[2] bachur n r, masek k, melmon k l, et al. fatty acid amides of ethanol-amine in mammalian tissues[j]. journal of biological chemistry, 1965, 240: 1019-1024.[3] ganley o h, graessle o e, robinson h j, et al. anti-inflammatory activity of compounds obtained from egg yolk, peanut oil, and soybean lecithin[j]. journal of laboratory and clinical medicine, 1958, 51: 709-714.[4] lambert d m, vandevoorde s, jonsson k o, et al. the palmitoylethanolamide family: a new class of anti-inflammatory agents [j]. current medicinal chemistry, 2002, 9(6): 663-674.

Upstream product

• 35320-23-1 (R)-2-aminopropan-1-ol 
• 112-39-0 hexadecanoic acid methyl ester 
• 57-10-3 1-hexadecylcarboxylic acid 

Relevant articles and documents

Different roles for the acyl chain and the amine leaving group in the substrate selectivity of N-Acylethanolamine acid amidase

N-acylethanolamine acid amidase (NAAA) is an N-terminal nucleophile (Ntn) hydrolase that catalyses the intracellular deactivation of the endogenous analgesic and anti-inflammatory agent palmitoylethanolamide (PEA). NAAA inhibitors counteract this process and exert marked therapeutic effects in animal models of pain, inflammation and neurodegeneration. While it is known that NAAA preferentially hydrolyses saturated fatty acid ethanolamides (FAEs), a detailed profile of the relationship between catalytic efficiency and fatty acid-chain length is still lacking. In this report, we combined enzymatic and molecular modelling approaches to determine the effects of acyl chain and polar head modifications on substrate recognition and hydrolysis by NAAA. The results show that, in both saturated and monounsaturated FAEs, the catalytic efficiency is strictly dependent upon fatty acyl chain length, whereas there is a wider tolerance for modifications of the polar heads. This relationship reflects the relative stability of enzyme-substrate complexes in molecular dynamics simulations.

COMPOSITIONS AND METHODS FOR THE MODULATION OF SPECIFIC AMIDASES FOR N-ACYLETHANOLAMINES FOR USE IN THE THERAPY OF INFLAMMATORY DISEASES

The present invention regards compositions and methods for the modulation of amidases capable of hydrolysing N-acylethanolamines useable in the therapy of inflammatory diseases. In particular, the present invention regards a compound of general formula (I): enantiomers, diastereoisomers, racemes and mixtures, polymorphs, salts, solvates thereof, wherein: (a) R is a linear alkyl radical having 13 to 19 carbon atoms or alkenyl radical having 13 to 19 carbon atoms carrying a double bond; (b) X is 0 or S; (c) Y is a 2 or 3 carbon atom alkylene residue, optionally substituted with one or two groups equal or different from each other and selected from among the group consisting of: -CH3, -CH2OH, -COOCH3, -COOH. Y may preferably be: -CH2-CH2-, -CH2-CH2-CH2-, CH (CH3) -CH2-, -CH2-CH (CH3) -, -CH2-C (CH3) 2-, -CH2-CH (CH2OH) -, -CH2-C ( (CH2OH) 2) -, -CH=CH-, -CH2-CH (COOCH3) -, -CH2-CH (COOH) -, for use as a medicine.