53832-59-0

Basic information

• Product Name: HEPTADECANOYL ETHANOLAMIDE
• Synonyms: N-(2-HYDROXYETHYL)HEPTADECANAMIDE;HEPTADECANOYL ETHANOLAMIDE
• CAS NO: 53832-59-0
• Molecular Formula: C19H39NO2
• Molecular Weight: 313.52
• Mol File: 53832-59-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: HEPTADECANOYL ETHANOLAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: HEPTADECANOYL ETHANOLAMIDE(53832-59-0)
• EPA Substance Registry System: HEPTADECANOYL ETHANOLAMIDE(53832-59-0)

Safety Data

• Hazardous Substances Data: 53832-59-0(Hazardous Substances Data)

Usage

General Description

Heptadecanoyl ethanolamide, also known as C17:0, is a naturally occurring fatty acid derivative that belongs to the family of N-acylethanolamines. It is found in various plant and animal tissues and has been implicated in various biological processes, including the regulation of inflammation, pain perception, and energy metabolism. Heptadecanoyl ethanolamide is also being studied for its potential therapeutic applications in conditions such as chronic pain, neuroinflammation, and metabolic disorders. Its activity is thought to be mediated through interactions with cannabinoid receptors and other lipid signaling pathways in the body. Overall, heptadecanoyl ethanolamide has shown potential as a bioactive molecule with diverse physiological effects and may have implications for the development of new drugs and therapies.

Upstream product

• 141-43-5 ethanolamine 
• 40480-10-2 heptadecanoyl chloride 
• 1731-92-6 methyl margarate 
• 14010-23-2 ethyl heptadecanoate 

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.