142-58-5

Basic information

• Product Name: N-(2-hydroxyethyl)myristamide
• Synonyms: N-(2-hydroxyethyl)myristamide;MYRISTAMIDE MEA;Tetradecanamide, N-(2-hydroxyethyl)-;N-(2-Hydroxyethyl)myristamid;Myristyl monoethanolamide;AM-3165;Myristic acid monoethanolamide;N-(2-Hydroxyethyl)myristic amide
• CAS NO: 142-58-5
• Molecular Formula: C₁₆H₃₃NO₂
• Molecular Weight: 271.43872
• EINECS: 205-546-5
• Mol File: 142-58-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 93-94 °C
• Boiling Point: 436.3°Cat760mmHg
• Flash Point: 217.7°C
• Appearance: /
• Density: 0.916g/cm³
• Vapor Pressure: 1.91E-09mmHg at 25°C
• Refractive Index: 1.461
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.49±0.10(Predicted)
• CAS DataBase Reference: N-(2-hydroxyethyl)myristamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-hydroxyethyl)myristamide(142-58-5)
• EPA Substance Registry System: N-(2-hydroxyethyl)myristamide(142-58-5)

Safety Data

• Hazardous Substances Data: 142-58-5(Hazardous Substances Data)

Usage

Definition

ChEBI: An N-(long-chain-acyl)ethanolamine resulting from the formal condensation of the carboxy group of tetradecanoic acid (myristic acid) with the amino group of ethanolamine.

InChI:InChI=1/C16H33NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-16(19)17-14-15-18/h18H,2-15H2,1H3,(H,17,19)

Upstream product

• 141-43-5 ethanolamine 
• 112-64-1 tetradecanoyl chloride 
• 544-63-8 n-tetradecanoic acid 
• 124-06-1 Ethyl myristate 
• 124-10-7 methyl myristoate 

Downstream Products

• 7596-88-5 N-dodecanoylglycine 
• 14246-55-0 N-myristoylglycine 
• 2441-41-0 N-palmitoyl glycine 
• 6333-54-6 N-stearoylglycine 
• 14305-32-9 N-n-decanoylglycine 
• 14246-53-8 N-(1-oxooctyl)glycine 

Relevant articles and documents

N-acylation of ethanolamine using lipase: A chemoselective catalyst

The N-acylation of ethanolamine (2) with various fatty acids 1a-d and esters of fatty acids 1e-h using Candida antarctica B lipase (Novozym 435) are described and optimum conditions for selective N-acylation rather than O-acylation are also discussed. Microwave assisted solution phase, solid supported and conventional methods were investigated and results were compared. There is a synergy between the enzyme catalysis and microwave irradiation.

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.

Synthesis and biological activity of N-acyl O-indolylalkyl ethanolamines

The plant-growth regulators, indole-3-carboxylic acids, were introduced into N-acyl ethanolamines, and a series of N-acyl O-indolylalkyl ethanolamines were prepared. Their biological activities to regulate rape hypocotyl elongation, cucumber cotyledon expansion and common wheat coleoptile growth were tested. The results indicate that the title compounds inhibited rape hypocotyl elongation, especially the indole-3-propionic acid derivatives, whose bioactivity was better than that of indole-3-acetic acid.