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Concept
Ethanolamine
Summary
Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is an organic chemical compound with the formula HOCH2CH2NH2 or C2H7NO. The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid with an odor reminiscent of ammonia. ETA molecules are a component in the formation of cellular membranes and are thus a molecular building block for life. It was thought to exist only on Earth and on certain asteroids, but in 2021 evidence was found that ETA molecules exist in interstellar space.
Derivatives of ethanolamine are widespread in nature; e.g., lipids, as precursor of a variety of N-acylethanolamines (NAEs), that modulate several animal and plant physiological processes such as seed germination, plant–pathogen interactions, chloroplast development and flowering, as well as precursor, combined with arachidonic acid C20H32O2 20:4, ω-6), to form the endocannabinoid anandamide (AEA: C22H37NO2; 20:4, ω-6).
The ethanolamines comprise a group of amino alcohols. A class of antihistamines is identified as ethanolamines, which includes carbinoxamine, clemastine, dimenhydrinate, chlorphenoxamine, diphenhydramine and doxylamine.
Monoethanolamine is produced by treating ethylene oxide with aqueous ammonia; the reaction also produces diethanolamine and triethanolamine. The ratio of the products can be controlled by the stoichiometry of the reactants.
Ethanolamine is biosynthesized by decarboxylation of serine:
HOCH2CH(CO2H)NH2 → HOCH2CH2NH2 +
Ethanolamine is the second-most-abundant head group for phospholipids, substances found in biological membranes (particularly those of prokaryotes); e.g., phosphatidylethanolamine. It is also used in messenger molecules such as palmitoylethanolamide, which has an effect on CB1 receptors.
Ethanolamine is commonly called monoethanolamine or MEA in order to be distinguished from diethanolamine (DEA) and triethanolamine (TEA). It is used as feedstock in the production of detergents, emulsifiers, polishes, pharmaceuticals, corrosion inhibitors, and chemical intermediates.
Official source
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