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Ethanolamine
Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is a naturally occurring organic chemical compound with the formula HOCH
2CH
2NH
2 or C
2H
7NO. 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.
Ethanolamine is commonly called monoethanolamine or MEA in order to be distinguished from diethanolamine (DEA) and triethanolamine (TEOA). 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.
Ethanolamines, or in particular, their salts, were discovered by Charles Adolphe Wurtz in 1860 by heating 2-chloroethanol with ammonia solution while studying derivatives of ethylene oxide he discovered a year earlier. He wasn't able to separate the salts or isolate any free bases.
In 1897 Ludwig Knorr developed the modern industrial route (see below) and separated the products, including MEA, by fractional distillation, for the first time studying their properties.
None of the ethanolamines were of any commercial importance until after the WWII industrial production of ethylene oxide took off.
MEA molecules are a component in the formation of cellular membranes and are thus a molecular building block for life. 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.
MEA was thought to exist only on Earth and on certain asteroids, but in 2021 evidence was found that these molecules exist in interstellar space.
Ethanolamine is biosynthesized by decarboxylation of serine:
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Ethanolamine
Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is a naturally occurring organic chemical compound with the formula HOCH
2CH
2NH
2 or C
2H
7NO. 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.
Ethanolamine is commonly called monoethanolamine or MEA in order to be distinguished from diethanolamine (DEA) and triethanolamine (TEOA). 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.
Ethanolamines, or in particular, their salts, were discovered by Charles Adolphe Wurtz in 1860 by heating 2-chloroethanol with ammonia solution while studying derivatives of ethylene oxide he discovered a year earlier. He wasn't able to separate the salts or isolate any free bases.
In 1897 Ludwig Knorr developed the modern industrial route (see below) and separated the products, including MEA, by fractional distillation, for the first time studying their properties.
None of the ethanolamines were of any commercial importance until after the WWII industrial production of ethylene oxide took off.
MEA molecules are a component in the formation of cellular membranes and are thus a molecular building block for life. 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.
MEA was thought to exist only on Earth and on certain asteroids, but in 2021 evidence was found that these molecules exist in interstellar space.
Ethanolamine is biosynthesized by decarboxylation of serine: