Etabonate or ethyl carbonate is the chemical group with formula –, or –. The names are also used for

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

s R–, for the

anion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conve ...

[], and for salt (chemistry), salts of the latter.

Pharmaceutical aspects

"Etabonate" is an international nonproprietary name (INN) and United States Adopted Name (USAN) for pharmaceutical substances and is the name almost universally used in

pharmacology Pharmacology is a branch of medicine, biology and pharmaceutical sciences concerned with drug or medication action, where a drug may be defined as any artificial, natural, or endogenous (from within the body) molecule which exerts a biochemi ...

. some important drugs featuring that group are * Loteprednol etabonate, a

corticosteroid Corticosteroids are a class of steroid hormones that are produced in the adrenal cortex of vertebrates, as well as the synthetic analogues of these hormones. Two main classes of corticosteroids, glucocorticoids and mineralocorticoids, are in ...

* Remogliflozin etabonate, an

anti-diabetic drug Drugs used in diabetes treat diabetes mellitus by altering the glucose level in the blood. With the exceptions of insulin, most GLP receptor agonists ( liraglutide, exenatide, and others), and pramlintide, all are administered orally and are t ...

Sergliflozin etabonate Sergliflozin etabonate (INN/USAN, codenamed GW869682X) is an investigational anti-diabetic drug being developed by GlaxoSmithKline. It did not undergo further development after phase II. Method of action Sergliflozin inhibits subtype 2 of the so ...

, another anti-diabetic drug

Chemical aspects

"Ethyl carbonate"is the name commonly used in chemistry. Important non-medical esters with that group are * Diethyl carbonate, * methyl ethyl carbonate, Alkali salts of that anion, such as sodium ethyl carbonate, are known and fairly stable at ambient conditions. They have been proposed as an economical and

environmentally friendly Environment friendly processes, or environmental-friendly processes (also referred to as eco-friendly, nature-friendly, and green), are sustainability and marketing terms referring to goods and services, laws, guidelines and policies that cl ...

intermediate for the synthesis of organic compounds from

carbon dioxide Carbon dioxide ( chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is t ...

. They can be obtained by reaction of carbon dioxide with alkali ethoxides: :[] [] + → [] [] where M could be sodium or potassium. The ethoxide could be produced on a laboratory scale by reaction of ethanol with alkali metal, : + M → [] [] + ½ or, more economically and safely, by reaction with alkali

hydroxide Hydroxide is a diatomic anion with chemical formula OH−. It consists of an oxygen and hydrogen atom held together by a single covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water ...

: + → [] [] + at about 80 °C, using calcium oxide (quicklime) as a Dehydration reaction, dehydrating agent to drive the reaction forward. Sodium ethyl carbonate is reported to be a white crystalline solid, nearly insoluble in many organic solvents (including diethyl ether, ethanol,

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscible wi ...

, and

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen ato ...

), that decomposes without melting at 380-400 °C. In contrast, the hypothetical conjugate ethylcarbonic acid is not known and (like carbonic acid) may be stable only at very low temperatures.

History

Ethyl carbonate esters were described in 1837 by

Jean-Baptiste André Dumas Jean Baptiste André Dumas (14 July 180010 April 1884) was a French chemist, best known for his works on organic analysis and synthesis, as well as the determination of atomic weights (relative atomic masses) and molecular weights by measuring ...

(1800-1884) and his assistant Eugène-Melchior Peligot (1811-1890), during their investigation of the nature of sugars (which had been incorrectly conjectured to be the same compounds).

References

Kh. A. Suerbaev, N. Zh. Kudaibergenov, N. R. Yesenzhanova, M. K. Kozhakhmet, and A. Gaini (2017): "Alkaline salts of alkyl carbonic acids as carboxylation reagents of phenols and naphtols". ''Известия Национальной академии наук Республики Казахстан'' (''News of the Academy of Sciences of the Republic of Kazakhstan''), Series Chemistry and Technology, volume 3, issue 423, pages 79-93. Quote: " ..sodium and potassium ethyl carbonates are effective carboxylating reagents of hydroxyarenes (phenols and naphthols) uch ashydroxybenzoic and hydroxynaphtoic acids." . Kh. A. Suerbaev, O. E. Mikhnenko, G. B. Akhmetova, K. M. Shalmagambetov, and E. G. Chepaikin (2005): "Phenol carboxylation with alkali metal salts of ethyl carbonic acid". ''Petroleum Chemistry'', volume 45,issue 1, pages 41-43. Quote: " ..phenol carboxylation with sodium ethyl carbonate under optimal conditions (P-Ar = 1 MPa, T = 200 °C, tau = 6 h) yielded o-hydroxybenzoic acid (69.9%) and p-hydroxybenzoic acid (17.5%). ..preparation of p-hydroxybenzoic acid by phenol carboxylation with potassium ethyl carbonate (P-CO2 = 2.5 MPa, T= 210 °C, and tau = 7 h) in a 71% yield was developed". J.-B. Dumas and E. Peligot (1837): "Note sur le carbométhylate de baryte". ''Comptes Rendus'', volume 2, pages 433-434. J.-B. Dumas and E. Peligot (1837): "Sur le carbovinate de potasse". ''Comptes Rendus'', volume 4 pages 563-565. J.-B Dumas, L.J. Thenard, J.L. Gay-Lussac, and J.B. Biot (1838): "Rapport sur un mémoire de M. Peligot, intitulé: Recherches sur la nature et les propriétés chimiques des sucres". ''Comptes Rendus'', volume 7 pages 106-113. M.E. Jungfleish (1891): "Notice sur la vie et les travaux - Eugène Melchior Peligot". ''Bulletin de la Société Chimique'', volume 5, pages xxi-xlvii, 1890 M.E. Jungfleish (1891): "Notice sur la vie et les travaux - Eugène Melchior Peligot". ''Annales du Conservatoire des arts et métiers'', volume 2, pages 85-102. Jaime Wisniak (2009): "Eugène Melchior Peligot". ''Educación Química'', volume 20, issue 1, pages 61-69. S. J. Han and J. H. Wee (2016): "Carbon dioxide fixation via synthesis of sodium ethyl carbonate in NaOH-dissolved ethanol", ''Industrial Engineering & Chemical Research'', volume 55, pages 12111-12118. {{doi, 10.1021/acs.iecr.6b03250 Carbonate esters

Pharmaceutical aspects

Chemical aspects

History

See also

References