Ethyl cinnamate is the ester of cinnamic acid and ethanol. It is present in the essential oil of cinnamon; pure ethyl cinnamate has a "fruity and balsamic odor, reminiscent of cinnamon with an amber note" (Merck Index). The p-methoxy substitute is reported to be a monoamine oxidase inhibitor[1]. Image File history File links Ethyl_cinnamate. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: Ï - Greek: rho) is a measure of mass per volume. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... General formula of a carboxylate ester. ... Cinnamic acid Cinnamic acid has the formula C6H5CHCHCOOH and is an odorless white crystalline acid, which is slightly soluble in water. ... Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless, mildly toxic chemical compound with a distinctive perfume-like odor, and is the alcohol found in alcoholic beverages. ... Binomial name Cinnamomum verum J.Presl Cassia (Indonesian cinnamon) is also commonly called (and sometimes sold as) cinnamon. ... Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ...
References
Budavari, Susan (Ed.) The Merck Index, 13 Ed. Merck & Co., Inc, Whitehouse Station, NJ, USA, 2001.
^ Noro T, Miyase T, Kuroyanagi M, Ueno A, Fukushima S. (1983). "Monoamine oxidase inhibitor from the rhizomes of Kaempferia galanga L.". Chem Pharm Bull (Tokyo).31 (8): 2708–11. PMID 6652816.
The thiomorpholide obtained by this Willgerodt-Kindler reaction is saponified in per se known manner with strong alkali lyes or with concentrated hydrochloric acid or with a mixture of sulphuric acid, glacial acetic acid and water, to give the carboxylic acid.
By hydrolysis of the ethylester analogously to Example 1, there is obtained 4-(2-methanesulphonamidoethyl)-benzoic acid in a yield of 93% of theory; m.p.
After cooling, the reaction mixture is extracted with ethyl acetate and, by the addition of hydrochloric acid, 4-(2-benzenesulphonamidoethyl)-phenylacetic acid, which, in all its physical properties, is identical with the product of Example 4 d, is precipitated from the aqueous phase; yield 56% of theory.
The ethyl acetate is distilled from a water bath and the remaining liquid is transferred to a Claisen flask and distilled from an oil bath under reduced pressure.
Ethylcinnamate can be prepared by the action of ethyl alcohol on cinnamic acid in the presence of hydrogen chloride or sulfuric acid,
and by the condensation of ethyl acetate and benzaldehyde in the presence of sodium.
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