page_title: Ester
section_title: IUPAC nomenclature
hierarchical_section_title: Ester / Nomenclature / IUPAC nomenclature
caption_attribution_description: English: improved (vs Ethylethanoate-parts.svg) image of ethyl acetate, a typical ester with color
context_page_description: In chemistry, an ester is a chemical compound derived from an acid in which at least one –OH group is replaced by an –O–alkyl group. Usually, esters are derived from substitution reaction of a carboxylic acid and an alcohol. Glycerides, which are fatty acid esters of glycerol, are important esters in biology, being one of the main classes of lipids, and making up the bulk of animal fats and vegetable oils. Esters with low molecular weight are commonly used as fragrances and found in essential oils and pheromones. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties, while polyesters are important plastics, with monomers linked by ester moieties. Esters usually have a sweet smell and are considered high-quality solvents for a broad array of plastics, plasticizers, resins, and lacquers. They are also one of the largest classes of synthetic lubricants on the commercial market.
context_section_description: Ester names are derived from the parent alcohol and the parent acid, where the latter may be organic or inorganic. Esters derived from the simplest carboxylic acids are commonly named according to the more traditional, so-called "trivial names" e.g. as formate, acetate, propionate, and butyrate, as opposed to the IUPAC nomenclature methanoate, ethanoate, propanoate and butanoate. Esters derived from more complex carboxylic acids are, on the other hand, more frequently named using the systematic IUPAC name, based on the name for the acid followed by the suffix -oate. For example, the ester hexyl octanoate, also known under the trivial name hexyl caprylate, has the formula CH₃(CH₂)₆CO₂(CH₂)₅CH₃.
  The chemical formulas of organic esters usually take the form RCO₂R′, where R and R′ are the hydrocarbon parts of the carboxylic acid and the alcohol, respectively. For example, butyl acetate (systematically butyl ethanoate), derived from butanol and acetic acid (systematically ethanoic acid) would be written CH₃CO₂C₄H₉. Alternative presentations are common including BuOAc and CH₃COOC₄H₉.
  Cyclic esters are called lactones, regardless of whether they are derived from an organic or an inorganic acid. One example of an organic lactone is γ-valerolactone.
caption: Ethyl acetate derived from an alcohol (blue) and an acyl group (yellow) derived from a carboxylic acid
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