List of esters

In chemistry, an ester is a compound derived from an acid (organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group (−OH) of that acid is replaced by an organyl group (−R). Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well (i.e. esters of acidic SH, SeH, TeH, PoH and LvH groups). According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well (e.g. amides), but not according to the IUPAC.[1]

An ester of carboxylic acid. R stands for any group (organic or inorganic) and R′ stands for organyl group.

An example of an ester formation is the substitution reaction between a carboxylic acid (R−C(=O)−OH) and an alcohol (R'OH), forming an ester (R−C(=O)−O−R'), where R and R′ are organyl groups, or H in the case of esters of formic acid. 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 of carboxylic acids 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 of carboxylic acids usually have a sweet smell and are considered high-quality solvents for a broad array of plastics, plasticizers, resins, and lacquers.[2] They are also one of the largest classes of synthetic lubricants on the commercial market.[3]

By number of R' group carbons (R−C(=O)−O−R')

1 carbon

NameStructure
Methyl nitrate[4]
Methyl formate[5]
Methyl acetate[6]
Methyl acrylate
Methyl propionate[7]
Methyl butyrate[8]
Methyl pentanoate[9]
Methyl benzoate[10]
Methyl anthranilate[11]
Methyl salicylate[12]
Methyl phenylacetate[13]
Methyl cinnamate[14]

2 carbons

NameStructure
Ethyl formate[15]
Ethyl acetate[16]
Ethyl propionate[17]
Ethyl lactate[18]
Ethyl butyrate[19]
Ethyl pentanoate[20]
Ethyl isovalerate[21]
Ethyl hexanoate[22]
Ethyl heptanoate[23]
Ethyl benzoate[24]
Ethyl salicylate[25]
Ethyl octanoate[26]
Ethyl cinnamate[27]
Ethyl decanoate[28]

3 carbons

NameStructure
Propyl acetate
Propyl propanoate
Propyl hexanoate
Allyl hexanoate
Isopropyl acetate
Isopropyl salicylate
Isopropyl palmitate

4 carbons

NameStructure
Butyl formate
Butyl acetate
Isobutyl formate
Isobutyl acetate
Sec-Butyl formate
Sec-Butyl acetate
Tert-Butyl formate
Tert-Butyl acetate
Butyl butyrate

5 carbons

NameStructure
Amyl acetate
Pentyl butyrate
Pentyl propanoate
Pentyl hexanoate
Sec-Amyl acetate

7 carbons

NameStructure
Benzyl acetate

8 carbons

NameStructure
Octyl acetate

10 carbons

NameStructure
Geranyl acetate
Bornyl acetate
Linalyl acetate

By number of R group carbons (R−C(=O)−O−R')

0 carbons

NameStructure
Methyl nitrate

1 carbon

NameStructure
Methyl formate
Ethyl formate
Isobutyl formate

2 carbons

NameStructure
Methyl acetate
Ethyl acetate
Propyl acetate
Butyl acetate
Amyl acetate
Benzyl acetate
Octyl acetate
Geranyl acetate
Bornyl acetate
Linalyl acetate

3 carbons

NameStructure
Methyl propionate
Ethyl propionate
Propyl propanoate
Pentyl propanoate
Ethyl lactate

4 carbons

NameStructure
Methyl butyrate
Ethyl butyrate
Butyl butyrate
Pentyl butyrate

5 carbons

NameStructure
Methyl pentanoate
Ethyl pentanoate
Pentyl pentanoate
Ethyl isovalerate

6 carbons

NameStructure
Ethyl hexanoate
Propyl hexanoate
Allyl hexanoate
Pentyl hexanoate

7 carbons

NameStructure
Ethyl heptanoate
Methyl benzoate
Ethyl benzoate
Methyl anthranilate
Methyl salicylate
Ethyl salicylate
Isopropyl salicylate

8 carbons

NameStructure
Ethyl octanoate
Methyl phenylacetate

9 carbons

NameStructure
Methyl cinnamate
Ethyl cinnamate

10 carbons

NameStructure
Ethyl decanoate

16 carbons

NameStructure
Isopropyl palmitate

List of ester odorants

Many esters of carboxylic acid have distinctive fruit-like odors, and many occur naturally in fruits and the essential oils of plants. This has also led to their common use in artificial flavorings and fragrances which aim to mimic those odors.

Ester nameStructureOdor or occurrence
Allyl hexanoate pineapple
Benzyl acetate pear, strawberry, jasmine
Bornyl acetate pine
Butyl acetate apple, honey
Butyl butyrate pineapple
Butyl propanoate pear drops
Ethyl acetate nail polish remover, model paint, model airplane glue
Ethyl benzoate sweet, wintergreen, fruity, medicinal, cherry, grape
Ethyl butyrate banana, pineapple, strawberry
Ethyl hexanoate pineapple, waxy-green banana
Ethyl cinnamate cinnamon
Ethyl formate lemon, rum, strawberry
Ethyl heptanoate apricot, cherry, grape, raspberry
Ethyl isovalerate apple
Ethyl lactate butter, cream
Ethyl nonanoate grape
Ethyl pentanoate apple
Geranyl acetate geranium
Geranyl butyrate cherry
Geranyl pentanoate apple
Isobutyl acetate cherry, raspberry, strawberry
Isobutyl formate raspberry
Isoamyl acetate pear, banana (flavoring in Pear drops)
Isopropyl acetate fruity
Linalyl acetate lavender, sage
Linalyl butyrate peach
Linalyl formate apple, peach
Methyl acetate glue
Methyl anthranilate grape, jasmine
Methyl benzoate fruity, ylang ylang, feijoa
Methyl butyrate (methyl butanoate) pineapple, apple, strawberry
Methyl cinnamate strawberry
Methyl pentanoate (methyl valerate) flowery
Methyl phenylacetate honey
Methyl salicylate (oil of wintergreen) Modern root beer, wintergreen, Germolene and Ralgex ointments (UK)
Nonyl caprylate orange
Octyl acetate fruity-orange
Octyl butyrate parsnip
Amyl acetate (pentyl acetate) apple, banana
Pentyl butyrate (amyl butyrate) apricot, pear, pineapple
Pentyl hexanoate (amyl caproate) apple, pineapple
Pentyl pentanoate (amyl valerate) apple
Propyl acetate pear
Propyl hexanoate blackberry, pineapple, cheese, wine
Propyl isobutyrate rum
Terpenyl butyrate cherry

Lactones

Lactones are a specific class cyclic carboxylic esters that are formed through intramolecular esterification.

Lactone nameStructure
β-propiolactone
γ-butyrolactone (GBL)
D-glucono-δ-lactone (E575)
ε-caprolactone

References