List of esters

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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

2 carbons

3 carbons

4 carbons

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5 carbons

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7 carbons

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Name Structure
Benzyl acetate
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8 carbons

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Name Structure
Octyl acetate
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10 carbons

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

0 carbons

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Name Structure
Methyl nitrate Thumb
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1 carbon

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2 carbons

3 carbons

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4 carbons

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5 carbons

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6 carbons

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7 carbons

8 carbons

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9 carbons

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10 carbons

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Name Structure
Ethyl decanoate Thumb
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16 carbons

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Name Structure
Isopropyl palmitate Thumb
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List of ester odorants

Summarize
Perspective

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.

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

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

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References

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