List of esters

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File:Ester-general.svg
An ester of carboxylic acid. R stands for any group (organic or inorganic) and R′ stands for organyl group.

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 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

Name Structure
Methyl nitrate[4] File:Methyl nitrate.svg
Methyl formate[5] File:Methyl formate.svg
Methyl acetate[6] File:Methyl-acetate-2D-structure.svg
Methyl acrylate File:Methylacrylat.svg
Methyl propionate[7] File:Methyl propionate structure.svg
Methyl butyrate[8] File:Methyl butyrate 200.svg
Methyl pentanoate[9] File:Methyl pentanoate.svg
Methyl benzoate[10] File:Methyl benzoate.svg
Methyl anthranilate[11] File:Methyl anthranilate.svg
Methyl salicylate[12] File:Methyl 2-hydroxybenzoate 200.svg
Methyl phenylacetate[13] File:Methyl phenylacetate.svg
Methyl cinnamate[14] File:Methyl cinnamate.svg

2 carbons

Name Structure
Ethyl formate[15] File:Ethyl formate Structural Formulae.svg
Ethyl acetate[16] File:Ethylacetat.svg
Ethyl propionate[17] File:Ethyl-propionate-2D-skeletal.svg
Ethyl lactate[18] File:Ethyl lactate.svg
Ethyl butyrate[19] File:Ethylbutyrat.svg
Ethyl pentanoate[20] File:Ethyl valerate.svg
Ethyl isovalerate[21] File:Ethyl-isovalerate.svg
Ethyl hexanoate[22] File:Ethyl-hexanoate.svg
Ethyl heptanoate[23] File:Ethyl-heptanoate.svg
Ethyl benzoate[24] File:Ethyl benzoate.svg
Ethyl salicylate[25] File:Ethyl-salicylate.svg
Ethyl octanoate[26] File:Ethyl octanoate structure.svg
Ethyl cinnamate[27] File:Ethyl-cinnamate.svg
Ethyl decanoate[28] File:Ethyl decanoate.svg

3 carbons

Name Structure
Propyl acetate File:Propyl-acetate-2D-skeletal.svg
Propyl propanoate File:Propyl propanoate.svg
Propyl hexanoate File:Propyl-hexanoate.svg
Allyl hexanoate File:Prop-2-enyl hexanoate.svg
Isopropyl acetate File:Isopropyl acetate.svg
Isopropyl salicylate File:Isopropyl salicylate.svg
Isopropyl palmitate File:Isopropyl-palmitate.svg

4 carbons

Name Structure
Butyl formate File:Structural formula of n-butyl formate.svg
Butyl acetate File:Butylacetat.svg
Isobutyl formate File:Isobutyl formate.svg
Isobutyl acetate File:Isobutyl acetate.svg
Sec-Butyl formate
Sec-Butyl acetate File:Sec-butyl acetate.svg
Tert-Butyl formate File:Tert-butyl formate.png
Tert-Butyl acetate File:Tert-Butylacetat.svg
Butyl butyrate File:Butyl butyrate2.svg

5 carbons

Name Structure
Amyl acetate File:Amyl acetate.svg
Pentyl butyrate File:Pentyl butyrate.svg
Pentyl propanoate
Pentyl hexanoate File:Pentyl hexanoate.svg
Sec-Amyl acetate File:2-Pentyl acetate.svg

7 carbons

Name Structure
Benzyl acetate File:Benzyl acetate-structure.svg

8 carbons

Name Structure
Octyl acetate File:Octyl acetate.svg

10 carbons

Name Structure
Geranyl acetate File:Geranyl acetate skeletal.svg
Bornyl acetate File:Bornyl acetate.svg
Linalyl acetate File:Linalyl acetate.svg

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

0 carbons

Name Structure
Methyl nitrate File:Methyl nitrate.svg

1 carbon

Name Structure
Methyl formate File:Methyl formate.svg
Ethyl formate File:Ethyl formate Structural Formulae.svg
Isobutyl formate File:Isobutyl formate.svg

2 carbons

Name Structure
Methyl acetate File:Methyl-acetate-2D-skeletal.svg
Ethyl acetate File:Ethylacetat.svg
Propyl acetate File:Propyl-acetate-2D-skeletal.svg
Butyl acetate File:Butylacetat.svg
Amyl acetate File:Amyl acetate.svg
Benzyl acetate File:Benzyl acetate-structure.svg
Octyl acetate File:Octyl acetate.svg
Geranyl acetate File:Geranyl acetate skeletal.svg
Bornyl acetate File:Bornyl acetate.svg
Linalyl acetate File:Linalyl acetate.svg

3 carbons

Name Structure
Methyl propionate File:Methyl propionate.svg
Ethyl propionate File:Ethyl-propionate-2D-skeletal.svg
Propyl propanoate File:Propyl propanoate.svg
Pentyl propanoate
Ethyl lactate File:Ethyl lactate.svg

4 carbons

Name Structure
Methyl butyrate File:Buttersauremethylester.svg
Ethyl butyrate File:Ethylbutyrat.svg
Butyl butyrate File:Butyl butyrate2.svg
Pentyl butyrate File:Pentyl butyrate.svg

5 carbons

Name Structure
Methyl pentanoate File:Methyl pentanoate.svg
Ethyl pentanoate File:Ethyl valerate.svg
Pentyl pentanoate File:Pentyl pentanoate.svg
Ethyl isovalerate File:Ethyl-isovalerate.svg

6 carbons

Name Structure
Ethyl hexanoate File:Hexansaureethylester.svg
Propyl hexanoate File:Propyl-hexanoate.svg
Allyl hexanoate File:Prop-2-enyl hexanoate.svg
Pentyl hexanoate File:Pentyl hexanoate.svg

7 carbons

Name Structure
Ethyl heptanoate File:Ethyl-heptanoate.svg
Methyl benzoate File:Methyl benzoate.svg
Ethyl benzoate File:Ethyl benzoate.svg
Methyl anthranilate File:Methyl anthranilate.svg
Methyl salicylate File:Methyl 2-hydroxybenzoate 200.svg
Ethyl salicylate File:Ethyl-salicylate.svg
Isopropyl salicylate File:Isopropyl salicylate.svg

8 carbons

Name Structure
Ethyl octanoate File:Ethyl octanoate structure.svg
Methyl phenylacetate File:Methyl phenylacetate.svg

9 carbons

Name Structure
Methyl cinnamate File:Methyl cinnamate.svg
Ethyl cinnamate File:Ethyl-cinnamate.svg

10 carbons

Name Structure
Ethyl decanoate File:Ethyl decanoate.svg

16 carbons

Name Structure
Isopropyl palmitate File:Isopropyl-palmitate.svg

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 name Structure Odor or occurrence
Allyl hexanoate File:Prop-2-enyl hexanoate.svg pineapple
Benzyl acetate File:Benzyl acetate-structure.svg pear, strawberry, jasmine
Bornyl acetate File:Bornyl acetate.svg pine
Butyl acetate File:Butylacetat.svg apple, honey
Butyl butyrate File:Butyl butyrate2.svg pineapple
Butyl propanoate File:Butyl propionate.svg pear drops
Ethyl acetate File:Ethyl-acetate-2D-skeletal.svg nail polish remover, model paint, model airplane glue
Ethyl benzoate File:Ethyl benzoate.svg sweet, wintergreen, fruity, medicinal, cherry, grape
Ethyl butyrate File:Ethyl butyrate2.svg banana, pineapple, strawberry
Ethyl hexanoate File:Ethyl-hexanoate.svg pineapple, waxy-green banana
Ethyl cinnamate File:Ethyl-cinnamate.svg cinnamon
Ethyl formate File:Ethyl-formate.svg lemon, rum, strawberry
Ethyl heptanoate File:Ethyl-heptanoate.svg apricot, cherry, grape, raspberry
Ethyl isovalerate File:Ethyl isovalerate structure.svg apple
Ethyl lactate File:Ethyl lactate.svg butter, cream
Ethyl nonanoate File:Ethyl-nonanoate-2D-skeletal.svg grape
Ethyl pentanoate File:Ethyl valerate.svg apple
Geranyl acetate File:Geranyl-acetate.svg geranium
Geranyl butyrate File:Geranyl butyrate.svg cherry
Geranyl pentanoate File:Geranyl pentanoate.svg apple
Isobutyl acetate File:Isobutyl-acetate.svg cherry, raspberry, strawberry
Isobutyl formate File:Isobutyl formate.svg raspberry
Isoamyl acetate File:Isoamyl acetate.svg pear, banana (flavoring in Pear drops)
Isopropyl acetate File:Isopropyl acetate.svg fruity
Linalyl acetate File:Linalyl acetate.svg lavender, sage
Linalyl butyrate File:Linalyl butyrate.svg peach
Linalyl formate File:Linalyl formate.svg apple, peach
Methyl acetate File:Methyl-acetate-2D-skeletal.svg glue
Methyl anthranilate File:Methyl anthranilate.svg grape, jasmine
Methyl benzoate File:Methyl benzoate.svg fruity, ylang ylang, feijoa
Methyl butyrate (methyl butanoate) File:Buttersauremethylester.svg pineapple, apple, strawberry
Methyl cinnamate File:Methyl cinnamate.svg strawberry
Methyl pentanoate (methyl valerate) File:Methyl pentanoate.svg flowery
Methyl phenylacetate File:Methyl phenylacetate.svg honey
Methyl salicylate (oil of wintergreen) File:Methyl salicylate.svg Modern root beer, wintergreen, Germolene and Ralgex ointments (UK)
Nonyl caprylate File:Nonyl caprylate.svg orange
Octyl acetate File:Octyl acetate.svg fruity-orange
Octyl butyrate File:Octyl butyrate.svg parsnip
Amyl acetate (pentyl acetate) File:Amyl acetate.svg apple, banana
Pentyl butyrate (amyl butyrate) File:Pentyl butyrate.svg apricot, pear, pineapple
Pentyl hexanoate (amyl caproate) File:Pentyl hexanoate.svg apple, pineapple
Pentyl pentanoate (amyl valerate) File:Pentyl pentanoate.svg apple
Propyl acetate File:Propyl acetate.svg pear
Propyl hexanoate File:Propyl-hexanoate.svg blackberry, pineapple, cheese, wine
Propyl isobutyrate File:Propyl isobutyrate.svg rum
Terpenyl butyrate File:Terpenyl butyrate.svg cherry

Lactones

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

Lactone name Structure
β-propiolactone File:Oxetan-2-one 200.svg
γ-butyrolactone (GBL)
File:Dihydrofuran-2(3H)-one 200.svg
D-glucono-δ-lactone (E575)
File:Glucono-delta-lactone-2D-skeletal.svg
ε-caprolactone
File:Caprolactone.svg

References

  1. ↑ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "esters". doi:10.1351/goldbook.E02219
  2. ↑ Cameron Wright (1986). A worker's guide to solvent hazards. The Group. p. 48. ISBN 9780969054542.
  3. ↑ E. Richard Booser (21 December 1993). CRC Handbook of Lubrication and Tribology, Volume III: Monitoring, Materials, Synthetic Lubricants, and Applications. CRC. p. 237. ISBN 978-1-4200-5045-5.
  4. ↑ Reichel, Marco; Krumm, Burkhard; Vishnevskiy, Yury V.; Blomeyer, Sebastian; Schwabedissen, Jan; Stammler, Hans‐Georg; Karaghiosoff, Konstantin; Mitzel, Norbert W. (2019-12-16). "Solid‐State and Gas‐Phase Structures and Energetic Properties of the Dangerous Methyl and Fluoromethyl Nitrates". Angewandte Chemie International Edition. 58 (51): 18557–18561. doi:10.1002/anie.201911300. ISSN 1433-7851. PMC 6916544. PMID 31573130.
  5. ↑ Werner Reutemann and Heinz Kieczka "Formic Acid" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a12_013
  6. ↑ Merck Index, 12th Edition, 6089.
  7. ↑ "Methyl Propionate Hazardous Substance Fact Sheet" (PDF). New Jersey Department of Health and Senior Services.
  8. ↑ Methyl butyrate, thegoodscentscompany.com
  9. ↑ Methyl pentanoate, thegoodscentscompany.com
  10. ↑ Methyl benzoate, thegoodscentscompany.com
  11. ↑ Methyl anthranilate, thegoodscentscompany.com
  12. ↑ Methyl salicylate, thegoodscentscompany.com
  13. ↑ Methyl phenylacetate, thegoodscentscompany.com
  14. ↑ Methyl cinnamate, thegoodscentscompany.com
  15. ↑ Ethyl formate, thegoodscentscompany.com
  16. ↑ Ethyl acetate, thegoodscentscompany.com
  17. ↑ Ethyl propionate, thegoodscentscompany.com
  18. ↑ Ethyl lactate, thegoodscentscompany.com
  19. ↑ Ethyl butyrate, thegoodscentscompany.com
  20. ↑ Ethyl pentanoate, thegoodscentscompany.com
  21. ↑ Ethyl isovalerate, thegoodscentscompany.com
  22. ↑ Ethyl hexanoate, thegoodscentscompany.com
  23. ↑ Ethyl heptanoate, thegoodscentscompany.com
  24. ↑ Ethyl benzoate, thegoodscentscompany.com
  25. ↑ Ethyl salicylate, thegoodscentscompany.com
  26. ↑ Ethyl octanoate, thegoodscentscompany.com
  27. ↑ Ethyl cinnamate, thegoodscentscompany.com
  28. ↑ Ethyl decanoate, thegoodscentscompany.com
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