Chemistry:List of esters

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Short description: List of esters
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] Methyl nitrate.svg
Methyl formate[5] Methyl formate.png
Methyl acetate[6] Methyl-acetate-2D-structure.svg
Methyl acrylate Methyl acrylate.png
Methyl propionate[7] Methyl propionate structure.svg
Methyl butyrate[8] Methyl butyrate 200.svg
Methyl pentanoate[9] Methyl pentanoate.svg
Methyl benzoate[10] Methyl benzoate.svg
Methyl anthranilate[11] Methyl anthranilate.png
Methyl salicylate[12] Methyl 2-hydroxybenzoate 200.svg
Methyl phenylacetate[13] Methyl phenylacetate.svg
Methyl cinnamate[14] Methyl cinnamate.svg

2 carbons

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

3 carbons

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

4 carbons

Name Structure
Butyl formate Structural formula of n-butyl formate.svg
Butyl acetate Butyl acetate.png
Isobutyl formate Isobutyl formate.svg
Isobutyl acetate Isobutyl acetate.png
Sec-Butyl formate
Sec-Butyl acetate S-butyl acetate.png
Tert-Butyl formate Tert-butyl formate.png
Tert-Butyl acetate T-butyl acetate.png
Butyl butyrate Butyl butyrate.png

5 carbons

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

7 carbons

Name Structure
Benzyl acetate Benzyl acetate-structure.svg

8 carbons

Name Structure
Octyl acetate Octyl acetate.svg

10 carbons

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

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

0 carbons

Name Structure
Methyl nitrate Methyl nitrate.svg

1 carbon

Name Structure
Methyl formate Methyl formate.png
Ethyl formate Ethyl formate Structural Formulae.svg
Isobutyl formate Isobutyl formate.svg

2 carbons

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

3 carbons

Name Structure
Methyl propionate Methyl propionate.svg
Ethyl propionate Ethylpropanoaat.png
Propyl propanoate Propyl propanoate.png
Pentyl propanoate
Ethyl lactate Ethyl lactate.svg

4 carbons

Name Structure
Methyl butyrate Methyl butanoate.png
Ethyl butyrate Ethyl butyrate.png
Butyl butyrate Butyl butyrate.png
Pentyl butyrate Pentyl butyrate.svg

5 carbons

Name Structure
Methyl pentanoate Methyl pentanoate.png
Ethyl pentanoate Ethyl valerate.svg
Pentyl pentanoate Pentyl pentanoate.svg
Ethyl isovalerate Ethyl-isovalerate.svg

6 carbons

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

7 carbons

Name Structure
Ethyl heptanoate Ethyl-heptanoate.svg
Methyl benzoate Methyl benzoate.svg
Ethyl benzoate Ethyl benzoate.png
Methyl anthranilate Methyl anthranilate.svg
Methyl salicylate Methyl 2-hydroxybenzoate 200.svg
Ethyl salicylate Ethyl salicylate.png
Isopropyl salicylate Isopropylsalicylatestruct.png

8 carbons

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

9 carbons

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

10 carbons

Name Structure
Ethyl decanoate Ethyl decanoate.svg

16 carbons

Name Structure
Isopropyl palmitate Isopropyl palmitate.png

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 Prop-2-enyl hexanoate.svg pineapple
Benzyl acetate Benzyl acetate-structure.svg pear, strawberry, jasmine
Bornyl acetate Bornyl acetate.svg pine
Butyl acetate Butylacetat.svg apple, honey
Butyl butyrate Butyl butyrate2.svg pineapple
Butyl propanoate Butyl propionate.svg pear drops
Ethyl acetate Ethyl acetate2.svg nail polish remover, model paint, model airplane glue
Ethyl benzoate Ethyl benzoate.svg sweet, wintergreen, fruity, medicinal, cherry, grape
Ethyl butyrate Ethyl butyrate2.svg banana, pineapple, strawberry
Ethyl hexanoate Ethyl-hexanoate.svg pineapple, waxy-green banana
Ethyl cinnamate Ethyl-cinnamate.svg cinnamon
Ethyl formate Ethyl-formate.svg lemon, rum, strawberry
Ethyl heptanoate Ethyl-heptanoate.svg apricot, cherry, grape, raspberry
Ethyl isovalerate Ethyl isovalerate structure.svg apple
Ethyl lactate Ethyl lactate.svg butter, cream
Ethyl nonanoate Ethyl-nonanoate.svg grape
Ethyl pentanoate Ethyl valerate.svg apple
Geranyl acetate Geranyl-acetate.svg geranium
Geranyl butyrate Geranyl butyrate.svg cherry
Geranyl pentanoate Geranyl pentanoate.svg apple
Isobutyl acetate Isobutyl-acetate.svg cherry, raspberry, strawberry
Isobutyl formate Isobutyl formate.svg raspberry
Isoamyl acetate Isoamyl acetate.svg pear, banana (flavoring in Pear drops)
Isopropyl acetate Isopropyl acetate.svg fruity
Linalyl acetate Linalyl acetate.svg lavender, sage
Linalyl butyrate Linalyl butyrate.svg peach
Linalyl formate Linalyl formate.svg apple, peach
Methyl acetate Methyl-acetate-2D-skeletal.svg glue
Methyl anthranilate Methyl anthranilate.svg grape, jasmine
Methyl benzoate Methyl benzoate.svg fruity, ylang ylang, feijoa
Methyl butyrate (methyl butanoate) Buttersauremethylester.svg pineapple, apple, strawberry
Methyl cinnamate Methyl cinnamate.svg strawberry
Methyl pentanoate (methyl valerate) Methyl pentanoate.svg flowery
Methyl phenylacetate Methyl phenylacetate.svg honey
Methyl salicylate (oil of wintergreen) Methyl salicylate.svg Modern root beer, wintergreen, Germolene and Ralgex ointments (UK)
Nonyl caprylate Nonyl caprylate.svg orange
Octyl acetate Octyl acetate.svg fruity-orange
Octyl butyrate Octyl butyrate.svg parsnip
Amyl acetate (pentyl acetate) Amyl acetate.svg apple, banana
Pentyl butyrate (amyl butyrate) Pentyl butyrate.svg apricot, pear, pineapple
Pentyl hexanoate (amyl caproate) Pentyl hexanoate.svg apple, pineapple
Pentyl pentanoate (amyl valerate) Pentyl pentanoate.svg apple
Propyl acetate Propyl acetate.svg pear
Propyl hexanoate Propyl-hexanoate.svg blackberry, pineapple, cheese, wine
Propyl isobutyrate Propyl isobutyrate.svg rum
Terpenyl butyrate Terpenyl butyrate.svg cherry

Lactones

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

Lactone name Structure
β-propiolactone Oxetan-2-one 200.svg
γ-butyrolactone (GBL)
D-glucono-δ-lactone (E575)
ε-caprolactone

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. https://books.google.com/books?id=sFRZAAAAYAAJ. 
  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. https://books.google.com/books?id=gnOJoug5R8IC&pg=PA237. 
  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" (in en). Angewandte Chemie International Edition 58 (51): 18557–18561. doi:10.1002/anie.201911300. ISSN 1433-7851. 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". New Jersey Department of Health and Senior Services. http://nj.gov/health/eoh/rtkweb/documents/fs/1290.pdf. 
  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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