List of esters

In chemistry, an ester is a chemical compound derived from an acid (organic or inorganic) in which at least one –OH (hydroxyl) group is replaced by an –O–alkyl (alkoxy) group.[1] Usually, esters are derived from a substitution reaction of 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.[2] They are also one of the largest classes of synthetic lubricants on the commercial market.[3]

A carboxylate ester. R′ denotes any alkyl or aryl group.

By number of alkyl group carbons

1 carbon
Name Structure
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
Name Structure
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
Name Structure
Propyl acetate
Propyl propanoate
Propyl hexanoate
Allyl hexanoate
Isopropyl acetate
Isopropyl salicylate
Isopropyl palmitate

4 carbons
Name Structure
Butyl formate
Butyl acetate
Isobutyl formate
Isobutyl acetate
Sec-Butyl formate
Sec-Butyl acetate
Tert-Butyl formate
Tert-Butyl acetate
Butyl butyrate

5 carbons
Name Structure
Amyl acetate
Pentyl butyrate
Pentyl propanoate
Pentyl hexanoate
Sec-Amyl acetate

7 carbons
Name Structure
Benzyl acetate

8 carbons
Name Structure
Octyl acetate

10 carbons
Name Structure
Geranyl acetate
Bornyl acetate
Linalyl acetate

By number of acid group carbons

0 carbons
Name Structure
Methyl nitrate

1 carbon
Name Structure
Methyl formate
Ethyl formate
Isobutyl formate

2 carbons
Name Structure
Methyl acetate
Ethyl acetate
Propyl acetate
Butyl acetate
Amyl acetate
Benzyl acetate
Octyl acetate
Geranyl acetate
Bornyl acetate
Linalyl acetate

3 carbons
Name Structure
Methyl propionate
Ethyl propionate
Propyl propanoate
Pentyl propanoate
Ethyl lactate

4 carbons
Name Structure
Methyl butyrate
Ethyl butyrate
Butyl butyrate
Pentyl butyrate

5 carbons
Name Structure
Methyl pentanoate
Ethyl pentanoate
Pentyl pentanoate
Ethyl isovalerate

6 carbons
Name Structure
Ethyl hexanoate
Propyl hexanoate
Allyl hexanoate
Pentyl hexanoate

7 carbons
Name Structure
Ethyl heptanoate
Methyl benzoate
Ethyl benzoate
Methyl anthranilate
Methyl salicylate
Ethyl salicylate
Isopropyl salicylate

8 carbons
Name Structure
Ethyl octanoate
Methyl phenylacetate

9 carbons
Name Structure
Methyl cinnamate
Ethyl cinnamate

10 carbons
Name Structure
Ethyl decanoate

16 carbons
Name Structure
Isopropyl palmitate

List of ester odorants

Many esters have distinctive fruit-like odors, and many occur naturally in 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 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 name Structure
β-propiolactone
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.
  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.
  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. {{cite journal}}: Cite journal requires |journal= (help)
  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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