Chemistry:List of esters

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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')

Template:Inc-science

1 carbon

Name Structure
Methyl nitrate[4] 75x75px
Methyl formate[5] 75x75px[6]
Methyl acetate[7][8] 75x75px
Methyl acrylate[9] 75x75px
Methyl propionate[10][11] 75x75px
Methyl butyrate[12] 75x75px
Methyl pentanoate[13] 75x75px
Methyl benzoate[14] 75x75px
Methyl anthranilate[15] 75x75px
Methyl salicylate[16] 75x75px
Methyl phenylacetate[17] 75x75px
Methyl cinnamate[18] 75x75px

2 carbons

Name Structure
Ethyl formate[19] 75x75px
Ethyl acetate[20] 75x75px
Ethyl propionate[21] 75x75px
Ethyl lactate[22] 75x75px
Ethyl butyrate[23] 75x75px
Ethyl pentanoate[24] 75x75px
Ethyl isovalerate[25] 75x75px
Ethyl hexanoate[26] 125x125px
Ethyl heptanoate[27] 125x125px
Ethyl benzoate[28] 75x75px
Ethyl salicylate[29] 75x75px
Ethyl octanoate[30] 125x125px
Ethyl cinnamate[31] 125x125px
Ethyl decanoate[32] 125x125px

3 carbons

Name Structure
Propyl acetate[33] 125x125px
Propyl propanoate[34] 125x125px
Propyl hexanoate[35] 150x150px
Allyl hexanoate[36] 150x150px
Isopropyl acetate[37] 85x85px
Isopropyl salicylate[38] 85x85px
Isopropyl palmitate[39] 150x150px

4 carbons

Name Structure
Butyl formate[40] 100x100px
Butyl acetate[41] 100x100px
Isobutyl formate[42] 100x100px
Isobutyl acetate[43] 100x100px
Sec-Butyl formate[44]
Sec-Butyl acetate[45][46][47] 100x100px
Tert-Butyl formate 100x100px
Tert-Butyl acetate[48] 100x100px
Butyl butyrate[49] 100x100px

5 carbons

Name Structure
Pentyl acetate[50] 100x100px
Pentyl butyrate[51] 100x100px
Pentyl propanoate[52]
Pentyl hexanoate[53] 100x100px
Sec-Amyl acetate[54] 100x100px

7 carbons

Name Structure
Benzyl acetate[55] 100x100px

8 carbons

Name Structure
Octyl acetate[56] 125x125px

10 carbons

Name Structure
Geranyl acetate[57] 125x125px
Bornyl acetate[58][59][60] 135x135px
Linalyl acetate[61][62][63] 125x125px

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

Template:Inc-science

0 carbons

Name Structure
Methyl nitrate 75x75px

1 carbon

Name Structure
Methyl formate 75x75px
Ethyl formate 75x75px
Isobutyl formate 75x75px

2 carbons

Name Structure
Methyl acetate 100x100px
Ethyl acetate 100x100px
Propyl acetate 100x100px
Butyl acetate 100x100px
Amyl acetate 100x100px
Benzyl acetate 100x100px
Octyl acetate 100x100px
Geranyl acetate 125x125px
Bornyl acetate 101x101px
Linalyl acetate 125x125px

3 carbons

Name Structure
Methyl propionate 75x75px
Ethyl propionate 75x75px
Propyl propanoate 75x75px
Pentyl propanoate
Ethyl lactate 75x75px

4 carbons

Name Structure
Methyl butyrate 100x100px
Ethyl butyrate 100x100px
Butyl butyrate 100x100px
Pentyl butyrate 100x100px

5 carbons

Name Structure
Methyl pentanoate 100x100px
Ethyl pentanoate 100x100px
Pentyl pentanoate 125x125px
Ethyl isovalerate 100x100px

6 carbons

Name Structure
Ethyl hexanoate 125x125px
Propyl hexanoate 125x125px
Allyl hexanoate 125x125px
Pentyl hexanoate 125x125px

7 carbons

Name Structure
Ethyl heptanoate 125x125px
Methyl benzoate 100x100px
Ethyl benzoate 100x100px
Methyl anthranilate 100x100px
Methyl salicylate 100x100px
Ethyl salicylate 100x100px
Isopropyl salicylate 85x85px

8 carbons

Name Structure
Ethyl octanoate 125x125px
Methyl phenylacetate 125x125px

9 carbons

Name Structure
Methyl cinnamate 125x125px
Ethyl cinnamate 125x125px

10 carbons

Name Structure
Ethyl decanoate 150x150px

16 carbons

Name Structure
Isopropyl palmitate 150x150px

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 75px pineapple
Benzyl acetate 75px pear, strawberry, jasmine
Bornyl acetate 75px pine
Butyl acetate 75px apple, honey
Butyl butyrate 75px pineapple
Butyl propanoate 75px pear drops
Ethyl acetate 75px nail polish remover, model paint, model airplane glue
Ethyl benzoate 75px sweet, wintergreen, fruity, medicinal, cherry, grape
Ethyl butyrate 75px banana, pineapple, strawberry
Ethyl hexanoate 75px pineapple, waxy-green banana
Ethyl cinnamate 75px cinnamon
Ethyl formate 75px lemon, rum, strawberry
Ethyl heptanoate 75px apricot, cherry, grape, raspberry
Ethyl isovalerate 75px apple
Ethyl lactate 75px butter, cream
Ethyl nonanoate 75px grape
Ethyl pentanoate 75px apple
Geranyl acetate 75px geranium
Geranyl butyrate 75px cherry
Geranyl pentanoate 75px apple
Isobutyl acetate 75px cherry, raspberry, strawberry
Isobutyl formate 75px raspberry
Isoamyl acetate 75px pear, banana (flavoring in Pear drops)
Isopropyl acetate 75px fruity
Linalyl acetate 75px lavender, sage
Linalyl butyrate 75px peach
Linalyl formate 75px apple, peach
Methyl acetate 75px glue
Methyl anthranilate 75px grape, jasmine
Methyl benzoate 75px fruity, ylang ylang, feijoa
Methyl butyrate (methyl butanoate) 75px pineapple, apple, strawberry
Methyl cinnamate 75px strawberry
Methyl pentanoate (methyl valerate) 75px flowery
Methyl phenylacetate 75px honey
Methyl salicylate (oil of wintergreen) 75px Modern root beer, wintergreen, Germolene and Ralgex ointments (UK)
Nonyl caprylate 75px orange
Octyl acetate 75px fruity-orange
Octyl butyrate 75px parsnip
Amyl acetate (pentyl acetate) 75px apple, banana
Pentyl butyrate (amyl butyrate) 75px apricot, pear, pineapple
Pentyl hexanoate (amyl caproate) 75px apple, pineapple
Pentyl pentanoate (amyl valerate) 75px apple
Propyl acetate 75px pear
Propyl hexanoate 75px blackberry, pineapple, cheese, wine
Propyl isobutyrate 75px rum
Terpenyl butyrate 75px cherry

Lactones

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

Lactone name Structure
β-propiolactone[64] 75px
γ-butyrolactone (GBL)[65]
D-glucono-δ-lactone (E575)[66]
ε-caprolactone[67]

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. ↑ "methyl formate". https://scentsandflavors.com/database/9dbb5186-3880-4548-aa35-eb990e9d6e0f. 
  7. ↑ Merck Index, 12th Edition, 6089.
  8. ↑ "methyl acetate". https://scentsandflavors.com/database/9dbb5125-5135-43f4-b9b0-3f6798025b43. 
  9. ↑ "methyl acrylate". https://scentsandflavors.com/database/9dbb5446-ac85-4f69-b1ce-c6ff2e610031. 
  10. ↑ "Methyl Propionate Hazardous Substance Fact Sheet". New Jersey Department of Health and Senior Services. http://nj.gov/health/eoh/rtkweb/documents/fs/1290.pdf. 
  11. ↑ "methyl propionate". https://scentsandflavors.com/database/9dbb4f5d-77d1-4057-9265-0fe4e17a524c. 
  12. ↑ "methyl butyrate". https://scentsandflavors.com/database/9dbb4fe1-443b-473c-9cbc-661035e6a0df. 
  13. ↑ "methyl valerate". https://scentsandflavors.com/database/9dbb4fe5-6ea9-4d6e-8393-f88c0c324030. 
  14. ↑ "methyl benzoate". https://scentsandflavors.com/database/9dbb505c-9208-4d0b-a219-d7a652f0e975. 
  15. ↑ "methyl anthranilate". https://scentsandflavors.com/database/9dbb4fd1-382e-47f0-98b0-f7a5193e5e41. 
  16. ↑ "methyl salicylate". https://scentsandflavors.com/database/9dbb4fda-f093-47b9-b6bb-6e31f7172adb. 
  17. ↑ "methyl phenyl acetate". https://scentsandflavors.com/database/9dbb4fd8-4c90-445c-ba4a-948d24236747. 
  18. ↑ "methyl cinnamate". https://scentsandflavors.com/database/9dbb5630-464b-46d7-beaa-93e9fe46473b. 
  19. ↑ "ethyl formate". https://scentsandflavors.com/database/9dbb505d-dcbe-4de9-a42b-020aaca51d95. 
  20. ↑ "ethyl acetate". https://scentsandflavors.com/database/9dbb4f71-1c5d-4c8b-a52e-e8cb5678777b. 
  21. ↑ "ethyl propionate". https://scentsandflavors.com/database/9dbb4f76-c426-40b9-89b0-01b1142277bf. 
  22. ↑ "ethyl lactate". https://scentsandflavors.com/database/9dbb512a-43d8-4872-9aeb-e12ef5603863. 
  23. ↑ "ethyl butyrate". https://scentsandflavors.com/database/9dbb4f72-ba4a-4e4b-9fce-9731b73e773b. 
  24. ↑ "ethyl valerate". https://scentsandflavors.com/database/9dbb4f0f-5658-4a01-abf4-1c1230860601. 
  25. ↑ "ethyl isovalerate". https://scentsandflavors.com/database/9dbb4fb2-dab9-445a-9d59-a0bc16b32ab2. 
  26. ↑ "ethyl hexanoate". https://scentsandflavors.com/database/9dbb4f73-8a79-48c2-99d6-3a5e736d9eed. 
  27. ↑ "ethyl heptanoate". https://scentsandflavors.com/database/9dbb4ff0-27a3-48db-8a70-ee45df918015. 
  28. ↑ "ethyl benzoate". https://scentsandflavors.com/database/9dbb4f72-3c00-40ba-b11f-c0a7a3534b3a. 
  29. ↑ "ethyl salicylate". https://scentsandflavors.com/database/9dbb4f23-e8dc-4a80-b461-7364f4e6128d. 
  30. ↑ "ethyl octanoate". https://scentsandflavors.com/database/9dbb51e9-fa86-43f3-abb9-446924771b56. 
  31. ↑ "ethyl cinnamate". https://scentsandflavors.com/database/9dbb5059-f561-48b9-9bfc-4742cd4a7330. 
  32. ↑ "ethyl decanoate". https://scentsandflavors.com/database/9dbb5063-5e66-4e9a-96ab-8fd63d562076. 
  33. ↑ "propyl acetate". https://scentsandflavors.com/database/9dbb513f-11c3-4053-b033-ee07331be173. 
  34. ↑ "propyl propionate". https://scentsandflavors.com/database/9dbb510d-7acf-4ff3-ac6b-b27e8cbd65ee. 
  35. ↑ "propyl hexanoate". https://scentsandflavors.com/database/9dbb5141-c41f-4df8-aa15-86dd4eb08c0f. 
  36. ↑ "allyl hexanoate". https://scentsandflavors.com/database/9dbb4f0f-a9f8-4352-9baf-72a16384ca0f. 
  37. ↑ "isopropyl acetate". https://scentsandflavors.com/database/9dbb5099-9659-46c7-895e-9c8dfc49b1b0. 
  38. ↑ "isopropyl salicylate". https://scentsandflavors.com/database/9dbb5670-3a40-4f9c-8518-12fd62084b33. 
  39. ↑ "isopropyl palmitate". https://scentsandflavors.com/database/9dbb508c-78d1-4ed1-816e-2de6c0419326. 
  40. ↑ "butyl formate". https://scentsandflavors.com/database/9dbb503e-18df-47e3-b7e0-8cf4743b32bf. 
  41. ↑ "butyl acetate". https://scentsandflavors.com/database/9dbb508d-db6f-4e24-b496-c13f93200fcc. 
  42. ↑ "isobutyl formate". https://scentsandflavors.com/database/9dbb505f-c07c-41d5-b85a-586d567a1206. 
  43. ↑ "isobutyl acetate". https://scentsandflavors.com/database/9dbb5043-dcb1-4681-9fe2-9e1febc8fa7b. 
  44. ↑ "sec-butyl formate". https://scentsandflavors.com/database/9dbb569e-4d9e-4dff-a0fc-bc242502d7cc. 
  45. ↑ "sec-butyl acetate". https://scentsandflavors.com/database/9dbb5188-fce1-4ebf-90f9-a17d847c7150. 
  46. ↑ "(+)-sec-butyl acetate". https://scentsandflavors.com/database/9dbb5222-f5f8-4d55-be65-e4fc7b11c0fc. 
  47. ↑ "(-)-sec-butyl acetate". https://scentsandflavors.com/database/9dbb5222-fe78-4de3-9a60-8a692af464de. 
  48. ↑ "tert-butyl acetate". https://scentsandflavors.com/database/9dbb5188-d781-44fa-9226-70ef6497b091. 
  49. ↑ "butyl butyrate". https://scentsandflavors.com/database/9dbb504e-b7ba-4226-be9f-551662ffd723. 
  50. ↑ "amyl acetate". https://scentsandflavors.com/database/9dbb5189-7542-4478-8b0f-b6e787d0e15b. 
  51. ↑ "amyl butyrate". https://scentsandflavors.com/database/9dbb4f66-3414-4d71-9bfc-4a969b1bcb8a. 
  52. ↑ "amyl propionate". https://scentsandflavors.com/database/9dbb5184-d9b0-4604-8c98-232ba2251fe1. 
  53. ↑ "amyl hexanoate". https://scentsandflavors.com/database/9dbb5097-3375-4a6c-baa2-c695ffbc03ff. 
  54. ↑ "2-pentyl acetate". https://scentsandflavors.com/database/9dbb558b-9d9c-4ccf-a8ff-08bbcadfe433. 
  55. ↑ "benzyl acetate". https://scentsandflavors.com/database/9dbb4f25-af09-457f-a883-83669519d01f. 
  56. ↑ "octyl acetate". https://scentsandflavors.com/database/9dbb4f5a-bf25-4019-8f2a-4409eb47ae52. 
  57. ↑ "geranyl acetate". https://scentsandflavors.com/database/9dbb5112-feb4-40d3-adc6-908475f042c3. 
  58. ↑ "bornyl acetate". https://scentsandflavors.com/database/9dbb5288-a2e5-4187-a0fa-c1a7b935845a. 
  59. ↑ "dextro-bornyl acetate". https://scentsandflavors.com/database/9dbb5289-15c5-4afd-9d42-078559594697. 
  60. ↑ "laevo-bornyl acetate". https://scentsandflavors.com/database/9dbb4fb7-a0f8-4c4c-97dc-6bc131d71628. 
  61. ↑ "linalyl acetate". https://scentsandflavors.com/database/9dbb4fc7-479d-44b9-8976-24828cd7502a. 
  62. ↑ "dextro-linalyl acetate". https://scentsandflavors.com/database/9dbb573b-de48-4942-94c7-84a94d213953. 
  63. ↑ "laevo-linalyl acetate". https://scentsandflavors.com/database/9dbb55e9-a9d0-46cb-a856-c519327fad24. 
  64. ↑ "beta-propiolactone". https://scentsandflavors.com/database/9dbb53a3-627c-450a-a5db-4cb7d5e85a8d. 
  65. ↑ "gamma-butyrolactone". https://scentsandflavors.com/database/9dbb5103-e1c8-4a54-84d6-d4b2deabefee. 
  66. ↑ "delta-gluconolactone". https://scentsandflavors.com/database/9dbb53e7-b7eb-47c9-9d6c-ab904a5ab36c. 
  67. ↑ "epsilon-caprolactone". https://scentsandflavors.com/database/9dbb53f9-0bb4-4172-af8e-8fcd22332472. 



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