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. 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]

Contents

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

NameStructure
Methyl nitrate [4] Methyl nitrate.svg
Methyl formate [5] Methyl formate.svg
Methyl acetate [6] Methyl-acetate-2D-structure.svg
Methyl acrylate Methylacrylat.svg
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.svg
Methyl salicylate [12] Methyl 2-hydroxybenzoate 200.svg
Methyl phenylacetate [13] Methyl phenylacetate.svg
Methyl cinnamate [14] Methyl cinnamate.svg

2 carbons

NameStructure
Ethyl formate [15] Ethyl formate Structural Formulae.svg
Ethyl acetate [16] Ethylacetat.svg
Ethyl propionate [17] Ethyl-propionate-2D-skeletal.svg
Ethyl lactate [18] Ethyl lactate.svg
Ethyl butyrate [19] Ethylbutyrat.svg
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.svg
Ethyl salicylate [25] Ethyl-salicylate.svg
Ethyl octanoate [26] Ethyl octanoate structure.svg
Ethyl cinnamate [27] Ethyl-cinnamate.svg
Ethyl decanoate [28] Ethyl decanoate.svg

3 carbons

NameStructure
Propyl acetate Propyl-acetate-2D-skeletal.svg
Propyl propanoate Propyl propanoate.svg
Propyl hexanoate Propyl-hexanoate.svg
Allyl hexanoate Prop-2-enyl hexanoate.svg
Isopropyl acetate Isopropyl acetate.svg
Isopropyl salicylate Isopropyl salicylate.svg
Isopropyl palmitate Isopropyl-palmitate.svg

4 carbons

NameStructure
Butyl formate Structural formula of n-butyl formate.svg
Butyl acetate Butylacetat.svg
Isobutyl formate Isobutyl formate.svg
Isobutyl acetate Isobutyl acetate.svg
Sec-Butyl formate
Sec-Butyl acetate Sec-butyl acetate.svg
Tert-Butyl formate Tert-butyl formate.png
Tert-Butyl acetate Tert-Butylacetat.svg
Butyl butyrate Butyl butyrate2.svg

5 carbons

NameStructure
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

NameStructure
Benzyl acetate Benzyl acetate-structure.svg

8 carbons

NameStructure
Octyl acetate Octyl acetate.svg

10 carbons

NameStructure
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

NameStructure
Methyl nitrate Methyl nitrate.svg

1 carbon

NameStructure
Methyl formate Methyl formate.svg
Ethyl formate Ethyl formate Structural Formulae.svg
Isobutyl formate Isobutyl formate.svg

2 carbons

NameStructure
Methyl acetate Methyl-acetate-2D-skeletal.svg
Ethyl acetate Ethylacetat.svg
Propyl acetate Propyl-acetate-2D-skeletal.svg
Butyl acetate Butylacetat.svg
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

NameStructure
Methyl propionate Methyl propionate.svg
Ethyl propionate Ethyl-propionate-2D-skeletal.svg
Propyl propanoate Propyl propanoate.svg
Pentyl propanoate
Ethyl lactate Ethyl lactate.svg

4 carbons

NameStructure
Methyl butyrate Buttersauremethylester.svg
Ethyl butyrate Ethylbutyrat.svg
Butyl butyrate Butyl butyrate2.svg
Pentyl butyrate Pentyl butyrate.svg

5 carbons

NameStructure
Methyl pentanoate Methyl pentanoate.svg
Ethyl pentanoate Ethyl valerate.svg
Pentyl pentanoate Pentyl pentanoate.svg
Ethyl isovalerate Ethyl-isovalerate.svg

6 carbons

NameStructure
Ethyl hexanoate Hexansaureethylester.svg
Propyl hexanoate Propyl-hexanoate.svg
Allyl hexanoate Prop-2-enyl hexanoate.svg
Pentyl hexanoate Pentyl hexanoate.svg

7 carbons

NameStructure
Ethyl heptanoate Ethyl-heptanoate.svg
Methyl benzoate Methyl benzoate.svg
Ethyl benzoate Ethyl benzoate.svg
Methyl anthranilate Methyl anthranilate.svg
Methyl salicylate Methyl 2-hydroxybenzoate 200.svg
Ethyl salicylate Ethyl-salicylate.svg
Isopropyl salicylate Isopropyl salicylate.svg

8 carbons

NameStructure
Ethyl octanoate Ethyl octanoate structure.svg
Methyl phenylacetate Methyl phenylacetate.svg

9 carbons

NameStructure
Methyl cinnamate Methyl cinnamate.svg
Ethyl cinnamate Ethyl-cinnamate.svg

10 carbons

NameStructure
Ethyl decanoate Ethyl decanoate.svg

16 carbons

NameStructure
Isopropyl palmitate 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 nameStructureOdor 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-acetate-2D-skeletal.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-2D-skeletal.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 nameStructure
β-propiolactone Oxetan-2-one 200.svg
γ-butyrolactone (GBL)
Dihydrofuran-2(3H)-one 200.svg
D-glucono-δ-lactone (E575)
Glucono-delta-lactone-2D-skeletal.svg
ε-caprolactone
Caprolactone.svg

Related Research Articles

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to an organyl group, or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a functional group derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Acetate</span> Salt compound formed from acetic acid and a base

An acetate is a salt formed by the combination of acetic acid with a base. "Acetate" also describes the conjugate base or ion typically found in aqueous solution and written with the chemical formula C
2
H
3
O
2
. The neutral molecules formed by the combination of the acetate ion and a positive ion are also commonly called "acetates". The simplest of these is hydrogen acetate with corresponding salts, esters, and the polyatomic anion CH
3
CO
2
, or CH
3
COO
.

In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the Nomenclature of Organic Chemistry. Ideally, every possible organic compound should have a name from which an unambiguous structural formula can be created. There is also an IUPAC nomenclature of inorganic chemistry.

<span class="mw-page-title-main">Ethyl butyrate</span> Chemical compound

Ethyl butyrate, also known as ethyl butanoate, or butyric ether, is an ester with the chemical formula CH3CH2CH2COOCH2CH3. It is soluble in propylene glycol, paraffin oil, and kerosene. It has a fruity odor, similar to pineapple, and is a key ingredient used as a flavor enhancer in processed orange juices. It also occurs naturally in many fruits, albeit at lower concentrations.

<span class="mw-page-title-main">Cinnamic acid</span> Chemical compound

Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.

<span class="mw-page-title-main">Valeric acid</span> Carboxylic acid – CH3(CH2)3COOH

Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula CH3(CH2)3COOH. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. It is found in the perennial flowering plant Valeriana officinalis, from which it gets its name. Its primary use is in the synthesis of its esters. Salts and esters of valeric acid are known as valerates or pentanoates. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Several, including ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.

<span class="mw-page-title-main">Methyl butyrate</span> Chemical compound

Methyl butyrate, also known under the systematic name methyl butanoate, is the methyl ester of butyric acid. Like most esters, it has a fruity odor, in this case resembling apples or pineapples. At room temperature, it is a colorless liquid with low solubility in water, upon which it floats to form an oily layer. Although it is flammable, it has a relatively low vapor pressure, so it can be safely handled at room temperature without special safety precautions.

In chemistry, solvolysis is a type of nucleophilic substitution (SN1/SN2) or elimination where the nucleophile is a solvent molecule. Characteristic of SN1 reactions, solvolysis of a chiral reactant affords the racemate. Sometimes however, the stereochemical course is complicated by intimate ion pairs, whereby the leaving anion remains close to the carbocation, effectively shielding it from an attack by the nucleophile. Particularly fast reactions can occur by neighbour group participation, with nonclassical ions as intermediates or transition states.

<span class="mw-page-title-main">Xanthate</span> Salt that is a metal-thioate/O-esters of dithiocarbonate

A xanthate is a salt or ester of a xanthic acid. The formula of the salt of xanthic acid is [R−O−CS2]M+. Xanthate also refers to the anion [R−O−CS2]. The formula of a xanthic acid is R−O−C(=S)−S−H, such as ethyl xanthic acid, while the formula of an ester of a xanthic acid is R−O−C(=S)−S−R', where R and R' are organyl groups. The salts of xanthates are also called O-organyl dithioates. The esters of xanthic acid are also called O,S-diorganyl esters of dithiocarbonic acid. The name xanthate is derived from Ancient Greek ξανθός (xanthos) meaning 'yellowish' or 'golden', and indeed most xanthate salts are yellow. They were discovered and named in 1823 by Danish chemist William Christopher Zeise. These organosulfur compounds are important in two areas: the production of cellophane and related polymers from cellulose and for extraction of certain sulphide bearing ores. They are also versatile intermediates in organic synthesis.

<span class="mw-page-title-main">Methyl benzoate</span> Chemical compound

Methyl benzoate is an organic compound. It is an ester with the chemical formula C6H5COOCH3, sometimes abbreviated as PhCO2Me, where Ph and Me are phenyl and methyl, respectively. Its structure is C6H5−C(=O)−O−CH3. It is a colorless liquid that is poorly soluble in water, but miscible with organic solvents. Methyl benzoate has a pleasant smell, strongly reminiscent of the fruit of the feijoa tree, and it is used in perfumery. It also finds use as a solvent and as a pesticide used to attract insects such as orchid bees.

<span class="mw-page-title-main">Propiolic acid</span> Chemical compound

Propiolic acid is the organic compound with the formula HC2CO2H. It is the simplest acetylenic carboxylic acid. It is a colourless liquid that crystallises to give silky crystals. Near its boiling point, it decomposes.

Enanthic acid, also called heptanoic acid, is an organic compound composed of a seven-carbon chain terminating in a carboxylic acid functional group. It is a colorless oily liquid with an unpleasant, rancid odor. It contributes to the odor of some rancid oils. It is slightly soluble in water, but very soluble in ethanol and ether. Salts and esters of enanthic acid are called enanthates or heptanoates.

<span class="mw-page-title-main">Butamben</span> Chemical compound

Butamben is a local anesthetic. Proprietary names includes Alvogil in Spain and Alvogyl in Switzerland. It is one of three components in the topical anesthetic Cetacaine.

<span class="mw-page-title-main">Ethyl benzoate</span> Chemical compound

Ethyl benzoate, C9H10O2, is an ester formed by the condensation of benzoic acid and ethanol. It is a colorless liquid that is almost insoluble in water, but miscible with most organic solvents.

<span class="mw-page-title-main">Methyl pentanoate</span> Chemical compound

Methyl pentanoate, commonly known as methyl valerate, is the methyl ester of pentanoic acid with a fruity odor.

The suffix -oate is the IUPAC nomenclature used in organic chemistry to form names of compounds formed from carboxylic acids. They are of two types:

Pentenoic acid is any of five mono-carboxylic acids whose molecule has an unbranched chain of five carbons connected by three single bonds and one double bond. That is, any compound with one of the formulas HO(O=)C−CH=CH−CH2−CH3 (2-pentenoic), HO(O=)C−CH2−CH=CH−CH3 (3-pentenoic), or HO(O=)C−CH2−CH2−CH=CH2 (4-pentenoic). In the IUPAC-recommended nomenclature, these acids are called pent-2-enoic, pent-3-enoic, and pent-4-enoic, respectively. All these compounds have the empirical formula C
5
H
8
O
2
.

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