List of esters explained
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 of that acid is replaced by an organyl group . Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well (i.e. esters of acidic,,, and 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.
An example of an ester formation is the substitution reaction between a carboxylic acid and an alcohol (R'OH), forming an ester, 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.[1] They are also one of the largest classes of synthetic lubricants on the commercial market.[2]
By number of R' group carbons (R−C(=O)−O−R')
5 carbons
10 carbons
By number of R group carbons (R−C(=O)−O−R')
1 carbon
3 carbons
8 carbons
9 carbons
16 carbons
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 |
---|
| | 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 |
| | pineapple, waxy-green banana |
Ethyl cinnamate | | cinnamon |
Ethyl formate | | lemon, rum, strawberry |
Ethyl heptanoate | | apricot, cherry, grape, raspberry |
Ethyl isovalerate | | apple |
| | 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) |
| | 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.
Notes and References
- Book: Cameron Wright. A worker's guide to solvent hazards. 1986. The Group. 48. 9780969054542 .
- Book: E. Richard Booser. CRC Handbook of Lubrication and Tribology, Volume III: Monitoring, Materials, Synthetic Lubricants, and Applications. 21 December 1993. CRC . 978-1-4200-5045-5. 237.
- 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. en. 58. 51. 18557–18561. 10.1002/anie.201911300. 31573130 . 6916544 . 1433-7851. free.
- Werner Reutemann and Heinz Kieczka "Formic Acid" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.
- Merck Index, 12th Edition, 6089.
- Web site: Methyl Propionate Hazardous Substance Fact Sheet. New Jersey Department of Health and Senior Services.
- http://www.thegoodscentscompany.com/data/rw1008721.html Methyl butyrate
- http://www.thegoodscentscompany.com/data/rw1008901.html Methyl pentanoate
- http://www.thegoodscentscompany.com/data/rw1015012.html Methyl benzoate
- http://www.thegoodscentscompany.com/data/rw1008211.html Methyl anthranilate
- http://www.thegoodscentscompany.com/data/rw1008471.html Methyl salicylate
- http://www.thegoodscentscompany.com/data/rw1008431.html Methyl phenylacetate
- http://www.thegoodscentscompany.com/data/rw1417571.html Methyl cinnamate
- http://www.thegoodscentscompany.com/data/rw1015051.html Ethyl formate
- http://www.thegoodscentscompany.com/data/rw1004691.html Ethyl acetate
- http://www.thegoodscentscompany.com/data/rw1004931.html Ethyl propionate
- http://www.thegoodscentscompany.com/data/rw1032431.html Ethyl lactate
- http://www.thegoodscentscompany.com/data/rw1004792.html Ethyl butyrate
- http://www.thegoodscentscompany.com/data/rw1000701.html Ethyl pentanoate
- http://www.thegoodscentscompany.com/data/rw1007041.html Ethyl isovalerate
- http://www.thegoodscentscompany.com/data/rw1004811.html Ethyl hexanoate
- http://www.thegoodscentscompany.com/data/rw1009172.html Ethyl heptanoate
- http://www.thegoodscentscompany.com/data/rw1004771.html Ethyl benzoate
- http://www.thegoodscentscompany.com/data/rw1001561.html Ethyl salicylate
- http://www.thegoodscentscompany.com/data/rw1056351.html Ethyl octanoate
- http://www.thegoodscentscompany.com/data/rw1014812.html Ethyl cinnamate
- http://www.thegoodscentscompany.com/data/rw1015411.html Ethyl decanoate