File: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 −S H , −Se H , −Te H , −Po H and −Lv H 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] 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] [ 3]
By number of R' group carbons (R−C(=O)−O−R') 1 carbon 2 carbons 3 carbons 4 carbons 5 carbons 7 carbons 8 carbons 10 carbons By number of R group carbons (R−C(=O)−O−R') 0 carbons 1 carbon 2 carbons 3 carbons 4 carbons 5 carbons 6 carbons 7 carbons 8 carbons 9 carbons 10 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
Allyl hexanoate
File:Prop-2-enyl hexanoate.svg pineapple
Benzyl acetate
File:Benzyl acetate-structure.svg pear , strawberry , jasmine
Bornyl acetate
File:Bornyl acetate.svg pine
Butyl acetate
File:Butylacetat.svg apple , honey
Butyl butyrate
File:Butyl butyrate2.svg pineapple
Butyl propanoate
File:Butyl propionate.svg pear drops
Ethyl acetate
File:Ethyl-acetate-2D-skeletal.svg nail polish remover , model paint , model airplane glue
Ethyl benzoate
File:Ethyl benzoate.svg sweet , wintergreen , fruity , medicinal, cherry , grape
Ethyl butyrate
File:Ethyl butyrate2.svg banana , pineapple , strawberry
Ethyl hexanoate
File:Ethyl-hexanoate.svg pineapple , waxy-green banana
Ethyl cinnamate
File:Ethyl-cinnamate.svg cinnamon
Ethyl formate
File:Ethyl-formate.svg lemon , rum , strawberry
Ethyl heptanoate
File:Ethyl-heptanoate.svg apricot , cherry , grape , raspberry
Ethyl isovalerate
File:Ethyl isovalerate structure.svg apple
Ethyl lactate
File:Ethyl lactate.svg butter , cream
Ethyl nonanoate
File:Ethyl-nonanoate-2D-skeletal.svg grape
Ethyl pentanoate
File:Ethyl valerate.svg apple
Geranyl acetate
File:Geranyl-acetate.svg geranium
Geranyl butyrate
File:Geranyl butyrate.svg cherry
Geranyl pentanoate
File:Geranyl pentanoate.svg apple
Isobutyl acetate
File:Isobutyl-acetate.svg cherry , raspberry , strawberry
Isobutyl formate
File:Isobutyl formate.svg raspberry
Isoamyl acetate
File:Isoamyl acetate.svg pear , banana (flavoring in Pear drops )
Isopropyl acetate
File:Isopropyl acetate.svg fruity
Linalyl acetate
File:Linalyl acetate.svg lavender , sage
Linalyl butyrate
File:Linalyl butyrate.svg peach
Linalyl formate
File:Linalyl formate.svg apple , peach
Methyl acetate
File:Methyl-acetate-2D-skeletal.svg glue
Methyl anthranilate
File:Methyl anthranilate.svg grape , jasmine
Methyl benzoate
File:Methyl benzoate.svg fruity, ylang ylang , feijoa
Methyl butyrate (methyl butanoate)
File:Buttersauremethylester.svg pineapple , apple , strawberry
Methyl cinnamate
File:Methyl cinnamate.svg strawberry
Methyl pentanoate (methyl valerate)
File:Methyl pentanoate.svg flowery
Methyl phenylacetate
File:Methyl phenylacetate.svg honey
Methyl salicylate (oil of wintergreen)
File:Methyl salicylate.svg Modern root beer , wintergreen , Germolene and Ralgex ointments (UK)
Nonyl caprylate
File:Nonyl caprylate.svg orange
Octyl acetate
File:Octyl acetate.svg fruity-orange
Octyl butyrate
File:Octyl butyrate.svg parsnip
Amyl acetate (pentyl acetate)
File:Amyl acetate.svg apple , banana
Pentyl butyrate (amyl butyrate)
File:Pentyl butyrate.svg apricot , pear , pineapple
Pentyl hexanoate (amyl caproate)
File:Pentyl hexanoate.svg apple , pineapple
Pentyl pentanoate (amyl valerate)
File:Pentyl pentanoate.svg apple
Propyl acetate
File:Propyl acetate.svg pear
Propyl hexanoate
File:Propyl-hexanoate.svg blackberry , pineapple , cheese , wine
Propyl isobutyrate
File:Propyl isobutyrate.svg rum
Terpenyl butyrate
File:Terpenyl butyrate.svg cherry
Lactones Lactones are a specific class cyclic carboxylic esters that are formed through intramolecular esterification .
References
↑ IUPAC , Compendium of Chemical Terminology esters ". doi :10.1351/goldbook.E02219 ↑ Cameron Wright (1986). A worker's guide to solvent hazards ISBN 9780969054542 ↑ E. Richard Booser (21 December 1993). CRC Handbook of Lubrication and Tribology, Volume III: Monitoring, Materials, Synthetic Lubricants, and Applications ISBN 978-1-4200-5045-5 ↑ 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 . ↑ Werner Reutemann and Heinz Kieczka "Formic Acid" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi :10.1002/14356007.a12_013
↑ Merck Index 6089 .↑ "Methyl Propionate Hazardous Substance Fact Sheet" (PDF) . New Jersey Department of Health and Senior Services.↑ Methyl butyrate , thegoodscentscompany.com↑ Methyl pentanoate , thegoodscentscompany.com↑ Methyl benzoate , thegoodscentscompany.com↑ Methyl anthranilate , thegoodscentscompany.com↑ Methyl salicylate , thegoodscentscompany.com↑ Methyl phenylacetate , thegoodscentscompany.com↑ Methyl cinnamate , thegoodscentscompany.com↑ Ethyl formate , thegoodscentscompany.com↑ Ethyl acetate , thegoodscentscompany.com↑ Ethyl propionate , thegoodscentscompany.com↑ Ethyl lactate , thegoodscentscompany.com↑ Ethyl butyrate , thegoodscentscompany.com↑ Ethyl pentanoate , thegoodscentscompany.com↑ Ethyl isovalerate , thegoodscentscompany.com↑ Ethyl hexanoate , thegoodscentscompany.com↑ Ethyl heptanoate , thegoodscentscompany.com↑ Ethyl benzoate , thegoodscentscompany.com↑ Ethyl salicylate , thegoodscentscompany.com↑ Ethyl octanoate , thegoodscentscompany.com↑ Ethyl cinnamate , thegoodscentscompany.com↑ Ethyl decanoate , thegoodscentscompany.com
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