List of esters#List of ester odorants

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File:Ester-general.svg. 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 ({{chem2|\sOH}}) of that acid is replaced by an organyl group ({{chem2|\sR}}). Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well (i.e. esters of acidic {{chem2|\sSH}}, {{chem2|\sSeH}}, {{chem2|\sTeH}}, {{chem2|\sPoH}} and {{chem2|\sLvH}} 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.{{GoldBookRef|title = esters | file = E02219}}

An example of an ester formation is the substitution reaction between a carboxylic acid ({{chem2|R\sC(\dO)\sOH}}) and an alcohol (R'OH), forming an ester ({{chem2|R\sC(\dO)\sO\sR'}}), 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.{{cite book|author=Cameron Wright|title=A worker's guide to solvent hazards|url=https://books.google.com/books?id=sFRZAAAAYAAJ|year=1986|publisher=The Group|page=48|isbn=9780969054542 }} They are also one of the largest classes of synthetic lubricants on the commercial market.{{cite book|author=E. Richard Booser|title=CRC Handbook of Lubrication and Tribology, Volume III: Monitoring, Materials, Synthetic Lubricants, and Applications|url=https://books.google.com/books?id=gnOJoug5R8IC&pg=PA237|date=21 December 1993|publisher=CRC |isbn=978-1-4200-5045-5|page=237}}

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

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= 1 carbon =

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!Name

!Structure

Methyl nitrate{{Cite journal|last1=Reichel|first1=Marco|last2=Krumm|first2=Burkhard|last3=Vishnevskiy|first3=Yury V.|last4=Blomeyer|first4=Sebastian|last5=Schwabedissen|first5=Jan|last6=Stammler|first6=Hans‐Georg|last7=Karaghiosoff|first7=Konstantin|last8=Mitzel|first8=Norbert W.|date=2019-12-16|title=Solid‐State and Gas‐Phase Structures and Energetic Properties of the Dangerous Methyl and Fluoromethyl Nitrates|journal=Angewandte Chemie International Edition|language=en|volume=58|issue=51|pages=18557–18561|doi=10.1002/anie.201911300|pmid=31573130 |pmc=6916544 |issn=1433-7851|doi-access=free}}

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Methyl formateWerner Reutemann and Heinz Kieczka "Formic Acid" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a12_013}}

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Methyl acetateMerck Index, 12th Edition, 6089.

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Methyl acrylate

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Methyl propionate{{cite web|title=Methyl Propionate Hazardous Substance Fact Sheet|url=http://nj.gov/health/eoh/rtkweb/documents/fs/1290.pdf|publisher=New Jersey Department of Health and Senior Services}}

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Methyl butyrate[http://www.thegoodscentscompany.com/data/rw1008721.html Methyl butyrate], thegoodscentscompany.com

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Methyl pentanoate[http://www.thegoodscentscompany.com/data/rw1008901.html Methyl pentanoate], thegoodscentscompany.com

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Methyl benzoate[http://www.thegoodscentscompany.com/data/rw1015012.html Methyl benzoate], thegoodscentscompany.com

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Methyl anthranilate[http://www.thegoodscentscompany.com/data/rw1008211.html Methyl anthranilate], thegoodscentscompany.com

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Methyl salicylate[http://www.thegoodscentscompany.com/data/rw1008471.html Methyl salicylate], thegoodscentscompany.com

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Methyl phenylacetate[http://www.thegoodscentscompany.com/data/rw1008431.html Methyl phenylacetate], thegoodscentscompany.com

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Methyl cinnamate[http://www.thegoodscentscompany.com/data/rw1417571.html Methyl cinnamate], thegoodscentscompany.com

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= 2 carbons =

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!Name

!Structure

Ethyl formate[http://www.thegoodscentscompany.com/data/rw1015051.html Ethyl formate], thegoodscentscompany.com

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Ethyl acetate[http://www.thegoodscentscompany.com/data/rw1004691.html Ethyl acetate], thegoodscentscompany.com

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Ethyl propionate[http://www.thegoodscentscompany.com/data/rw1004931.html Ethyl propionate], thegoodscentscompany.com

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Ethyl lactate[http://www.thegoodscentscompany.com/data/rw1032431.html Ethyl lactate], thegoodscentscompany.com

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Ethyl butyrate[http://www.thegoodscentscompany.com/data/rw1004792.html Ethyl butyrate], thegoodscentscompany.com

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Ethyl pentanoate[http://www.thegoodscentscompany.com/data/rw1000701.html Ethyl pentanoate], thegoodscentscompany.com

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Ethyl isovalerate[http://www.thegoodscentscompany.com/data/rw1007041.html Ethyl isovalerate], thegoodscentscompany.com

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Ethyl hexanoate[http://www.thegoodscentscompany.com/data/rw1004811.html Ethyl hexanoate], thegoodscentscompany.com

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Ethyl heptanoate[http://www.thegoodscentscompany.com/data/rw1009172.html Ethyl heptanoate], thegoodscentscompany.com

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Ethyl benzoate[http://www.thegoodscentscompany.com/data/rw1004771.html Ethyl benzoate], thegoodscentscompany.com

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Ethyl salicylate[http://www.thegoodscentscompany.com/data/rw1001561.html Ethyl salicylate], thegoodscentscompany.com

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Ethyl octanoate[http://www.thegoodscentscompany.com/data/rw1056351.html Ethyl octanoate], thegoodscentscompany.com

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Ethyl cinnamate[http://www.thegoodscentscompany.com/data/rw1014812.html Ethyl cinnamate], thegoodscentscompany.com

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Ethyl decanoate[http://www.thegoodscentscompany.com/data/rw1015411.html Ethyl decanoate], thegoodscentscompany.com

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= 3 carbons =

= 4 carbons =

= 5 carbons =

= 7 carbons =

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!Name

!Structure

Benzyl acetate

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= 8 carbons =

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!Name

!Structure

Octyl acetate

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= 10 carbons =

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!Name

!Structure

Geranyl acetate

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Bornyl acetate

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Linalyl acetate

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

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= 0 carbons =

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!Name

!Structure

Methyl nitrate

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= 1 carbon =

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!Name

!Structure

Methyl formate

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Ethyl formate

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Isobutyl formate

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= 2 carbons =

= 3 carbons =

= 4 carbons =

= 5 carbons =

= 6 carbons =

= 7 carbons =

= 8 carbons =

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!Name

!Structure

Ethyl octanoate

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Methyl phenylacetate

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= 9 carbons =

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!Name

!Structure

Methyl cinnamate

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Ethyl cinnamate

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= 10 carbons =

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!Name

!Structure

Ethyl decanoate

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= 16 carbons =

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!Name

!Structure

Isopropyl palmitate

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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.

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valign="top" align="left"| Ester name

! valign="top" align="left"| Structure

! valign="top" align="left"| Odor or occurrence

Allyl hexanoate

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| pineapple

Benzyl acetate

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| pear, strawberry, jasmine

Bornyl acetate

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| pine

Butyl acetate

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apple, honey
Butyl butyrate

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pineapple
Butyl propanoate

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pear drops
Ethyl acetate

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| nail polish remover, model paint, model airplane glue

Ethyl benzoate

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| sweet, wintergreen, fruity, medicinal, cherry, grape

Ethyl butyrate

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| banana, pineapple, strawberry

Ethyl hexanoate

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| pineapple, waxy-green banana

Ethyl cinnamate

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| cinnamon

Ethyl formate

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| lemon, rum, strawberry

Ethyl heptanoate

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| apricot, cherry, grape, raspberry

Ethyl isovalerate

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| apple

Ethyl lactate

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| butter, cream

Ethyl nonanoate

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| grape

Ethyl pentanoate

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| apple

Geranyl acetate

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| geranium

Geranyl butyrate

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| cherry

Geranyl pentanoate

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| apple

Isobutyl acetate

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| cherry, raspberry, strawberry

Isobutyl formate

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| raspberry

Isoamyl acetate

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| pear, banana (flavoring in Pear drops)

Isopropyl acetate

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| fruity

Linalyl acetate

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| lavender, sage

Linalyl butyrate

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| peach

Linalyl formate

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| apple, peach

Methyl acetate

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| glue

Methyl anthranilate

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| grape, jasmine

Methyl benzoate

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| fruity, ylang ylang, feijoa

Methyl butyrate (methyl butanoate)

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| pineapple, apple, strawberry

Methyl cinnamate

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| strawberry

Methyl pentanoate (methyl valerate)

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| flowery

Methyl phenylacetate

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| honey

Methyl salicylate (oil of wintergreen)

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| Modern root beer, wintergreen, Germolene and Ralgex ointments (UK)

Nonyl caprylate

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| orange

Octyl acetate

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| fruity-orange

Octyl butyrate

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| parsnip

Amyl acetate (pentyl acetate)

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| apple, banana

Pentyl butyrate (amyl butyrate)

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| apricot, pear, pineapple

Pentyl hexanoate (amyl caproate)

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| apple, pineapple

Pentyl pentanoate (amyl valerate)

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| apple

Propyl acetate

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| pear

Propyl hexanoate

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| blackberry, pineapple, cheese, wine

Propyl isobutyrate

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| rum

Terpenyl butyrate

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| | cherry

Lactones

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

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valign="top" align="left"| Lactone name

! valign="top" align="left"| Structure

β-propiolactone

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γ-butyrolactone (GBL)

| File:Dihydrofuran-2(3H)-one 200.svg

D-glucono-δ-lactone (E575)

|File:Glucono-delta-lactone-2D-skeletal.svg

ε-caprolactone

|File:Caprolactone.svg

References

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Category:Esters

Esters