Isoamyl acetate, also known as isopentyl acetate, is an

ester In chemistry, an ester is a compound derived from an acid (either 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 (R). These compounds contain a distin ...

formed from isoamyl alcohol and

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

, with the molecular formula . It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isoamyl acetate has a strong odor which is described as similar to both

banana A banana is an elongated, edible fruit – botanically a berry – produced by several kinds of large treelike herbaceous flowering plants in the genus '' Musa''. In some countries, cooking bananas are called plantains, distinguishing the ...

and

pear Pears are fruits produced and consumed around the world, growing on a tree and harvested in late summer into mid-autumn. The pear tree and shrub are a species of genus ''Pyrus'' , in the Family (biology), family Rosaceae, bearing the Pome, po ...

. Pure isoamyl acetate, or mixtures of isoamyl acetate, amyl acetate, and other flavors in

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

may be referred to as banana oil or pear oil.

Natural occurrence

Isoamyl acetate occurs naturally in many plants, including

apple An apple is a round, edible fruit produced by an apple tree (''Malus'' spp.). Fruit trees of the orchard or domestic apple (''Malus domestica''), the most widely grown in the genus, are agriculture, cultivated worldwide. The tree originated ...

coffee Coffee is a beverage brewed from roasted, ground coffee beans. Darkly colored, bitter, and slightly acidic, coffee has a stimulating effect on humans, primarily due to its caffeine content, but decaffeinated coffee is also commercially a ...

grape A grape is a fruit, botanically a berry, of the deciduous woody vines of the flowering plant genus ''Vitis''. Grapes are a non- climacteric type of fruit, generally occurring in clusters. The cultivation of grapes began approximately 8,0 ...

guava Guava ( ), also known as the 'guava-pear', is a common tropical fruit cultivated in many tropical and subtropical regions. The common guava '' Psidium guajava'' (lemon guava, apple guava) is a small tree in the myrtle family (Myrtaceae), nativ ...

lychee Lychee ( , ; ''Litchi chinensis''; ) is a monotypic taxon and the sole member in the genus ''Litchi'' in the soapberry family, Sapindaceae. There are three distinct subspecies of lychee. The most common is the Indochinese lychee found in So ...

papaya The papaya (, ), papaw, () or pawpaw () is the plant species ''Carica papaya'', one of the 21 accepted species in the genus '' Carica'' of the family Caricaceae, and also the name of its fruit. It was first domesticated in Mesoamerica, within ...

peach The peach (''Prunus persica'') is a deciduous tree first domesticated and Agriculture, cultivated in China. It bears edible juicy fruits with various characteristics, most called peaches and the glossy-skinned, non-fuzzy varieties called necta ...

pomegranate The pomegranate (''Punica granatum'') is a fruit-bearing deciduous shrub in the family Lythraceae, subfamily Punica, Punicoideae, that grows between tall. Rich in symbolic and mythological associations in many cultures, it is thought to have o ...

, and

tomato The tomato (, ), ''Solanum lycopersicum'', is a plant whose fruit is an edible Berry (botany), berry that is eaten as a vegetable. The tomato is a member of the nightshade family that includes tobacco, potato, and chili peppers. It originate ...

. It is also released by fermentation processes, including those used for making

beer Beer is an alcoholic beverage produced by the brewing and fermentation of starches from cereal grain—most commonly malted barley, although wheat, maize (corn), rice, and oats are also used. The grain is mashed to convert starch in the ...

sake Sake, , or saki, also referred to as Japanese rice wine, is an alcoholic beverage of Japanese origin made by fermenting rice that has been polished to remove the bran. Despite the name ''Japanese rice wine'', sake, and indeed any East Asi ...

cognac Cognac ( , also , ) is a variety of brandy named after the Communes of France, commune of Cognac, France. It is produced in the surrounding wine-growing region in the Departments of France, departments of Charente and Charente-Maritime. Cogn ...

, and

whisky Whisky or whiskey is a type of liquor made from Fermentation in food processing, fermented grain mashing, mash. Various grains (which may be Malting, malted) are used for different varieties, including barley, Maize, corn, rye, and wheat. Whisky ...

. Isoamyl acetate is released by a

honey bee A honey bee (also spelled honeybee) is a eusocial flying insect within the genus ''Apis'' of the bee clade, all native to mainland Afro-Eurasia. After bees spread naturally throughout Africa and Eurasia, humans became responsible for the ...

's sting apparatus where it serves as a

pheromone A pheromone () is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavio ...

beacon to attract other bees and provoke them to sting.

Production

Isoamyl acetate is prepared by the acid-catalyzed reaction ( Fischer esterification) between isoamyl alcohol and glacial

as shown in the reaction equation below. Typically,

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...

is used as the

catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

. Alternatively, ''p''-toluenesulfonic acid or an acidic ion exchange resin can be used as the catalyst. : It is also produced synthetically by the rectification of amyl acetate.

Applications

Isoamyl acetate is used to confer banana or pear flavor in foods such as circus peanuts,

Juicy Fruit Juicy Fruit is an American brand of chewing gum made by the Wrigley Company, a U.S. company that since 2008 has been a subsidiary of the privately held Mars, Incorporated. It was introduced in 1893, and in the 21st century the brand name is reco ...

and pear drops. ''Banana oil'' and ''pear oil'' commonly refer to a solution of isoamyl acetate in

that is used as an artificial flavor. It is also used as a

solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

for some

varnish Varnish is a clear Transparency (optics), transparent hard protective coating or film. It is not to be confused with wood stain. It usually has a yellowish shade due to the manufacturing process and materials used, but it may also be pigmente ...

es,

oil paint Oil paint is a type of slow-drying paint that consists of particles of pigment suspended in a drying oil, commonly linseed oil. Oil paint also has practical advantages over other paints, mainly because it is waterproof. The earliest surviving ...

s, and

nitrocellulose lacquer Lacquer is a type of hard and usually shiny coating or finish applied to materials such as wood or metal. It is most often made from resin extracted from trees and waxes and has been in use since antiquity. Asian lacquerware, which may be c ...

s. As a solvent and carrier for materials such as

nitrocellulose Nitrocellulose (also known as cellulose nitrate, flash paper, flash cotton, guncotton, pyroxylin and flash string, depending on form) is a highly flammable compound formed by nitrating cellulose through exposure to a mixture of nitric acid and ...

, it was extensively used in the aircraft industry for stiffening and wind-proofing fabric flying surfaces, where it and its derivatives were generally known as '

aircraft dope Aircraft dope is a plasticised lacquer that is applied to fabric-covered aircraft. It tightens and stiffens fabric stretched over airframes, which renders them airtight and weatherproof, increasing their durability and lifespan.Crane, Dale: ...

'. Now that most aircraft wings are made of metal, such use is mostly limited to historically accurate reproductions and scale models. Because of its intense, pleasant odor and its low toxicity, isoamyl acetate is used to test the effectiveness of

respirators A respirator is a device designed to protect the wearer from inhaling hazardous atmospheres including lead, lead fumes, vapors, gases and particulate matter such as dusts and airborne pathogens such as viruses. There are two main categories o ...

gas masks A gas mask is a piece of personal protective equipment used to protect the wearer from inhaling airborne pollutants and toxic gases. The mask forms a sealed cover over the nose and mouth, but may also cover the eyes and other vulnerable soft ...

References

{{DEFAULTSORT:Isoamyl Acetate Flavors Insect pheromones Ester solvents Acetate esters Acetate, Isoamyl Sweet-smelling chemicals