Isoamyl acetate
4164654
216110850
2008-05-31T03:13:16Z
Cacycle
83784
+ [[Category:Esters]]
{{Chembox new
| Name = Isoamyl acetate
| ImageFile = Isoamyl_acetate.png
<!-- | ImageSize = 200px -->
| ImageName = Isoamyl acetate
| ImageFile2 = Isoamyl-acetate-3D-balls.png
| IUPACName = 3-methyl-1-butyl acetate
| OtherNames = isopentyl acetate<br />banana oil<br />isopentyl ethanoate<br />pear essence<br />3-methylbutyl acetate
| Section1 = {{Chembox Identifiers
| CASNo = 123-92-2
| SMILES = CC(C)CCOC(C)=O
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>7</sub>H<sub>14</sub>O<sub>2</sub>
| MolarMass = 130.19 g/mol
| Density = 0.876 g/cm<sup>3</sup>
| MeltingPt = -78 °C
| BoilingPt = 142 °C
}}
| Section7 = {{Chembox Hazards
| NFPA-H = 1
| NFPA-F = 3
| NFPA-R = 0
| FlashPt = 25 °C
}}
}}<!--
| [[Refractive index]]
| {{{refractive_index_(nD20)|1.4020}}}-->
'''Isoamyl acetate''', also known as '''isopentyl acetate''', is an [[organic compound]] that is the [[ester]] formed from [[isoamyl alcohol]] and [[acetic acid]]. It is a clear colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents.
Isoamyl acetate has a strong odor (similar to juicy fruit) which is also described as similar to both [[banana]] and [[pear]]. '''Banana oil''' is a term that is applied either to pure isoamyl acetate or to flavorings that are mixtures of isoamyl acetate, [[amyl acetate]], [[nitrocellulose]] and other flavors. ''Pear oil'' commonly refers to a solution of isoamyl acetate in [[ethanol]] that is used as an artificial flavor.
Isoamyl acetate is also used to test the effectiveness of [[respirator]]s or [[gas mask]]s because it has a strong smell which is generally not experienced as unpleasant that can be detected at low concentrations, and has low toxicity.
It is also used as a solvent for some varnishes and nitrocellulose lacquers, as well as being a honey bee [[pheromone]] and can be used to attract large groups of honeybees to a small area.
Isoamyl acetate is released by a [[honey bee]]'s [[Stinger|sting]] apparatus where it serves as a [[Honey_bee_pheromones#Alarm_ pheromone |pheromone]] beacon to attract other bees and provoke them to sting. <ref>{{cite journal | author = Boch R | coauthors = Shearer DA, Stone BC | date = [[September 8]], [[1962]] | title = Identification of isoamyl acetate as an active component in the sting pheromone of the honey bee. | journal = Nature | volume = 195 | pages = 1018-20 | publisher = Nature Publishing Group | location = England | issn = 0028-0836 | pmid = 13870346 }}</ref>
==Laboratory Synthesis==
Isoamyl acetate can be prepared in the laboratory by the acid catalyzed [[Fischer esterification]] reaction between [[isoamyl alcohol]] and glacial [[acetic acid]] as shown in the reaction equation below. Typically, concentrated [[sulfuric acid]] is used as the [[catalyst]]. The reactants are [[refluxed]] in order to promote the reaction, the acid is neutralized and extracted, and the product is dried, then distilled.
[[Image:Isoamyl_acetate_synthesis.png|450px]]
==References==
<references/>
[[Category:Esters]]
[[Category:Carboxylate esters]]
[[Category:Acetates]]
[[Category:Flavors]]
[[Category:Ester solvents]]
[[Category:Pheromones]]
[[fr:Acétate d'isoamyle]]
[[it:Acetato di isoamile]]
[[nl:Isoamylacetaat]]
[[ja:酢酸イソアミル]]
[[fi:Isoamyyliasetaatti]]