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Revision as of 13:53, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 471520280 of page Isoamyl_acetate for the Chem/Drugbox validation project (updated: '').  Latest revision as of 12:11, 3 September 2024 edit Prince Quilliam (talk | contribs)29 editsmNo edit summary 
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{{Short description|Chemical compound with banana odor}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 443880449 | verifiedrevid = 477004274
| Name = Isoamyl acetate | Name = Isoamyl acetate
| ImageFile1 = Isoamyl_acetate.svg | ImageFile =
| ImageFile1 = Isoamyl_acetate.svg
| ImageSize1 = 200px | ImageSize1 = 200px
| ImageName1 = Isoamyl acetate | ImageName1 = Isoamyl acetate
| ImageFile2 = Isoamyl-acetate-3D-balls.png | ImageFile2 = Isoamyl-acetate-3D-balls.png
| ImageSize2 = 200px | ImageSize2 = 200px
| ImageFile3 = Isopentyl acetate.jpg
| IUPACName = 3-methylbut-1-yl ethanoate
| ImageSize3 = 50px
| OtherNames = isopentyl acetate<br />banana oil<br />isopentyl ethanoate<br />pear essence<br />3-methylbutyl acetate<br />3-methylbutyl ethanoate
| PIN = 3-Methylbutyl acetate
| SystematicName = 3-Methylbutyl ethanoate
| OtherNames = Isopentyl acetate<br />Isopentyl ethanoate<br />Isoamyl acetate<br />Banana oil<br />Pear essence
| IUPACName =
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 31725 | ChEBI = 31725
| PubChem = 31276
| Beilstein = 1744750
| Gmelin = 101452
| EC_number = 204-662-3
| RTECS = NS9800000
| UNNumber = 1104 1993
| SMILES = O=C(OCCC(C)C)C | SMILES = O=C(OCCC(C)C)C
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = C<sub>7</sub>H<sub>14</sub>O<sub>2</sub> | C=7 | H =14 | O=2
| MolarMass = 130.19 g/mol
| Density = 0.876 g/cm<sup>3</sup> | Density = 0.876 g/cm<sup>3</sup>
| Appearance = Colorless liquid
| Odor = Banana-like<ref name=PGCH/>
| MeltingPtC = −78 | MeltingPtC = −78
| BoilingPtC = 142<!--Ref Index: nD-20 = 1.4006--> | BoilingPtC = 142<!--Ref Index: nD-20 = 1.4006-->
| Solubility = 0.3% (20{{nbsp}}°C)<ref name=PGCH/>
| VaporPressure = 4{{nbsp}}mmHg or 0.533{{nbsp}}kPa (20{{nbsp}}°C)<ref name=PGCH/>
| MagSus = −89.4·10<sup>−6</sup>{{nbsp}}cm<sup>3</sup>/mol
| RefractIndex =1.4020 at 20°
}} }}
| Section7 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| NFPA-H = 1 | NFPA-H = 1
| NFPA-F = 3 | NFPA-F = 3
| NFPA-R = 0 | NFPA-R = 0
| FlashPt = 25 °C | FlashPtC = 25
| PEL = TWA 100{{nbsp}}ppm (525{{nbsp}}mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0347}}</ref>
| ExploLimits = 1.0% (100{{nbsp}}°C) – 7.5%<ref name=PGCH/>
| REL = TWA 100{{nbsp}}ppm (525{{nbsp}}mg/m<sup>3</sup>)<ref name=PGCH/>
| IDLH = 1000{{nbsp}}ppm<ref name=PGCH/>
| LCLo = 6470{{nbsp}}ppm (cat)<ref name=IDLH>{{IDLH|123922|Isoamyl acetate}}</ref>
| LD50 = 7422{{nbsp}}mg/kg (rabbit, oral)<br/>16,600{{nbsp}}mg/kg (rat, oral)<ref name=IDLH/>
| GHSPictograms = {{GHS02}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|226|315|319|335|336|372}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|270|271|280|302+352|303+361+353|304+340|305+351+338|312|314|321|332+313|337+313|362|370+378|403+233|403+235|405|501}}
}} }}
| Section4 = {{Chembox Related
| OtherCompounds = ]
}} }}
}}<!--
| ]
| {{{Refractive index (nD20)|1.4020}}}-->

'''Isoamyl acetate''', also known as '''isopentyl acetate''', is an ] formed from ] and ], with the molecular formula {{chem2|C7H14O2}}. 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 ] and ].<ref>{{Cite web | url = http://www.chemicalland21.com/specialtychem/perchem/ISO-AMYL%20ACETATE.htm | title = Iso-amyl acetate | publisher = chemicalland21.com}}</ref> Pure isoamyl acetate, or mixtures of isoamyl acetate, ], and other flavors in ] may be referred to as '''banana oil'''<ref>Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2002. {{doi|10.1002/14356007.a11_141}}.</ref> or '''pear oil'''.<ref>{{cite web |title=T3DB: Isopentyl acetate |url=http://www.t3db.ca/toxins/T3D4851 |website=Toxin and Toxin Target Database (T3DB) |publisher=Canadian Institutes of Health Research, Canada Foundation for Innovation, and by The Metabolomics Innovation Centre (TMIC) |access-date=2 April 2023}}</ref>

==Natural occurrence==
Isoamyl acetate occurs naturally in many plants, including ], ], ], ], ], ], ], ], ], and ].<ref name="ntp" /><ref>{{cite web |title=Isoamyl acetate Taxonomy |url=https://pubchem.ncbi.nlm.nih.gov/compound/Isoamyl-acetate#section=Taxonomy&fullscreen=true |website=PubChem |publisher=National Center for Biotechnology Information |access-date=2 April 2023 |language=en}}</ref> It is also released by fermentation processes, including those used for making ], ], ], and ].<ref name="ntp">{{cite web |author1=Technical Resources International, Inc |title=SUMMARY OF DATA FOR CHEMICAL SELECTION: Isoamyl Acetate |url=https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/isoamylacetate_508.pdf |website=National Toxicology Program |publisher=U.S. Department of Health and Human Services |access-date=2 April 2023 |date=November 1994}}</ref>

Isoamyl acetate is released by a ]'s ] apparatus where it serves as a ] beacon to attract other bees and provoke them to sting.<ref>{{cite journal|author=Boch R|author2=Shearer DA |author3=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 |issue=4845 |pages=1018–20 |publisher=Nature Publishing Group |location=England |pmid=13870346|doi=10.1038/1951018b0 |bibcode=1962Natur.195.1018B |s2cid=4224788 }}</ref>

==Production==
Isoamyl acetate is prepared by the acid-catalyzed reaction (]) between ] and glacial ] as shown in the reaction equation below. Typically, ] is used as the ]. Alternatively, ] or an acidic ion exchange resin can be used as the catalyst.

:]

It is also produced synthetically by the ] of ].<ref>{{cite web |title=Isoamyl acetate Methods of Manufacturing |url=https://pubchem.ncbi.nlm.nih.gov/compound/Isoamyl-acetate#section=Methods-of-Manufacturing |website=PubChem |publisher=National Center for Biotechnology Information |language=en}}</ref>

==Applications==
Isoamyl acetate is used to confer banana or pear flavor in foods such as ]s, ] and ]s.<ref>{{cite web |title=Isoamyl acetate |url=https://www.acs.org/content/acs/en/molecule-of-the-week/archive/i/isoamyl-acetate.html |website=American Chemical Society |access-date=27 October 2022 |language=en}}</ref> ''Banana oil'' and ''pear oil'' commonly refer to a solution of isoamyl acetate in ] that is used as an ].

It is also used as a ] for some ]es, ]s, and ]s. As a solvent and carrier for materials such as ], 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 ']'. 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 ] or ].<ref>{{Cite web|url=https://www.osha.gov/pls/oshaweb/owadisp.show_document?p_id=9780&p_table=STANDARDS|title=Fit Testing Procedures (Mandatory). - 1910.134 App A {{!}} Occupational Safety and Health Administration|website=www.osha.gov|access-date=2020-02-04}}</ref>

== References ==
{{Reflist}}

{{Esters}}

{{DEFAULTSORT:Isoamyl Acetate}}
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