Ethyl butyrate: Difference between revisions

| Watchedfields = changed

| verifiedrevid = 407477713

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageFile = Ethyl butyrate-2D-by-AHRLS-2012.png

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| ImageFile1 = Ethyl-butyrate3D.png

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| PIN = Ethyl butanoate <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->

| OtherNames = Butanoic acid ethyl ester<br />Ethyl butyrate<br />Butyric acid ethyl ester<br />Ethyl n-butanoate<br />Ethyl n-butyrate<br />Butyric ether<br />UN 1180

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 88764

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 44800

| EINECS = 203-306-4

| PubChem = 7762

| SMILES = CCCC(=O)OCC

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|Section2={{Chembox Properties

| Properties_ref = <ref name=Merck>''[[Merck Index]]'', 12th Edition, '''3822'''</ref>

| C=6 | H=12 | O=2

| Appearance = Colorless liquid with fruity odor (typically pineapple)

| Density = 0.879 g/cm³

| MeltingPtC = −93

| BoilingPtC = 120–121

| Solubility = Soluble in 150 parts

| VaporPressure = 1510{{nbsp}}Pa (11.3{{nbsp}}mmHg)

| MagSus = −77.7×10⁻⁶ cm³/mol

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|Section7={{Chembox Hazards

| NFPA-H = 1

| NFPA-F = 2

| NFPA-R = 0

| NFPA-S =

| GHSPictograms = {{GHS02}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|226}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|280|303+361+353|370+378|403+235|501}}

| FlashPtF = 78

| FlashPt_notes = c.c.

| AutoignitionPtC = 463

| LD50 = 1350 mg/kg (oral, rat)<ref name=Merck/>

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'''Ethyl butyrate''', also known as '''ethyl butanoate''', or '''butyric ether''', is an [[ester]] with the chemical formula CH₃CH₂CH₂COOCH₂CH₃. It is soluble in [[propylene glycol]], [[Mineral oil|paraffin oil]], and [[kerosene]]. It has a fruity odor, similar to [[pineapple]], and is a key ingredient used as a flavor enhancer in processed orange juices.<ref name=Merck/> It also occurs naturally in many fruits, albeit at lower concentrations.<ref name=Schieberle09>{{cite book|last1=Schieberle|first1=H.-D. Belitz, W. Grosch, P.|title=Food chemistry|date=2009|publisher=Springer|location=Berlin|isbn=9783540699330|edition=4th rev. and extended}}</ref>

==Uses==

It is commonly used as [[artificial flavor]]ing resembling [[orange juice]]<ref>{{cite magazine|url=http://www.newyorker.com/online/blogs/books/2009/05/ask-an-academic-orange-juice.html|title=Ask an Academic: Orange Juice|author=Andrea Walker|date=12 May 2009|magazine=The New Yorker}}</ref> and is hence used in nearly all orange juices sold in the US, including those sold as "[[Tropicana Products|fresh]]" or “concentrated".<ref>{{cite book |last1=Hamilton |first1=Alissa |title=Squeezed |publisher=Yale University}}</ref> It is also used in alcoholic beverages (e.g. martinis, daiquiris etc.), as a solvent in [[perfume]]ry products, and as a [[plasticizer]] for [[cellulose]].

Ethyl butyrate is one of the most common chemicals used in [[Flavoring|flavor]]s and [[fragrance]]s. It can be used in a variety of flavors: orange (most common), cherry, pineapple, mango, guava, bubblegum, peach, apricot, fig, and plum. Ethyl butyrate is synthesised in Jamaican rum upon the estrification of butyric acid from muck and ethanol during the distillation process. This gives Jamaican rum its pleasant flavour. In industrial use, it is also one of the cheapest chemicals, which only adds to its popularity.

==Production==

It can be synthesized by reacting [[ethanol]] and [[butyric acid]]. This is a [[condensation reaction]], meaning water is produced in the reaction as a byproduct. Ethyl butyrate from natural sources can be distinguished from synthetic ethyl butyrate by [[Isotope analysis|Stable Isotope Ratio Analysis]] (SIRA).<ref name=Ashurst98>{{cite book|last1=Ashurst|first1=P.R.|last2=Dennis|first2=M.J.|title=Analytical methods of food authentication|date=1998|publisher=Blackie Academic & Professional|location=London|isbn=9780751404265|edition=1st|url=https://books.google.com/books?id=80qArVT12FwC&pg=PA22|access-date=27 January 2016}}</ref>

{{Refimprove-section|date=January 2017}}

| 296&nbsp;°C (569 K)

| 2.38&nbsp;mol.l⁻¹

| [[Refractive index]] (n) at 20&nbsp;°C

{{reflist}}

* [http://www.sigmaaldrich.com/catalog/product/aldrich/w242705?lang=en&region=GB MSDS sheet]

* [http://cat.inist.fr/?aModele=afficheN&cpsidt=3822500 Sorption of ethyl butyrate and octanal constituents of orange essence by polymeric adsorbents] {{Webarchive|url=https://web.archive.org/web/20090501145609/http://cat.inist.fr/?aModele=afficheN&cpsidt=3822500 |date=2009-05-01 }}

* [http://cat.inist.fr/?aModele=afficheN&cpsidt=16129526 Biosynthesis of ethyl butyrate using immobilized lipase: a statistical approach] {{Webarchive|url=https://web.archive.org/web/20090501145557/http://cat.inist.fr/?aModele=afficheN&cpsidt=16129526 |date=2009-05-01 }}

{{Esters}}

{{Authority control}}

[[Category:Butyrate esters]]

[[Category:Sweet-smelling chemicals]]