Ethyl butyrate
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| Watchedfields = changed
| verifiedrevid = 407477713
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Ethyl butyrate-2D-by-AHRLS-2012.png
| ImageSize =
| ImageFile1 = Ethyl-butyrate3D.png
| ImageFile2 =
| PIN = Ethyl butanoate
| OtherNames = Butanoic acid ethyl ester
Ethyl butyrate
Butyric acid ethyl ester
Ethyl n-butanoate
Ethyl n-butyrate
Butyric ether
UN 1180
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7475
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 88764
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = UFD2LZ005D
| InChI = 1/C6H12O2/c1-3-5-6(7)8-4-2/h3-5H2,1-2H3
| InChIKey = OBNCKNCVKJNDBV-UHFFFAOYAO
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 44800
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H12O2/c1-3-5-6(7)8-4-2/h3-5H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OBNCKNCVKJNDBV-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 105-54-4
| EINECS = 203-306-4
| PubChem = 7762
| SMILES = CCCC(=O)OCC
}}
|Section2={{Chembox Properties
| Properties_ref = Merck Index, 12th Edition, 3822
| 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)
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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, 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. It also occurs naturally in many fruits, albeit at lower concentrations.{{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}}
Uses
It is commonly used as artificial flavoring resembling orange juice{{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}} and is hence used in nearly all orange juices sold in the US, including those sold as "fresh" or “concentrated".{{cite book |last1=Hamilton |first1=Alissa |title=Squeezed |publisher=Yale University}} It is also used in alcoholic beverages (e.g. martinis, daiquiris etc.), as a solvent in perfumery products, and as a plasticizer for cellulose.
Ethyl butyrate is one of the most common chemicals used in flavors and fragrances. 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 Stable Isotope Ratio Analysis (SIRA).{{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}}
Table of physical properties
{{Refimprove-section|date=January 2017}}
| class="wikitable"
! Property ! Value |
| Critical temperature (Tc)
| 296 °C (569 K) |
| Critical pressure (pc)
| 3.10 MPa (30.64 bar) |
| Critical density (ρc)
| 2.38 mol.l−1 |
| Refractive index (n) at 20 °C
| 1.390 - 1.394 |
See also
References
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External links
- [http://www.sigmaaldrich.com/catalog/product/aldrich/w242705?lang=en®ion=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 }}
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