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.[1] It also occurs naturally in many fruits, albeit at lower concentrations.[2]
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| Names | |
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| Preferred IUPAC name
Ethyl butanoate | |
| Other names
Butanoic acid ethyl ester
Ethyl butyrate Butyric acid ethyl ester Ethyl n-butanoate Ethyl n-butyrate Butyric ether UN 1180 | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.007 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties[1] | |
| C6H12O2 | |
| Molar mass | 116.160 g·mol−1 |
| Appearance | Colorless liquid with fruity odor (typically pineapple) |
| Density | 0.879 g/cm3 |
| Melting point | −93 °C (−135 °F; 180 K) |
| Boiling point | 120–121 °C (248–250 °F; 393–394 K) |
| Soluble in 150 parts | |
| Vapor pressure | 1510 Pa (11.3 mmHg) |
| −77.7×10−6 cm3/mol | |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H226 | |
| P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 26 °C; 78 °F; 299 K c.c. |
| 463 °C (865 °F; 736 K) | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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1350 mg/kg (oral, rat)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Uses
editIt is commonly used as artificial flavoring resembling orange juice[3] and is hence used in nearly all orange juices sold in the US, including those sold as "fresh" or “concentrated".[4] 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
editIt 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).[5]
Table of physical properties
editThis section needs additional citations for verification. (January 2017) |
| 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
editReferences
edit- ^ a b c Merck Index, 12th Edition, 3822
- ^ Schieberle, H.-D. Belitz, W. Grosch, P. (2009). Food chemistry (4th rev. and extended ed.). Berlin: Springer. ISBN 9783540699330.
{{cite book}}: CS1 maint: multiple names: authors list (link) - ^ Andrea Walker (12 May 2009). "Ask an Academic: Orange Juice". The New Yorker.
- ^ Hamilton, Alissa. Squeezed. Yale University.
- ^ Ashurst, P.R.; Dennis, M.J. (1998). Analytical methods of food authentication (1st ed.). London: Blackie Academic & Professional. ISBN 9780751404265. Retrieved 27 January 2016.