Ethyl butyrate Names Preferred IUPAC name Other names Identifiers ChEBI ChEMBL ChemSpider ECHA InfoCard 100.003.007 EC Number UNII 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: 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): 1350 mg/kg (oral, rat)[1]
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]
It 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.
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).[5]
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
- Butyric acid
- Butyrates
- Methyl butyrate
- MSDS sheet
- Sorption of ethyl butyrate and octanal constituents of orange essence by polymeric adsorbents Archived 2009-05-01 at the Wayback Machine
- Biosynthesis of ethyl butyrate using immobilized lipase: a statistical approach Archived 2009-05-01 at the Wayback Machine
