Ethyl butyrate

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]

Ethyl butyrate
Names
Preferred IUPAC name
Ethyl butanoate
Other names
Butanoic acid methyl ester
Ethyl butyrate
Butyric acid ethyl ester
Ethyl n-butanoate
Ethyl n-butyrate
Butyric ether
UN 1180
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.007
EC Number
  • 203-306-4
PubChem CID
UNII
CompTox Dashboard (EPA)
Properties[1]
Chemical formula
 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)
Solubility in water
 Soluble in 150 parts
Vapor pressure 1510 Pa (11.3 mmHg)
Magnetic susceptibility (χ)
 −77.7×10−6 cm3/mol
Hazards
Main hazards Irritant (Xi)
Safety data sheet See: data page
R-phrases (outdated) R10 R36/37/38
S-phrases (outdated) S16 S26 S36
NFPA 704 (fire diamond)
2
1
0
Flash point 26 °C; 78 °F; 299 K c.c.
Autoignition
temperature
 463 °C (865 °F; 736 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 13050 mg/kg (oral, rat)[1]
Supplementary data page
Structure and
properties
 Refractive index (n),
Dielectric constant (εr), etc.
Thermodynamic
data
 Phase behaviour
solid–liquid–gas
Spectral data
 UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Uses

It is commonly used as artificial flavoring resembling orange juice[3] and is hence used in nearly all orange juices sold, 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. 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).[5]

Table of physical properties
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
  1. Merck Index, 12th Edition, 3822
  2. Schieberle, H.-D. Belitz, W. Grosch, P. (2009). Food chemistry (4th rev. and extended ed.). Berlin: Springer. ISBN 9783540699330.
  3. Andrea Walker (12 May 2009). "Ask an Academic: Orange Juice". The New Yorker.
  4. Hamilton, Alissa. Squeezed. Yale University.
  5. Ashurst, P.R.; Dennis, M.J. (1998). Analytical methods of food authentication (1st ed.). London: Blackie Academic & Professional. ISBN 9780751404265. Retrieved 27 January 2016.
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