Ethyl propionate

Ethyl propionate is an organic compound with formula C2H5O2CCH2CH3. It is the ethyl ester of propionic acid. It is a colorless volatile liquid with a pineapple-like odor.[3] Some fruits such as kiwis[4] and strawberries[5] contain ethyl propionate in small amounts.

Ethyl propionate
Names
Preferred IUPAC name
Ethyl propanoate
Other names
  • Ethyl propionate
  • n-Ethyl propanoate
  • Propanoic acid ethyl ester
Identifiers
3D model (JSmol)
506287
ChemSpider
ECHA InfoCard 100.002.993
EC Number
  • 203-291-4
RTECS number
  • UF3675000
UNII
UN number N119
  • InChI=1/C5H10O2/c1-3-5(6)7-4-2/h3-4H2,1-2H3
  • CCOC(=O)CC
Properties
C5H10O2
Molar mass 102.133 g·mol−1
Appearance Colorless Liquid
Density 0.884325 g/cm3
Melting point −73.6 °C (−100.5 °F; 199.6 K)
Boiling point 98.9 °C (210.0 °F; 372.0 K)
-66.5·10−6 cm3/mol
Hazards
GHS labelling:[1]
Danger
H225
P403+P235
NFPA 704 (fire diamond)
2
2
0
Flash point 12 °C (54 °F; 285 K)
440 °C (824 °F; 713 K)
Explosive limits 1.9-11 %
Safety data sheet (SDS) [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Uses and reactions

It is also used in the production of some antimalarial drugs including pyrimethamine.

Ethyl propionate can be synthesized by the Fischer esterification of ethanol and propionic acid:

CH3CH2OH + CH3CH2CO2H → CH3CH2O2CCH2CH3 + H2O

It participates in condensation reactions by virtue of the weakly acidic methylene group.[6]

See also

References
  1. GHS: Record of Ethyl propionate in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. "Material Safety Data Sheet : Ethyl propionate" (PDF). Chemblink.com. Retrieved 2015-02-27.
  3. "Ethyl Propionate | Cameo Chemicals | Noaa". Cameochemicals.noaa.gov. Retrieved 2015-02-27.
  4. Bartley, J. P.; Schwede, A. M. (1989). "Production of volatile compounds in ripening kiwi fruit (Actinidia chinensis)". Journal of Agricultural and Food Chemistry. 37 (4): 1023. doi:10.1021/jf00088a046.
  5. Perez, A. G.; Rios, J. J.; Sanz, C.; Olias, J. M. (1992). "Aroma components and free amino acids in strawberry variety Chandler during ripening". Journal of Agricultural and Food Chemistry. 40 (11): 2232. doi:10.1021/jf00023a036.
  6. Cox, Richard F. B.; McElvain, S. M. (1937). "Ethyl Ethoxalylpropionate". Organic Syntheses. 17: 54. doi:10.15227/orgsyn.017.0054.
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