:Ethyl propionate
{{Chembox
| Name =
| ImageFileL1 = Ethyl-propionate-2D-skeletal.svg
| ImageNameL1 = Skeletal formula of ethyl propionate
| ImageSizeL1 = 120px
| ImageFileR1 = Ethyl propionate 3D ball.png
| ImageNameR1 = Ball-and-stick model of ethyl propionate
| ImageSizeR1 = 120px
| ImageFile2 = Ethyl propionate.jpg
| ImageSize2 = 50px
| ImageAlt = Skeletal formula of ethyl propionate
| PIN = Ethyl propanoate
| OtherNames = {{bulleted list|Ethyl propionate |n-Ethyl propanoate|Propanoic acid ethyl ester}}
|Section1={{Chembox Identifiers
| Abbreviations =
| CASNo = 105-37-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = AT9K8FY49U
| PubChem = 7749
| ChemSpiderID = 7463
| EINECS = 203-291-4
| UNNumber = N119
| RTECS = UF3675000
| SMILES = CCOC(=O)CC
| InChI = 1/C5H10O2/c1-3-5(6)7-4-2/h3-4H2,1-2H3
| Beilstein = 506287}}
|Section2={{Chembox Properties
| C=5|H=10|O=2
| Density = 0.884325 g/cm3
| MeltingPtC = -73.6
| BoilingPtC = 98.9
| Appearance = Colorless Liquid
| MagSus = −66.5·10−6 cm3/mol
}}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS02}}
| GHSSignalWord = danger
| HPhrases = {{HPhrases|H225}}
| PPhrases = {{PPhrases|P403+P235}}
| GHS_ref = GHS: {{GESTIS|ZVG=28580|CAS=105-37-3|Name=Ethyl propionate}}
| NFPA-H = 2
| NFPA-F = 2
| NFPA-R = 0
| FlashPtC = 12
| AutoignitionPtC = 440
| ExploLimits = 1.9-11 %
}}
}}
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.{{cite web|url=http://cameochemicals.noaa.gov/chemical/710 |title=Ethyl Propionate | Cameo Chemicals | Noaa |publisher=Cameochemicals.noaa.gov |access-date=2015-02-27}} Some fruits such as kiwis{{Cite journal | last1 = Bartley | first1 = J. P. | last2 = Schwede | first2 = A. M. | doi = 10.1021/jf00088a046 | title = Production of volatile compounds in ripening kiwi fruit (Actinidia chinensis) | journal = Journal of Agricultural and Food Chemistry | volume = 37 | issue = 4 | pages = 1023 | year = 1989 }} and strawberries{{Cite journal | last1 = Perez | first1 = A. G. | last2 = Rios | first2 = J. J. | last3 = Sanz | first3 = C. | last4 = Olias | first4 = J. M. | title = Aroma components and free amino acids in strawberry variety Chandler during ripening | doi = 10.1021/jf00023a036 | journal = Journal of Agricultural and Food Chemistry | volume = 40 | issue = 11 | pages = 2232 | year = 1992 }} contain ethyl propionate in small amounts.
Uses and reactions
It is also used in the production of some antimalarial drugs including pyrimethamine.{{cite web|title=Pyrimethamine synthesis: Status at end of 2015|website=Daraprim Synthesis|publisher=Open Source Malaria|date=29 January 2016|first=Thomas|last=MacDonald|archive-url=https://web.archive.org/web/20180426233859/http://malaria.ourexperiment.org/daraprim_synthesis/13962/Pyrimethamine_synthesis_Status_at_end_of_2015.html|archive-date=26 April 2018|url=http://malaria.ourexperiment.org/daraprim_synthesis/13962/Pyrimethamine_synthesis_Status_at_end_of_2015.html}}
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.{{cite journal|first1=Richard F. B.|last1=Cox|first2=S. M.|last2=McElvain |doi=10.15227/orgsyn.017.0054|title=Ethyl Ethoxalylpropionate|journal=Organic Syntheses|year=1937|volume=17|page=54}}
See also
- Methyl propionate, a similar compound