Oleic acid ethyl ester
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||310.522 g·mol−1|
|Appearance||Colorless to light yellow liquid|
|Melting point||−32 °C (−26 °F; 241 K)|
|Boiling point||216–218 °C (421–424 °F; 489–491 K) (15 hPa)|
|Flash point||> 113 °C|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids. It also finds use as a lubricant and a plasticizer. Louis Bouveault used ethyl oleate to demonstrate Bouveault–Blanc reduction, producing oleyl alcohol and ethanol, a method which was subsequently refined and published in Organic Syntheses.
Ethyl oleate is one of the fatty acid ethyl esters (FAEE) that is formed in the body after ingestion of ethanol. There is a growing body of research literature that implicates FAEEs such as ethyl oleate as the toxic mediators of ethanol in the body (pancreas, liver, heart, and brain). Among the speculations is that ethyl oleate may be the toxic mediator of alcohol in fetal alcohol syndrome. The oral ingestion of ethyl oleate has been carefully studied and due to rapid degradation in the digestive tract it appears safe for oral ingestion. Ethyl oleate is not currently approved by the U.S. Food and Drug Administration for any injectable use. However, it is used by compounding pharmacies as a vehicle for intramuscular drug delivery, in some cases to prepare the daily doses of progesterone in support of pregnancy. Studies which document the safe use of ethyl oleate in pregnancy for both the mother and the fetus have never been performed.
- Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
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- Bouveault, Louis; Blanc, Gustave Louis (1904). "Hydrogénation des éthers des acides possédant en outre les fonctions éther-oxyde ou acétal" [Hydrogenation of the ether of the acids furthermore possessing the ether-oxide or acetal functions]. Bull. Soc. Chim. Fr. (in French). 31 (3): 1210–1213.
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- Laposata M. (1998). "Fatty acid ethyl esters: nonoxidative metabolites of ethanol". Addiction Biology. 3: 5–14. doi:10.1080/13556219872308.
- Laposata M. (1999). "Fatty acid ethyl esters: current facts and speculations". Prostaglandins, Leukotrienes and Essential Fatty Acids. 60 (5&6): 313–315. doi:10.1016/S0952-3278(99)80005-2.
- Laposata M, et al. (2002). "Fatty acid ethyl esters: recent observations". Prostaglandins, Leukotrienes and Essential Fatty Acids. 67 (2–3): 193–196. doi:10.1054/plef.2002.0418.
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