Ethyl oleate
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| Names | |
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| IUPAC name
Ethyl (Z)-octadec-9-enoate
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| Other names
Oleic acid ethyl ester
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| Identifiers | |
111-62-6  |
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| ChEBI | CHEBI:84940  |
| ChemSpider | 4515636 |
| Jmol 3D model | Interactive image |
| KEGG | D04090 |
| PubChem | 5363269 |
| UNII | Z2Z439864Y |
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| Properties | |
| C20H38O2 | |
| Molar mass | 310.52 g·mol−1 |
| Appearance | Colorless to light yellow liquid[1] |
| Density | 0.87 g/cm³[1] |
| Melting point | −32 °C (−26 °F; 241 K)[1] |
| Boiling point | 216–218 °C (421–424 °F; 489–491 K)[1] (15 hPa) |
| Insoluble[1] | |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. It is a colorless to light yellow liquid. Ethyl oleate is produced by the body during ethanol intoxication.[2]
Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.[3] It also finds use as a lubricant and a plasticizer.
Ethyl oleate is regulated as a food additive by the Food and Drug Administration under "Food Additives Permitted for Direct Addition to Food for Human Consumption", 21CFR172.515.
Ethyl oleate has been identified as a primer pheromone in honeybees.[4]
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).[5][6][7] Among the speculations is that ethyl oleate may be the toxic mediator of alcohol in fetal alcohol syndrome.[8] 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.[9] 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.
See also
References
- ↑ 1.0 1.1 1.2 1.3 1.4 Record in the GESTIS Substance Database of the IFA
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