Ethyl oleate
Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. It is a colorless oil although degraded samples can appear yellow.
Use and occurrenceEdit
AdditiveEdit
Ethyl oleate 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 that document the safe use of ethyl oleate in pregnancy for both the mother and the fetus have never been performed. It is regulated as a food additive in the U.S. by the Food and Drug Administration.<ref>"Food Additives Permitted for Direct Addition to Food for Human Consumption", 21CFR172.515</ref> Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.<ref>Template:Cite journal</ref>
ChemistryEdit
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,<ref>Template:Cite journal</ref> a method which was subsequently refined and published in Organic Syntheses.<ref>Template:OrgSynth</ref>
OccurrenceEdit
Ethyl oleate has been identified as a primer pheromone in honeybees.<ref>Template:Cite journal</ref>
Precursor to other chemicalsEdit
By the process of ethenolysis, the methyl ester of oleic acid, converts to 1-decene and methyl 9-decenoate:<ref>Template:Cite journal</ref>
- Template:Chem2 CH2=CH2 → CH3(CH2)7CH=CH2 + MeO2C(CH2)7CH=CH2
Medical aspectsEdit
Ethyl oleate is produced by the body during ethanol intoxication.<ref>Template:Cite journal</ref> It is one of the fatty acid ethyl esters (FAEE) produced after ingestion of ethanol. Some research literature implicates FAEEs such as ethyl oleate as the toxic mediators of ethanol in the body (pancreas, liver, heart, and brain).<ref name="Laposata 1998">Template:Cite journal</ref><ref>Template:Cite journal</ref> Ethyl oleate may be the toxic mediator of alcohol in fetal alcohol syndrome.<ref name="Laposata 1998"/> 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.<ref>Template:Cite journal</ref>