Ethyl oleate is a fatty acid ester formed by the

condensation Condensation is the change of the state of matter from the gas phase into the liquid phase, and is the reverse of vaporization. The word most often refers to the water cycle. It can also be defined as the change in the state of water vapor to ...

of oleic acid and ethanol. It is a colorless oil although degraded samples can appear yellow.

Use and occurrence

Additive

Ethyl oleate is used by compounding pharmacies as a vehicle for intramuscular drug delivery, in some cases to prepare the daily doses of

progesterone Progesterone (P4) is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens and is the m ...

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. Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as

steroid A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and a ...

s. It also finds use as a lubricant and a plasticizer. Louis Bouveault used ethyl oleate to demonstrate Bouveault–Blanc reduction, producing

oleyl alcohol Oleyl alcohol , or ''cis''-9-octadecen-1-ol, is an unsaturated fatty alcohol with the molecular formula or the condensed structural formula . It is a colorless oil, mainly used in cosmetics. It can be produced by the hydrogenation of oleic a ...

and ethanol, a method which was subsequently refined and published in '' Organic Syntheses''.

Occurrence

Ethyl oleate has been identified as a primer pheromone in honeybees.

Precursor to other chemicals

By the process of ethenolysis, the ''methyl ester'' of oleic acid, converts to

1-decene Decene is an organic compound with the chemical formula . Decene contains a chain of ten carbon atoms with one double bond, making it an alkene. There are many isomers of decene depending on the position and geometry of the double bond. Dec-1- ...

and methyl 9- decenoate: : CH₂=CH₂ → CH₃(CH₂)₇CH=CH₂ + MeO₂C(CH₂)₇CH=CH₂

Medical aspects

Ethyl oleate is produced by the body during ethanol intoxication. 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). 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.

References