Ethyl oleate is a

fatty acid ester Fatty acid esters (FAEs) are a type of ester that result from the combination of a fatty acid with an alcohol. When the alcohol component is glycerol, the fatty acid esters produced can be monoglycerides, diglycerides, or triglycerides. Dietary ...

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 ...

oleic acid Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish due to the presence of impurities. In chemical terms, oleic acid is cl ...

and

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

. 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 ma ...

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 The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respo ...

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

lipophilic Lipophilicity (from Greek language, Greek λίπος "fat" and :wikt:φίλος, φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are c ...

substances such as

steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...

Chemistry

It also finds use as a lubricant and a

plasticizer A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticizer ...

Louis Bouveault Louis Bouveault (11 February 1864 – 5 September 1909) was a French scientist who became professor of organic chemistry at the Faculty of Sciences of the University of Paris. He is known for the Bouveault aldehyde synthesis and the Bouveault� ...

used ethyl oleate to demonstrate Bouveault–Blanc reduction, producing oleyl alcohol and

, a method which was subsequently refined and published in ''

Organic Syntheses ''Organic Syntheses'' is a peer-reviewed scientific journal that was established in 1921. It publishes detailed and checked procedures for the synthesis of organic compounds. A unique feature of the review process is that all of the data and expe ...

''.

Occurrence

Ethyl oleate has been identified as a primer

pheromone A pheromone () is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavio ...

honeybee A honey bee (also spelled honeybee) is a eusocial flying insect within the genus ''Apis'' of the bee clade, all native to mainland Afro-Eurasia. After bees spread naturally throughout Africa and Eurasia, humans became responsible for the c ...

Precursor to other chemicals

By the process of

ethenolysis In organic chemistry, ethenolysis is a chemical process in which internal olefins are degraded using ethylene () as the reagent. The reaction is an example of olefin metathesis, cross metathesis. The utility of the reaction is driven by the low ...

, 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 Fetal alcohol spectrum disorders (FASDs) are a group of conditions that can occur in a person who is exposed to alcohol during gestation. FASD affects 1 in 20 Americans, but is highly misdiagnosed and underdiagnosed. The several forms of the ...

. 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

{{Reflist Ethyl esters Food additives Insect pheromones Semiochemicals