Ethyl oleate 1297260 221010249 2008-06-22T17:18:46Z DOI bot 6652755 Citation maintenance. You can [[WP:DOI|use this bot]] yourself! Please [[User:DOI_bot/bugs|report any bugs]]. {{Chembox new | ImageFile = Ethyl oleate.png | ImageSize = 250px | IUPACName = Ethyl (''Z'')-octadec-9-enoate | OtherNames = Oleic acid ethyl ester | Section1 = {{Chembox Identifiers | CASNo = 111-62-6 | PubChem = 5363269 | SMILES = CCCCCCCC\C=C/CCCCCCCC(=O)OCC }} | Section2 = {{Chembox Properties | C=20|H=38|O=2 | MolarMass = 310.51 g/mol | Appearance = Colorless to light yellow liquid | Density = 0.87 g/cm³, liquid | MeltingPtC = -32 | BoilingPtC = 210 | Solubility = Insoluble }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | Autoignition = }} }} '''Ethyl oleate''' is the [[ester]] formed by the condensation of the [[fatty acid]] [[oleic acid]] and [[ethanol]]. It is a colorless to light yellow liquid. Ethyl oleate is produced by the body during ethanol intoxication.<ref>{{cite journal |author=Dan L, Laposata M |title=Ethyl palmitate and ethyl oleate are the predominant fatty acid ethyl esters in the blood after ethanol ingestion and their synthesis is differentially influenced by the extracellular concentrations of their corresponding fatty acids |journal=Alcohol. Clin. Exp. Res. |volume=21 |issue=2 |pages=286–92 |year=1997 |pmid=9113265 |doi=}}</ref> Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving [[lipophilicity|lipophilic]] substances such as [[steroid]]s.<ref>{{cite journal |author=Ory SJ, Hammond CB, Yancy SG, Hendren RW, Pitt CG |title=The effect of a biodegradable contraceptive capsule (Capronor) containing levonorgestrel on gonadotropin, estrogen, and progesterone levels |journal=Am. J. Obstet. Gynecol. |volume=145 |issue=5 |pages=600–5 |year=1983 |pmid=6402933 |doi=}}</ref> 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", [[21CFR]]172.515. Ethyl oleate has been identified as a primer [[pheromone]] in [[honeybee]]s.{{Fact|date=June 2007}} 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).<ref>Laposata M. Fatty acid ethyl esters: nonoxidative metabolites of ethanol. Addiction Biology. 1998; vol 3, pg 5-14.</ref><ref>Laposata M. Fatty acid ethyl esters: currnet facts and speculations. Prostaglandins, Leukotrienes and essential fatty acids 1999; vol 60, no 5&6, pg 313-315.</ref><ref>Laposata M et al. Fatty acid ethyl esters: recent observations. Prostaglandins, Leukotrienes and essential fatty acids 2002; vol 67, no 2-3, pg 193-196.</ref> Among the speculations is that ethyl oleate may be the toxic mediator of alcohol in Fetal Alcohol Syndrome.<ref>Laposata M. Fatty acid ethyl esters: nonoxidative metabolites of ethanol. Addiction Biology. 1998; vol 3, pg 5-14.</ref> 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>Saghir M. Rapid in vivo hydrolysis of fatty acid ethyl esters, toxic nonoxidative ethanol metabolites. Am J Physiol. 1997 Jul; 273(1 pt 1):G184-190.</ref> Ethyl oleate is not currently approved by the FDA 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. ==References== {{Reflist}} ==External links== [[Category:Carboxylate esters]] [[Category:Food additives]] [[Category:Pheromones]]