Ethyl oleate

Ethyl oleate
Ethyl oleate
IUPAC name
Ethyl (Z)-octadec-9-enoate
Other names
Oleic acid ethyl ester
Identifiers
CAS number 111-62-6 YesY
PubChem 5363269
ChemSpider 4515636 YesY
UNII Z2Z439864Y YesY
KEGG D04090 YesY
Jmol-3D images Image 1
Properties
Molecular formula C20H38O2
Molar mass 310.51 g mol−1
Appearance Colorless to light yellow liquid
Density 0.87 g/cm³, liquid
Melting point

-32 °C, 241 K, -26 °F
Boiling point

210 °C, 483 K, 410 °F
Solubility in water Insoluble
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.[1]

Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.[2] 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.[3]

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).[4][5][6] Among the speculations is that ethyl oleate may be the toxic mediator of alcohol in Fetal Alcohol Syndrome.[7] 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. [8] 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.

References

  1. ^ Dan L, Laposata M (1997). "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". Alcohol. Clin. Exp. Res. 21 (2): 286–92. PMID 9113265. 
  2. ^ Ory SJ, Hammond CB, Yancy SG, Hendren RW, Pitt CG (1983). "The effect of a biodegradable contraceptive capsule (Capronor) containing levonorgestrel on gonadotropin, estrogen, and progesterone levels". Am. J. Obstet. Gynecol. 145 (5): 600–5. PMID 6402933. 
  3. ^ Leoncini I.; Le Conte, Y; Costagliola, G; Plettner, E; Toth, AL; Wang, M; Huang, Z; Bécard, JM et al. (2004). "Regulation of behavioral maturation by a primer pheromone produced by adult worker honey bees". Proc. Natl. Acad. Sci. U. S. A. 101 (50): 17559–17564. doi:10.1073/pnas.0407652101. PMC 536028. PMID 15572455. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=536028. 
  4. ^ Laposata M. Fatty acid ethyl esters: nonoxidative metabolites of ethanol. Addiction Biology. 1998; vol 3, pg 5-14.
  5. ^ Laposata M. Fatty acid ethyl esters: current facts and speculations. Prostaglandins, Leukotrienes and essential fatty acids 1999; vol 60, no 5&6, pg 313-315.
  6. ^ 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.
  7. ^ Laposata M. Fatty acid ethyl esters: nonoxidative metabolites of ethanol. Addiction Biology. 1998; vol 3, pg 5-14.
  8. ^ 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.

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