Ethyl oleate

Ethyl oleate
Names
	Preferred IUPAC name Ethyl (9Z)-octadec-9-enoate
	Other names Oleic acid ethyl ester
Identifiers
CAS Number	111-62-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:84940 ;
ChEMBL	ChEMBL2106289 ;
ChemSpider	4515636 ;
ECHA InfoCard	100.003.536
KEGG	D04090 ;
PubChem CID	5363269;
UNII	Z2Z439864Y ;
CompTox Dashboard (EPA)	DTXSID3047633 ;
	InChI InChI=1S/C20H38O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h11-12H,3-10,13-19H2,1-2H3/b12-11- Key: LVGKNOAMLMIIKO-QXMHVHEDSA-N ;
	SMILES O=C(OCC)CCCCCCC\C=C/CCCCCCCC;
Properties
Chemical formula	C20H38O2
Molar mass	310.522 g·mol−1
Appearance	Colorless to light yellow liquid
Density	0.87 g/cm3
Melting point	−32 °C (−26 °F; 241 K)
Boiling point	216–218 °C (421–424 °F; 489–491 K) (15 hPa)
Solubility in water	Insoluble
Hazards
Flash point	> 113 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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 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 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.^[2] Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.^[3] 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,^[4] a method which was subsequently refined and published in Organic Syntheses.^[5]

Occurrence

Ethyl oleate has been identified as a primer pheromone in honeybees.^[6]

Precursor to other chemicals

By the process of ethenolysis, the methyl ester of oleic acid, converts to 1-decene and methyl 9-decenoate:^[7]

CH₃(CH₂)₇CH=CH(CH₂)₇CO₂Me + CH₂=CH₂ → CH₃(CH₂)₇CH=CH₂ + MeO₂C(CH₂)₇CH=CH₂

Medical aspects

Ethyl oleate is produced by the body during ethanol intoxication.^[8] 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).^[9]^[10] Ethyl oleate may be the toxic mediator of alcohol in fetal alcohol syndrome.^[9] 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.^[11]

References

^ ^a ^b ^c ^d ^e ^f Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ "Food Additives Permitted for Direct Addition to Food for Human Consumption", 21CFR172.515
^ 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. doi:10.1016/0002-9378(83)91204-8. PMID 6402933.
^ Bouveault, Louis; Blanc, Gustave Louis (1904). "Hydrogénation des éthers des acides possédant en outre les fonctions éther-oxyde ou acétal" [Hydrogenation of the ether of the acids furthermore possessing the ether-oxide or acetal functions]. Bull. Soc. Chim. Fr. (in French). 31 (3): 1210–1213.
^ Adkins, Homer; Gillespie, R. H. (1949). "Oleyl alcohol". Organic Syntheses. 29: 80. doi:10.15227/orgsyn.029.0080; Collected Volumes, vol. 3, p. 671.
^ 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.
^ Marinescu, Smaranda C.; Schrock, Richard R.; Müller, Peter; Hoveyda, Amir H. (2009). "Ethenolysis Reactions Catalyzed by Imido Alkylidene Monoaryloxide Monopyrrolide (MAP) Complexes of Molybdenum". J. Am. Chem. Soc. 131 (31): 10840–10841. doi:10.1021/ja904786y. PMID 19618951.
^ 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. doi:10.1111/j.1530-0277.1997.tb03762.x. PMID 9113265.
^ ^a ^b Laposata M. (1998). "Fatty acid ethyl esters: nonoxidative metabolites of ethanol". Addiction Biology. 3 (1): 5–14. doi:10.1080/13556219872308. PMID 26736076. S2CID 22486675.
^ Laposata M, et al. (2002). "Fatty acid ethyl esters: recent observations". Prostaglandins, Leukotrienes, and Essential Fatty Acids. 67 (2–3): 193–196. doi:10.1054/plef.2002.0418. PMID 12324241.
^ Saghir M. (1997). "Rapid in vivo hydrolysis of fatty acid ethyl esters, toxic nonoxidative ethanol metabolites". Am J Physiol. 273 (1 Pt 1): G184–190. doi:10.1152/ajpgi.1997.273.1.G184. PMID 9252525.

[GESTIS-1] ^ ^a ^b ^c ^d ^e ^f Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[2] "Food Additives Permitted for Direct Addition to Food for Human Consumption", 21CFR172.515

[3] 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. doi:10.1016/0002-9378(83)91204-8. PMID 6402933.

[4] Bouveault, Louis; Blanc, Gustave Louis (1904). "Hydrogénation des éthers des acides possédant en outre les fonctions éther-oxyde ou acétal" [Hydrogenation of the ether of the acids furthermore possessing the ether-oxide or acetal functions]. Bull. Soc. Chim. Fr. (in French). 31 (3): 1210–1213.

[5] Adkins, Homer; Gillespie, R. H. (1949). "Oleyl alcohol". Organic Syntheses. 29: 80. doi:10.15227/orgsyn.029.0080; Collected Volumes, vol. 3, p. 671.

[6] 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.

[7] Marinescu, Smaranda C.; Schrock, Richard R.; Müller, Peter; Hoveyda, Amir H. (2009). "Ethenolysis Reactions Catalyzed by Imido Alkylidene Monoaryloxide Monopyrrolide (MAP) Complexes of Molybdenum". J. Am. Chem. Soc. 131 (31): 10840–10841. doi:10.1021/ja904786y. PMID 19618951.

[8] 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. doi:10.1111/j.1530-0277.1997.tb03762.x. PMID 9113265.

[Laposata_1998-9] Laposata M. (1998). "Fatty acid ethyl esters: nonoxidative metabolites of ethanol". Addiction Biology. 3 (1): 5–14. doi:10.1080/13556219872308. PMID 26736076. S2CID 22486675.

[10] Laposata M, et al. (2002). "Fatty acid ethyl esters: recent observations". Prostaglandins, Leukotrienes, and Essential Fatty Acids. 67 (2–3): 193–196. doi:10.1054/plef.2002.0418. PMID 12324241.

[11] Saghir M. (1997). "Rapid in vivo hydrolysis of fatty acid ethyl esters, toxic nonoxidative ethanol metabolites". Am J Physiol. 273 (1 Pt 1): G184–190. doi:10.1152/ajpgi.1997.273.1.G184. PMID 9252525.

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