| Revision as of 15:40, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 477191045 of page Ethyl_oleate for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 15:55, 3 December 2023 edit OAbot (talk | contribs)Bots440,440 editsm Open access bot: doi updated in citation with #oabot. |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 443800502 |
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| verifiedrevid = 477198559 |
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| ImageFile = Ethyl oleate.png |
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| ImageFile = Ethyl oleate.png |
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| ImageSize = 250px |
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| ImageSize = 250px |
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| IUPACName = Ethyl (''Z'')-octadec-9-enoate |
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| PIN = Ethyl (9''Z'')-octadec-9-enoate |
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| OtherNames = Oleic acid ethyl ester |
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| OtherNames = Oleic acid ethyl ester |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4515636 |
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| ChemSpiderID = 4515636 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D04090 |
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| KEGG = D04090 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| InChI = 1/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- |
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| ChEBI = 84940 |
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| InChIKey = LVGKNOAMLMIIKO-QXMHVHEDBH |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 2106289 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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- |
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| StdInChI = 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- |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 111-62-6 |
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| CASNo = 111-62-6 |
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| PubChem = 5363269 |
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| PubChem = 5363269 |
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| SMILES = O=C(OCC)CCCCCCC\C=C/CCCCCCCC |
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| SMILES = O=C(OCC)CCCCCCC\C=C/CCCCCCCC |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=20|H=38|O=2 |
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| C=20 | H=38 | O=2 |
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| Appearance = Colorless to light yellow liquid<ref name=GESTIS>{{GESTIS|ZVG=101777}}</ref> |
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| MolarMass = 310.51 g/mol |
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| Density = 0.87 g/cm<sup>3</sup><ref name=GESTIS/> |
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| Appearance = Colorless to light yellow liquid |
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| MeltingPtC = -32 |
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| Density = 0.87 g/cm³ |
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| MeltingPt_ref = <ref name=GESTIS/> |
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| MeltingPtC = -32 |
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| BoilingPtC = 210 |
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| BoilingPtC = 216-218 |
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| BoilingPt_notes = (15 ]) |
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| Solubility = Insoluble |
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| BoilingPt_ref = <ref name=GESTIS/> |
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| Solubility = Insoluble<ref name=GESTIS/> |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = > 113 °C<ref name=GESTIS/> |
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| Autoignition = |
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'''Ethyl oleate''' is a ] formed by the ] of ] and ]. It is a colorless oil although degraded samples can appear yellow. |
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==Use and occurrence== |
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===Additive=== |
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Ethyl oleate is used by compounding pharmacies as a vehicle for intramuscular drug delivery, in some cases to prepare the daily doses of ] 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 ].<ref>"Food Additives Permitted for Direct Addition to Food for Human Consumption", ]172.515</ref> Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving ] substances such as ]s.<ref>{{cite journal |vauthors=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=10.1016/0002-9378(83)91204-8}}</ref> It also finds use as a lubricant and a ]. ] used ethyl oleate to demonstrate ], producing ] and ],<ref>{{cite journal |last1 = Bouveault |first1 = Louis |authorlink1 = Louis Bouveault |last2 = Blanc |first2 = Gustave Louis | journal = ] | year = 1904 | volume = 31 | issue = 3 | pages = 1210–1213 | title = Hydrogénation des éthers des acides possédant en outre les fonctions éther-oxyde ou acétal | language = French | trans-title = Hydrogenation of the ether of the acids furthermore possessing the ether-oxide or acetal functions | url = http://gallica.bnf.fr/ark:/12148/bpt6k5469971k/f1214.image}}</ref> a method which was subsequently refined and published in '']''.<ref>{{OrgSynth|last1 = Adkins|first1 = Homer|authorlink1 = Homer Burton Adkins|last2 = Gillespie|first2 = R. H.|title = Oleyl alcohol|collvol = 3|collvolpages = 671|year = 1949|volume = 29|pages = 80|doi = 10.15227/orgsyn.029.0080|prep = cv3p0671}}</ref> |
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===Occurrence=== |
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Ethyl oleate has been identified as a primer ] in ]s.<ref>{{cite journal |author=Leoncini I. |title=Regulation of behavioral maturation by a primer pheromone produced by adult worker honey bees|journal=Proc. Natl. Acad. Sci. U.S.A. |volume=101 |issue=50 |pages=17559–17564 |year=2004|doi=10.1073/pnas.0407652101 |pmid=15572455 |last2=Le Conte |first2=Y |last3=Costagliola |first3=G |last4=Plettner |first4=E |last5=Toth |first5=AL |last6=Wang |first6=M |last7=Huang |first7=Z |last8=Bécard |first8=JM |last9=Crauser |first9=D |last10=Slessor|first10=K. N.|last11=Robinson|first11=G. E.|pmc=536028|display-authors=8|doi-access=free}}</ref> |
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===Precursor to other chemicals=== |
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By the process of ], the ''methyl ester'' of oleic acid, converts to ] and methyl 9-]:<ref>{{ cite journal | last1 = Marinescu | first1 = Smaranda C. | last2 = Schrock | first2 = Richard R. | last3 = Müller | first3 = Peter | last4 = Hoveyda | first4 = Amir H. | title = Ethenolysis Reactions Catalyzed by Imido Alkylidene Monoaryloxide Monopyrrolide (MAP) Complexes of Molybdenum | journal = J. Am. Chem. Soc. | year = 2009 | volume = 131 | issue = 31 | pages = 10840–10841 | doi = 10.1021/ja904786y | pmid=19618951}}</ref> |
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:{{chem2|CH3(CH2)7CH\dCH(CH2)7CO2Me +}} <span style="color:#008000">'''CH<sub>2</sub>=CH<sub>2</sub>'''</span> → CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub>CH=<span style="color:#008000">'''CH<sub>2</sub>'''</span> + MeO<sub>2</sub>C(CH<sub>2</sub>)<sub>7</sub>CH=<span style="color:#008000">'''CH<sub>2</sub>'''</span> |
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===Medical aspects=== |
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Ethyl oleate is produced by the body during ethanol intoxication.<ref>{{cite journal |vauthors=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=10.1111/j.1530-0277.1997.tb03762.x}}</ref> It is one of the ] (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).<ref name="Laposata 1998">{{Cite journal | author = Laposata M.|title=Fatty acid ethyl esters: nonoxidative metabolites of ethanol|journal=]|year=1998|volume=3|issue=1|pages=5–14 |doi=10.1080/13556219872308|pmid=26736076|s2cid=22486675|doi-access=free}}</ref><ref>{{cite journal | author = Laposata M | title = Fatty acid ethyl esters: recent observations | journal = Prostaglandins, Leukotrienes, and Essential Fatty Acids | year = 2002 | volume = 67 | issue = 2–3 | pages = 193–196 |name-list-style=vanc | display-authors = 1 | doi = 10.1054/plef.2002.0418 | last2 = Hasaba | first2 = Ali | last3 = Best | first3 = Catherine A. | last4 = Yoerger | first4 = Danita M. | last5 = McQuillan | first5 = Brendan M. | last6 = Salem | first6 = Raneem O. | last7 = Refaai | first7 = Majed A. | last8 = Soderberg | first8 = Britt L.| pmid = 12324241 }}</ref> Ethyl oleate may be the toxic mediator of alcohol in ].<ref name="Laposata 1998"/> 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>{{cite journal | author = Saghir M. | title = Rapid in vivo hydrolysis of fatty acid ethyl esters, toxic nonoxidative ethanol metabolites | journal = Am J Physiol | year = 1997 | volume = 273 | issue = 1 Pt 1 | pages = G184–190| doi = 10.1152/ajpgi.1997.273.1.G184 | pmid = 9252525 }}</ref> |
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==See also== |
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== References == |
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{{Reflist}} |
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