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Wikipedia

Ethyl oleate

April 14, 2024

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.

Ethyl oleate
Names
Preferred IUPAC name
Ethyl (9Z)-octadec-9-enoate
Other names
Oleic acid ethyl ester
Identifiers
  • 111-62-6 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:84940 N
ChEMBL
  • ChEMBL2106289 N
ChemSpider
  • 4515636 Y
ECHA InfoCard 100.003.536
KEGG
  • D04090 Y
  • 5363269
UNII
  • Z2Z439864Y Y
  • DTXSID3047633
  • 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- Y
    Key: LVGKNOAMLMIIKO-QXMHVHEDSA-N Y
  • O=C(OCC)CCCCCCC\C=C/CCCCCCCC
Properties
C20H38O2
Molar mass 310.522 g·mol−1
Appearance Colorless to light yellow liquid[1]
Density 0.87 g/cm3[1]
Melting point −32 °C (−26 °F; 241 K)[1]
Boiling point 216–218 °C (421–424 °F; 489–491 K)[1] (15 hPa)
Insoluble[1]
Hazards
Flash point > 113 °C[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Use and occurrence edit

Additive edit

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 edit

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

Precursor to other chemicals edit

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 edit

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]

See also edit

References edit

  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.
  9. ^ 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.
  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.

April 14, 2024
ethyl, oleate, fatty, acid, ester, formed, condensation, oleic, acid, ethanol, colorless, although, degraded, samples, appear, yellow, namespreferred, iupac, name, ethyl, octadec, enoateother, names, oleic, acid, ethyl, esteridentifierscas, number, model, jsmo. 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 Ethyl oleate NamesPreferred IUPAC name Ethyl 9Z octadec 9 enoateOther names Oleic acid ethyl esterIdentifiersCAS Number 111 62 6 Y3D model JSmol Interactive imageChEBI CHEBI 84940 NChEMBL ChEMBL2106289 NChemSpider 4515636 YECHA InfoCard 100 003 536KEGG D04090 YPubChem CID 5363269UNII Z2Z439864Y YCompTox Dashboard EPA DTXSID3047633InChI 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 YKey LVGKNOAMLMIIKO QXMHVHEDSA N YSMILES O C OCC CCCCCCC C C CCCCCCCCPropertiesChemical formula C 20H 38O 2Molar mass 310 522 g mol 1Appearance Colorless to light yellow liquid 1 Density 0 87 g cm3 1 Melting point 32 C 26 F 241 K 1 Boiling point 216 218 C 421 424 F 489 491 K 1 15 hPa Solubility in water Insoluble 1 HazardsFlash point gt 113 C 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Use and occurrence 1 1 Additive 1 2 Occurrence 1 3 Precursor to other chemicals 1 4 Medical aspects 2 See also 3 ReferencesUse and occurrence editAdditive edit 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 edit Ethyl oleate has been identified as a primer pheromone in honeybees 6 Precursor to other chemicals edit 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 CH2Medical aspects edit 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 See also editButyl oleate OleateReferences edit 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 Hydrogenation des ethers des acides possedant en outre les fonctions ether oxyde ou acetal 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 Becard 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 Muller 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 Retrieved from https en wikipedia org w index php title Ethyl oleate amp oldid 1188139940, wikipedia, wiki, book, books, library,

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