ETHYL OLEATE

Base Information

• Chemical Name: ETHYL OLEATE
• CAS No.: 111-62-6
• Molecular Formula: C20H38O2
• Molecular Weight: 310.521
• Hs Code.: 29161900
• European Community (EC) Number: 228-082-5
• DSSTox Substance ID: DTXSID00110052
• Nikkaji Number: J47.116J,J227.303I
• Wikidata: Q63409543
• Metabolomics Workbench ID: 46554
• Mol file: 111-62-6.mol

Synonyms:9-Octadecenoicacid (Z)-, ethyl ester;Oleic acid, ethyl ester (6CI,8CI);Crodamol EO;Esterol123;Ethyl (Z)-9-octadecenoate;Ethyl cis-9-octadecenoate;Ethyl oleate;NikkolEOO;Nofable EO 99;

Chemical Property of ETHYL OLEATE

Chemical Property:

• Appearance/Colour: clear pale yellow oily liquid
• Vapor Pressure: 3.67E-06mmHg at 25°C
• Melting Point: - 32 °C(lit.)
• Refractive Index: n20/D 1.451(lit.)
• Boiling Point: 385.9 °C at 760 mmHg
• Flash Point: 91.8 °C
• PSA: 26.30000
• Density: 0.872 g/cm³
• LogP: 6.58700
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive
• Solubility.: chloroform: soluble10%
• XLogP3: 8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 17
• Exact Mass: 310.287180451
• Heavy Atom Count: 22
• Complexity: 258

Purity/Quality:

99% ^*data from raw suppliers

Ethyl Oleate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OCC
• Isomeric SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)OCC
• Uses: Pharmaceutical Industry Ethyl oleate is utilized as an ingredient for the preparations of pharmaceutical drugs that involves lipophilic substances such as steroids. Due to its quick degradation of the digestive system, ethyl oleate is employed as a way for intramuscular drug delivery by compounding pharmacies. In some cases, the compound is used in the preparation of day-to-day doses of progesterone in the sustenance of pregnancy. Transport Industry It is used in the transport industry as a lubricant and as a plasticiser. It is also used as a planting agent and for treating surfaces. Food Industry Ethyl oleate is used as a food additive and is regulated by the Food and Drug Administration. It is also used as a flavouring agent in food. Ethyl oleate is a flavoring and fragrance agent. It was obtained by the hydrolysis of various animal and vegetable fats and oils. Usually used to prepare the oily phase of self-microemulsifying drug delivery system (SMEDDS) for tacrolimus (Tac).
• Description: Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. It is a colorless to light yellow liquid. Ethyl oleate is produced by the body during ethanol intoxication. Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids. 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. 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). Among the speculations is that ethyl oleate may be the toxic mediator of alcohol in fetal alcohol syndrome. 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. 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.

Technology Process of ETHYL OLEATE

There total 18 articles about ETHYL OLEATE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

ethanol (64-17-5) + cis-Octadecenoic acid (112-80-1,2027-47-6) → oleic acid ethyl ester (111-62-6)

Guidance literature:

With sulfuric acid; at 110 ℃; for 2h;

DOI:10.1007/BF02523427

Reference yield: 99.0%

→ oleic acid ethyl ester (111-62-6)

Guidance literature:

With toluene-4-sulfonic acid; at 125 ℃; for 3h; under 2052.14 Torr; Sealed tube;

Reference yield: 90.0%

cis-Octadecenoic acid (112-80-1,2027-47-6) + Triethyl orthoacetate (78-39-7) → oleic acid ethyl ester (111-62-6)

Guidance literature:

In various solvent(s); at 80 ℃; for 4h;

DOI:10.1016/j.tet.2005.09.147

upstream raw materials:

ethanol

cis-Octadecenoic acid

(+/-)-threo-9,10-dibromo-octadecanoic acid ethyl ester

potassium oleate

Downstream raw materials:

azelaic acid

octane-1,8-dioic acid

Octanoic acid

nonanoic acid

Refernces

• 1、 Choo, Yuen-May,Ooi, Kay-Eng,Ooi, Ing-Hong. "Synthesis of Civetone from Palm Oil Products". . p. 911 - 913. Retrieved 1994.
• 2、 Santos, Joicy S.,Dias, José A.,Dias, Sílvia C.L.,De MacEdo, Julio L.,Garcia, Fillipe A.C.,Almeida, Liana S.,De Carvalho, Eduardo N.C.B.. "Acidic characterization and activity of (NH4)xCs 2.5-xH0.5PW12O40 catalysts in the esterification reaction of oleic acid with ethanol". . p. 33 - 39. Retrieved 2012.
• 3、 Kita, Hidetoshi,Tanaka, Kazuhiro,Okamoto, Ken-ichi,Yamamoto, Masuji. "The Esterification of Oleic Acid with Ethanol Accompanied by Membrane Separation". . p. 2053 - 2056. Retrieved 1987.
• 4、 Krupickova, Jana,Vcelak, Jaroslav,Hetflejs, Jiri. "HYDROGENATION OF FATTY ACIDS ESTERS. II. KINETICS OF HYDROGENATION OF METHYL (Z)- AND (E)-9-OCTADECENOATE CATALYZED BY A ZIEGLER NICKEL CATALYST". . p. 2583 - 2592. Retrieved 1992.
• 5、 Ong, Huei Ruey,Rahman Khan, Md Maksudur,Yousuf, Abu,Hussain, Nor Amalina,Cheng, Chin Kui. "Synthesis and characterization of a CaFe2O4 catalyst for oleic acid esterification". . p. 100362 - 100368. Retrieved 2015.
• 6、 Selva, Elisabet,Soto, J. Javier,Nájera, Carmen,Foubelo, Francisco,Sansano, José M.. "Proline derivatives incorporating hydrophobic long-chain derived from natural and synthetic fatty acids". . p. 1378 - 1386. Retrieved 2019.
• 7、 Luvino, Delphine,Khiati, Salim,Oumzil, Khalid,Rocchi, Palma,Camplo, Michel,Barthélémy, Philippe. "Efficient delivery of therapeutic small nucleic acids to prostate cancer cells using ketal nucleoside lipid nanoparticles". . p. 954 - 961. Retrieved 2013.
• 8、 De Souza, Stefania P.,Bassut, Jonathan,Marquez, Heiddy V.,Junior, Ivaldo I.,Miranda, Leandro S. M.,Huang, Youkui,Mackenzie, Grahame,Boa, Andrew N.,De Souza, Rodrigo O. M. A.. "Sporopollenin as an efficient green support for covalent immobilization of a lipase". . p. 3130 - 3136. Retrieved 2015.
• 9、 Sebah, Majda,Maddala, Sai P.,Haycock, Peter,Sullivan, Alice,Toms, Harold,Wilson, John. "New phosphonic acid polysilsesquioxane mild solid acid catalysts". . p. 59 - 65. Retrieved 2013.
• 10、 Kumar, Davender,Nagar, Sushil,Bhushan, Indu,Kumar, Lalit,Parshad, Rajinder,Gupta, Vijay Kumar. "Covalent immobilization of organic solvent tolerant lipase on aluminum oxide pellets and its potential application in esterification reaction". . p. 51 - 61. Retrieved 2013.