ETHYL OLEATE (ETL OLEAT)
ETHYL OLEATE
ETHYLE OLEATE; ethyl oleate; etil oleate; etil oleate; Ethyl oleate; Ethyl oleate; 111-62-6; Oleic acid ethyl ester; Ethyl cis-9-octadecenoate; Oleic acid, ethyl ester; 9-Octadecenoic acid (Z)-, ethyl ester; ethyl (Z)-octadec-9-enoate; Ethyl oleate [NF]; UNII-Z2Z439864Y; MFCD00009579; CHEBI:84940; (Z)-9-Octadecenoic acid ethyl ester; Ethyl oleate (NF); Z2Z439864Y; Ethyl oleate (natural); FEMA No. 2450; Ethyl 9-octadecenoate, (Z)-; EINECS 203-889-5; NSC 229428; 9-Octadecenoic acid (9Z)-, ethyl ester; AI3-00657; Ethyl Z-9-octadecenoate; Ethyl oleate, 98%, mixture of homologeous fatty acid esters; Ethylis oleas; Oleic acid, ethyl ester (6CI,8CI); Oleic acid ethyl; 85049-36-1; 9-Octadecenoic acid, (Z)-, ethyl ester; Ethyl Oleate, NF; Ethyl oleate, 98%; ethyl (9Z)-octadecenoate; SCHEMBL2797; DSSTox_CID_27633; DSSTox_RID_82464; DSSTox_GSID_47633; ethyl (9Z)octadec-9-enoate; ethyl (9Z)-octadec-9-enoate; CHEMBL2106289; DTXSID3047633; Ethyl (9Z)-9-octadecenoate #; Ethyl oleate, natural, >=85%; CIS-9-OCTADECENYL ACETATE; Ethyl oleate, analytical standard; HMS3650O15; HY-N7103; ZINC8214560; Tox21_303521; Ethyl oleate, technical grade, 70%; NSC229428; s5367; SBB060320; AKOS025117011; CCG-267586; CS-W009922; NSC-229428; NCGC00257457-01; CAS-111-62-6; SC-79350; Ethyl oleate, tested according to Ph.Eur.; O0054; O0143; Ethyl oleate, Vetec(TM) reagent grade, 98%; D04090; SR-01000946820; Q6578680; SR-01000946820-1; Ethyl (Z)-9-Octadecenoate.;ethyl oleate;ETHYL OLEATE; UNII-0962034MCM component LVGKNOAMLMIIKO-QXMHVHEDSA-N; UNII-2351QH8W1N component LVGKNOAMLMIIKO-QXMHVHEDSA-N; UNII-89IR26S11S component LVGKNOAMLMIIKO-QXMHVHEDSA-N; UNII-ANA2NCS6V1 component LVGKNOAMLMIIKO-QXMHVHEDSA-N; NII-PY7890FR5M component LVGKNOAMLMIIKO-QXMHVHEDSA-N; Ethyl oleate, United States Pharmacopeia (USP) Reference Standar;
ETHYL OLEATE
CAS No.：111-62-6
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.[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, a method which was subsequently refined and published in Organic Syntheses. 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).[7][8][9] 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.[10] 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. Appearance of Ethyl Oleate: Colorless to pale yellow clear liquid. Almost insoluble in water, can be miscible with ethanol, dichloride methane or petroleum ether. It can be miscible with isopropanol in any proportion.
Application of Ethyl Oleate:
This product is mainly used as a solvent, a transdermal absorption enhancer, a lubricant and a plasticizer in pharmaceuticals. This product is a suitable solvent for steroids and other lipophilic drugs. Its properties are similar to almond oil and peanut oil, and its viscosity is low, and it is easily absorbed by body tissues. This product is also used for biodegradable microcapsules and microemulsions of cyclosporine implanted under the dermis.
Overview to Ethyl Oleate
Ethyl oleate is a colourless liquid that is normally formed by condensing ethanol and oleic acid. Notably, the compound is normally produced by the body during intoxication of ethanol. Its other names are 9-Octadecenoic acid (Z)-, Ethyl cis-9-octadecenoate, (Z)-9-Octadecenoic acid ethyl ester, and Oleic acid, ethyl ester. The compound contributed to approximately 17% of the total fatty acids esterified to phosphatidylcholine in porcine platelets. Ethyl oleate is neutral and is a more lipid-soluble form of oleic acid.
The compound is one of the fatty acid ethyl esters that is generated after the breakdown of ethanol in the body. Moreover, ethyl oleate usually acts as a toxic mediator of ethanol in the heart, liver, pancreas, and brain.
Uses of Ethyl Oleate
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.
Description of Ethyl Oleate
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.
Chemical Properties of Ethyl Oleate
Ethyl oleate has a faint, floral note.
Chemical Properties of Ethyl Oleate
clear pale yellow oily liquid
Chemical Properties of Ethyl Oleate
Ethyl oleate occurs as a pale yellow to almost colorless, mobile, oily liquid with a taste resembling that of olive oil and a slight, but not rancid odor.
Ethyl oleate is described in the USP32-NF27 as consisting of esters of ethyl alcohol and high molecular weight fatty acids, principally oleic acid. A suitable antioxidant may be included.
Occurrence
Reported found in cocoa, buckwheat, elderberry and babaco fruit (Carica pentagona Heilborn).
Uses
Ethyl oleate is a flavoring and fragrance agent.
Uses
It was obtained by the hydrolysis of various animal and vegetable fats and oils.
Uses
Usually used to prepare the oily phase of self-microemulsifying drug delivery system (SMEDDS) for tacrolimus (Tac).
Production Methods
Ethyl oleate is prepared by the reaction of ethanol with oleoyl chloride in the presence of a suitable hydrogen chloride acceptor.
Pharmaceutical Applications of Ethyl Oleate
Ethyl oleate is primarily used as a vehicle in certain parenteral preparations intended for intramuscular administration. It has also been used as a solvent for drugs formulated as biodegradable capsules for subdermal implantation) and in the preparation of microemulsions containing cyclosporinand norcantharidin.
Microemulsion formulations containing ethyl oleate have also been proposed for topical and ocular delivery, and for liver targeting following parenteral administration. Ethyl oleate has been used in topical gel formulations, and in self-microemulsifying drug delivery systems for oral administration.
Ethyl oleate is a suitable solvent for steroids and other lipophilic drugs. Its properties are similar to those of almond oil and peanut oil. However, it has the advantage that it is less viscous than fixed oils and is more rapidly absorbed by body tissues.
Ethyl oleate has also been evaluated as a vehicle for subcutaneous injection.
Safety
Ethyl oleate is generally considered to be of low toxicity but ingestion should be avoided. Ethyl oleate has been found to cause minimal tissue irritation. No reports of intramuscular irritation during use have been recorded.
Carcinogenicity
Not listed by ACGIH, California Proposition 65, IARC, NTP, or OSHA.
Storage of Ethyl Oleate
Ethyl oleate should be stored in a cool, dry place in a small, wellfilled, well-closed container, protected from light. When a partially filled container is used, the air should be replaced by nitrogen or another inert gas. Ethyl oleate oxidizes on exposure to air, resulting in an increase in the peroxide value. It remains clear at 5°C, but darkens in color on standing. Antioxidants are frequently used to extend the shelf life of ethyl oleate. Protection from oxidation for over 2 years has been achieved by storage in amber glass bottles with the addition of combinations of propyl gallate, butylated hydroxyanisole, butylated hydroxytoluene, and citric or ascorbic acid. A concentration of 0.03% w/v of a mixture of propyl gallate (37.5%), butylated hydroxytoluene (37.5%), and butylated hydroxyanisole (25%) was found to be the best antioxidant for ethyl oleate.
Ethyl oleate may be sterilized by heating at 150°C for 1 hour.
Incompatibilities
Ethyl oleate dissolves certain types of rubber and causes others to swell. It may also react with oxidizing agents.
Regulatory Status
Included in the FDA Inactive Ingredients Database (transdermal preparation). Included in parenteral (intramuscular injection) and nonparenteral (transdermal patches) medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
Etil oleat a, yal asit esteri ile oluturulan younlatrma ve oleik asit ve etanol . Renksiz ila açk sar bir svdr. Etil oleat, etanol zehirlenmesi srasnda vücut tarafndan üretilir. Etil oleat, steroidler gibi lipofilik maddeler içeren farmasötik ilaç terkipleri için bir çözücü olarak kullanlr . Ayn zamanda bir yalayc ve bir plastikletirici olarak kullanm alan bulur . Louis Bouveault , Bouveault-Blanc indirgemesini göstermek için etil oleat kulland , oleil alkol ve etanol üretti , bu daha sonra rafine edilen ve Organik Sentezlerde yaynlanan bir yöntem . Etil oleat, Gda ve laç daresi tarafndan “nsan Tüketimi için Gdaya Dorudan Katlmasna zin Verilen Gda Katk Maddeleri”, 21CFR 172.515 altnda bir gda katk maddesi olarak düzenlenmitir . Etil oleat bir primer olarak tanmlanmtr feromon olarak bal arlar . Etil oleat, etanol almndan sonra vücutta oluan ya asidi etil esterlerinden (FAEE) biridir. Etil oleat gibi FAEE’leri vücuttaki etanolün toksik araclar olarak (pankreas, karacier, kalp ve beyin) içeren büyüyen bir aratrma literatürü vardr. Spekülasyonlar arasnda etil oleatn fetal alkol sendromunda alkolün toksik aracs olabilecei yer alyor . Etil oleatn azdan yutulmas dikkatle incelenmitir ve sindirim sistemindeki hzl bozulma nedeniyle azdan yutulmas için güvenli görünmektedir. Etil oleat u anda herhangi bir enjekte edilebilir kullanm için ABD Gda ve laç Dairesi tarafndan onaylanmamtr . Bununla birlikte, eczanelerin kas içi ilaç datm için bir araç olarak birletirilmesi, baz durumlarda hamilelii desteklemek için günlük progesteron dozlarnn hazrlanmas için kullanlr . Etil oleatn gebelikte hem anne hem de fetüs için güvenli kullanmn belgeleyen çalmalar hiçbir zaman yaplmamtr. Etil Oleat Uygulamas:
Bu ürün esas olarak farmasötiklerde solvent, transdermal absorpsiyon arttrc, yalayc ve plastikletirici olarak kullanlr. Bu ürün, steroidler ve dier lipofilik ilaçlar için uygun bir çözücüdür. Özellikleri badem ya ve fstk yana benzer, viskozitesi düüktür ve vücut dokular tarafndan kolayca emilir. Bu ürün ayrca biyolojik olarak parçalanabilen mikrokapsüller ve dermisin altna implante edilen siklosporin mikroemülsiyonlar için kullanlr.
Etil Oleata Genel Bak
Etil oleat, normalde etanol ve oleik asidin younlatrlmasyla oluan renksiz bir svdr. Özellikle, bileik normal olarak etanolün zehirlenmesi srasnda vücut tarafndan üretilir. Dier isimleri 9-Oktadesenoik asit (Z) -, Etil cis-9-oktadesenoat, (Z) -9-Oktadekenoik asit etil ester ve Oleik asit, etil esterdir. Bileik, domuz trombositlerinde fosfatidilkoline esterlenen toplam ya asitlerinin yaklak% 17’sine katkda bulunmutur. Etil oleat nötrdür ve oleik asidin yada daha çözünür bir eklidir.
Bileik, vücutta etanolün parçalanmasndan sonra oluan ya asidi etil esterlerinden biridir. Dahas, etil oleat genellikle kalp, karacier, pankreas ve beyinde etanolün toksik bir aracs olarak görev yapar.
Etil Oleatn Kullanm Alanlar
laç endüstrisi
Etil oleat, steroidler gibi lipofilik maddeler içeren farmasötik ilaçlarn preparasyonlarnda bir bileen olarak kullanlr. Sindirim sistemindeki hzl bozunmas nedeniyle, etil oleat, eczaneleri birletirerek kas içi ilaç datmnn bir yolu olarak kullanlr. Baz durumlarda, bileik hamileliin sürdürülmesinde günlük progesteron dozlarnn hazrlanmasnda kullanlr.
Tama Sektörü
Tamaclk endüstrisinde yalayc ve plastikletirici olarak kullanlr. Ayrca ekim ajan olarak ve yüzeyleri ilemek için kullanlr.
Gda endüstrisi
Etil oleat bir gda katk maddesi olarak kullanlr ve Gda ve laç daresi tarafndan düzenlenir. Ayrca gdalarda aroma maddesi olarak kullanlr.
Ethyl Oleate açklamas
Etil oleat, oleik asit ve etanolün younlamasyla oluan bir ya asidi esteridir. Renksiz ila açk sar bir svdr. Etil oleat, etanol zehirlenmesi srasnda vücut tarafndan üretilir.
Etil oleat, steroidler gibi lipofilik maddeleri içeren farmasötik ilaç terkipleri için bir çözücü olarak kullanlr. Ayrca yalayc ve plastikletirici olarak kullanm alan bulur.
Etil oleat, Gda ve laç daresi tarafndan “nsan Tüketimi için Gdaya Dorudan Katlmasna zin Verilen Gda Katk Maddeleri”, 21CFR172.515 altnda bir gda katk maddesi olarak düzenlenmitir.
Etil oleat, bal arlarnda bir primer feromon olarak tanmlanmtr.
Etil oleat, etanol almndan sonra vücutta oluan ya asidi etil esterlerinden (FAEE) biridir. Etil oleat gibi FAEE’leri vücuttaki etanolün toksik araclar olarak (pankreas, karacier, kalp ve beyin) içeren büyüyen bir aratrma literatürü vardr. Spekülasyonlar arasnda etil oleatn fetal alkol sendromunda alkolün toksik aracs olabilecei de var. Etil oleatn azdan yutulmas dikkatle incelenmitir ve sindirim sistemindeki hzl bozulma nedeniyle azdan yutulmas için güvenli görünmektedir. Etil oleat u anda herhangi bir enjekte edilebilir kullanm için ABD Gda ve laç Dairesi tarafndan onaylanmamtr. Bununla birlikte, eczanelerin kas içi ilaç datm için bir araç olarak birletirilmesi, baz durumlarda hamilelii desteklemek için günlük progesteron dozlarnn hazrlanmas için kullanlr. Etil oleatn gebelikte hem anne hem de fetüs için güvenli kullanmn belgeleyen çalmalar hiçbir zaman yaplmamtr. Etil Oleatn Kimyasal Özellikleri
Etil oleatn soluk, çiçeksi bir notas vardr.
Etil Oleatn Kimyasal Özellikleri
berrak soluk sar yal sv
Etil Oleatn Kimyasal Özellikleri
Etil oleat, zeytinyana benzeyen bir tada ve hafif ama kokusuz bir kokuya sahip, soluk sar ila neredeyse renksiz, hareketli, yal bir sv olarak ortaya çkar.
Etil oleat, USP32 – NF27’de etil alkol esterlerinden ve yüksek moleküler arlkl ya asitlerinden, özellikle oleik asitten olutuu eklinde tanmlanmaktadr. Uygun bir antioksidan dahil edilebilir.
Oluum
Kakao, karabuday, mürver ve babaco meyvesinde (Carica pentagona Heilborn) bulunduu bildirilmitir.
Kullanmlar
Etil oleat bir tatlandrc ve koku verici ajandr.
Kullanmlar
Çeitli hayvansal ve bitkisel kat ve sv yalarn hidrolizi ile elde edilmitir.
Kullanmlar
Genellikle takrolimus (Tac) için kendi kendine mikroemülsifiye edici ilaç datm sisteminin (SMEDDS) yal fazn hazrlamak için kullanlr.
Üretim yöntemleri
Etil oleat, etanolün oleoil klorür ile uygun bir hidrojen klorür alcs varlnda reaksiyonuyla hazrlanr.
Etil Oleatn Farmasötik Uygulamalar
Etil oleat, öncelikle kas içi uygulama için amaçlanan baz parenteral preparatlarda bir araç olarak kullanlr. Ayrca deri altna implantasyon için biyolojik olarak parçalanabilir kapsüller olarak formüle edilen ilaçlar için bir çözücü olarak ve siklosporin ve norkantaridin içeren mikroemülsiyonlarn hazrlanmasnda da kullanlmtr.
Etil oleat içeren mikroemülsiyon formülasyonlar da topikal ve oküler uygulama için ve parenteral uygulamay takiben karacier hedeflemesi için önerilmitir. Etil oleat, topikal jel formülasyonlarnda ve oral uygulama için kendi kendine mikroemülsifiye edici ilaç verme sistemlerinde kullanlmtr.
Etil oleat, steroidler ve dier lipofilik ilaçlar için uygun bir çözücüdür. Özellikleri badem ya ve yerfst yana benzer. Bununla birlikte, sabit yalardan daha az viskoz olmas ve vücut dokular tarafndan daha hzl emilmesi avantajna sahiptir.
Etil oleat ayrca subkutan enjeksiyon için bir araç olarak deerlendirilmitir.
Emniyet
Etil oleat genellikle düük toksisiteye sahip olarak kabul edilir ancak yutulmasndan kaçnlmaldr. Etil oleatn minimal doku tahriine neden olduu bulunmutur. Kullanm srasnda herhangi bir kas içi tahri raporu kaydedilmemitir.
Kanserojenlik
ACGIH, California Proposition 65, IARC, NTP veya OSHA tarafndan listelenmemitir.
Ethyl Oleate saklanmas
Etil oleat, serin ve kuru bir yerde küçük, iyi doldurulmu, iyi kapatlm bir kapta, ktan korunarak saklanmaldr. Ksmen dolu bir kap kullanldnda, havann nitrojen veya baka bir inert gazla deitirilmesi gerekir. Etil oleat havaya maruz kaldnda oksitlenerek peroksit deerinde bir arta neden olur. 5 ° C’de berrak kalr, ancak bekletildiinde rengi koyular. Antioksidanlar sklkla etil oleatn raf ömrünü uzatmak için kullanlr. 2 yldan fazla bir süredir oksidasyondan koruma, propil gallat, butile hidroksianisol, butile hidroksitoluen ve sitrik veya askorbik asit kombinasyonlarnn eklenmesiyle amber cam ielerde saklanarak salanmtr. Etil oleat için en iyi antioksidan propil galat (% 37.5), bütillenmi hidroksitoluen (% 37.5) ve bütillenmi hidroksianisol (% 25) karmnn arlk / hac% 0.03’lük bir konsantrasyonunun olduu bulunmutur.
Etil oleat 150 ° C’de 1 saat stlarak sterilize edilebilir.
Uyumsuzluklar
Etil oleat, belirli kauçuk türlerini çözer ve dierlerinin imesine neden olur. Oksitleyici maddelerle de reaksiyona girebilir.
Düzenleyici statü
FDA Inactive Ingredients Database’e (transdermal hazrlk) dahildir. Birleik Krallk’ta ruhsatl parenteral (kas içi enjeksiyon) ve parenteral olmayan (transdermal bantlar) ilaçlara dahildir. Kanada’da Kabul Edilebilir Tbbi Olmayan Bileenler Listesinde yer almaktadr.