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CAS NO:111-62-6
EC NO:285-206-0
Oleic Acid Ethyl Ester is a long-chain fatty acid ethyl ester resulting from the formal condensation of the carboxy group of oleic acid with the hydroxy group of ethanol.
Oleic Acid Ethyl Ester has a role as a plant metabolite and an acaricide.
Oleic Acid Ethyl Ester derives from an oleic acid.
Oleic Acid Ethyl Ester is a natural product found in Azadirachta indica, Cinnamomum camphora, and other organisms with data available.
Oleic Acid Ethyl Ester is a fatty acid ester formed by the condensation of oleic acid and ethanol.
Oleic Acid Ethyl Ester is a colorless oil although degraded samples can appear yellow.
Use and occurrence
Oleic Acid Ethyl Ester 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.
Oleic Acid Ethyl Ester is regulated as a food additive in the U.S. by the Food and Drug Administration.
Oleic Acid Ethyl Ester is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.
Oleic Acid Ethyl Ester 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.
Occurrence
Oleic Acid Ethyl Ester has been identified as a primer pheromone in honeybees.
Precursor to other chemicals
By the process of ethenolysis, the methyl ester of oleic acid, converts to 1-decene and methyl 9-decenoate:
CH3(CH2)7CH=CH(CH2)7CO2Me + CH2=CH2 → CH3(CH2)7CH=CH2 + MeO2C(CH2)7CH=CH2
Medical aspects
Oleic Acid Ethyl Ester is produced by the body during ethanol intoxication.
Oleic Acid Ethyl Ester 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).
Oleic Acid Ethyl Ester 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.
Properties:
Chemical formula: C20H38O2
Molar mass: 310.522 g·mol−1
Appearance: Colorless to light yellow liquid
Density: 0.87 g/cm3[1]
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
Industry Uses:
-Lubricants and lubricant additives
-Plating agents and surface treating agents
Industry Processing Sectors:
-Paint and coating manufacturing
-Petroleum lubricating oil and grease manufacturing
Oleic Acid ethyl ester is a neutral, more lipid-soluble form of oleic acid.
Oleic Acid ethyl ester is a monounsaturated fatty acid and is one of the major components of membrane phospholipids.
Oleic Acid ethyl ester contributes about 17% of the total fatty acids esterified to phosphatidylcholine in porcine platelets. As the free acid, it inhibits collagen-stimulated platelet aggregation by approximately 90% at a concentration of 10 μg/ml.
Oleic Acid ethyl ester inhibits fMLF-induced neutrophil aggregation and degranulation by 55% and 68%, respectively, at 5 μM .
Oleic Acid ethyl ester, whether applied extracellularly (EC50= ~60 μM) to human platelets or released from membrane phospholipids, causes an increase in intracellular calcium levels.
Uses
Pharmaceutical Industry
Oleic Acid ethyl ester 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
Oleic Acid ethyl ester is used in the transport industry as a lubricant and as a plasticiser.
Oleic Acid ethyl ester is also used as a planting agent and for treating surfaces.
Food Industry
Oleic Acid ethyl ester is used as a food additive and is regulated by the Food and Drug Administration.
Oleic Acid ethyl ester is also used as a flavouring agent in food.
Description
Oleic Acid ethyl ester is a fatty acid ester formed by the condensation of oleic acid and ethanol.
Oleic Acid ethyl ester is a colorless to light yellow liquid.
Oleic Acid ethyl ester is produced by the body during ethanol intoxication.
Oleic Acid ethyl ester is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.
Oleic Acid ethyl ester also finds use as a lubricant and a plasticizer.
Oleic Acid ethyl ester 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.
Oleic Acid ethyl ester has been identified as a primer pheromone in honeybees.
Oleic Acid ethyl ester is one of the fatty acid ethyl esters (FAEE) that is formed in the body after ingestion of ethanol.
Oleic Acid ethyl ester 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.
Chemical Properties
clear pale yellow oily liquid
Chemical Properties
Oleic Acid ethyl ester 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.
Oleic Acid ethyl ester 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.
Chemical Properties
Oleic Acid ethyl ester has a faint, floral note.
Occurrence
Reported found in cocoa, buckwheat, elderberry and babaco fruit (Carica pentagona Heilborn).
Preparation
By direct esterification of oleic acid with ethyl alcohol in the presence of HCl at the boil; in the presence of Twitchell’s reagent or chlorosulfonic acid.
Definition
ChEBI: A long-chain fatty acid ethyl ester resulting from the formal condensation of the carboxy group of oleic acid with the hydroxy group of ethanol.
Pharmaceutical Applications
Oleic Acid ethyl ester is primarily used as a vehicle in certain parenteral preparations intended for intramuscular administration.
Oleic Acid ethyl ester 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.
Oleic Acid ethyl ester has been used in topical gel formulations, and in self-microemulsifying drug delivery systems for oral administration.
Oleic Acid ethyl ester is a suitable solvent for steroids and other lipophilic drugs.
Oleic Acid ethyl esters 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.
Oleic Acid ethyl ester has also been evaluated as a vehicle for subcutaneous injection.
IUPAC names:
9-Octadecenoic acid (9Z)-, ethyl ester
ethyl (9Z)-octadec-9-enoate
ethyl (Z)-octadec-9-enoate
ethyl octadec-9-enoate
ethyl oleate
SYNONYMS:
(9Z)-9-Octadécénoate d'éthyle [French] [ACD/IUPAC Name]
(Z)-9-Octadecenoic Acid Ethyl Ester
111-62-6 [RN]
203-889-5 [EINECS]
2450
9-Octadecenoic acid, ethyl ester, (9Z)- [ACD/Index Name]
9Z-octadecenoic acid, ethyl ester
Ethyl (9Z)-9-octadecenoate [ACD/IUPAC Name]
Ethyl (9Z)-octadec-9-enoate
Ethyl cis-9-octadecenoate
Ethyl oleate
Ethyl-(9Z)-9-octadecenoat [German] [ACD/IUPAC Name]
Ethylis oleas
MFCD00009579 [MDL number]
Oleic Acid ethyl ester
Oleic acid, ethyl ester
RG3715000
(9Z)-9-Octadecenoic acid ethyl ester
(Z)-octadec-9-enoic acid ethyl ester
[111-62-6]
85049-36-1 [RN]
9-Octadecenoic acid (Z)-, ethyl ester
CIS-9-OCTADECENYL ACETATE
D04090
Elhyl oleate
ethyl (9Z)octadec-9-enoate
ethyl (9Z)-octadecenoate
ethyl (Z)-octadec-9-enoate
