ETHYL OLEATE
Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol.
Ethyl oleate is a colorless oil although degraded samples can appear yellow.
Ethyl oleate 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.
Ethyl oleate, also known as ethyl oleic acid, belongs to the class of organic compounds known as fatty acid esters.
Oleic acid ethyl ester is a neutral, more lipid-soluble form of oleic acid.
Ethyl oleate is a fatty acid ester used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.
In vivo studies have demonstrated that Ethyl oleate and other fatty acid esters are also rapidly hydrolyzed to ethanol and free fatty acid.
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 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 formula: C20H38O2
Molar mass: 310.522 g·mol−1
Appearance: Colorless to light yellow liquid
Density: 0.87 g/cm3
Melting point: −32 °C (−26 °F; 241 K)
Boiling point: 216–218 °C (421–424 °F; 489–491 K)
Solubility in water: Insoluble
Flash point: > 113 °C
Odor: Delicate fragrance with a faint floral note
Use Classification
Food additives -> Flavoring Agents
Flavoring Agents -> JECFA Flavorings Index
Cosmetics -> Emollient
Use: Ethyl oleate is an excellent solvent and good moisturiser. It is suitable for skin care, hair care and colour cosmetics.
Pharma -> Solvent
Ethyl Oleate (Oleic acid ethyl ester) is a fatty acid ester formed by the condensation of oleic acid and ethanol, usually used as a solvent for pharmaceutical drug preparations
Applications in Pharmaceutical Formulation or Technology
Ethyl oleate is primarily used as a vehicle in certain parenteral preparations intended for intramuscular administration.
Ethyl oleate has also been used as a solvent for drugs formulated as biodegradable capsules for subdermal implantation and in the preparation of microemulsions containing cyclosporin and 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.
Description
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.
Industry Uses of Ethyl oleate:
Lubricants and lubricant additives
Plating agents and surface treating agents
Industry Processing Sectors
Paint and coating manufacturing
Petroleum lubricating oil and grease manufacturing
Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. It is a colorless to pale yellow liquid. Ethyl oleate is produced by the body during ethanol poisoning.
Ethyl oleate is used as a solvent for pharmaceutical preparations containing lipophilic substances such as steroids. It is also used 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 then 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 Add To Food for Human Consumption”, 21CFR172.515.
Ethyl oleate has been identified as a primer pheromone in honey bees.
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 implying FAEEs such as ethyl oleate as the toxic mediators of ethanol in the body (pancreas, liver, heart and brain). One speculation is that ethyl oleate may be the toxic mediator of alcohol in fetal alcohol syndrome. The oral intake of ethyl oleate has been carefully studied and due to its rapid breakdown in the digestive tract, it appears to be safe for oral intake. Ethyl oleate is not currently approved by the U.S. Food and Drug Administration for injectable use.
Oleate Esters Market, By Product
• Methyl Oleate
• Ethyl Oleate
• Butyl Oleate
• Others
Oleate Esters Market, By Application
• Agrochemical
• Cosmetics
• Lubricant
• Absorbent
Use and occurrence
Additive
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.
Ethyl oleate is regulated as a food additive in the U.S. by the Food and Drug Administration.
Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.
Ethyl oleate also finds use as a lubricant and a plasticizer.
Ethyl oleate 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.
Ethyl oleate has a role as a plant metabolite and an acaricide.
Ethyl oleate derives from an oleic acid.
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 a fatty acid ester formed by the condensation of oleic acid and ethanol.
Ethyl oleate is the liquid lipid component in nanostructured lipid carriers (NLCs).
NLC is a promising vehicle for oral trans-Ferulic acid (TFA) administration.
Occurrence
Ethyl oleate 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
Ethyl oleate is a natural product found in Aristolochia fontanesii, Portulaca oleracea, and other organisms with data available.
Medical aspects
Ethyl oleate is produced by the body during ethanol intoxication.
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).
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 a kind of fatty acid ester, and ethyl oleate is mainly used in lubricant, water repellent agent, the tough agent of resin, tensio-active agent, pharmaceutical auxiliary material, the softening agent of plastics, the preparation of ointment base and other organic chemicals, is also used as spices.
The acquisition of current ethyl oleate is mainly by the way of chemosynthesis, namely obtained or carry out transesterification reaction by another kind of oleic acid ester together with ethanol and obtain through esterification by ethanol and oleic acid.
Overview
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
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
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
Ethyl oleate has a faint, floral note.
Chemical Properties
clear pale yellow oily liquid
Chemical Properties
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.
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.
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.
Aroma threshold values
Detection: 130 to 610 ppm
Pharmaceutical Applications
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
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.
Ethyl oleate
111-62-6
ethyl (Z)-octadec-9-enoate
Ethyl cis-9-octadecenoate
Oleic acid, ethyl ester
Oleic acid ethyl ester
9-Octadecenoic acid (Z)-, ethyl ester
Ethyl oleate [NF]
UNII-Z2Z439864Y
MFCD00009579
CHEBI:84940
(Z)-9-Octadecenoic acid ethyl ester
Ethyl oleate (NF)
Z2Z439864Y
ethyl octadec-9-enoate
9-Octadecenoic acid (9Z)-, ethyl ester
Ethyl Z-9-octadecenoate
ETHYLOLEATE
Ethyl oleate (natural)
Ethylis oleas
FEMA No. 2450
Ethyl 9-octadecenoate, (Z)-
Oleic acid ethyl
85049-36-1
Ethyl Oleate, NF
EINECS 203-889-5
NSC 229428
Ethyl oleate, 98%
Oleic acid-ethyl ester
AI3-00657
ethyl (9Z)-octadecenoate
SCHEMBL2797
DSSTox_CID_27633
DSSTox_RID_82464
DSSTox_GSID_47633
ethyl (9Z)-octadec-9-enoate
Synonyms:
crodamol EO
ethyl (9Z)-octadec-9-enoate
ethyl (Z)-9-octadecenoate
ethyl (Z)-octadec-9-enoate
(Z)- ethyl 9-octadecenoate
ethyl cis-9-octadecenoate
ethyl oleate FCC
ethyl oleate N.F.
ethyl oleate natural
ethyl oleate naturel
ethyl oleate synthetic
ethyloleate
9- octadecenoic acid (Z)-, ethyl ester
(9Z)-9- octadecenoic acid ethyl ester
(Z)-9- octadecenoic acid ethyl ester
9- octadecenoic acid, ethyl ester, (9Z)-
(Z)- oleic acid ethyl ester
(Z)- oleic acid, ethyl ester
(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
ethyl oleate 95%
Ethyl oleate (NF)
ethyl oleate food grade
ethyl oleate(c18:1)
ethyl oleate, ??? 95.0%
ethyl oleate, 98%, mixture of homologeous fatty acid esters
ethyl oleate, tech. 70%
Ethyl oleate, USP grade
Ethyl Z-9-octadecenoate
ethyloleate
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:84940
Jsp000872
oleic acid ethyl ester,98%
Oleic Acid ethyl ester|9Z-octadecenoic acid, ethyl ester
tech., 70%
Ethyl oleate acts emollient, solvent and glossing agent.
Elhyl oleate is a natural origin ingredient according to ISO 16128.
Ethyl oleate is used in makeup, skincare and vegetal products.
Claims
Emollients
Solvents & Carriers
glossy/ultra-glossy
vegetal origin
Ethyl Oleate (High Oleic- No Methyl)
Product Description
Ethyl Oleate is a fatty ester derived from natural oils that has excellent solvency properties, is readily biodegradable and has low toxicity characteristics.
COMMON AND OTHER NAMES: Ethyl Oleate, Ethylated Seed Oil
CHEMICAL COMPOSITION: Ethyl Esters of High Oleic Oil
CHARACTERISTICS: Ethyl Oleate is a pale yellow oily liquid with a pleasant fatty ester odour.
Product Performance
Ethyl Oleate as a fatty ester product has excellent solvency powers and hence can easily be formulated with a wide range of oils, surfactants and oil soluble materials.
Based on High Oleic Oil, its fatty acids are predominantly oleic (approx. 80%) which results in liquid product which has superior oxidative stability when compared with other fatty esters.
Ethyl Oleate is nonvolatile and is safe to handle.
Natural or synthetic antioxidants can be added to Ethyl Oleate on request which will further increase its oxidative stability.
Product Usage
Ethyl Oleate contains less than 0.1% of methyl esters enabling the use of a fatty ester where methyl esters may be undesirable.
Key Points
Excellent solvency properties can provide formulators with replacements for petroleum derived solvents.
High lubricity and low volatility characteristics can provide the properties required of oily bases in specialised lubricant products.
Low Methyl Ester content enables use where methyl esters are undesirable.
Oxidative stability ensures a longer life or a wider range of conditions before any natural deterioration is observed.
When stored indoors at temperatures below 40ºC and in closed original containers, this product can be stored for at least 1 year.
HEALTH, SAFETY & ENVIRONMENT
Ethyl Oleate is nontoxic, biodegradable and not classified as a dangerous good.
Low toxicity means that it poses a low health and safety risk for users.
Readily Biodegradable means that it will have a low environmental impact.
According to experience this product is considered to be harmless to health if used in the correct manner.
Skin and eye contact should be avoided.
Ethyl Oleate used in many applications such as cosmetic, health, food, perfume, industrial, medical & beauty preparations. Ethyl Oleate can function as solvent, glossing agent and emollient. E
thyl oleate is used as a solvent for pharmaceutical preparations involving lipophilic substances.
It also finds use as a lubricant and a plasticizer.
It is used by compounding pharmacies as a vehicle for enhanced intramuscular compound delivery.
Typical Properties
Boiling point 205–2088C (some decomposition)
Flash point 175.38C
Freezing point 328C
Moisture content At 208C and 52% relative humidity, the
equilibrium moisture content of ethyl oleate is 0.08%.
Solubility Miscible with chloroform, ethanol (95%), ether, fixed oils, liquid paraffin, and most other organic solvents; practically insoluble in water.
Surface tension 32.3 mN/m (32.3 dynes/cm) at 258C(9)
Viscosity (dynamic) 3.9 mPa s (3.9 cP) at 258C(9)
Viscosity (kinematic) 0.046 mm2/s (4.6 cSt) at 258C(9)
Ethyl oleate is primarily used as a vehicle in parenteral applications such as intramuscular drug administration.
Recommended as a solvent for many lipophilic drugs, ethyl oleate is less viscous than certain other nonaqueous solvents such as fixed oils, and is more rapidly absorbed by body tissues.
Stability and Storage Conditions
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 58C, 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 1508C for 1 hour.
Incompatibilities
Ethyl oleate dissolves certain types of rubber and causes others to swell.
It may also react with oxidizing agents.
Method of Manufacture
Ethyl oleate is prepared by the reaction of ethanol with oleoyl chloride in the presence of a suitable hydrogen chloride acceptor.
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.
Ethyl oleate by ATAMAN KIMYA acts as an emollient, spreading agent, moisturiser and solvent.
Ethyl oleate imparts gloss, shine and vibrancy.
Ethyl oleate is preservative free and readily biodegradable.
Ethyl oleate is used in skin care, hair styling, rinse off conditioners, hair coloring, shaving/ hair removal, body care, antiperspirants/deodorants, face/ neck skin care, eye color and sun protection formulations.
Claims
Emollients > Esters
Solvents & Carriers > Esters
shine / radiance
glossy/ultra-glossy
spreading