Natural Ethyl Oleate

Product Name:

Natural ethyl oleate

Synonyms:

(Z)-9-Octadecenoic acid ethyl ester;(Z)-9-Octadecenoicacidethylester;ethyl (Z)-octadec-9-enoate;Ethyl oleate, 75.0%(GC);9-Octadecenoicacid(Z)-,ethylester;oleic;OLEIC ACID ETHYL ESTER;FEMA 2450

CAS:

111-62-6

MF:

C20H38O2

MW:

310.51

EINECS:

203-889-5

Mol File:

111-62-6.mol

Melting point 

−32 °C(lit.)

Boiling point 

216-218 °C15 mm Hg

density 

0.87 g/mL at 25 °C(lit.)

FEMA 

2450 | ETHYL OLEATE

refractive index 

n20/D 1.451(lit.)

Fp 

>230 °F

storage temp. 

−20°C

solubility 

chloroform: soluble10%

form 

Oily Liquid

color 

Clear

Sensitive 

Light Sensitive

JECFA Number

345

Merck 

14,6828

BRN 

1727318

InChIKey

LVGKNOAMLMIIKO-VAWYXSNFSA-N

CAS DataBase Reference

111-62-6(CAS DataBase Reference)

NIST Chemistry Reference

9-Octadecenoic acid (Z)-, ethyl ester(111-62-6)

EPA Substance Registry System

Ethyl oleate (111-62-6)

Safety Statements 

23-24/25-22

WGK Germany 

2

RTECS 

RG3715000

F 

10-23

TSCA 

Yes

HS Code 

29161900

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

 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.