Ethyl Oleate

Product Name:

ETHYL OLEATE

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

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.

Preparation Products

Oleyl alcohol-->coconut oil alcohol acylamide

Raw materials

Etanol-->Calcium chloride-->cis-9-Octadecenoic acid