Oleic acid ethyl ester

Structural formula
General
Surname	Oleic acid ethyl ester
other names	Ethyl oleate; ethyl cis-9-octadecenoate;
Molecular formula	C 20 H 38 O 2
Brief description	colorless to yellowish liquid
External identifiers / databases
EC number	203-889-5
ECHA InfoCard	100.003.536
PubChem	5363269
ChemSpider	4515636
Wikidata	Q6578680
properties
Molar mass	310.52 g mol −1
Physical state	liquid
density	0.87 g cm −3
Melting point	−32 ° C
boiling point	168 ° C (1.3 hPa)
solubility	practically insoluble in water; soluble in chloroform ; soluble in ethanol and diethyl ether ;
Refractive index	1.451 (20 ° C)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , rabbit / mouse , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Oleic acid ethyl ester is a chemical compound from the group of fatty acid esters .

Occurrence

Ethyl oleic acid has been found in cocoa , buckwheat , elder and babaco fruits ( Carica pentagona Heilborn).

Extraction and presentation

Ethyl oleic ester can be obtained by the direct esterification of oleic acid with ethyl alcohol in the presence of hydrogen chloride , Twitchell's reagent, or chlorosulfonic acid.

properties

Ethyl oleic ester is a flammable, difficult to ignite, viscous, colorless to yellowish liquid that is practically insoluble in water.

use

Ethyl oleic ester is used to prepare the oily phase of the self-microemulsifying drug delivery system (SMEDDS) for tacrolimus (Tac). The compound is also used as a flavoring agent.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on oleic acid ethyl ester in the GESTIS substance database of the IFA , accessed on January 1, 2019(JavaScript required) .
↑ ^a ^b ^c data sheet Ethyl oleate, 98% from Sigma-Aldrich , accessed on January 1, 2019 ( PDF ).
↑ ^a ^b ^c ^d George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . CRC Press, 2004, ISBN 978-1-4200-3787-6 , pp. 618 ( limited preview in Google Book search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on oleic acid ethyl ester in the GESTIS substance database of the IFA , accessed on January 1, 2019(JavaScript required) .

[Sigma-2] ta sheet Ethyl oleate, 98% from Sigma-Aldrich , accessed on January 1, 2019 ( PDF ).

[George_A._Burdock-3] George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . CRC Press, 2004, ISBN 978-1-4200-3787-6 , pp. 618 ( limited preview in Google Book search).