γ-Linolenic Acid Ethyl Ester Chemical Properties

Boiling point:

390.6±31.0 °C(Predicted)

Density 

0.893±0.06 g/cm3(Predicted)

storage temp. 

−20°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

liquid

color 

Colourless

Stability:

Light Sensitive

InChI

InChI=1S/C20H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h8-9,11-12,14-15H,3-7,10,13,16-19H2,1-2H3/b9-8-,12-11-,15-14-

InChIKey

MJLYTDAIYLGSRZ-ORZIMQNZSA-N

SMILES

C(OCC)(=O)CCCC/C=C\C/C=C\C/C=C\CCCCC

LogP

7.562 (est)

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

γ-Linolenic Acid Ethyl Ester Usage And Synthesis

Description

γ-Linolenic acid (GLA) is an ω-6 fatty acid which can be elongated to arachidonic acid for endogenous eicosanoid synthesis. It is a weak leukotriene B₄ (LTB₄) receptor antagonist, inhibiting [³H]-LTB₄ binding to porcine neutrophil membranes with a K_i value of 1 μM. GLA produces 53% inhibition at a 1 mg/kg dose in an in vivo model of LTB₄-induced bronchoconstriction. GLA ethyl ester is an esterified version of the free acid which is less water soluble but more amenable for the formulation of GLA-containing diets.

Uses

γ-Linolenic Acid Ethyl Ester is used in biological studies for neoplasm inhibition of cultured carcinoma cells of human breast. This analog is also used in the evaluation of hypocholesterolemic activity in rats by comparing it with γ-Linolenic Acid (L467660).

Definition

ChEBI: Gamma-Linolenic acid ethyl ester is a long-chain fatty acid ethyl ester.

Purification Methods

To highly purify γ-linolenic acid (GLA) from microbial lipids, various types of zeolites were investigated in a fixed-bed column system, where a two-step desoprtion operation mode was found to be superior in selective separation of GLA. By this system, GLA ethyl ester of 98 mol% purity was obtained from a mixture of various polysaturated and unsaturated fatty acid esters using cesium Y and methyl-, dimethyl- and ethylammonium Y zeolites^[1].

References

[1] MAKOTO ARAI Hisashi M Hideki Fukuda. Selective separation of γ-linolenic acid ethyl ester using y-zeolite[J]. Journal of Fermentation Technology, 1987. DOI:10.1016/0385-6380(87)90118-X.

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