γ-Linolenic Acid Ethyl Ester Property

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

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

γ-Linolenic Acid Ethyl Ester Chemical Properties,Usage,Production

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.