γ-Linolenic Acid Ethyl Ester

γ-Linolenic Acid Ethyl Ester Structure
CAS No.
31450-14-3
Chemical Name:
γ-Linolenic Acid Ethyl Ester
Synonyms
Ethyl linolenate gamma;Ethyl gamma-linolenate;Ethyl gamma-linolenic acid;GAMMA-LINOLENIC ACID ETHYL ESTER;Ethyl Gamma-Linolenic Acid(C18:3);Gamma Linolenic Acid Ethyl Ester (90%);Ethyl 6(Z),9(Z),12(Z)-octadecatrienoate;6,9,12-OCTADECATRIENOIC ACID ETHYL ESTER;Gamma Linolenic acid ethyl ester (GLA-EE);Ethyl linolenate gamma@10 mg/mL in Hexane
CBNumber:
CB5229451
Molecular Formula:
C20H34O2
Molecular Weight:
306.48
MOL File:
31450-14-3.mol
Modify Date:
2024/5/14 14:33:17

γ-Linolenic Acid Ethyl Ester 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

Risk and Safety Statements

Symbol(GHS) 
GHS02,GHS07
Signal word  Danger
Hazard statements  H225-H319
Precautionary statements  P210-P233-P240-P241-P242-P243-P264-P280-P303+P361+P353-P305+P351+P338-P337+P313-P370+P378-P403+P235-P501
WGK Germany  3
NFPA 704
3
2 0

γ-Linolenic Acid Ethyl Ester Chemical Properties,Uses,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 Ki 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).

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.

γ-Linolenic Acid Ethyl Ester Preparation Products And Raw materials

Raw materials

Preparation Products

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6,9,12-OCTADECATRIENOIC ACID ETHYL ESTER GAMMA-LINOLENIC ACID ETHYL ESTER DELTA 6 CIS 9 CIS 12 CIS OCTADECATRIENOIC ACID ETHYL ESTER 6,9,12-Octadecatrienoic acid, ethyl ester, (6Z,9Z,12Z)- γ-Linolenic acid ethyl ester, 6,9,12-Octadecatrienoic acid ethyl ester Ethyl linolenate gamma (6Z,9Z,12Z)-6,9,12-Octadecatrienoic acid ethyl ester Ethyl gamma-linolenate Ethyl gamma-linolenic acid Ethyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate Gamma Linolenic Acid Ethyl Ester (90%) Gamma Linolenic acid ethyl ester (GLA-EE) Ethyl linolenate gamma@10 mg/mL in Hexane cis-6,cis-9,cis-12 Octadecadienoic acid ethyl ester Ethyl Gamma-Linolenic Acid(C18:3) (6Z,9Z,12Z)-ethyl octadeca-6,9,12-trienoate Ethyl 6(Z),9(Z),12(Z)-octadecatrienoate Ethyl (6Z,9Z,12Z)-6,9,12- octadecatrienoic acid 31450-14-3 Biochemicals and Reagents BioChemical Fatty Acids Ethyl Ester Esters Lipids Unsaturated fatty acids and derivatives