31450-14-3

Basic information

• Product Name: GAMMA-LINOLENIC ACID ETHYL ESTER
• Synonyms: 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
• CAS NO: 31450-14-3
• Molecular Formula: C20H34O2
• Molecular Weight: 306.48
• Mol File: 31450-14-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 390.575oC at 760 mmHg
• Flash Point: 100.751oC
• Appearance: /liquid
• Density: 0.894g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: GAMMA-LINOLENIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: GAMMA-LINOLENIC ACID ETHYL ESTER(31450-14-3)
• EPA Substance Registry System: GAMMA-LINOLENIC ACID ETHYL ESTER(31450-14-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 31450-14-3(Hazardous Substances Data)

Usage

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).

InChI:InChI=1/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-

Upstream product

• 847019-77-6 BGC-20-0134 
• 64-17-5 ethanol 
• 959510-75-9 cis-6,cis-9-octadecadienoic acid ethyl ester 

Relevant articles and documents

Fatty acid desaturation and elongation reactions of trichoderma sp. 1-OH-2-3

The fatty acid desaturation and elongation reactions catalyzed by Trichoderma sp. 1-OH-2-3 were investigated. This strain converted palmitic acid (16:0) mainly to stearic acid (18:0), and further to oleic acid (c9-18:1), linoleic acid (c9,c12-18:2), and α-linolenic acid (c9,c12,c15-18:3) through elongation, and Δ9, Δ12, and Δ15 desaturation reactions, respectively. Palmitoleic acid (c9-16:1) and cis-9,cis-12- hexadecadienoic acid were also produced from 16:0 by the strain. This strain converted n-tridecanoic acid (13:0) to cis-9-heptadecenoic acid and further to cis-9,cis-12-heptadecadienoic acid through elongation, and Δ9 and Δ12 desaturation reactions, respectively. trans-Vaccenic acid (t11-18:1) and trans-12-octadecenoic acid (t12-18:1) were desaturated by the strain through Δ9 desaturation. The products derived from t11-18:1 were identified as the conjugated linoleic acids (CLAs) of cis-9,trans-11-octadecadienoic acid and trans-9,trans-11-octadecadienoic acid. The product derived from t12-18:1 was identified as cis-9,trans-12-octadecadienoic acid. cis-6,cis-9-Octadecadienoic acid was desaturated to cis-6,cis-9,cis-12-octadecatrienoic acid by this strain through Δ12 desaturation. The broad substrate specificity of the elongation, and Δ9 and Δ12 desaturation reactions of the strain is useful for fatty acid biotransformation.