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

GAMMA-LINOLENIC ACID ETHYL ESTER is an esterified version of GAMMA-LINOLENIC ACID (GLA), an ω-6 fatty acid that 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. The ethyl ester form is less water-soluble but more suitable for formulating GLA-containing diets.

Uses

Used in Pharmaceutical Industry:
GAMMA-LINOLENIC ACID ETHYL ESTER is used as a pharmaceutical agent for neoplasm inhibition of cultured carcinoma cells of human breast. It plays a crucial role in biological studies focused on cancer research and treatment.
Used in Nutritional Research:
GAMMA-LINOLENIC ACID ETHYL ESTER is used as a nutritional supplement in the evaluation of hypocholesterolemic activity in rats, where it is compared with GAMMA-LINOLENIC ACID (L467660) to determine its effectiveness in managing cholesterol levels.

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.