GAMMA-LINOLENIC ACID METHYL ESTER Chemical Properties

Boiling point:

162 °C0.5 mm Hg(lit.)

Density 

0.9019 g/cm3

refractive index 

n20/D 1.476(lit.)

Flash point:

62 °C

storage temp. 

-20°C

solubility 

≤100mg/ml in DMSO;100mg/ml in dimethyl formamide

form 

Liquid

Safety Information

Hazard Codes 

F

Risk Statements 

11

Safety Statements 

16

RIDADR 

UN 1993 / PGIII

WGK Germany 

3

F 

8-10-23

MSDS

• Language:English Provider:SigmaAldrich

GAMMA-LINOLENIC ACID METHYL ESTER Usage And Synthesis

Description

Polyunsaturated fatty acids (PUFAs) are essential nutrients that show distinct deficiency syndromes when not present in adequate amounts in the diet. γ-Linolenic Acid methyl ester (Methyl GLA) is an esterified version of the free acid which is less water soluble but more amenable for the formulation of GLA-containing diets and dietary supplements. 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 of 1 μM. GLA produces 53% inhibition at a 1 mg/kg dose in an in vivo model of LTB₄-induced bronchoconstriction.

Uses

Methyl γ-linolenate may be used as an analytical standard for the determination of aldehydes such as pentanal and hexanal via peroxidation, further analyzed by gas chromatography technique. It may also be used as an analytical reference standard for the quantification of the analyte in serum lipid extract and Arthrospira (Spirulina) platensis using the gas-chromatography technique.

Definition

ChEBI: Methyl gamma-linolenate is a fatty acid methyl ester obtained from the formal condensation of methanol and gamma-linolenic acid. It has a role as a bacterial metabolite, an apoptosis inducer, an antineoplastic agent and an antibacterial agent. It is functionally related to a gamma-linolenic acid.

Biochem/physiol Actions

Methyl γ-linolenate (C18:6,9,12) differs from methyl α-linolenate (C18:9,12,15) in the positions of the double bonds. Methyl γ-linolenate may be used in nutritional studies regarding weight regain and as a possible tumor suppression agent.

in vitro

γ-linolenic acid methyl ester is an esterified version of the free acid which is less water soluble but more amenable for the formulation of gla-containing diets and dietary supplements. gla was identified as an ω-6 fatty acid which could be elongated to arachidonic acid for endogenous eicosanoid synthesis. gla was found to be a weak leukotriene b4 (ltb4) receptor antagonist, which was able to inhibit [3h]-ltb4 binding to porcine neutrophil membranes with a ki of 1 μm [1].

in vivo

in an in-vivo model of ltb4-induced bronchoconstriction, ricinelaidic acid andγ-linolenic acid methyl ester at a 1 mg/kg i.v. dose could result in 46% and 53% inhibition, respectively, indicating that essential fatty acids are ltb4 receptor antagonists, which may account in part for their reported anti-inflammatory activities [1].

References

[1] yagaloff, k. a.,franco, l.,simko, b., et al. essential fatty acids are antagonists of the leukotriene b4 receptor. prostaglandins, leukotrienes and essential fatty acids 52, 293-297 (1995).

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