Methyl γ-linolenate

Names

[ Name ]:
Methyl γ-linolenate

[Synonym ]:
6,9,12-Octadecatrienoic acid, methyl ester, (6Z,9Z,12Z)-
6,9,12-Octadecatrienoic acid, methyl ester, (Z,Z,Z)-
γ-LINOLENIC ACID METHYL ESTER
Methyl (6Z,9Z,12Z)-6,9,12-octadecatrienoate
Methyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate
MFCD00010455
Methyl g-linolenate

Biological Activity

[Description]:

γ-Linolenic Acid methyl ester (Methyl GLA) is an esterified version of γ-Linolenic Acid (GLA), which is an ω-6 fatty acid, serves as melanoma cell proliferation inhibitors. γ-Linolenic Acid methyl ester inhibits ADP-induced blood platelet aggregation and induces apoptosis[1][2][3][4][5].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

[In Vitro]

γ-Linolenic Acid methyl ester (1-4 μg/mL; 72 h) induces apoptosis in vitro A-549 lung cancer cell lines using SRB assay. However GLA is due to its action at the gene/oncogene level and by altering BCl-2 expression[1]. Apoptosis Analysis[1] Cell Line: A-549 lung cancer cell line Concentration: 1, 2, 3, and 4 μg/mL Incubation Time: 72 hours; observed at 24 h, 48 h, and 72 h Result: Showed cytotoxicity potentially due to the induction of apoptosis of tumor cells by augmenting free radical generation only in the tumor cells but not normal cells.

[In Vivo]

γ-Linolenic Acid methyl ester decreases the hepatic triglycerides and histological evidence of fatty liver induced by EtOH[2]. γ-Linolenic Acid methyl ester could significantly decrease levels of plasma total cholesterol (TC), triglycerides (TG), low density lipoprotein cholesterol (LDL-C), MDA, atherosclerosis index (AI) and liver TC, MDA, and increase levels of high density lipoprotein cholesterol (HDL-C) in both normal and hyperlipidemic rats[3]. Animal Model: Hepatic pathol rats model induced by EtOH (male Sprague-Dawley rats, 250-300 g)[2] Dosage: 90 mL, 50-60 mL Administration: Intraperitoneal injection; once daily; administrated 90 mL during day 1-5 and day 9, 50-60 mL during day 6-8 Result: Decreased the hepatic triglycerides of 25.6 mg/g compared with saline (40.2 mg/g) or olive oil (42.8 mg/g) treatment. Decreased liver index (the ratio of liver weight and body wight) in hyperlipidemic rats, but had no significant effect in normal rats.

[References]

[1]. Jubie S, et al. Isolation of methyl gamma linolenate from Spirulina platensis using flash chromatography and its apoptosis inducing effect. BMC Complement Altern Med. 2015 Aug 4;15:263.

[2]. Segarnick DJ, et al. Gamma-linolenic acid inhibits the development of the ethanol-induced fatty liver. Prostaglandins Leukot Med. 1985 Mar;17(3):277-82.

[3]. Xiuqin K, et al. Studies on the hypolipidemic effects of gamma-linolenic acid methyl ester derived from Spirulina maxima[J]. Zhongguo hai Yang yao wu= Chinese Journal of Marine Drugs, 2003, 22(6): 30-34.

[4]. Williams, et al. Antithrombosis agent containing γ-linolenic acid or a functional derivative of it: Federal Republic of Germany, DE2749492[P]. 1978-05-11.

[5]. Hiyamuta, et al. Melanoma cell proliferation inhibitors containing γ-linolenic acid or its derivatives: Japan, JP2014141427[P]. 2014-08-07.

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
385.4±0.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₉H₃₂O₂

[ Molecular Weight ]:
292.456

[ Flash Point ]:
101.5±23.2 °C

[ Exact Mass ]:
292.240234

[ PSA ]:
26.30000

[ LogP ]:
7.03

[ Appearance of Characters ]:
Liquid

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.476

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H319

[ Precautionary Statements ]:
P210-P280-P305 + P351 + P338-P337 + P313-P403 + P235

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
F

[ Risk Phrases ]:
11

[ Safety Phrases ]:
16

[ RIDADR ]:
UN 1993 / PGIII

[ WGK Germany ]:
3

[ HS Code ]:
2916190090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2916190090

[ Summary ]:
2916190090 unsaturated acyclic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:6.5%。general tariff:30.0%

Articles

Weight regain after Roux-en-Y: a significant 20% complication related to PYY.

Nutrition 24 , 832-842, (2008)

Roux-en-Y gastric bypass (RYGB) produces rapid and dramatic weight loss in very heavy obese patients. Up to 20% cannot sustain their weight loss beyond 2 to 3 y after surgery.To identify putative etio...

Effect of long-term dietary supplementation of high-gamma-linolenic canola oil versus borage oil on growth, hematology, serum biochemistry, and N-6 fatty acid metabolism in rats.

J. Agric. Food Chem. 52 , 3960-3966, (2004)

Dietary supplementation of a high-gamma-linolenic acid canola oil (HGCO) containing approximately 36% (w/w) of gamma-linolenic acid (GLA, 18:3n-6) from the seeds of a genetically transformed canola st...

Gamma-linolenate reduces weight regain in formerly obese humans.

J. Nutr. 137 , 1430-1435, (2007)

The purpose of this study was to determine whether gamma-linolenate (GLA) supplementation would suppress weight regain following major weight loss. Fifty formerly obese humans were randomized into a d...

Related Compounds

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