Gamma Linoleic Acid - CAS 506-26-3
Catalog number: B0005-293430
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C18H30O2
Molecular Weight:
278.43
COA:
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Chemical Family:
Other Natural Compounds
Description:
Gamma Linoleic acid is an omega-6 fatty acid generated from linoleic acid. It is converted to dihomo-gamma-linolenic acid, which is a biosynthetic precursor of monoenoic prostaglandins such as PGE1.
Nutritional supplement in health care products.
Purity:
95%
Synonyms:
gamma-Linolenicacid; GAMOLENICACID; (6Z,9Z,12Z)-octadeca-6,9,12-trienoicacid; 506-26-3; Ligla; (Z,Z,Z)-6,9,12-Octadecatrienoicacid
Storage:
-20ºC
MSDS:
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Application:
Ingredient of health care products.
Quantity:
Data not available, please inquire.
Boiling Point:
379.5ºC at 760mmHg
Density:
0.924g/cm3
InChIKey:
VZCCETWTMQHEPK-QNEBEIHSSA-N
InChI:
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-
Canonical SMILES:
CCCCCC=CCC=CCC=CCCCCC(=O)O
1.[The importance of γ-linolenic acid in the prevention and treatment].
Białek M1, Rutkowska J1. Postepy Hig Med Dosw (Online). 2015 Jul 27;69:892-904.
The etiology of diet-related disorders is closely associated with dietary factors. A special role is attributed to intake of fat and fatty acid profile, both quantitative and qualitative. For prevention and treatment of the abovementioned diseases a proper supply of unsaturated fatty acids plays a significant role, because of their particular importance to health. γ-Linolenic acid (GLA), with three double bonds in the carbon chain, also known as all-cis 6,9,12-octadecatrienoic acid, belongs to the n-6 family of fatty acids. It plays biologically important functions in the human body, such as being a substrate for eicosanoids synthesis, involvement in the transport and oxidation of cholesterol, and being one of the components of lipid membrane. Its inadequate dietary intake or impaired formation is the cause of many inflammatory and degenerative diseases. A rich source of this fatty acid is vegetable oils, until recently used mainly in folk medicine.
2.Gamma linolenic acid: an antiinflammatory omega-6 fatty acid.
Kapoor R1, Huang YS. Curr Pharm Biotechnol. 2006 Dec;7(6):531-4.
Inflammation plays an important role in health and disease. Most of the chronic diseases of modern society, including cancer, diabetes, heart disease, arthritis, Alzheimer's disease, etc. have inflammatory component. At the same time, the link between diet and disease is also being recognized. Amongst dietary constituents, fat has gained most recognition in affecting health. Saturated and trans fatty acids have been implicated in obesity, heart disease, diabetes and cancer while polyunsaturated fatty acids (PUFAs) generally have a positive effect on health. The PUFAs of omega-3 and omega-6 series play a significant role in health and disease by generating potent modulatory molecules for inflammatory responses, including eicosanoids (prostaglandins, and leukotrienes), and cytokines (interleukins) and affecting the gene expression of various bioactive molecules. Gamma linolenic acid (GLA, all cis 6, 9, 12-Octadecatrienoic acid, C18:3, n-6), is produced in the body from linoleic acid (all cis 6,9-octadecadienoic acid), an essential fatty acid of omega-6 series by the enzyme delta-6-desaturase.
3.Activating omega-6 polyunsaturated fatty acids and inhibitory purine nucleotides are high affinity ligands for novel mitochondrial uncoupling proteins UCP2 and UCP3.
Zackova M1, Skobisová E, Urbánková E, Jezek P. J Biol Chem. 2003 Jun 6;278(23):20761-9. Epub 2003 Apr 1.
UCP2 (the lowest Km values: 20 and 29 microm, respectively) for omega-6 polyunsaturated FAs (PUFAs), all-cis-8,11,14-eicosatrienoic and all-cis-6,9,12-octadecatrienoic acids, which are also the most potent agonists of the nuclear PPARbeta receptor in the activation of UCP2 transcription. omega-3 PUFA, cis-5,8,11,14,17-eicosapentaenoic acid had lower affinity (Km, 50 microm), although as an omega-6 PUFA, arachidonic acid exhibited the same low affinity as lauric acid (Km, approximately 200 microm). These findings suggest a possible dual role of some PUFAs in activating both UCPn expression and uncoupling activity. UCP2 (UCP3)-dependent H+ translocation activated by all tested FAs was inhibited by purine nucleotides with apparent affinity to UCP2 (reciprocal Ki) decreasing in order: ADP > ATP approximately GTP > GDP >> AMP. Also [3H]GTP ([3H]ATP) binding to isolated Escherichia coli (Kd, approximately 5 microm) or yeast-expressed UCP2 (Kd, approximately 1.
4.Screening of microbial lipases and evalutaion of their potential to produce glycerides with high gamma linolenic acid concentration.
Fregolente PB1, Fregolente LV, Maciel MR, Carvalho PO. Braz J Microbiol. 2009 Oct;40(4):747-56. doi: 10.1590/S1517-83822009000400004. Epub 2009 Dec 1.
Gamma linolenic acid (GLA, 18:3, cis- 6,9,12- octadecatrienoic acid), an important compound in n- 6 eicosanoid family biosynthesis, occurs in the lipids of a few plant and microbial sources. This study focused on the screening of microbial strains with suitable lipase activity for enrichment of GLA by selective hydrolysis of the borage oil (21.6 % of GLA/total fatty acids). Firstly, 352 microrganisms were tested for their lipolytic capacity using screening techniques on agar plates containing borage oil, strains were then selected and screened for their activity (U/mg) using both submerged fermentation (SmF) and solid state fermentation (SSF). The rate of hydrolysis and the selective preference of these hydrolytic enzymes towards fatty acids, with a special focus on enrichment of GLA were studied and compared with those obtained by two commercially-available lipases. Only one of the lipases tested during this study displayed selectivity, discriminating the GLA during the hydrolysis reaction.
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CAS 506-26-3 Gamma Linoleic Acid

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