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gamma-Linolenic acid

gamma-Linolenic acid
gamma-Linolenic acid structure
CAS No.
506-26-3
Chemical Name:
gamma-Linolenic acid
Synonyms
C06426;Gamolenic;18:3(n-6);R- flax acid;gamolenic acid;γ-linolenicaci;G-LINOLENICACID;LINOLEIC ACID(P);r-linolenic acid;GAMMALINOLEICACID
CBNumber:
CB3238150
Molecular Formula:
C18H30O2
Formula Weight:
278.43
MOL File:
506-26-3.mol

gamma-Linolenic acid Properties

Melting point:
-12~-11℃
Boiling point:
379.5±11.0 °C(Predicted)
Density 
0.92
refractive index 
n20/D 1.471
Flash point:
110 °C
storage temp. 
-20°C
pka
4.74±0.10(Predicted)
form 
liquid
Merck 
14,5507
BRN 
1712253
InChIKey
VZCCETWTMQHEPK-QNEBEIHSSA-N
CAS DataBase Reference
506-26-3(CAS DataBase Reference)
FDA UNII
78YC2MAX4O
ATC code
D11AX02,D11AX52
NIST Chemistry Reference
Gamolenic acid(506-26-3)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  3
8-10-23
HS Code  29161500

gamma-Linolenic acid price More Price(32)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 62174 γ-Linolenic acid analyticalstandard 506-26-3 100 mg $175 2021-12-16 Buy
Sigma-Aldrich 62174 γ-Linolenic acid analyticalstandard 506-26-3 500 mg $483 2021-12-16 Buy
Sigma-Aldrich 62174 γ-Linolenic acid analytical standard 506-26-3 100mg-f $170 2021-12-16 Buy
Sigma-Aldrich 62174 γ-Linolenic acid analytical standard 506-26-3 500mg-f $468 2021-12-16 Buy
TCI Chemical L0152 γ-Linolenic Acid >98.0%(GC)(T) 506-26-3 100mg $85 2021-12-16 Buy

gamma-Linolenic acid Chemical Properties,Uses,Production

Description

γ-Linolenic acid (gamma-linolenic acid or GLA, INN and USAN gamolenic acid) is a fatty acid found primarily in vegetable oils. It is sold as a dietary supplement for treating problems with inflammation and auto-immune diseases, although its efficacy is disputed.

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 LTB4 receptor antagonist, inhibiting [3H]-LTB4 binding to porcine neutrophil membranes with a Ki of 1 μM. GLA produces 53% inhibition at a 1 mg/kg dose in an in vivo model of LTB4-induced bronchoconstriction.

Chemical Properties

GLA is categorized as an n?6 (also called ω?6 or omega-6) fatty acid, meaning that the first double bond on the methyl end (designated with n or ω) is the sixth bond. In physiological literature, GLA is designated as 18:3 (n?6). GLA is a carboxylic acid with an 18-carbon chain and three cis double bonds. It is an isomer of α-linolenic acid, which is a polyunsaturated n?3 (omega-3) fatty acid, found in rapeseed canola oil, soy beans, walnuts, flax seed (linseed oil), perilla, chia, and hemp seed.

Occurrence

GLA is obtained from vegetable oils such as GLA safflower oil (Carthamus tinctorius), evening primrose (Oenothera biennis) oil, blackcurrant seed oil, borage oil, and hemp seed oil. GLA is also found in edible hemp seeds, oats, barley, and spirulina. Each contains varying amounts of the fatty acid, with GLA safflower oil at 40% GLA being a novel concentrated form. This is a new genetically modified oil and has been available in commercial quantities since 2011. It should be noted that conventional safflower oils have zero GLA. Borage oil ranges from 15 % to 20 % and evening primrose oil ranges from 8 % to 10 % GLA.
The human body produces GLA from linoleic acid (LA). This reaction is catalyzed by Δ6 - desaturase (D6D), an enzyme that allows the creation of a double bond on the sixth carbon counting from the carboxyl terminus. LA is consumed sufficiently in most diets, from such abundant sources as cooking oils and meats. However, a lack of GLA can occur when there is a reduction of the efficiency of the D6D conversion (for instance, as people grow older or when there are specific dietary deficiencies) or in disease states wherein there is excessive consumption of GLA metabolites.

History

GLA was first isolated from the seed oil of evening primrose. This herbal plant was grown by Native Americans to treat swelling in the body. In the 17th century, it was introduced to Europe and became a popular folk remedy, earning the name king's cure-all. in 1919, Heiduschka and Lüft extracted the oil from evening primrose seeds and described an unusual linolenic acid, which they name γ-. Later, the exact chemical structure was characterized by Riley.
Although there are α- and γ- forms of linolenic acid, there is no β- form. One was once identified, but it turned out to be an artifact of the original analytical process.

Uses

γ-linolenic acid has been used as an analytical standard in gas chromatography. It may be used in nutritional studies regarding weight regain and as a possible tumor suppression agent. γ-linolenic acid is used in studies on the mechanisms and prevention of oxidation/peroxidation of unsaturated fatty acids.

Uses

γ-Linolenic Acid is a fatty acid found mainly in vegetable oil. Studies suggest that γ-Linolenic Acid may have immune regulating and anti-inflammatory effects. γ-Linolenic Acid has also been used in the treatment of atopic eczeme although its efficacy is

Definition

ChEBI: A C18, omega-6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12.

Biochem/physiol Actions

Gamma-linolenate (C18:6,9,12) differs from α-linolenate (C18:9,12,15) in the positions of the double bonds.

gamma-Linolenic acid synthesis

60-33-3
506-26-3
Synthesis of gamma-Linolenic acid from Linoleic acid

gamma-Linolenic acid Preparation Products And Raw materials

Raw materials

Preparation Products


gamma-Linolenic acid Suppliers

Global( 185)Suppliers
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career henan chemical co
+86-0371-55982848
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Shaanxi Pioneer Biotech Co., Ltd .
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8485655694
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0371-55170695
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Masteam Bio-tech Co., Ltd.
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View Lastest Price from gamma-Linolenic acid manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2019-07-06 gamma-Linolenic acid
506-26-3
US $8.00 / kg 1kg 98% 10MT Career Henan Chemical Co

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