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gamma-Linolenic acid

Product Name
gamma-Linolenic acid
CAS No.
506-26-3
Chemical Name
gamma-Linolenic acid
Synonyms
gamolenic acid;C06426;Gamolenic;18:3(n-6);Flunarizin;Flunarizina;R- flax acid;Flunarizinum;γ-linolenicaci;G-LINOLENICACID
CBNumber
CB3238150
Molecular Formula
C18H30O2
Formula Weight
278.43
MOL File
506-26-3.mol
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gamma-Linolenic acid Property

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
solubility 
Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
pka
4.74±0.10(Predicted)
form 
liquid
color 
Colourless
biological source
synthetic
Merck 
14,5507
BRN 
1712253
Stability:
Light Sensitive
InChIKey
VZCCETWTMQHEPK-QNEBEIHSSA-N
LogP
6.570 (est)
CAS DataBase Reference
506-26-3(CAS DataBase Reference)
NIST Chemistry Reference
Gamolenic acid(506-26-3)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
F 
8-10-23
HS Code 
29161500
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
62174
Product name
γ-Linolenic acid
Purity
analyticalstandard
Packaging
100mg
Price
$226
Updated
2024/03/01
Sigma-Aldrich
Product number
62174
Product name
γ-Linolenic acid
Purity
analyticalstandard
Packaging
500mg
Price
$624
Updated
2024/03/01
TCI Chemical
Product number
L0152
Product name
γ-Linolenic Acid
Purity
>98.0%(GC)(T)
Packaging
100mg
Price
$98
Updated
2024/03/01
TCI Chemical
Product number
L0152
Product name
γ-Linolenic Acid
Purity
>98.0%(GC)(T)
Packaging
1g
Price
$485
Updated
2024/03/01
Cayman Chemical
Product number
90220
Product name
γ-Linolenic Acid
Purity
≥98%
Packaging
50mg
Price
$25
Updated
2024/03/01
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gamma-Linolenic acid Chemical Properties,Usage,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.

References

[1] yagaloff k a, franco l, simko b, et al. essential fatty acids are antagonists of the leukotriene b4 receptor[j]. prostaglandins, leukotrienes and essential fatty acids, 1995, 52(5): 293-297.
[2] crooks s w, stockley r a. leukotriene b4[j]. the international journal of biochemistry & cell biology, 1998, 30(2): 173-178.
[3] tasset-cuevas i, fernández-bedmar z, lozano-baena m d, et al. protective effect of borage seed oil and gamma linolenic acid on dna: in vivo and in vitro studies[j]. plos one, 2013, 8(2): e56986.
[4] jamal g a, carmichael h. the effect of γ‐linolenic acid on human diabetic peripheral neuropathy: a double‐blind placebo‐controlled trial[j]. diabetic medicine, 1990, 7(4): 319-323.
[5] andreassi m, forleo p, dilohjo a, et al. efficacy of γ-linolenic acid in the treatment of patients with atopic dermatitis[j]. journal of international medical research, 1997, 25(5): 266-274.

gamma-Linolenic acid Preparation Products And Raw materials

Raw materials

Preparation Products

Linolenic acid
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View Lastest Price from gamma-Linolenic acid manufacturers

Hebei Mujin Biotechnology Co.,Ltd
Product
gamma-Linolenic acid 506-26-3
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-07-26
BINBO BIOLOGICAL CO.,LTD
Product
Gamma Linolenic Acid Powder（GLA） 506-26-3
Price
US $0.00/kg
Min. Order
1kg
Purity
10% 12% 20%
Supply Ability
3000 kg
Release date
2024-04-17
Career Henan Chemical Co
Product
gamma-Linolenic acid 506-26-3
Price
US $8.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
10MT
Release date
2018-12-16

506-26-3, gamma-Linolenic acidRelated Search:

Linolenic acid Docosahexaenoic Acid EPA Linoleic acid 6-Amino-4-hydroxy-2-naphthalenesulfonic acid Ethyl 2-(Chlorosulfonyl)acetate Arachidonic acid 4-Aminobutyric acid Folic acid Citric acid Ascoric Acid OLEIC ACID-1-13C OCTADECENEDIOIC ACID GAMMA-LINOLENIC ACID METHYL ESTER 1,2-OLEIN-3-LINOLENIN GAMMA-LINOLENIC ACID ETHYL ESTER HOMO-GAMMA-LINOLENIC ACID,DIHOMO-GAMMA-LINOLENIC ACID,(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid,DIHOMO-GAMMA-LINOLENIC ACID-CONTAINING TRIGLYCERIDE EVENING PRIMROSE OIL 10% GAMMA LINOLENIC ACID (GLA) OENOTHERA BIENNIS

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  • Gamolenic
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  • LINOLEIC ACID(P)
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  • 506-26-3
  • Unsaturated fatty acids and derivatives
  • Lipids
  • Polyunsaturated
  • Omega 6 fatty acids and derivatives
  • BioChemical
  • Biochemicals and Reagents
  • Anti-proliferative Agents