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Gamma-Linolenic acid

CAT: 0804-HY-N7140-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N7140-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Gamma-linolenic acid (γ-Linolenic acid) is an orally active unsaturated fatty acid. Gamma-linolenic acid exerts anti-inflammatory effects by inhibiting the NF-κB pathway and the phosphorylation of ERK1/2 and JNK. At the same time, it exerts anticancer effects by inducing apoptosis (Apoptosis) in cancer cells. Additionally, Gamma-linolenic acid also has antioxidant and memory-improving effects. It holds promise for research in the fields of inflammation, neurology, and cancer diseases[1][2][3][4][5].
CAS Number
506-26-3
Product Name Alternative
γ-Linolenic acid
UNSPSC
12352211
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; Endogenous Metabolite; ERK; JNK; NF-κB
Type
Natural Products
Related Pathways
Apoptosis; MAPK/ERK Pathway; Metabolic Enzyme/Protease; NF-κB; Stem Cell/Wnt
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Cancer; Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/gamma-linolenic-acid.html
Purity
99.86
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
CCCCC/C=C\C/C=C\C/C=C\CCCCC(O)=O
Molecular Formula
C18H30O2
Molecular Weight
278.43
Precautions
H302, H315, H319, H335
References & Citations
[1]Sergeant S, et al. Gamma-linolenic acid, Dihommo-gamma linolenic, Eicosanoids and Inflammatory Processes. Eur J Pharmacol. 2016 Aug 15;785:77-86.|[2]Youn K, et al. Gamma-linolenic acid ameliorates Aβ-induced neuroinflammation through NF-κB and MAPK signalling pathways[J]. Journal of Functional Foods, 2018, 42: 30-37.|[3]Andreoli Miyake J, et al. Gamma-Linolenic acid alters migration, proliferation and apoptosis in human and rat glioblastoma cells. Prostaglandins Other Lipid Mediat. 2020 Oct;150:106452.|[4]Rahimi K, et al. The protective effects of Gamma-linolenic acid against indomethacin-induced gastric ulcer in rats[J]. British Journal of Nutrition, 2024, 131 (11) : 1844-1851.|[5]Khan SA, et al. Gamma-linolenic acid ameliorated glycation-induced memory impairment in rats. Pharm Biol. 2017 Dec;55 (1) :1817-1823.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, protect from light, stored under nitrogen)
Scientific Category
Natural Products
Clinical Information
Launched
Isoform
ERK1; ERK2; Human Endogenous Metabolite

Chemical Information

Gamma-Linolenic acid

Gamma-linolenic acid is a C18, -6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12. It has a role as a mouse metabolite, a plant metabolite and a human metabolite. It is a linolenic acid and an omega-6 fatty acid. It is a conjugate acid of a gamma-linolenate.

CAS Number506-26-3
PubChem CID5280933
IUPAC Name(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Molecular FormulaC18H30O2
Molecular Weight278.4
XLogP5.9
Topological Polar Surface Area37.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count13
Heavy Atom Count20
Formal Charge0
Complexity301
SMILES
CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O
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-
InChIKey
VZCCETWTMQHEPK-QNEBEIHSSA-N
Chemical Structure
2D Structure
2D structure of Gamma-Linolenic acid
CAS: 506-26-3
CID: 5280933
Formula: C18H30O2
MW: 278.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight278.4
XLogP35.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count13
Exact Mass278.224580195
Monoisotopic Mass278.224580195
Topological Polar Surface Area37.3 Ų
Heavy Atom Count20
Formal Charge0
Complexity301
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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