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Basic Description
| Synonyms | gamma-Linolenic acid|GAMOLENIC ACID|506-26-3|(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid|(Z,Z,Z)-6,9,12-Octadecatrienoic acid|Ligla|(6,9,12)-linolenic acid|gamma Linolenic Acid|6,9,12-Octadecatrienoic acid, (Z,Z,Z)-|CCRIS 7668|.gamma.-Linolenic Acid|all-cis |
|---|---|
| Specifications & Purity | Moligand™, 10mM in DMSO |
| Biochemical and Physiological Mechanisms | Unsaturated fatty acid. Putative anticancer agent. Linoleic acid derivative. Induces ROS generation. Inactivates NFκB. May also act via peroxisome proliferator activated receptors (PPARs) by stimulating their phosphorylation and translocation |
| Storage Temp | Store at -80°C |
| Shipped In | Ice chest + Ice pads |
| Grade | Moligand™ |
| Product Description | Usually used as an analytical standard in gas chromatography,and also 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. |
Associated Targets
CHERP Tbio Calcium homeostasis endoplasmic reticulum protein 0 Activities
DRD1 Tclin D(1A) dopamine receptor 0 Activities
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ESR1 Tclin Estrogen receptor 0 Activities
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GABRA1 Tclin Gamma-aminobutyric acid receptor subunit alpha-1 0 Activities
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EHMT2 Tchem Histone-lysine N-methyltransferase EHMT2 0 Activities
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POLH Tchem DNA polymerase eta 0 Activities
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VDR Tclin Vitamin D3 receptor 0 Activities
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FFAR1 Tchem Free fatty acid receptor 1 0 Activities
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HRH3 Tclin Histamine H3 receptor 0 Activities
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HDAC6 Tclin Histone deacetylase 6 0 Activities
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SLC6A2 Tclin Sodium-dependent noradrenaline transporter 0 Activities
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SLC6A3 Tclin Sodium-dependent dopamine transporter 0 Activities
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SRD5A2 Tclin 3-oxo-5-alpha-steroid 4-dehydrogenase 2 0 Activities
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SLC6A4 Tclin Sodium-dependent serotonin transporter 0 Activities
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PGR Tclin Progesterone receptor 0 Activities
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PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 0 Activities
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POLI Tchem DNA polymerase iota 0 Activities
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PLK1 Tchem Serine/threonine-protein kinase PLK1 0 Activities
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PDE3A Tclin cGMP-inhibited 3',5'-cyclic phosphodiesterase A 0 Activities
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PTGS1 Tclin Prostaglandin G/H synthase 1 0 Activities
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PDE4A Tclin cAMP-specific 3',5'-cyclic phosphodiesterase 4A 0 Activities
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RGS4 Tchem Regulator of G-protein signaling 4 0 Activities
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L3MBTL1 Tchem Lethal(3)malignant brain tumor-like protein 1 0 Activities
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CASP6 Tchem Caspase-6 1 Activities
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DRD3 Tclin D(3) dopamine receptor 0 Activities
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KDR Tclin Vascular endothelial growth factor receptor 2 0 Activities
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CHRM2 Tclin Muscarinic acetylcholine receptor M2 0 Activities
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ACHE Tclin Acetylcholinesterase 0 Activities
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CHRM1 Tclin Muscarinic acetylcholine receptor M1 0 Activities
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ADRA2A Tclin Alpha-2A adrenergic receptor 0 Activities
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ADRA1A Tclin Alpha-1A adrenergic receptor 0 Activities
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AR Tclin Androgen receptor 0 Activities
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MAOA Tclin Amine oxidase [flavin-containing] A 0 Activities
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HTR1A Tclin 5-hydroxytryptamine receptor 1A 0 Activities
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ADORA3 Tchem Adenosine receptor A3 0 Activities
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HTR2B Tclin 5-hydroxytryptamine receptor 2B 0 Activities
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TBXA2R Tclin Thromboxane A2 receptor 0 Activities
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F2 Tclin Prothrombin 0 Activities
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KCNH2 Tclin Potassium voltage-gated channel subfamily H member 2 0 Activities
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GLP1R Tclin Glucagon-like peptide 1 receptor 0 Activities
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GLS Tchem Glutaminase kidney isoform, mitochondrial 0 Activities
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IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic 0 Activities
| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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OPRM1 Tclin Mu-type opioid receptor 0 Activities
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PPARA Tclin Peroxisome proliferator-activated receptor alpha 0 Activities
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PPARD Tchem Peroxisome proliferator-activated receptor delta 0 Activities
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PPARG Tclin Peroxisome proliferator-activated receptor gamma 0 Activities
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Names and Identifiers
| IUPAC Name | (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid |
|---|---|
| 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- |
| InChi Key | VZCCETWTMQHEPK-QNEBEIHSSA-N |
| Canonical SMILES | CCCCCC=CCC=CCC=CCCCCC(=O)O |
| Isomeric SMILES | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O |
| WGK Germany | 3 |
| PubChem CID | 5280933 |
| Molecular Weight | 278.43 |
| Beilstein | 1712253 |
Certificates
Certificate of Analysis(COA)
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Chemical and Physical Properties
| Sensitivity | Light & Air & Heat sensitive |
|---|---|
| Refractive Index | 1.48 |
| Flash Point(°F) | 230.0 °F |
| Flash Point(°C) | 110°C |
Safety and Hazards(GHS)
| Pictogram(s) | GHS07 |
|---|---|
| Signal | Warning |
| Hazard Statements | H315:Causes skin irritation H319:Causes serious eye irritation H335:May cause respiratory irritation |
| Precautionary Statements | P261:Avoid breathing dust/fume/gas/mist/vapors/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P321:Specific treatment (see ... on this label). P405:Store locked up. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P271:Use only outdoors or in a well-ventilated area. P304+P340:IF INHALED: Remove person to fresh air and keep comfortable for breathing. P403+P233:Store in a well-ventilated place. Keep container tightly closed. P362+P364:Take off contaminated clothing and wash it before reuse. P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes. P337+P317:If eye irritation persists: Get medical help. P332+P317:If skin irritation occurs: Get medical help. P319:Get medical help if you feel unwell. |
| WGK Germany | 3 |
| Merck Index | 5507 |