γ-Linolenic acid - 97%, high purity , CAS No.506-26-3

Item Number
L111861
Grouped product items
SKUSizeAvailabilityPrice Qty
L111861-50mg
50mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$65.90
L111861-100mg
100mg
In stock
$92.90
L111861-500mg
500mg
In stock
$325.90
L111861-1g
1g
Available within 1-2 weeks(?)
Item is derived from our semi-finished stock and is processed in 1-2 weeks.
$459.90

Unsaturated fatty acid

Basic Description

Synonyms(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid | gamma-Linolenic acid | (Z,Z,Z)-6,9,12-Octadecatrienoic acid
Specifications & PurityMoligand™, ≥97%
Biochemical and Physiological MechanismsUnsaturated 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 TempStore at -20°C,Argon charged
Shipped InIce chest + Ice pads
GradeMoligand™
NoteWherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.
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(Human)

CASP6 Tchem Caspase-6 (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
F2 Tclin Thrombin (11687 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PGR Tclin Progesterone receptor (8562 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AR Tclin Androgen Receptor (11781 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
VDR Tclin Vitamin D receptor (26531 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOA Tclin Monoamine oxidase A (11911 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD1 Tclin Dopamine D1 receptor (9720 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A2 Tclin Norepinephrine transporter (10102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SRD5A2 Tclin Steroid 5-alpha-reductase 2 (937 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A4 Tclin Serotonin transporter (12625 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRM1 Tclin Mu opioid receptor (19785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD3 Tclin Dopamine D3 receptor (14368 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A3 Tclin Dopamine transporter (10535 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE3A Tclin Phosphodiesterase 3A (3309 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE4A Tclin Phosphodiesterase 4A (1943 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH3 Tclin Histamine H3 receptor (10389 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FASN Tchem Fatty acid synthase (3390 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CASP6 Tchem Caspase-6 (1213 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FFAR1 Tchem Free fatty acid receptor 1 (4763 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLK Tbio DNA polymerase kappa (8653 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLI Tchem DNA polymerase iota (116820 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLH Tchem DNA polymerase eta (21678 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L3MBTL1 Tchem Lethal(3)malignant brain tumor-like protein 1 (14536 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PMP22 Tbio Peripheral myelin protein 22 (699 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
F7 Tchem Coagulation factor VII/tissue factor (740 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLS Tchem Glutaminase kidney isoform, mitochondrial (16997 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypsin (394 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ppard Peroxisome proliferator-activated receptor delta (358 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hdac6 Histone deacetylase 6 (222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GCN5 Histone acetyltransferase GCN5 (89 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TGR Thioredoxin glutathione reductase (28579 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Names and Identifiers

Pubchem Sid488195218
Pubchem Sid Urlhttps://pubchem.ncbi.nlm.nih.gov/substance/488195218
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)

Enter Lot Number to search for COA:

Find and download the COA for your product by matching the lot number on the packaging.

19 results found

Lot NumberCertificate TypeDateItem
F2405476Certificate of AnalysisApr 18, 2024 L111861
F2405466Certificate of AnalysisApr 18, 2024 L111861
F2405465Certificate of AnalysisApr 18, 2024 L111861
D2407373Certificate of AnalysisMar 08, 2024 L111861
H2328681Certificate of AnalysisAug 21, 2023 L111861
H2328673Certificate of AnalysisAug 21, 2023 L111861
H2328671Certificate of AnalysisAug 21, 2023 L111861
F2312931Certificate of AnalysisJun 01, 2023 L111861
F2312897Certificate of AnalysisJun 01, 2023 L111861
D2324866Certificate of AnalysisApr 03, 2023 L111861
D2324901Certificate of AnalysisApr 03, 2023 L111861
D2324896Certificate of AnalysisApr 03, 2023 L111861
D2324868Certificate of AnalysisApr 03, 2023 L111861
D2324844Certificate of AnalysisApr 03, 2023 L111861
F2221133Certificate of AnalysisJun 01, 2022 L111861
F2221132Certificate of AnalysisJun 01, 2022 L111861
F2221125Certificate of AnalysisJun 01, 2022 L111861
J2227058Certificate of AnalysisJun 01, 2022 L111861
K2214110Certificate of AnalysisJun 01, 2022 L111861

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Chemical and Physical Properties

SensitivityLight & Air & Heat sensitive
Refractive Index1.48
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

Related Documents

Citations of This Product

1. Hongshuai Lv, Weiping Jia, Li Yang, Peng Dong, Jiaojiao Liu, Si Wang, Xiaohai Li, Jinghua Hu, Ling Zhao, Yikang Shi.  (2023)  Influence of unsaturated fatty acids on the antitumor activity of polymeric conjugates grafted with cabazitaxel against prostate cancer.  BIOMEDICINE & PHARMACOTHERAPY,  169  (115902).  [PMID:37989031] [10.1016/j.biopha.2023.115902]
2. Lei He, Qian Hu, Liyang Wei, Xuliyang Ge, Ning Yu, Ying Chen.  (2023)  Unravelling dynamic changes in non-volatile and volatile metabolites of pulses during soaking: An integrated metabolomics approach.  FOOD CHEMISTRY,  422  (136231).  [PMID:37141754] [10.1016/j.foodchem.2023.136231]
3. Ge Tang, Kuaqian Deng, Panyang Li, Jiali Huang, Fanglin Dao, Hao Jiang, Jing Wang, Jianfang Jiang.  (2023)  One-pot method of recyclable lipase-nanocatalyst based on chitosan magnetic nanomaterial for ethyl levulinate synthesis.  COMPOSITES SCIENCE AND TECHNOLOGY,  236  (110002).  [PMID:] [10.1016/j.compscitech.2023.110002]
4. Yang-Yang Li, Xin-Xin Ma, Xin-Yan Song, Lin-Lin Ma, Yu-Ying Li, Xin Meng, Yu-Jie Chen, Ke-Xin Xu, Ali Akbar Moosavi-Movahedi, Bao-Lin Xiao, Jun Hong.  (2023)  Glucose Biosensor Based on Glucose Oxidase Immobilized on BSA Cross-Linked Nanocomposite Modified Glassy Carbon Electrode.  SENSORS,  23  (6): (3209).  [PMID:36991919] [10.3390/s23063209]

References

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8. Undurti N Das.  (2006-12-16)  Tumoricidal and anti-angiogenic actions of gamma-linolenic acid and its derivatives..  Current pharmaceutical biotechnology,  ((6)): (457-466).  [PMID:17168663]
9. Marie A Schirmer,Stephen D Phinney.  (2007-05-22)  Gamma-linolenate reduces weight regain in formerly obese humans..  The Journal of nutrition,  137  ((6)): (1430-1435).  [PMID:17513402]
10. Michael M Meguid,Michael J Glade,Frank A Middleton.  (2008-08-30)  Weight regain after Roux-en-Y: a significant 20% complication related to PYY..  Nutrition (Burbank, Los Angeles County, Calif.),  24  ((9)): (832-842).  [PMID:18725080]
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16. Fengyun Qin,Linzhi Kang,Liqiong Guo,Junfang Lin,Jingshen Song,Yinhua Zhao.  (2012-02-14)  Composition of transgenic soybean seeds with higher γ-linolenic acid content is equivalent to that of conventional control..  Journal of agricultural and food chemistry,  60  ((9)): (2200-2204).  [PMID:22324875]
17. O Ya Lukivskaya,E Naruta,V Sadovnichy,S Kirko,V U Buko.  (2012-02-24)  Reversal of experimental ethanol-induced liver steatosis by borage oil..  Phytotherapy research : PTR,  26  ((11)): (1626-1631).  [PMID:22359349]
18. C Vaquerizo Alonso,T Grau Carmona,M Juan Díaz.  (2012-03-21)  Guidelines for specialized nutritional and metabolic support in the critically-ill patient: update. Consensus SEMICYUC-SENPE: hyperglycemia and diabetes mellitus..  Nutricion hospitalaria,  26 Suppl 2  (46-49).  [PMID:22411519]
19. Hector L Lopez.  (2012-06-01)  Nutritional interventions to prevent and treat osteoarthritis. Part I: focus on fatty acids and macronutrients..  PM & R : the journal of injury, function, and rehabilitation,  ((5 Suppl)): (S145-S154).  [PMID:22632694]
20. Jie Fu,Xue-Wei Zhang,Kai Liu,Qing-Shan Li,Li-Rong Zhang,Xian-Hui Yang,Zhi-Ming Zhang,Chang-Zhu Li,Yin Luo,Zhen-Xiang He,Hai-Liang Zhu.  (2012-07-04)  Hypolipidemic activity in Sprague-Dawley rats and constituents of a novel natural vegetable oil from Cornus wilsoniana fruits..  Journal of food science,  77  ((8)): (H160-H169).  [PMID:22747885]
21. Jutta Auberger,Stefan Vogt,Georg Hopfinger,Johannes Clausen,Richard Greil.  (2012-12-25)  Topical evening primrose oil for reduction of bortezomib-induced skin reactions..  Annals of hematology,  92  ((7)): (995-996).  [PMID:23262668]
22. Brian R Jacobs,Vinay Nadkarni,Brahm Goldstein,Paul Checchia,Onsy Ayad,Judy Bean,Stephen DeMichele.  (2013-01-09)  Nutritional immunomodulation in critically ill children with acute lung injury: feasibility and impact on circulating biomarkers..  Pediatric critical care medicine : a journal of the Society of Critical Care Medicine and the World Federation of Pediatric Intensive and Critical Care Societies,  14  ((1)): (e45-e56).  [PMID:23295853]
23. Inmaculada Tasset-Cuevas,Zahira Fernández-Bedmar,María Dolores Lozano-Baena,Juan Campos-Sánchez,Antonio de Haro-Bailón,Andrés Muñoz-Serrano,Angeles Alonso-Moraga.  (2013-03-06)  Protective effect of borage seed oil and gamma linolenic acid on DNA: in vivo and in vitro studies..  PloS one,  ((2)): (e56986-e56986).  [PMID:23460824]
24. I S Mysiakina,Ia É Sergeeva,A A Ivashechkin,E P Feofilova.  (2013-04-25)  [Lipid composition of fungus Mucor hiemalis mycelium grown in the presence of trehalose, triacylglycerols, and itraconazole]..  Mikrobiologiia,  81  ((6)): (726-732).  [PMID:23610922]
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26. Tiffany T Mayo,Farhan Khan,Christine Hunt,Kristy Fleming,Ramsey Markus.  (2013-08-01)  Comparative study on bruise reduction treatments after bruise induction using the pulsed dye laser..  Dermatologic surgery : official publication for American Society for Dermatologic Surgery [et al.],  39  ((10)): (1459-1464).  [PMID:23899131]
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30. J Hindo,C Hauville,S Rémita,P Thérond,M Couturier,D Jore,M Gardès-Albert.  (2000-01-12)  Evidence of the formation of different hydroperoxides in irradiated gamma-linolenate solutions: effect of micelle formation..  Radiation research,  153  ((2)): (201-207).  [PMID:10629620]
31. Undurti N Das.  (2007-06-30)  Gamma-linolenic acid therapy of human glioma-a review of in vitro, in vivo, and clinical studies..  Medical science monitor : international medical journal of experimental and clinical research,  13  ((7)): (RA119-RA131).  [PMID:17599036]
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Solution Calculators