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

4 Citations

Moligand™

≥97%

CAS#: 506-26-3
Molecular Weight: 278.43
Beilstein Registry Number: 1712253
MDL number: MFCD00065718
PubChem CID: 5280933
PubChem SID: 488195218

Item Number

L111861

Grouped product items
SKU	Size	Availability	Price
L111861-50mg	50mg	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$65.90
L111861-100mg	100mg	3	$92.90
L111861-500mg	500mg	1	$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

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carboxylic acid (0) Carboxylic acid capping agent (0)

Basic Description

Synonyms	(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid \| gamma-Linolenic acid \| (Z,Z,Z)-6,9,12-Octadecatrienoic acid
Specifications & Purity	Moligand™, ≥97%
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 -20°C,Argon charged
Shipped In	Ice chest + Ice pads
Grade	Moligand™
Note	Wherever 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.

AI Insight

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Names and Identifiers

Pubchem Sid	488195218
Pubchem Sid Url	https://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（CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):

Analytical Chart:

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

19 results found

Lot Number	Certificate Type	Date	Item
F2405476	Certificate of Analysis	Apr 18, 2024	L111861
F2405466	Certificate of Analysis	Apr 18, 2024	L111861
F2405465	Certificate of Analysis	Apr 18, 2024	L111861
D2407373	Certificate of Analysis	Mar 08, 2024	L111861
H2328681	Certificate of Analysis	Aug 21, 2023	L111861
H2328673	Certificate of Analysis	Aug 21, 2023	L111861
H2328671	Certificate of Analysis	Aug 21, 2023	L111861
F2312931	Certificate of Analysis	Jun 01, 2023	L111861
F2312897	Certificate of Analysis	Jun 01, 2023	L111861
D2324866	Certificate of Analysis	Apr 03, 2023	L111861
D2324901	Certificate of Analysis	Apr 03, 2023	L111861
D2324896	Certificate of Analysis	Apr 03, 2023	L111861
D2324868	Certificate of Analysis	Apr 03, 2023	L111861
D2324844	Certificate of Analysis	Apr 03, 2023	L111861
F2221133	Certificate of Analysis	Jun 01, 2022	L111861
F2221132	Certificate of Analysis	Jun 01, 2022	L111861
F2221125	Certificate of Analysis	Jun 01, 2022	L111861
J2227058	Certificate of Analysis	Jun 01, 2022	L111861
K2214110	Certificate of Analysis	Jun 01, 2022	L111861

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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

Alternative Products

Reviews

Citations of This Product

How to Cite Aladdin Scientific Products?

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

1. D F Horrobin. (1992-01-01) The use of gamma-linolenic acid in diabetic neuropathy.. Agents and actions. Supplements, 37 (120-144). [PMID:1321553]
2. A Bordoni. (1990-03-31) [Significance and motivation of the clinical use of essential fatty acid derivatives, especially gamma-linolenic acid].. La Clinica terapeutica, 132 ((6)): (383-392). [PMID:2158408]
3. V A Ziboh,C C Miller,Y Cho. (2000-01-05) Metabolism of polyunsaturated fatty acids by skin epidermal enzymes: generation of antiinflammatory and antiproliferative metabolites.. The American journal of clinical nutrition, 71 ((1 Suppl)): (361S-366S). [PMID:10617998]
4. Elizabeth C Leigh-Firbank,Anne M Minihane,David S Leake,John W Wright,Margaret C Murphy,Bruce A Griffin,Christine M Williams. (2002-05-16) Eicosapentaenoic acid and docosahexaenoic acid from fish oils: differential associations with lipid responses.. The British journal of nutrition, 87 ((5)): (435-445). [PMID:12010583]
5. Berthold Koletzko,Ulrike Sauerwald,Ursula Keicher,Helmut Saule,Susanne Wawatschek,Hansjosef Böhles,Karin Bervoets,Mathilde Fleith,Gayle Crozier-Willi. (2003-10-22) Fatty acid profiles, antioxidant status, and growth of preterm infants fed diets without or with long-chain polyunsaturated fatty acids. A randomized clinical trial.. European journal of nutrition, 42 ((5)): (243-253). [PMID:14569405]
6. . (2004-03-10) Gamma-linolenic acid (GLA). Monograph.. Alternative medicine review : a journal of clinical therapeutic, 9 ((1)): (70-78). [PMID:15005646]
7. Jim-Wen Liu,Stephen J DeMichele,John Palombo,Lu-Te Chuang,Christine Hastilow,Emil Bobik,Yung-Sheng Huang. (2004-06-10) Effect of long-term dietary supplementation of high-gamma-linolenic canola oil versus borage oil on growth, hematology, serum biochemistry, and N-6 fatty acid metabolism in rats.. Journal of agricultural and food chemistry, 52 ((12)): (3960-3966). [PMID:15186123]
8. Undurti N Das. (2006-12-16) Tumoricidal and anti-angiogenic actions of gamma-linolenic acid and its derivatives.. Current pharmaceutical biotechnology, 7 ((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]
11. David S Wishart,Craig Knox,An Chi Guo,Roman Eisner,Nelson Young,Bijaya Gautam,David D Hau,Nick Psychogios,Edison Dong,Souhaila Bouatra,Rupasri Mandal,Igor Sinelnikov,Jianguo Xia,Leslie Jia,Joseph A Cruz,Emilia Lim,Constance A Sobsey,Savita Shrivastava,Paul Huang,Philip Liu,Lydia Fang,Jun Peng,Ryan Fradette,Dean Cheng,Dan Tzur,Melisa Clements,Avalyn Lewis,Andrea De Souza,Azaret Zuniga,Margot Dawe,Yeping Xiong,Derrick Clive,Russ Greiner,Alsu Nazyrova,Rustem Shaykhutdinov,Liang Li,Hans J Vogel,Ian Forsythe. (2008-10-28) HMDB: a knowledgebase for the human metabolome.. Nucleic acids research, 37 ((Database issue)): (D603-D610). [PMID:18953024]
12. Julianne Lindemann,E David Pampe,Joanna J Peterkin,Patti Orozco-Cronin,Gil Belofsky,Dean Stull. (2009-10-09) Clinical study of the effects on asthma-related QOL and asthma management of a medical food in adult asthma patients.. Current medical research and opinion, 25 ((12)): (2865-2875). [PMID:19811112]
13. Nikolaos Psychogios,David D Hau,Jun Peng,An Chi Guo,Rupasri Mandal,Souhaila Bouatra,Igor Sinelnikov,Ramanarayan Krishnamurthy,Roman Eisner,Bijaya Gautam,Nelson Young,Jianguo Xia,Craig Knox,Edison Dong,Paul Huang,Zsuzsanna Hollander,Theresa L Pedersen,Steven R Smith,Fiona Bamforth,Russ Greiner,Bruce McManus,John W Newman,Theodore Goodfriend,David S Wishart. (2011-03-02) The human serum metabolome.. PloS one, 6 ((2)): (e16957-e16957). [PMID:21359215]
14. Klemens König,Peter Rosenberger,Valbona Mirakaj. (2012-01-12) Supplementation in acute lung injury.. JAMA, 307 ((2)): (145-145). [PMID:22235080]
15. Patrick Tso,Jody Caldwell,Dana Lee,Gregory P Boivin,Stephen J DeMichele. (2012-01-24) Comparison of growth, serum biochemistries and n-6 fatty acid metabolism in rats fed diets supplemented with high-gamma-linolenic acid safflower oil or borage oil for 90 days.. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 50 ((6)): (1911-1919). [PMID:22265940]
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, 4 ((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, 8 ((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]
25. I S Mysiakina,Ia É Sergeeva,A A Ivashechkin,E P Feofilova. (2013-04-25) [Effect of biological factors on morphogenesis, growth, and lipid composition of fungus Mucor hiemalis mycelium].. Mikrobiologiia, 81 ((6)): (733-740). [PMID:23610923]
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]
27. Milan Gautam,Atsushi Izawa,Yuji Shiba,Hirohiko Motoki,Takahiro Takeuchi,Ayako Okada,Takeshi Tomita,Yusuke Miyashita,Jun Koyama,Uichi Ikeda. (2014-09-06) Importance of fatty acid compositions in patients with peripheral arterial disease.. PloS one, 9 ((9)): (e107003-e107003). [PMID:25191963]
28. Minho Kim,JaeGoo Kim,Yu-Kyong Shin,Ki-Young Kim. (2020-03-27) Gentisic Acid Stimulates Keratinocyte Proliferation through ERK1/2 Phosphorylation.. International journal of medical sciences, 17 ((5)): (626-631). [PMID:32210712]
29. D F Horrobin. (1993-01-01) The effects of gamma-linolenic acid on breast pain and diabetic neuropathy: possible non-eicosanoid mechanisms.. Prostaglandins, leukotrienes, and essential fatty acids, 48 ((1)): (101-104). [PMID:8380930]
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]
32. Tomáš Řezanka,Jaromír Lukavský,Lucie Siristova,Karel Sigler. (2012-03-27) Regioisomer separation and identification of triacylglycerols containing vaccenic and oleic acids, and α- and γ-linolenic acids, in thermophilic cyanobacteria Mastigocladus laminosus and Tolypothrix sp.. Phytochemistry, 78 (147-155). [PMID:22445652]
33. Ola M Omran. (2012-05-12) Histopathological study of evening primrose oil effects on experimental diabetic neuropathy.. Ultrastructural pathology, 36 ((4)): (222-227). [PMID:22574767]
34. Ulrike Mütze,Skadi Beblo,Linda Kortz,Claudia Matthies,Berthold Koletzko,Mathias Bruegel,Carmen Rohde,Joachim Thiery,Wieland Kiess,Uta Ceglarek. (2012-08-23) Metabolomics of dietary fatty acid restriction in patients with phenylketonuria.. PloS one, 7 ((8)): (e43021-e43021). [PMID:22912778]
35. Selvaraj Jubie,Palanisamy Dhanabal,Mohammed Afzal Azam,Nithyanantham Muruganantham,Rajagopal Kalirajan,Kannan Elango. (2013-03-30) Synthesis and characterization of some novel fatty acid analogues: a preliminary investigation on their activity against human lung carcinoma cell line.. Lipids in health and disease, 12 (45-45). [PMID:23537396]
36. Zosia Kmietowicz. (2013-05-01) Evening primrose oil and borage oil do not help eczema symptoms, finds Cochrane review.. BMJ (Clinical research ed.), 346 (f2712-f2712). [PMID:23628953]
37. Xiaofei Bai,Leng-Jie Huang,Sheng-Wen Chen,Benjamin Nebenfuehr,Brian Wysolmerski,Jui-Ching Wu,Sara K Olson,Andy Golden,Chao-Wen Wang. (2020-08-21) Loss of the seipin gene perturbs eggshell formation in Caenorhabditis elegans.. Development (Cambridge, England), 147 ((20)): [PMID:32820022]
38. 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]
39. 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]
40. 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]
41. 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]

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