Gamolenic acid
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540270

CAS#: 506-26-3

Description: Gamolenic acid is an omega-6 fatty acid PPAR agonist found in vegetable oils. It is a precursor to prostaglandin E1 and eicsapentaenoic acid. It regulates insuilin secretion, inhibits diabetes mellitus-induced albuminuria, and induces apoptosis in leukemia cells.


Price and Availability

Size
Price

100mg
USD 230
Size
Price

1g
USD 830
Size
Price

Gamolenic acid, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 540270
Name: Gamolenic acid
CAS#: 506-26-3
Chemical Formula: C18H30O2
Exact Mass: 278.2246
Molecular Weight: 278.43
Elemental Analysis: C, 77.65; H, 10.86; O, 11.49


Synonym: γ-Linolenic Acid; Gamolenic acid

IUPAC/Chemical Name: (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid

InChi Key: VZCCETWTMQHEPK-QNEBEIHSSA-N

InChi Code: 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-

SMILES Code: CCCCC/C=C\C/C=C\C/C=C\CCCCC(O)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Simon D, Eng PA, Borelli S, Kägi R, Zimmermann C, Zahner C, Drewe J, Hess L, Ferrari G, Lautenschlager S, Wüthrich B, Schmid-Grendelmeier P. Gamma-linolenic acid levels correlate with clinical efficacy of evening primrose oil in patients with atopic dermatitis. Adv Ther. 2014 Feb;31(2):180-8. doi: 10.1007/s12325-014-0093-0. Epub 2014 Jan 17. PubMed PMID: 24435467; PubMed Central PMCID: PMC3930832.

2: Antal O, Péter M, Hackler L Jr, Mán I, Szebeni G, Ayaydin F, Hideghéty K, Vigh L, Kitajka K, Balogh G, Puskás LG. Lipidomic analysis reveals a radiosensitizing role of gamma-linolenic acid in glioma cells. Biochim Biophys Acta. 2015 Sep;1851(9):1271-82. doi: 10.1016/j.bbalip.2015.06.003. Epub 2015 Jun 16. PubMed PMID: 26092623.

3: Jubie S, Dhanabal P, Afzal Azam M, Muruganantham N, Kalirajan R, Elango K. Synthesis and characterization of some novel fatty acid analogues: a preliminary investigation on their activity against human lung carcinoma cell line. Lipids Health Dis. 2013 Mar 28;12:45. doi: 10.1186/1476-511X-12-45. PubMed PMID: 23537396; PubMed Central PMCID: PMC3621780.

4: Klempova T, Basil E, Kubatova A, Certik M. Biosynthesis of gamma-linolenic acid and beta-carotene by Zygomycetes fungi. Biotechnol J. 2013 Jul;8(7):794-800. doi: 10.1002/biot.201200099. Epub 2013 Jun 7. PubMed PMID: 23625863.

5: Arm JP, Boyce JA, Wang L, Chhay H, Zahid M, Patil V, Govindarajulu U, Ivester P, Weaver KL, Sergeant S, Israel E, Chilton FH. Impact of botanical oils on polyunsaturated fatty acid metabolism and leukotriene generation in mild asthmatics. Lipids Health Dis. 2013 Oct 2;12:141. doi: 10.1186/1476-511X-12-141. PubMed PMID: 24088297; PubMed Central PMCID: PMC3851449.

6: Cheung KL. Management of cyclical mastalgia in oriental women: pioneer experience of using gamolenic acid (Efamast) in Asia. Aust N Z J Surg. 1999 Jul;69(7):492-4. PubMed PMID: 10442919.

7: Fejerčáková A, Vašková J, Bača M, Vaško L, Marcinčák S, Hertelyová Z, Petrášová D, Guothová L. Effect of dietary microbially produced gamma-linolenic acid and plant extracts on enzymatic and non-enzymatic antioxidants in various broiler chicken organs. J Anim Physiol Anim Nutr (Berl). 2014 Oct;98(5):860-6. doi: 10.1111/jpn.12146. Epub 2013 Nov 20. PubMed PMID: 24251917.

8: Park SO, Hwangbo J, Yuh IS, Park BS. Gamma-linolenic acid egg production enriched with hemp seed oil and evening primrose oil in diet of laying hens. J Environ Biol. 2014 Jul;35(4):635-40. PubMed PMID: 25004746.

9: Li C, Bo L, Liu W, Lu X, Jin F. Enteral Immunomodulatory Diet (Omega-3 Fatty Acid, γ-Linolenic Acid and Antioxidant Supplementation) for Acute Lung Injury and Acute Respiratory Distress Syndrome: An Updated Systematic Review and Meta-Analysis. Nutrients. 2015 Jul 9;7(7):5572-85. doi: 10.3390/nu7075239. Review. PubMed PMID: 26184293; PubMed Central PMCID: PMC4517016.

10: Sergeant S, Rahbar E, Chilton FH. Gamma-linolenic acid, Dihommo-gamma linolenic, Eicosanoids and Inflammatory Processes. Eur J Pharmacol. 2016 Aug 15;785:77-86. doi: 10.1016/j.ejphar.2016.04.020. Epub 2016 Apr 12. Review. PubMed PMID: 27083549; PubMed Central PMCID: PMC4975646.

11: Miyake JA, Benadiba M, Ribeiro G, DE Oliveira Silva D, Colquhoun A. Novel ruthenium - gamma-linolenic acid complex inhibits C6 rat glioma cell proliferation in vitro and in the orthotopic C6 model in vivo after osmotic pump infusion. Anticancer Res. 2014 Apr;34(4):1901-11. PubMed PMID: 24692725.

12: Das UN. n-3 fatty acids, γ-linolenic acid, and antioxidants in sepsis. Crit Care. 2013 Apr 19;17(2):312. doi: 10.1186/cc12574. Review. PubMed PMID: 23597172; PubMed Central PMCID: PMC3672630.

13: Shin KO, Kim K, Jeon S, Seo CH, Lee YM, Cho Y. Mass Spectrometric Confirmation of γ-Linolenic Acid Ester-Linked Ceramide 1 in the Epidermis of Borage Oil Fed Guinea Pigs. Lipids. 2015 Oct;50(10):1051-6. doi: 10.1007/s11745-015-4056-2. Epub 2015 Aug 2. PubMed PMID: 26233818.

14: Safarinejad MR, Shafiei N, Safarinejad S. Effects of EPA, γ-linolenic acid or coenzyme Q10 on serum prostate-specific antigen levels: a randomised, double-blind trial. Br J Nutr. 2013 Jul 14;110(1):164-71. doi: 10.1017/S0007114512004783. Epub 2012 Nov 30. PubMed PMID: 23199523.

15: Saad N, Abdeshahian P, Kalil MS, Yusoff WM, Hamid AA. Optimization of aeration and agitation rate for lipid and gamma linolenic acid production by Cunninghamella bainieri 2A1 in submerged fermentation using response surface methodology. ScientificWorldJournal. 2014;2014:280146. doi: 10.1155/2014/280146. Epub 2014 Dec 31. PubMed PMID: 25610901; PubMed Central PMCID: PMC4295020.

16: Chenoy R, Hussain S, Tayob Y, O'Brien PM, Moss MY, Morse PF. Effect of oral gamolenic acid from evening primrose oil on menopausal flushing. BMJ. 1994 Feb 19;308(6927):501-3. PubMed PMID: 8136666; PubMed Central PMCID: PMC2542782.

17: Ribeiro P, Carvalho FD, Abreu Ade A, Sant'anna Mde T, Lima RJ, Carvalho Pde O. Effect of fish oil supplementation in pregnancy on the fatty acid composition of erythrocyte phospholipids and breast milk lipids. Int J Food Sci Nutr. 2012 Feb;63(1):36-40. doi: 10.3109/09637486.2011.593714. Epub 2011 Jun 28. Erratum in: Int J Food Sci Nutr. 2012 Nov;63(7):893. PubMed PMID: 21707451.

18: Chen Q, Nimal J, Li W, Liu X, Cao W. Delta-6 desaturase from borage converts linoleic acid to gamma-linolenic acid in HEK293 cells. Biochem Biophys Res Commun. 2011 Jul 8;410(3):484-8. doi: 10.1016/j.bbrc.2011.06.003. Epub 2011 Jun 7. PubMed PMID: 21679695.

19: Tasset-Cuevas I, Fernández-Bedmar Z, Lozano-Baena MD, Campos-Sánchez J, de Haro-Bailón A, Muñoz-Serrano A, Alonso-Moraga A. Protective effect of borage seed oil and gamma linolenic acid on DNA: in vivo and in vitro studies. PLoS One. 2013;8(2):e56986. doi: 10.1371/journal.pone.0056986. Epub 2013 Feb 27. PubMed PMID: 23460824; PubMed Central PMCID: PMC3584109.

20: Tso P, Caldwell J, Lee D, Boivin GP, DeMichele SJ. 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 Chem Toxicol. 2012 Jun;50(6):1911-9. doi: 10.1016/j.fct.2012.01.001. Epub 2012 Jan 12. PubMed PMID: 22265940; PubMed Central PMCID: PMC4520314.