Gamolenic acid | γ-Linolenic Acid | CAS#506-26-3 | omega-6 fatty acid PPAR agonist

MedKoo Cat#: 540270 | Name: Gamolenic acid

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Description:

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

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.

Chemical Structure

Gamolenic acid

CAS#506-26-3

Theoretical Analysis

MedKoo Cat#: 540270

Name: Gamolenic acid

CAS#: 506-26-3

Chemical Formula: C18H30O2

Exact Mass: 278.2246

Molecular Weight: 278.44

Elemental Analysis: C, 77.65; H, 10.86; O, 11.49

Price and Availability

Size	Price	Availability
100mg	USD 285.00	2 Weeks
250mg	USD 550.00	2 Weeks
1g	USD 950.00	2 Weeks

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Synonym

γ-Linolenic Acid; Gamolenic acid; gamma-Linolenic acid; FA 18:3; GLA

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

Appearance

Liquid

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).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Biological target: Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from human milk and several botanical seed oils.

In vitro activity:

GLA (gamma-linolenic acid) at 30 μM, a concentration reportedly within the range of circulating concentrations in clinical studies, caused apoptotic cell death. GLA caused an elevation in mitochondrial Ca2+ level and a decrease in mitochondrial membrane potential. GLA treatment depleted cyclopiazonic acid (CPA)-sensitive Ca2+ store and triggered substantial Ca2+ influx. Reference: Chin J Physiol. 2021 Jul-Aug;64(4):202-209. https://pubmed.ncbi.nlm.nih.gov/34472451/

In vivo activity:

The initial study revealed that of all the fatty acids tested, GLA was the most effective in protecting the animals from radiation-induced mortality (see Figure 9 for the protocol of the studies; the protocol is shown for GLA only, and the same protocol was used for studying the effect of other fatty acids, including LXA4). Reference: Biomolecules. 2022 Jun 7;12(6):797. https://pubmed.ncbi.nlm.nih.gov/35740923/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	359.15

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 278.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Chen CY, Wu CH, Wu KC, Shiao LR, Chuang CM, Leung YM, Chow LWC. A basal level of γ-linolenic acid depletes Ca2+ stores and induces endoplasmic reticulum and oxidative stresses to cause death of breast cancer BT-474 cells. Chin J Physiol. 2021 Jul-Aug;64(4):202-209. doi: 10.4103/cjp.cjp_30_21. PMID: 34472451. 2. Wang Y, Shi J, Gong L. Gamma linolenic acid suppresses hypoxia-induced gastric cancer cell growth and epithelial-mesenchymal transition by inhibiting the Wnt/b-catenin signaling pathway. Folia Histochem Cytobiol. 2020;58(2):117-126. doi: 10.5603/FHC.a2020.0012. Epub 2020 Jul 1. PMID: 32608501. 3. Rengachar P, Bhatt AN, Polavarapu S, Veeramani S, Krishnan A, Sadananda M, Das UN. Gamma-Linolenic Acid (GLA) Protects against Ionizing Radiation-Induced Damage: An In Vitro and In Vivo Study. Biomolecules. 2022 Jun 7;12(6):797. doi: 10.3390/biom12060797. PMID: 35740923; PMCID: PMC9221136. 4. Cui H, Han F, Zhang L, Wang L, Kumar M. Gamma linolenic acid regulates PHD2 mediated hypoxia and mitochondrial apoptosis in DEN induced hepatocellular carcinoma. Drug Des Devel Ther. 2018 Dec 13;12:4241-4252. doi: 10.2147/DDDT.S178519. PMID: 30587920; PMCID: PMC6296206.

In vitro protocol:

In vivo protocol:

1. Rengachar P, Bhatt AN, Polavarapu S, Veeramani S, Krishnan A, Sadananda M, Das UN. Gamma-Linolenic Acid (GLA) Protects against Ionizing Radiation-Induced Damage: An In Vitro and In Vivo Study. Biomolecules. 2022 Jun 7;12(6):797. doi: 10.3390/biom12060797. PMID: 35740923; PMCID: PMC9221136. 2. Cui H, Han F, Zhang L, Wang L, Kumar M. Gamma linolenic acid regulates PHD2 mediated hypoxia and mitochondrial apoptosis in DEN induced hepatocellular carcinoma. Drug Des Devel Ther. 2018 Dec 13;12:4241-4252. doi: 10.2147/DDDT.S178519. PMID: 30587920; PMCID: PMC6296206.

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.