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MedKoo Cat#: 591831 | Name: Linoleic acid
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Description:

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

Linoleic acid is a doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes.

Chemical Structure

Linoleic acid
CAS#60-33-3

Theoretical Analysis

MedKoo Cat#: 591831

Name: Linoleic acid

CAS#: 60-33-3

Chemical Formula: C18H32O2

Exact Mass: 280.2402

Molecular Weight: 280.45

Elemental Analysis: C, 77.09; H, 11.50; O, 11.41

Price and Availability

Size Price Availability Quantity
5g USD 350.00 2 Weeks
25g USD 750.00 2 Weeks
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Synonym
Linoleic acid
IUPAC/Chemical Name
9,12-Octadecadienoic acid (9Z,12Z)-
InChi Key
OYHQOLUKZRVURQ-HZJYTTRNSA-N
InChi Code
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
SMILES Code
CCCCC/C=C\C/C=C\CCCCCCCC(O)=O
Appearance
Liquid
Purity
>97% (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
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Linoleic acid is a common polyunsaturated (PUFA) found in plant-based oils, nuts and seeds.
In vitro activity:
Among them, linoleic acid was found to have the greatest interaction with SARS-CoV-2 RdRp, with its direct binding to the cavity formed by the RNA double helix and protein. Linoleic acid forms hydrophobic interactions with multiple residues, and at the same time forms electrostatic interactions including the hydrogen bond with Lys593 and Asp865. In line with these results, a dose-dependent inhibition of HCoV-OC43 replication in vitro was observed, additionally strengthened by data from in vivo study, which also confirmed anti-inflammatory potential of linoleic acid. Reference: Sci Rep. 2022 Nov 9;12(1):19114. https://pubmed.ncbi.nlm.nih.gov/36352079/
In vivo activity:
To study the effect of linoleic acid on red blood cells and to examine the pathogenesis of hidden blood loss in vivo, this study generated an animal model by injecting linoleic acid into the tail veins of rats. Hidden blood loss occurred when linoleic acid was administered at a concentration of 60 mmol/L; RBC and Hb levels were significantly reduced by 24 h post-injection. These findings suggest that linoleic acid enhances acute red blood cell injury. Hb and RBC began to increase by 72 h, potentially resulting from linoleic acid metabolism. Reference: Int J Clin Exp Pathol. 2015 May 1;8(5):5044-52. https://pubmed.ncbi.nlm.nih.gov/26191198/
Solvent mg/mL mM comments
Solubility
DMSO 100.0 356.57
0.1 M NaOH 8.3 29.70
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 280.45 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.

Recalculate based on batch purity %
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. Goc A, Sumera W, Rath M, Niedzwiecki A. Linoleic acid binds to SARS-CoV-2 RdRp and represses replication of seasonal human coronavirus OC43. Sci Rep. 2022 Nov 9;12(1):19114. doi: 10.1038/s41598-022-23880-9. PMID: 36352079; PMCID: PMC9645759. 2. Alarcon-Gil J, Sierra-Magro A, Morales-Garcia JA, Sanz-SanCristobal M, Alonso-Gil S, Cortes-Canteli M, Niso-Santano M, Martínez-Chacón G, Fuentes JM, Santos A, Perez-Castillo A. Neuroprotective and Anti-Inflammatory Effects of Linoleic Acid in Models of Parkinson's Disease: The Implication of Lipid Droplets and Lipophagy. Cells. 2022 Jul 26;11(15):2297. doi: 10.3390/cells11152297. PMID: 35892594; PMCID: PMC9331796. 3. Azemi NA, Azemi AK, Abu-Bakar L, Sevakumaran V, Muhammad TST, Ismail N. Effect of Linoleic Acid on Cholesterol Levels in a High-Fat Diet-Induced Hypercholesterolemia Rat Model. Metabolites. 2022 Dec 30;13(1):53. doi: 10.3390/metabo13010053. PMID: 36676979; PMCID: PMC9864559. 4. Yuan T, Fan WB, Cong Y, Xu HD, Li CJ, Meng J, Bao NR, Zhao JN. Linoleic acid induces red blood cells and hemoglobin damage via oxidative mechanism. Int J Clin Exp Pathol. 2015 May 1;8(5):5044-52. PMID: 26191198; PMCID: PMC4503070.
In vitro protocol:
1. Goc A, Sumera W, Rath M, Niedzwiecki A. Linoleic acid binds to SARS-CoV-2 RdRp and represses replication of seasonal human coronavirus OC43. Sci Rep. 2022 Nov 9;12(1):19114. doi: 10.1038/s41598-022-23880-9. PMID: 36352079; PMCID: PMC9645759. 2. Alarcon-Gil J, Sierra-Magro A, Morales-Garcia JA, Sanz-SanCristobal M, Alonso-Gil S, Cortes-Canteli M, Niso-Santano M, Martínez-Chacón G, Fuentes JM, Santos A, Perez-Castillo A. Neuroprotective and Anti-Inflammatory Effects of Linoleic Acid in Models of Parkinson's Disease: The Implication of Lipid Droplets and Lipophagy. Cells. 2022 Jul 26;11(15):2297. doi: 10.3390/cells11152297. PMID: 35892594; PMCID: PMC9331796.
In vivo protocol:
1. Azemi NA, Azemi AK, Abu-Bakar L, Sevakumaran V, Muhammad TST, Ismail N. Effect of Linoleic Acid on Cholesterol Levels in a High-Fat Diet-Induced Hypercholesterolemia Rat Model. Metabolites. 2022 Dec 30;13(1):53. doi: 10.3390/metabo13010053. PMID: 36676979; PMCID: PMC9864559. 2. Yuan T, Fan WB, Cong Y, Xu HD, Li CJ, Meng J, Bao NR, Zhao JN. Linoleic acid induces red blood cells and hemoglobin damage via oxidative mechanism. Int J Clin Exp Pathol. 2015 May 1;8(5):5044-52. PMID: 26191198; PMCID: PMC4503070.
1: Mazoochian L, Mohammad Sadeghi HM, Pourfarzam M. The effect of FADS2 gene rs174583 polymorphism on desaturase activities, fatty acid profile, insulin resistance, biochemical indices, and incidence of type 2 diabetes. J Res Med Sci. 2018 May 30;23:47. doi: 10.4103/jrms.JRMS_961_17. eCollection 2018. PubMed PMID: 29937909; PubMed Central PMCID: PMC5996566. 2: Zozaya C, García-Serrano A, Fontecha J, Redondo-Bravo L, Sánchez-González V, Montes MT, Saenz de Pipaón M. Fat Loss in Continuous Enteral Feeding of the Preterm Infant: How Much, What and When Is It Lost? Nutrients. 2018 Jun 23;10(7). pii: E809. doi: 10.3390/nu10070809. PubMed PMID: 29937492. 3: Giacomini A, Stagni F, Emili M, Guidi S, Salvalai ME, Grilli M, Vidal-Sanchez V, Martinez-Cué C, Bartesaghi R. Treatment with corn oil improves neurogenesis and cognitive performance in the Ts65Dn mouse model of Down syndrome. Brain Res Bull. 2018 Jun 20. pii: S0361-9230(18)30330-7. doi: 10.1016/j.brainresbull.2018.06.009. [Epub ahead of print] PubMed PMID: 29935232. 4: Zhuang P, Shou Q, Wang W, He L, Wang J, Chen J, Zhang Y, Jiao J. Essential Fatty Acids Linoleic Acid and Α-Linolenic Acid Sex-Dependently Regulate Glucose Homeostasis in Obesity. Mol Nutr Food Res. 2018 Jun 23:e1800448. doi: 10.1002/mnfr.201800448. [Epub ahead of print] PubMed PMID: 29935107. 5: Thakur VR, Beladiya JV, Chaudagar KK, Mehta AA. An anti-asthmatic activity of Natural Toll like receptor-4 antagonist in OVA-LPS induced asthmatic rats. Clin Exp Pharmacol Physiol. 2018 Jun 23. doi: 10.1111/1440-1681.13002. [Epub ahead of print] PubMed PMID: 29935094. 6: Petropoulos SA, Pereira C, Ntatsi G, Danalatos N, Barros L, Ferreira ICFR. Nutritional value and chemical composition of Greek artichoke genotypes. Food Chem. 2018 Nov 30;267:296-302. doi: 10.1016/j.foodchem.2017.01.159. Epub 2017 Feb 2. PubMed PMID: 29934171. 7: Hatami A, Zhu C, Relaño-Gines A, Elias C, Galstyan A, Jun M, Milne G, Cantor CR, Chesselet MF, Shchepinov MS. Deuterium-reinforced linoleic acid lowers lipid peroxidation and mitigates cognitive impairment in the Q140 knock in mouse model of Huntington's disease. FEBS J. 2018 Jun 22. doi: 10.1111/febs.14590. [Epub ahead of print] PubMed PMID: 29933522. 8: Bernat P, Nykiel-Szymańska J, Stolarek P, Słaba M, Szewczyk R, Różalska S. 2,4-dichlorophenoxyacetic acid-induced oxidative stress: Metabolome and membrane modifications in Umbelopsis isabellina, a herbicide degrader. PLoS One. 2018 Jun 22;13(6):e0199677. doi: 10.1371/journal.pone.0199677. eCollection 2018. PubMed PMID: 29933393. 9: Gao HL, Zhang AH, Yu JB, Sun H, Kong L, Wang XQ, Yan GL, Liu L, Wang XJ. High-throughput lipidomics characterize key lipid molecules as potential therapeutic targets of Kaixinsan protects against Alzheimer's disease in APP/PS1 transgenic mice. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Jun 18;1092:286-295. doi: 10.1016/j.jchromb.2018.06.032. [Epub ahead of print] PubMed PMID: 29933222. 10: Dogan A, Dalar A, Sadullahoglu C, Battal A, Uzun Y, Celik I, Demirel K. Investigation of the protective effects of horse mushroom (Agaricus arvensis Schaeff.) against carbon tetrachloride-induced oxidative stress in rats. Mol Biol Rep. 2018 Jun 21. doi: 10.1007/s11033-018-4218-4. [Epub ahead of print] PubMed PMID: 29931536. 11: Li XZ, Yan CG, Gao QS, Yan Y, Choi SH, Smith SB. Adipogenic/lipogenic gene expression and fatty acid composition in chuck, loin, and round muscles in response to grain feeding of Yanbian Yellow cattle. J Anim Sci. 2018 Jun 21. doi: 10.1093/jas/sky161. [Epub ahead of print] PubMed PMID: 29931237. 12: Ribeiro FA, Domenech-Pérez KI, Contreras-Castillo CJ, Wilkerson EK, Voegele HR, Ballard Hart K, Herrera NJ, Calkins CR. Effects of dietary fat source on beef strip loin steak display life. J Anim Sci. 2018 Jun 19. doi: 10.1093/jas/sky113. [Epub ahead of print] PubMed PMID: 29924329. 13: Mboma J, Leblanc N, Angers P, Rocher A, Vigor C, Oger C, Reversat G, Vercauteren J, Galano JM, Durand T, Jacques H. Effects of Cyclic Fatty Acid Monomers from Heated Vegetable Oil on Markers of Inflammation and Oxidative Stress in Male Wistar Rats. J Agric Food Chem. 2018 Jun 19. doi: 10.1021/acs.jafc.8b01836. [Epub ahead of print] PubMed PMID: 29920087. 14: Stoessel D, Stellmann JP, Willing A, Behrens B, Rosenkranz SC, Hodecker SC, Stürner KH, Reinhardt S, Fleischer S, Deuschle C, Maetzler W, Berg D, Heesen C, Walther D, Schauer N, Friese MA, Pless O. Metabolomic Profiles for Primary Progressive Multiple Sclerosis Stratification and Disease Course Monitoring. Front Hum Neurosci. 2018 Jun 4;12:226. doi: 10.3389/fnhum.2018.00226. eCollection 2018. PubMed PMID: 29915533; PubMed Central PMCID: PMC5994544. 15: Osowska S, Kunecki M, Sobocki J, Tokarczyk J, Majewska K, Omidi M, Radkowski M, Fisk HL, Calder PC. Effect of changing the lipid component of home parenteral nutrition in adults. Clin Nutr. 2018 Jun 6. pii: S0261-5614(18)30214-0. doi: 10.1016/j.clnu.2018.05.028. [Epub ahead of print] PubMed PMID: 29907355. 16: Poomanee W, Chaiyana W, Mueller M, Viernstein H, Khunkitti W, Leelapornpisid P. In-vitro investigation of anti-acne properties of Mangifera indica L. kernel extract and its mechanism of action against Propionibacterium acnes. Anaerobe. 2018 May 17;52:64-74. doi: 10.1016/j.anaerobe.2018.05.004. [Epub ahead of print] PubMed PMID: 29906773. 17: Valenti B, Luciano G, Pauselli M, Mattioli S, Biondi L, Priolo A, Natalello A, Morbidini L, Lanza M. Dried tomato pomace supplementation to reduce lamb concentrate intake: Effects on growth performance and meat quality. Meat Sci. 2018 Jun 9;145:63-70. doi: 10.1016/j.meatsci.2018.06.009. [Epub ahead of print] PubMed PMID: 29906738. 18: Yang F, Wu J, Zheng Y. [Difference of fatty acids in human milk, bovine milk and powdered formulas with the change of lactation period or suitable object]. Wei Sheng Yan Jiu. 2017 Jul;46(4):579-614. Chinese. PubMed PMID: 29903179. 19: Hanana M, Mezghenni H, Ben Ayed R, Ben Dhiab A, Jarradi S, Jamoussi B, Hamrouni L. Nutraceutical potentialities of Tunisian Argan oil based on its physicochemical properties and fatty acid content as assessed through Bayesian network analyses. Lipids Health Dis. 2018 Jun 15;17(1):138. doi: 10.1186/s12944-018-0782-9. PubMed PMID: 29903007. 20: Weng LC, Guan W, Steffen LM, Pankow JS, Pankratz N, Chen MH, Cushman M, Basu S, Folsom AR, Tang W. Pleiotropic effects of n-6 and n-3 fatty acid-related genetic variants on circulating hemostatic variables. Thromb Res. 2018 Jun 1;168:53-59. doi: 10.1016/j.thromres.2018.05.032. [Epub ahead of print] PubMed PMID: 29902632.