Palmitic acid | CAS#57-10-3 | saturated fatty acid

MedKoo Cat#: 591740 | Name: Palmitic acid

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Description:

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

Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common saturated fatty acid found in animals, plants and microorganisms.

Chemical Structure

Palmitic acid

CAS#57-10-3

Theoretical Analysis

MedKoo Cat#: 591740

Name: Palmitic acid

CAS#: 57-10-3

Chemical Formula: C16H32O2

Exact Mass: 256.2402

Molecular Weight: 256.43

Elemental Analysis: C, 74.94; H, 12.58; O, 12.48

Price and Availability

Size	Price	Availability	Quantity
10g	USD 240.00
25g	USD 400.00

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Related CAS #

No Data

Synonym

Palmitic acid; NSC 5030; NSC-5030; NSC5030

IUPAC/Chemical Name

Hexadecanoic acid

InChi Key

IPCSVZSSVZVIGE-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)

SMILES Code

CCCCCCCCCCCCCCCC(O)=O

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

>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:

PA (palmitic acid) can induce the expression of glucose-regulated protein 78 (GRP78) and CCAAT/enhancer binding protein homologous protein (CHOP) in in mouse granulosa cells.

In vitro activity:

PA (palmitic acid) functions as a ligand for TLR4 on human monocyte derived dendritic cells (MoDCs). Treatment of human MoDCs with PA resulted in endocytosis of TLR4, further supporting the function of PA as a TLR4 agonist. In addition, PA stimulated DC maturation and activation based on the upregulation of DC costimulatory factors CD86 and CD83. Further experiments showed that PA induced TLR4 dependent secretion of the pro-inflammatory cytokine IL-1β. Lastly, the experimental data show that PA stimulation of NF-κB canonical pathway activation is regulated by TLR4 signaling and that reactive oxygen species may be important in upregulating this pro-inflammatory response. Reference: PLoS One. 2017 May 2;12(5):e0176793. https://pubmed.ncbi.nlm.nih.gov/28463985/

In vivo activity:

In a dose-dependent fashion, palmitic acid rapidly reduced mouse locomotor activity by a mechanism that did not rely on TLR4, MyD88, IL-1, IL-6 or TNFα but was dependent on fatty acid chain length. Twenty-four hours after palmitic acid administration mice exhibited anxiety-like behavior without impairment in locomotion, food intake, depressive-like behavior or spatial memory. Additionally, the serotonin metabolite 5-HIAA was increased by 33% in the amygdala 24h after palmitic acid treatment. Reference: Metabolism. 2014 Sep;63(9):1131-40. https://pubmed.ncbi.nlm.nih.gov/25016520/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	77.99
	DMSO	57.0	222.28
	Ethanol	60.3	235.28
	Ethanol:PBS (pH 7.2) (1:2)	0.3	0.97

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 256.43 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. Nicholas DA, Zhang K, Hung C, Glasgow S, Aruni AW, Unternaehrer J, Payne KJ, Langridge WHR, De Leon M. Palmitic acid is a toll-like receptor 4 ligand that induces human dendritic cell secretion of IL-1β. PLoS One. 2017 May 2;12(5):e0176793. doi: 10.1371/journal.pone.0176793. PMID: 28463985; PMCID: PMC5413048. 2. Liang H, Zhong Y, Zhou S, Li QQ. Palmitic acid-induced apoptosis in pancreatic β-cells is increased by liver X receptor agonist and attenuated by eicosapentaenoate. In Vivo. 2011 Sep-Oct;25(5):711-8. PMID: 21753123. 3. Moon ML, Joesting JJ, Lawson MA, Chiu GS, Blevins NA, Kwakwa KA, Freund GG. The saturated fatty acid, palmitic acid, induces anxiety-like behavior in mice. Metabolism. 2014 Sep;63(9):1131-40. doi: 10.1016/j.metabol.2014.06.002. Epub 2014 Jun 9. PMID: 25016520; PMCID: PMC4151238. 4. Harada H, Yamashita U, Kurihara H, Fukushi E, Kawabata J, Kamei Y. Antitumor activity of palmitic acid found as a selective cytotoxic substance in a marine red alga. Anticancer Res. 2002 Sep-Oct;22(5):2587-90. PMID: 12529968.

In vitro protocol:

In vivo protocol:

1. Moon ML, Joesting JJ, Lawson MA, Chiu GS, Blevins NA, Kwakwa KA, Freund GG. The saturated fatty acid, palmitic acid, induces anxiety-like behavior in mice. Metabolism. 2014 Sep;63(9):1131-40. doi: 10.1016/j.metabol.2014.06.002. Epub 2014 Jun 9. PMID: 25016520; PMCID: PMC4151238. 2. Harada H, Yamashita U, Kurihara H, Fukushi E, Kawabata J, Kamei Y. Antitumor activity of palmitic acid found as a selective cytotoxic substance in a marine red alga. Anticancer Res. 2002 Sep-Oct;22(5):2587-90. PMID: 12529968.

1: Jain A, Mathur A, Pandey U, Sarma HD, Dash A. Synthesis and evaluation of (68)Ga labeled palmitic acid for cardiac metabolic imaging. Appl Radiat Isot. 2018 Jun 5;140:35-40. doi: 10.1016/j.apradiso.2018.06.003. [Epub ahead of print] PubMed PMID: 29936274. 2: Ahmed Z, Malli S, Diaz-Salmeron R, Destruel PL, Da Costa A, Guigner JM, Porcher F, Baptiste B, Ponchel G, Bouchemal K. New insights on the structure of hexagonally faceted platelets from hydrophobically modified chitosan and α-cyclodextrin. Int J Pharm. 2018 Jun 21. pii: S0378-5173(18)30433-2. doi: 10.1016/j.ijpharm.2018.06.035. [Epub ahead of print] PubMed PMID: 29936201. 3: 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. 4: Lucarini M, Durazzo A, Sánchez Del Pulgar J, Gabrielli P, Lombardi-Boccia G. Determination of fatty acid content in meat and meat products: The FTIR-ATR approach. Food Chem. 2018 Nov 30;267:223-230. doi: 10.1016/j.foodchem.2017.11.042. Epub 2017 Nov 11. PubMed PMID: 29934161. 5: Sugawara T, Onoue S, Takimoto H, Kawahara K. Modification of lipid A structure and activity by the introduction of palmitoyltransferase gene to the acyltransferase-knockout mutant of Escherichia coli. Microbiol Immunol. 2018 Jun 22. doi: 10.1111/1348-0421.12631. [Epub ahead of print] PubMed PMID: 29932223. 6: 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. 7: 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. 8: Ye JZ, Li YT, Wu WR, Shi D, Fang DQ, Yang LY, Bian XY, Wu JJ, Wang Q, Jiang XW, Peng CG, Ye WC, Xia PC, Li LJ. Dynamic alterations in the gut microbiota and metabolome during the development of methionine-choline-deficient diet-induced nonalcoholic steatohepatitis. World J Gastroenterol. 2018 Jun 21;24(23):2468-2481. doi: 10.3748/wjg.v24.i23.2468. PubMed PMID: 29930468; PubMed Central PMCID: PMC6010937. 9: Das S, Reddy MA, Senapati P, Stapleton K, Lanting L, Wang M, Amaram V, Ganguly R, Zhang L, Devaraj S, Schones DE, Natarajan R. Diabetes Mellitus-Induced Long Noncoding RNA Dnm3os Regulates Macrophage Functions and Inflammation via Nuclear Mechanisms. Arterioscler Thromb Vasc Biol. 2018 Jun 21. pii: ATVBAHA.117.310663. doi: 10.1161/ATVBAHA.117.310663. [Epub ahead of print] PubMed PMID: 29930005. 10: Lacombe RJS, Giuliano V, Chouinard-Watkins R, Bazinet RP. Natural Abundance Carbon Isotopic Analysis Indicates the Equal Contribution of Local Synthesis and Plasma Uptake to Palmitate Levels in the Mouse Brain. Lipids. 2018 Jun 20. doi: 10.1002/lipd.12046. [Epub ahead of print] PubMed PMID: 29923600. 11: Li X, Jin SJ, Su J, Li XX, Xu M. Acid Sphingomyelinase Down-Regulation Alleviates Vascular Endothelial Insulin Resistance in Diabetic Rats. Basic Clin Pharmacol Toxicol. 2018 Jun 19. doi: 10.1111/bcpt.13073. [Epub ahead of print] PubMed PMID: 29923306. 12: Park SH, Kyndt J, Chougule K, Park JJ, Brown JK. Low-phosphate-selected Auxenochlorella protothecoides redirects phosphate to essential pathways while producing more biomass. PLoS One. 2018 Jun 19;13(6):e0198953. doi: 10.1371/journal.pone.0198953. eCollection 2018. PubMed PMID: 29920531; PubMed Central PMCID: PMC6007911. 13: Schiffer JM, Luo M, Dommer AC, Thoron G, Pendergraft MA, Santander MV, Lucero D, Pecora de Barros E, Prather KA, Grassian VH, Amaro RE. Impacts of Lipase Enzyme on the Surface Properties of Marine Aerosols. J Phys Chem Lett. 2018 Jun 19. doi: 10.1021/acs.jpclett.8b01363. [Epub ahead of print] PubMed PMID: 29916254. 14: Ortiz-Rodriguez A, Acaz-Fonseca E, Boya P, Arevalo MA, Garcia-Segura LM. Lipotoxic Effects of Palmitic Acid on Astrocytes Are Associated with Autophagy Impairment. Mol Neurobiol. 2018 Jun 18. doi: 10.1007/s12035-018-1183-9. [Epub ahead of print] PubMed PMID: 29916142. 15: Wu JY, Liao JH, Shieh CJ, Hsieh FC, Liu YC. Kinetic analysis on precursors for iturin A production from Bacillus amyloliquefaciens BPD1. J Biosci Bioeng. 2018 Jun 12. pii: S1389-1723(18)30236-6. doi: 10.1016/j.jbiosc.2018.05.002. [Epub ahead of print] PubMed PMID: 29907529. 16: Ozseyhan ME, Li P, Na G, Li Z, Wang C, Lu C. Improved fatty acid profiles in seeds of Camelina sativa by artificial microRNA mediated FATB gene suppression. Biochem Biophys Res Commun. 2018 Jun 14. pii: S0006-291X(18)31363-9. doi: 10.1016/j.bbrc.2018.06.051. [Epub ahead of print] PubMed PMID: 29906463. 17: Béghin L, Marchandise X, Lien E, Bricout M, Bernet JP, Lienhardt JF, Jeannerot F, Menet V, Requillart JC, Marx J, De Groot N, Jaeger J, Steenhout P, Turck D. Growth, stool consistency and bone mineral content in healthy term infants fed sn-2-palmitate-enriched starter infant formula: A randomized, double-blind, multicentre clinical trial. Clin Nutr. 2018 Jun 1. pii: S0261-5614(18)30200-0. doi: 10.1016/j.clnu.2018.05.015. [Epub ahead of print] PubMed PMID: 29903473. 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: Athanázio-Heliodoro JC, Okino-Delgado CH, Fernandes CJDC, Zanutto MR, Prado DZD, da Silva RA, Facanali R, Zambuzzi WF, Marques MOM, Fleuri LF. Improvement of lipase obtaining system by orange waste-based solid-state fermentation: production, characterization and application. Prep Biochem Biotechnol. 2018 Jun 14:1-9. doi: 10.1080/10826068.2018.1476879. [Epub ahead of print] PubMed PMID: 29902112. 20: Takeda M, Sakaguchi T, Hiraide T, Shibasaki Y, Morita Y, Kikuchi H, Ikegami K, Setou M, Konno H, Takeuchi H. Role of caveolin-1 in hepatocellular carcinoma arising from non-alcoholic fatty liver disease. Cancer Sci. 2018 Jun 13. doi: 10.1111/cas.13659. [Epub ahead of print] PubMed PMID: 29896915.