Capric acid

Manufactured by Merck Group

Sourced in United States, Germany

Capric acid is a medium-chain fatty acid commonly used in laboratory settings. It serves as a chemical building block and precursor for the synthesis of various compounds. The core function of capric acid is to provide a stable and versatile platform for further chemical reactions and formulations.

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Capric (4 citations)

22 protocols using capric acid

Synthesis of Fatty Acid Derivatives

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Capric acid (CA; purity degree: ≥ 98%; melting point: 27–32 °C), palmitic acid (PA; purity degree: ≥ 98%; melting point: 62–65 °C) and stearic acid (SA; purity degree: ≥ 98%; melting point: 67–72 °C) were obtained from Merck company (Germany), and used without further purifications. Thionly chloride (SOCl₂) and nitric acid (HNO₃) were purchased from BDH Chemicals Ltd. The CNTs were supplied from Cheap Tubes Inc. (Grafton, USA).

Al-Ahmed A., Sarı A., Mazumder M.A., Salhi B., Hekimoğlu G., Al-Sulaiman F.A, & I.n.a.m.u.d.d.i.n. (2020). Thermal energy storage and thermal conductivity properties of fatty acid/fatty acid-grafted-CNTs and fatty acid/CNTs as novel composite phase change materials. Scientific Reports, 10, 15388.

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Enzymatic Cottonseed Oil Esterification

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Experiments were performed using Lipozyme RM IM (lipase from R. miehei), kindly donated by Novozymes^® (Araucária, PR, Brazil). Cottonseed (Gossypium spp.) oil (Distriol^®, Ipiranga, SP, Brazil) and capric acid (Merck^®, Darmstadt, Germany) were used as raw materials. All other reagents were of analytical grade.

Remonatto D., Santaella N., Lerin L.A., Bassan J.C., Cerri M.O, & de Paula A.V. (2023). Solvent-Free Enzymatic Synthesis of Dietary Triacylglycerols from Cottonseed Oil in a Fluidized Bed Reactor. Molecules, 28(14), 5384.

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Synthesis and Antimicrobial Evaluation of Lipopeptides

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All amino acid residues and coupling reagents were purchased from GL Biochem (Shanghai, China). The fatty acids: caprylic acid, capric acid, lauric acid, myristic acid and palmitic acid, were acquired from Merck (Darmstadt, Germany), Sigma-Aldrich (Darmstadt, Germany) and Acros Organics (Geel, Belgium). The resin and solvents were purchased from Rapp Polymere (Tübingen, Germany) and Merck (Darmstadt, Germany). The phospholipids, 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), 1,2-dipalmitoyl-sn-glycero-3-[phospho-rac-(1-glycerol)] (DPPG), 1-palmitoyl-2-oleoyl-glycero-3-phosphocholine (POPC) and 1-palmitoyl-2-oleoyl-sn-glycero-3-[phospho-rac-(1-glycerol)] (POPG) were purchased from Avanti Polar Lipids (Alabaster, AL, USA). The Mueller Hinton broth was bought from BIOCORP (Warsaw, Poland) and the RPMI-1640 medium from Sigma-Aldrich (Darmstadt, Germany). Bacterial strains Staphylococcus aureus PCM 1650, Staphylococcus aureus PCM 2054, Staphylococcus epidermidis PCM 521, Staphylococcus epidermidis PCM 2118, Escherichia coli PCM 2057 obtained from the Polish Collection of Microorganisms (PCM, II TD PAN, Wrocław), Candida albicans PCM 2566, Candida glabrata CCM 8270, Candida krusei CCM 8271, Candida parapsilosis CCM 8260 were purchased from Czech Collection of Microorganisms (CCM, Department of Experimental Biology Faculty of Science, Masaryk University, Brno).

Makowska M., Kosikowska-Adamus P., Zdrowowicz M., Wyrzykowski D., Prahl A, & Sikorska E. (2023). Lipidation of Naturally Occurring α-Helical Antimicrobial Peptides as a Promising Strategy for Drug Design. International Journal of Molecular Sciences, 24(4), 3951.

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Curcumin-Loaded Nanoemulsion Preparation

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Glycerol from Golden Bell (Mexico City, México), 3 Å molecular mesh, Kolliphor^® EL from Sigma-Aldrich (Mexico City, México), caproic acid (purity ≥ 99.5%), caprylic acid (purity ≥ 98%), and capric acid (purity ≥ 98%) were purchased from Sigma-Aldrich (Mexico City, México). For the quantification of acylglycerides, chlorotrimethylsilane (TMC), hexamethyldisilazane (HMDS), and pyridine were also obtained from Sigma-Aldrich (Mexico City, México). Novozym 435 enzyme (Lipase from Candida antarctica fraction B) from NOVO (Salem City, VA, USA). Solvents used were of HPLC grade from Tecsiquim (Mexico City, México). Curcumin with a purity ≥98% was bought from LKT Laboratories (St. Paul, MN, USA). Swanson medium chain triacylglycerides (MCTs) form Fargo (ND) and Milli-Q water (Milli-Q corp. Bedford, MA, USA) were used to prepare the NE. A Zetasizer Nano- ZS90 dynamic light scattering device (Malvern Instruments Inc., Worcestershire, UK) was used to characterize the nanoemulsions (NEs).

Agame-Lagunes B., Grube-Pagola P., García-Varela R., Alexander-Aguilera A, & García H.S. (2021). Effect of Curcumin Nanoemulsions Stabilized with MAG and DAG-MCFAs in a Fructose-Induced Hepatic Steatosis Rat Model. Pharmaceutics, 13(4), 509.

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Lipid Droplet Imaging Assay

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Insulin, glucose, Nile Red, Hoechst 33342, BSA, capric acid, lauric acid, palmitic acid, and oleic acid, were purchased from Sigma-Aldrich. Bafilomycin A1 was purchased from Tocris. Antibodies purchased from Cell Signaling Technology, Abcam, and Santa Cruz Biotechnology were listed in Supplementary Table 1.

Wang M.E., Singh B.K., Hsu M.C., Huang C., Yen P.M., Wu L.S., Jong D.S, & Chiu C.H. (2017). Increasing Dietary Medium-Chain Fatty Acid Ratio Mitigates High-fat Diet-Induced Non-Alcoholic Steatohepatitis by Regulating Autophagy. Scientific Reports, 7, 13999.

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Synthesis and Characterization of Novel Lipid Compounds

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Purchased from commercial vendors: 6-OAU (Cayman Chemical 17687), DL-175 (Tocris 7082), capric acid (Sigma C1875), myristic acid (Sigma M2138), forskolin (Cambridge Bioscience SM18-2), cmpd101 (Tocris 5642), MK-2206 (APExBio A3010), U0126 (Cell Guidance Systems SM106), calyculin A (ab141784), pertussis toxin (Tocris 3097), DMSO (Sigma D8418), Tween-80 (Sigma 8.22187), BSA (Sigma A7906), PBS (Thermo 14190094), Tris-buffered saline (Sigma T5941, T6066, S9888), Tween-20 (Sigma P1379), RIPA buffer (Millipore 20-188), protease and phosphatase inhibitors (Sigma 11836170001, P5726, P5726; CST 8553), non-fat dry skim milk powder (Sigma 70166), collagen I (Merck C3867), formaldehyde (Thermo 28906), Hoechst 33342 (ImmunoChemistry technologies 639).
Antagonist 8 (2-((1,4-Dioxan-2-yl)methoxy)-9-hydroxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4- one, CAS ID 1445846-30-9) was synthesised as previously described [2]. DL-222 (2-(2-((4-chloronaphthalen-1-yl)oxy)ethyl)pyridine 1-oxide) was synthesised as previously described [11].
Synthesis of (rac)-3-hydroxy capric acid is provided in Supplementary Information.

Luscombe V.B., Baena-López L.A., Bataille C.J., Russell A.J, & Greaves D.R. (2023). Kinetic insights into agonist-dependent signalling bias at the pro-inflammatory G-protein coupled receptor GPR84. European Journal of Pharmacology, 956, 175960.

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Osteoclastogenesis Signaling Pathways

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Capric acid was purchased from Sigma (USA). RANKL and MCSF were obtained from R&D Systems (USA). Antibodies against phospho-IκBα, phospho-JNK, phospho-p38, phospho-ERK, IκBα, JNK, p38, ERK, phospho-c-Jun, and nucleophosmin were purchased from Cell Signaling Technology (USA). Anti-Bim antibody was obtained from BD Biosciences (USA). Anti-p65 antibody was obtained from Santa Cruz Biotechnology (USA). Anti-NFATc1 antibody was purchased from BD Pharmingen (USA).

Kim H.J., Yoon H.J., Kim S.Y, & Yoon Y.R. (2014). A Medium-Chain Fatty Acid, Capric Acid, Inhibits RANKL-Induced Osteoclast Differentiation via the Suppression of NF-κB Signaling and Blocks Cytoskeletal Organization and Survival in Mature Osteoclasts. Molecules and Cells, 37(8), 598-604.

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Preparation of Therapeutic Deep Eutectic Solvents

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The reagents used in the preparation of THEDES were S-Limonene (LIM, ref.218367 Sigma Aldrich), myristic acid (MA; ref.70082, Sigma Aldrich), Capric acid (CA, ref. A14788.30, Sigma Aldrich), menthol (ref.M2772, Sigma Aldrich) and Ibuprofen (IBU, ref. I4883, Sigma Aldrich). THEDES of MA:LIM, CA:LIM, menthol:LIM and IBU:LIM were prepared at different molar ratios. The systems were prepared by gently mixing the two components at the given molar ratio. The mixture was heated to 40 °C, under constant stirring, until a clear liquid solution was formed.

Pereira C.V., Silva J.M., Rodrigues L., Reis R.L., Paiva A., Duarte A.R, & Matias A. (2019). Unveil the Anticancer Potential of Limomene Based Therapeutic Deep Eutectic Solvents. Scientific Reports, 9, 14926.

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Lipid Signaling Pathway Reagents

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αLA, DHA, capric acid, palmitic acid, oleic acid, Fura 2-AM, EGTA, 2-aminoethoxydiphenylborane (2-APB), pertussis toxin (PTX), 8-bromo-cyclic adenosine diphosphate ribose (8-Bro-cADPR), 2,2′-dihydroxyazobenzene (DAB), and thapsigargin were purchased from Sigma-Aldrich (St Louis, MO, USA). EPA, lauric acid, myristic acid, stearic acid, linoleic acid, γ-linolenic acid, TUG-891, and edelfosine were obtained from Cayman (Ann Arbor, MI, USA).

Kim J.M., Lee K.P., Park S.J., Kang S., Huang J., Lee J.M., Sato K., Chung H.Y., Okajima F, & Im D.S. (2015). Omega-3 fatty acids induce Ca2+ mobilization responses in human colon epithelial cell lines endogenously expressing FFA4. Acta Pharmacologica Sinica, 36(7), 813-820.

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Purification and Characterization of Rat NADPH-P450 Reductase

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Lauric acid, capric acid, glucose-6-phosphate, glucose-6-phosphate dehydrogenase, dilauroyl-ʟ-phosphatidylcholine (DLPC), imidazole, and NADP⁺ were purchased from Sigma-Aldrich (St. Louis, MO, USA). Ni²⁺-nitrilotriacetate (NTA) agarose was purchased from Thermo Fisher Scientific (Waltham, MA, USA). 3-[(3-Cholamidopropyl) dimethylammonio]-1-propanesulfonate (CHAPS) was purchased from GoldBio (St. Louis, MO, USA). Rat NADPH-P450 reductase (NPR) was heterologously expressed in E. coli HMS174 (DE3) cells and purified as described previously (Park et al., 2017 (link)). All the other chemicals used were of the highest commercially available grade.

Lee S.A., Kim V., Choi B., Lee H., Chun Y.J., Cho K.S, & Kim D. (2022). Functional Characterization of Drosophila melanogaster CYP6A8 Fatty Acid Hydroxylase. Biomolecules & Therapeutics, 31(1), 82-88.

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