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9 protocols using lauric acid

1

Characterization of Lipid Compounds

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β-sitosterol (≥70%) and oleic acid (≥90%) were purchased from Sigma-Aldrich (Brondby, Denmark). Linoleic acid (97%) was obtained from TCI Europe (Zwijndrecht, Belgium) and stearic acid (97%), palmitic acid (98%) and lauric acid (99%) from Acros Organics (Geel, Belgium). β-sitosterol and oleic acid were analyzed for their chemical composition since their purity was lower than that of the other starting materials. Table 6 shows the sterol composition of β-sitosterol as measured by the method described in Ryckebosch et al. (2012a) [34 (link)]. Table 7 reports the fatty acid composition of oleic acid as determined by the method described in Ryckebosch et al. (2012b) [35 (link)].
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2

Fatty Acid Standards for Analytical LC-MS

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All solvents used were of LC–MS analytical grade. Acetonitrile was purchased from Carlo Erba (Val De Reuil, France), isopropanol and methanol from Fisher Scientific (Laughborough, UK) and formic acid 98–100% from Chem-Lab (Zedelgem, Belgium). Lauric acid was purchased from Acros Organics (>99%), myristic acid from Sigma Aldrich (>99.5%), myristoleic acid from Sigma Aldrich (>99%), pentadecanoic acid from Sigma Aldrich (>99%), palmitic acid from Fluka (analytical standard), 9-palmitoleic acid from Fluka (analytical standard), margaric acid from Sigma Aldrich (>98%), 10-Z-heptadecenoic acid from Cayman Chemical Company (>98%), stearic acid from Fluka (analytical standard), oleic acid from Fluka (analytical standard), linoleic acid from Sigma Aldrich (>99%), linolenic acid from Sigma Aldrich (>99%), arachidic acid from Cayman Chemical Company (>98%), bihomo-γ-linolenic acid from Cayman Chemical Company (>98%), arachidonic acid from Sigma Aldrich (>99), 5,8,11,14,17-cis-eicosapentanoic acid from Fluka (analytical standard), 7,10,13,16,19-cis-docosapentaenoic acid from Cayman Chemical Company (>98%), 4,7,10,13,16,19-cis-docosahexaenoic acid from Sigma Aldrich (>98%) and lignoceric acid from Cayman Chemical Company (>98%).
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3

Fatty Acid Profiling Protocol

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Ethyl acetate (EtOAc), methanol (MeOH), acetonitrile (ACN), chloroform (CHCl3), sulfuric acid 96% (H2SO4) and propan-2-ol were purchased from Carlo Erba (Val de Reuil, France). Ammonium formate and the following standards were purchased from Sigma Aldrich (Saint-Quentin Fallavier, France): dodecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, γ-linolenic acid, arachidic acid, arachidonic acid, nervonic acid, eicosapentaenoic acid and eicosatrienoic acid. Dimethyl carbonate (DMC) and lauric acid 99% were purchased from Acros Organics (Geel, Belgium). Formic acid was purchased from Fisher Scientific SAS (Illkirch, France). Nonanoic acid 98% and decanoic acid 99% were purchased from Alfa Aesar (Haverhill, MA, USA). Water was purified using a Milli-Q system (Millipore Corporation, Bedford, MA, USA). Phosphoric acid 85–90% (H3PO4) and Formic acid were purchased from Fisher Scientific SAS (Illkirch, France). Vanillin was purchased from Extrasynthese (Genay, France).
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4

Comprehensive Lipid Standards for Analytical Protocols

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Methanol (Optima grade), formic acid (Optima grade), ammonium acetate, hexane, acetonitrile, and ammonium hydroxide were purchased from Fisher Scientific (Fair Lawn, NJ, USA). Oxalyl chloride, oleic acid, erucic acid, petroselaidic acid, heptane HPLC grade, methyl-tert-butyl-ether HPLC grade, isopropanol HPLC grade, acetic acid, and anhydrous dichloromethane were from Sigma Aldrich (St Louis, MO, USA). N, N-dimethylformamide, heptadecanoic acid, and eicosanoic acid were purchased from Aldrich Chemical Company (Milwaukee, WI, USA). Lauric acid, myristic acid, palmitic acid, stearic acid, and docosanoic acid were purchased from Acros Organics (New Jersey, USA). Elaidic acid was from MP Biomedical Inc. (Solon, OH, USA) and linoleamide was purchased from Enzo Life Sciences (Ann Arbor, MI, USA). Stearoyl ethanolamine, oleoylglycine, linoleoylglycine, palmitoylglycine, arachidonoylglycine, and arachidoylglycine were purchased from Cayman Chemicals (Ann Arbor, MI, USA). 1 monopalmitoyl-rac-glycerol (MAG) and tristearin (TAG) were from Sigma (St. Louis, MO) 99% purity and 1,2-dipalmitoyl-rac-glycerol (DAG) was from MP Biomedicals (Solon, Ohio).
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5

Synthesis of Fatty Acid-Polylysine Conjugates

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As previously reported [19 , 20 ], fatty acids and PLL were used to synthesize fatty acid-PLLs. The saturated fatty acids used were caproic acid (C6, Sigma-Aldrich), caprylic acid (C8, Acros Organics), capric acid (C10, Sigma-Aldrich), lauric acid (C12, Acros Organics), myristic acid (C14, Acros Organics), and palmitic acid (C16, Acros Organics), whereas the unsaturated fatty acids used were palmitoleic acid (C16:1, Fluka), oleic acid (C18:1, Sigma-Aldrich), and linoleic acid (C18:2, Sigma-Aldrich). The cationic α-PLL (Alamanda Polymers; molecular mass around 21,000 Da) is a polypeptide composed of repeated structural units of 100 lysine residues and PLL was analyzed by gas chromatography and nuclear magnetic resonance for molecular mass determination and polydispersity index.
Each fatty acid was activated by ethyl chloroformate (ECF), which acts as a coupling agent by activating the carboxylic group of the fatty acids. The intermediate compound was linked to the ε-amine group of the lysine residue through amide-bond formation [21 (link)]. This was then purified by dialysis in buffer solutions and lyophilized for analysis. Thus, the final compounds were called fatty acid-PLLs. For example, lauric acid linked to PLL was called lauryl-PLL (see Figure 1).
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6

Characterization of Phase Change Materials and Recycled Tire Rubber Composites

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Paraffin (P), palmitic acid (PA), and stearic acid (SA) were acquired from Merck Chemical, Aldrich, and TEKKIM, respectively, while amyristic acid (MA) and lauric acid were obtained (LA) from Acros Organics. Molecular and structural formulas of fatty acids are summarized in Table 1. Figure 1 shows chemical structures of the fatty acids and image of the PCMs used in this study. Epoxy and epoxy hardener behave as the auxiliary.
The ELT rubber powder (also can be called as tire rubber powder, rubber powder or regenerated tire rubber) provided from UN-SAL (Turkey) was used as a composite matrix. The properties of the ELT rubber powder sample as indicated in the certificate analysis of the products are presented in Table 2.
The particle size distribution analyses of ELT rubber powder used in this study were determined by laser diffraction particle size analyser (Malvern-Mastersizer 3000). According to the particle size distribution analyses presented in Figure 2, the ELT rubber powder has a median grain size (d50) of 381μm and d90 value of 717μm.
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7

Preparation of Glycosylated Surfaces

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Lauric acid was purchased from Alfa Aesar. Sodium dodecylbenzenesulfonate (SDBS) and cetyltrimethylammonium tosylate (CTAT) were purchased from TCI America and Merck, respectively. N,N′-dicyclohexylcarbodiimide (DCC) coupling reagent was purchased from TCI America. High-binding polystyrene 96-well ELISA plates were purchased from Santa Cruz Biotechnology, Inc. Biotin-ConA and biotin-SNA were purchased from Vector Laboratories. Galectin-3 with a His tag at the N-terminus was purchased from Abcam. All other chemicals were purchased from Sigma-Aldrich unless sated otherwise and used as received.
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8

Synthesis of 64Cu-Incorporated Iron Oxide Nanoparticles

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To synthesize 64Cu-incorporated iron oxide (64Cu-IO) NPs, we purchased the reagents acetylacetone, sodium acetate, copper chloride, benzyl ether, iron acetylacetonate, lauric acid, dodecylamine, cyclohexane, ammonia hydroxide, and tetraethylorthosilicate from Alfa Aesar. In addition, reagents 1,2-hexadicanediol and igepal CO-520 were purchased from Sigma Aldrich (Burlington, MA, USA). 64Cu was supplied by Korea Institute of Radiological & Medical Sciences.
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9

Melanogenesis Inhibition Screening Assay

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Paeonol (≥98%), tyrosinase (≥500 U mg−1), penicillin–streptomycin solution (100X), l-glutamine (≥99%), and cholesterol (≥99.5%) were purchased from Macklin. Lauric acid (≥99%) was supplied by Alfa Aesar. Phosphate buffered saline (PBS, pH = 6.8, 0.01 M) was purchased from Biorigin. l-Dopa (≥98%) was supplied by Duly Biotech. Co. Ltd (Nanjing, China). Lecithin (from soybean, >90%) was purchased from Aladdin. DMSO (Greagent, ≥99%) and dichloromethane (Greagent, 99.5%) were from Tansoole (Titan Co. Shanghai, China). CCK-8 was from Invigentech. RPMI 1640 cell culture medium and fetal bovine serum (FBS) were supplied by Biological Industries.
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