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Palmitoyl chloride

Manufactured by Merck Group
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Sourced in United States, New Zealand, India, United Kingdom, France

Palmitoyl chloride is a chemical compound used as an intermediate in organic synthesis. It is a clear, colorless liquid with a distinctive odor. Palmitoyl chloride is commonly used in the production of various chemicals, pharmaceuticals, and personal care products.

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Lab products found in correlation

C18 redisep rf gold 15 g, by Teledyne (2 mentions) Stearoyl chloride, by Merck Group (2 mentions) Oleoyl chloride, by Merck Group (2 mentions) 4 dimethylaminopyridine, by Merck Group (2 mentions) Lauroyl chloride, by Merck Group (2 mentions) 4 6 diamidino 2 phenylindole (dapi), by Thermo Fisher Scientific (2 mentions) Palmitic acid, by Merck Group (1 mentions) Horseradish peroxidase hrp conjugated goat anti rabbit igg, by Abcam (1 mentions) Hela cell, by American Type Culture Collection (1 mentions) A549 cell, by American Type Culture Collection (1 mentions) Hydroxylamine, by Merck Group (1 mentions) Rapigest, by Waters Corporation (1 mentions) Dithiothreitol (dtt), by Merck Group (1 mentions) Ammonium bicarbonate, by Merck Group (1 mentions) 2 5 dihydroxybenzoic acid dhb, by Bruker (1 mentions) Ammonium hydrogen carbonate, by Merck Group (1 mentions) Pyridine, by Avantor (1 mentions) Methanol, by Merck Group (1 mentions) Formic acid, by Merck Group (1 mentions) Ammonium formate, by Merck Group (1 mentions)

12 protocols using palmitoyl chloride

1

Palmitoyl Peptide Synthesis on Wang Resin

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Wang resins with preloaded amino acids were purchased from Matrix Innovation. Coupling reagents (PyBOP and Cl-HOBt) were purchased from P3 BioSystems. Palmitoyl chloride and all other reagents were purchased from Sigma-Aldrich. Dimethylformamide (DMF) was added to preloaded Wang resins (~80 mg) and incubated for 30 minutes. Removal of N-Fmoc from swollen resins was accomplished by two rounds of piperidine treatment [20% solution in DMF (v/v), 3 ml] for 3 and 10 minutes, followed by several washes with DMF. Palmitoyl chloride (1 equivalent) in DMF was then added and the resin suspension was shaken for 2 hours at room temperature. The N-acylated amino acid product was cleaved from the resins by treatment with trifluoroacetic acid (TFA) supplemented with 2.5% (v/v) water and 2.5% (v/v) triisopropylsilane (TIPS). After evaporation of TFA the crude product was purified by automated reversed phase flash chromatography (Teledyne Isco, C18 RediSep RF GoldTm 15 g), binary solvent system: water and acetonitrile supplemented with 0.1% acetic acid. All final products were verified by MS (Supplementary Table 3).
Cohen L.J., Esterhazy D., Kim S.H., Lemetre C., Aguilar R.R., Gordon E.A., Pickard A.J., Cross J.R., Emiliano A.B., Han S.M., Chu J., Vila-Farres X., Kaplitt J., Rogoz A., Calle P.Y., Hunter C., Bitok J.K, & Brady S.F. (2017). Commensal bacteria produce GPCR ligands that mimic human signaling molecules. Nature, 549(7670), 48-53.
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2

Peptide-Liposome Nanoparticle Synthesis

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PEI (branched, 25 kDa), palmitic acid (PA) (≥99%), and palmitoyl chloride (98%) were purchased from Sigma-Aldrich (St. Louis, MO). Fmoc-l-arginine and 2-chlorotrityl chloride resins were purchased from JiEr Biochemistry Company (Shanghai, China). O-benzotriazol-1-yl-tetramethyluronium hexafluorophosphate (HBTU), 1-hydroxybenzotriazole (Hobt), and N,N-diisopropyl ethylamine (DIEA) were purchased from Xiya Chemical Technology Co., Ltd. (Chengdu, China). Egg phosphatidylcholine (ePC) and cholesterol were purchased from Avanti Polar Lipids, Inc. (Shanghai, China). LOR-2501 (5′-CTC TAG CGT CTT AAA GCC GA-3′) and 5′-Cy3-labled LOR-2501 were synthesized by Biomics Biotechnologies (Jiangsu, China). 4′,6-Diamidino-2-phenylindole (DAPI) was purchased from Thermo Fisher Scientific (Rockford, IL). Roswell Park Memorial Institute 1640 (RPMI 1640), Dulbecco’s modified Eagle’s medium (DMEM) and fetal bovine serum (FBS) were purchased from HyClone (Logan, UT). GAPDH, anti-R1 antibody and horseradish peroxidase (HRP)-conjugated goat anti-rabbit IgG were obtained from Abcam Inc. (Cambridge, MA). HeLa cells and A549 cells were purchased from American Type Culture Collection (ATCC). All other analytical reagents were commercially obtained in reagent grade.
Yang S., Wang D., Sun Y, & Zheng B. (2019). Delivery of antisense oligonucleotide using polyethylenimine-based lipid nanoparticle modified with cell penetrating peptide. Drug Delivery, 26(1), 965-974.
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3

Peptide Synthesis and Modification

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Synthetic peptide GCLGNAK was acquired from AnaSpec (San Jose, CA). Palmitoyl chloride, dithiothreitol (DTT), hydroxylamine (HA), and ammonium bicarbonate (ABC) were purchased from Sigma-Aldrich (St. Louis, MO). Trifluoroacetic acid (TFA), formic acid (FA), and iodoacetamide (IAM) were purchased from Pierce (Rockford, IL). RapiGest™ was obtained from Waters (Milford, MA). 2,5-dihydroxybenzoic acid (DHB) was obtained from Bruker Daltonics (Billerica, MA). Acetonitrile (ACN) and isopropanol (IPA) were obtained from Burdick and Jackson (Muskegon, MI).
Ji Y., Bachschmid M.M., Costello C.E, & Lin C. (2016). S- to N-Palmitoyl Transfer during Proteomic Sample Preparation. Journal of the American Society for Mass Spectrometry, 27(4), 677-685.
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4

Lipid Synthesis and Characterization

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Methanol, acetonitrile, methyl‐tert‐butyl ether (MTBE), dichloromethane, palmitoyl chloride, heptadecanoyl chloride, stearoyl chloride, oleoyl chloride, 4‐dimethylaminopyridine, ammonium hydrogen carbonate, ammonium formate, 2‐propanol, formic acid, and acetic acid were purchased from Sigma–Aldrich (St Louis, MO, USA), and pyridine was purchased from VWR (Radnor, PA, USA). Deionized water was obtained from a MilliQ Gradient A10 system (Millipore, Billerica, MA, USA).
1,2‐Di‐(9Z‐octadecenoyl)‐sn‐glycero‐3‐phosphoethanolamine‐N‐nonadecanoyl (PE 18:1/18:1‐N‐19:0) and 1,2‐dioleoyl‐sn‐glycero‐3‐phosphoethanolamine‐N‐arachidonoyl (ammonium salt) (PE 18:1/18:1‐N‐20:4) were purchased from Avanti Polar Lipids (Alabaster, AL, USA) and l‐α‐phosphatidylethanolamine from Larodan Fine Chemicals AB (Malmö, Sweden). Lipid standard stock solutions at concentrations of 1 mmol/L were prepared in chloroform/Methanol (1:1, v/v).
Triebl A., Weissengruber S., Trötzmüller M., Lankmayr E, & Köfeler H. (2016). Quantitative analysis of N‐acylphosphatidylethanolamine molecular species in rat brain using solid‐phase extraction combined with reversed‐phase chromatography and tandem mass spectrometry. Journal of Separation Science, 39(13), 2474-2480.
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5

Phenolic Compounds Extraction and Derivatization

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Commercial standards include (+)-catechin hydrate (≥98%), (−)-epicatechin (≥90%), rutin hydrate (≥95%) and quercetin (≥95%) were purchased from Sigma-Aldrich (Auckland, New Zealand). Acetonitrile (MeCN, HPLC grade), L-(+)-tartaric acid (reagent grade), acetone (analytical grade) and ethanol (analytical grade) were purchased from ECP (Auckland, New Zealand). Glacial acetic acid (AcOH, HPLC grade) was purchased from ThermoFisher Scientific (Auckland, New Zealand). Ultrapure water (H2O) had resistivity of 18.2 MΩ cm and was obtained from Sartorius Arium® Pro system. Pinot noir grape pomace (seeds, skins and stems) was industrially sourced from a New Zealand vineyard in 2015. Acylating agents (octanoyl chloride, lauroyl chloride and palmitoyl chloride) were purchased from Sigma-Aldrich (Auckland, New Zealand).
Lo S., Pilkington L.I., Barker D, & Fedrizzi B. (2022). Attempts to Create Products with Increased Health-Promoting Potential Starting with Pinot Noir Pomace: Investigations on the Process and Its Methods. Foods, 11(14), 1999.
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6

Palmitoyl Peptide Synthesis on Wang Resin

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Wang resins with preloaded amino acids were purchased from Matrix Innovation. Coupling reagents (PyBOP and Cl-HOBt) were purchased from P3 BioSystems. Palmitoyl chloride and all other reagents were purchased from Sigma-Aldrich. Dimethylformamide (DMF) was added to preloaded Wang resins (~80 mg) and incubated for 30 minutes. Removal of N-Fmoc from swollen resins was accomplished by two rounds of piperidine treatment [20% solution in DMF (v/v), 3 ml] for 3 and 10 minutes, followed by several washes with DMF. Palmitoyl chloride (1 equivalent) in DMF was then added and the resin suspension was shaken for 2 hours at room temperature. The N-acylated amino acid product was cleaved from the resins by treatment with trifluoroacetic acid (TFA) supplemented with 2.5% (v/v) water and 2.5% (v/v) triisopropylsilane (TIPS). After evaporation of TFA the crude product was purified by automated reversed phase flash chromatography (Teledyne Isco, C18 RediSep RF GoldTm 15 g), binary solvent system: water and acetonitrile supplemented with 0.1% acetic acid. All final products were verified by MS (Supplementary Table 3).
Cohen L.J., Esterhazy D., Kim S.H., Lemetre C., Aguilar R.R., Gordon E.A., Pickard A.J., Cross J.R., Emiliano A.B., Han S.M., Chu J., Vila-Farres X., Kaplitt J., Rogoz A., Calle P.Y., Hunter C., Bitok J.K, & Brady S.F. (2017). Commensal bacteria produce GPCR ligands that mimic human signaling molecules. Nature, 549(7670), 48-53.
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7

Fluorometric Lipase Activity Assay

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Resorufin, Resorufin sodium salt, naphthofluorescein, palmitoyl chloride, phospholipase A2 from porcine pancreas, arachidonyl trifluoromethyl ketone, bromoenol lactone, ionomycin, and H2O2 30% (w/w) were purchased from Sigma-Aldrich. DDAO, arachidonoyl chloride, and LY311727 were purchased from Santa Cruz Biotechnology. 7-HCA was purchased from Cayman Chemical. Syto 9 was purchased from Life Technologies. Egg phosphatidylcholine was purchased from Avanti Polar Lipids, Inc.
Chiorazzo M.G., Bloch N.B., Popov A.V, & Delikatny E.J. (2015). Synthesis and Evaluation of Cytosolic Phospholipase A2 Activatable Fluorophores for Cancer Imaging. Bioconjugate chemistry, 26(12), 2360-2370.
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8

Synthesis and Purification of Fatty Acid Derivatives

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Decanoylchloride (N10), laurylchloride (N12), myristoyl-chloride (N14), palmitoylchloride (N16), stearoylchloride (N18), tromethamine hydrochloride (TM), 8-anilinonapthalene sulfonic acid (ANS), laurdan and prodan were purchased from Sigma, India. All other reagents were of reagent grade and were obtained from local suppliers. Solvents were distilled and dried prior to usage.
Megarajan S., Subramaniyan S.B., Muthuswamy S., Anthony S.P., Arunachalam J., Moon D, & Veerappan A. (2018). Synthesis, supramolecular organization and thermotropic phase behaviour of N-acyltris(hydroxymethyl)aminomethane. RSC Advances, 8(57), 32823-32831.
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9

Synthesis of Novel Acyl Chlorides

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Hesperetin, Oleoyl chloride, Lauroyl chloride, Palmitoyl chloride, 4-nitrobenzoyl chloride, and Methoxyacetyl chloride, were bought from Sigma-Aldrich Chemicals Pvt. Ltd, USA. Triethylamine, Sodium sulphate, and solvents were bought from SRL, India. It comes with high purity so we can use it without any further purification. Column chromatography was performed on Silica Gel 60 (100–200 mesh). 1H &13C NMR spectra were recorded on Bruker DRX 500. Elemental analyses were performed using Perkin-Elmer 2400 elemental analyzer and optical rotations were determined by using a Rudolph Autopol II digital polarimeter.
, & Rajasekar M. (2021). Synthesis and characterization of hesperetin derivatives and toxicity level of the zebrafish model. Heliyon, 7(1), e06066.
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10

Synthesis and Characterization of PEGylated Polyplexes

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PEG (5 kDa, α-methoxy-ω-NHS ester activated) was purchased from NanoCS (New York, NY). Branched PEI (bPEI), deoxycholate (DOC), N-hydroxy succinimide, 4-dimethylaminopyridine, 1-ethyl-3-(3-dimethyl aminopropyl) carbodiimide hydrochloride (EDC HCl), palmitoyl chloride, resazurin sodium salt, sulforhodamine B based in vitro toxicology assay kit (TOX6), and poly(L-lysine) (PLL, 30-70 kDa) were purchased from Sigma Aldrich (St. Louis, MO). RNAiMAX, 4-12% NuPAGE Bis-Tris precast gels, HEPES buffer (pH 8.0, 1 M), MES buffer (0.1 M, pH 5.0), RIPA buffer, pyridine, NuSieve GTG agarose, dialysis membrane with molecular cut-off (MWCO) of 6-8 and 100 kDa, and other organic solvents were purchased from Fisher Scientific (Waltham, MA). siRNA (5′-GUUGGCACCAGCAGCGCACUU-3′) was purchased from GE Dharmacon (Lafayette, CO). Opti-MEM was purchased from Life Technologies (Carlsbad, CA). Mitochondrial ToxGlo™ assay kit and Bradford assay kit were purchased from Promega (Madison, WI). McCoy's 5A, 0.05% trypsin/EDTA, and phosphate buffered saline (PBS) were from GE Healthcare (Logan, UT). Fetal bovine serum (FBS) was purchased from Atlanta Biologicals (Flowery Branch, GA).
Rheiner S., Reichel D., Rychahou P., Izumi T., Yang H.S, & Bae Y. (2017). Polymer Nanoassemblies with Hydrophobic Pendant Groups in the Core Induce False Positive siRNA Transfection in Luciferase Reporter Assays. International journal of pharmaceutics, 528(1-2), 536-546.
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