All chemicals and solvents used in this study such as hexane, ethanol, hydrogen peroxide, toluene and acetic acid were from the analar grade and were used without further purification. Oleic acid (OA), LinOleic acid (LA), p-toluenesulfonic acid (PTSA), oleyl alcohol (OL) and oleoyl chloride (OLC) were acquired from Fisher and Merck.
Linoleic acid
Manufactured by Thermo Fisher Scientific
Sourced in United States, United Kingdom, Japan, Germany, Belgium
Linoleic acid is a polyunsaturated fatty acid that is commonly used in various laboratory applications. It serves as a key component in the formulation of culture media, buffers, and other reagents utilized in scientific research and analysis.
Automatically generated - may contain errors
Lab products found in correlation
Oleic acid, by Thermo Fisher Scientific (5 mentions)
Tween 80, by Merck Group (4 mentions)
Trolox, by Thermo Fisher Scientific (3 mentions)
Palmitic acid, by Thermo Fisher Scientific (3 mentions)
Oleic acid, by Merck Group (3 mentions)
Gallic acid, by Thermo Fisher Scientific (2 mentions)
Hexane, by Thermo Fisher Scientific (2 mentions)
Ethanol, by Thermo Fisher Scientific (2 mentions)
Folin ciocalteu s reagent, by Merck Group (2 mentions)
Potassium persulfate, by Thermo Fisher Scientific (2 mentions)
Anhydrous sodium carbonate, by Thermo Fisher Scientific (2 mentions)
Chloroform, by Thermo Fisher Scientific (2 mentions)
Iron 3 chloride anhydrous, by Thermo Fisher Scientific (2 mentions)
Tween 40, by Thermo Fisher Scientific (2 mentions)
2 2 azinodi 3 ethyl benzthiazoline sulfonate, by Merck Group (2 mentions)
Milli q water purification unit, by Merck Group (2 mentions)
Sodium acetate, by Merck Group (2 mentions)
Methanol, by Merck Group (2 mentions)
Acetone, by Merck Group (2 mentions)
Kanamycin sulfate, by Carl Roth (2 mentions)
28 protocols using linoleic acid
1
Chemical Reagent Purification Protocol
2
Characterization of Lipid Compounds
3
Analytical Reagents and Solvents Procurement
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All the chemicals and reagents were of analytical grades. Ethanol, hexane, gallic acid, linoleic acid, Trolox, Tween 40, sodium carbonate anhydrous, chloroform, iron (III) chloride anhydrous, and potassium persulfate were purchased from Fisher Scientifi c Co. (Fisher Scientifi c, Loughborough, UK). Acetone, mEthanol, Folin-Ciocalteu's reagent, and 2,2'-azinodi[3-ethyl-benzthiazoline sulfonate] (ABTS) were from Merck KGaA (Lichrosolv, Darmstadt, Germany), while 2,2-diphenyl-1-picryhydrazyl (DPPH), β-carotene, butylated hydroxy anisole (BHA), acetic acid, and sodium acetate were purchased from Sigma-Aldrich (St. Louis, MO, USA). Distilled water used was obtained from a Milli-Q water purifi cation unit (Millipore, Milford, MA, USA).
4
Antioxidant Activity Characterization
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All the chemicals and reagents were of analytical grade. Ethanol, hexane, gallic acid, linoleic acid, Trolox, Tween 40, sodium carbonate anhydrous, chloroform, iron(III) chloride anhydrous, and potassium persulfate were purchased from Fisher Scientifi c Co. (Fisher Scientifi c, Loughborough, UK). Acetone, mEthanol, Folin-Ciocalteu's reagent, and 2,2'-azinodi[3-ethyl-benzthiazoline sulfonate] (ABTS) were from Merck KGaA (Lichrosolv, Darmstadt, Germany), while 2,2-diphenyl-1-picrylhydrazyl (DPPH), β-carotene, butylated hydroxy anisole (BHA), acetic acid, and sodium acetate were purchased from Sigma-Aldrich (St. Louis, MO, USA). Distilled water was obtained from a Milli-Q water purifi cation unit (Millipore, Milford, MA, USA).
5
Topical Delivery System Optimization
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RLX, peppermint oil, Tween® 80, n-propranolol, n-butanol, polyethylene glycol (PEG) 200, propylene glycol, gellan gum, TPGS, and HPLC-grade methanol and acetonitrile were purchased from Sigma-Aldrich (St Louis, MO, USA). Sefsol® 218 was kindly supplied by Nikko Chemicals Company, Ltd. (Tokyo, Japan), linoleic acid was purchased from Thermo Fisher Scientific (Waltham, MA, USA), and Kolliphor® RH 40 was purchased from BASF Corp. (Ludwigshafen, Germany).
6
Safflower Oil Fatty Acid Composition Analysis
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Safflower oil was purchased from Gefro (Germany) and had a fatty acid composition of 77.2% linoleic acid, 13.3% oleic acid, 2.4% stearic acid, 6.7% palmitic acid, and 0.4% of other fatty acids [11 (link)]. 13S-HPODE, 12-oxo-9(Z)-dodecenoic acid, and 12-oxo-10(E)-dodecenoic acid standards were from Larodan (Sweden). Hexanal, hexanol, and 12-hydroxydodecanoic acid standards, Glycine max LOX-1, and P. fluorescens Amano lipase were obtained from Sigma-Aldrich (USA). linoleic acid was purchased from Thermo Fisher Scientific (USA), and δ-aminolevulinic acid (ALA), Triton X-100, isopropyl β-d-1-thiogalactopyranoside (IPTG), as well as kanamycin sulfate and ampicillin sodium salt were obtained from Carl Roth (Germany). All other solvents and chemicals were supplied by Carl Roth (Germany), Sigma-Aldrich (USA), or Thermo Fisher Scientific (USA). For PCR, Phusion Hot Start DNA polymerase with 5 × Phusion High-fidelity buffer and dNTPs were obtained from Thermo Fisher Scientific (USA). PageRuler™ Prestained Protein ladder, restriction enzymes, and the monoclonal AP-conjugated Anti-His (C-term) antibody (AB_2556555) were purchased from Thermo Fisher Scientific (USA) as well. Alkaline phosphatase was obtained from New England Biolabs GmbH (Germany).
7
Identification of Compounds in P. maliformis Flowers
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For positive identification of the compounds in P. maliformis flowers, β-pinene, borneol, indole, terpin, raspberry ketone (4-(4-hydroxyphenyl)-2-butanone), cuelure (4-(4-acetoxyphenyl)-2-butanone), zingerone (4-(4-hydroxy-3-methoxyphenyl)-2-butanone), farnesol, palmitic acid, ethyl palmitate, phytol, linolenic acid, ethyl linoleate, ethyl linolenate, stearic acid, ethyl stearate, and squalene were purchased from Sigma-Aldrich (Merck KGaA, Darmstadt, Germany). Nonanoic acid was purchased from Acros Organics (Thermo Fisher Scientific, Geel, Belgium). Propyl laurate was purchased from AbovChem (AbovChem LLC, San Diego, CA, USA). Farnesyl acetate (a mixture of isomers) was purchased from TCI (Tokyo Chemical Industry Co., Ltd. Tokyo, Japan). Linoleic acid was purchased from Alfa-Aesar (Thermo Fisher Scientific, Lancashire, UK). The chemicals were analytical or reagent grade with 98% or higher purity and used without further purifications. Zingerol (4-(4-hydroxy-3-methoxyphenyl)-2-butanol) was synthesized by the reduction of zingerone with sodium borohydride in methanol (See Supplementary Materials for synthetic details).
8
Enzymatic Synthesis of Oxidized Lipids
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The 12-aminododecanoic acid standard was purchased from Alfa Aesar (Haverhill, MA, USA), while the 12-oxo-9(Z)-dodecenoic acid and 12-oxo-10(E)-dodecenoic acid standards were purchased from Larodan (Solna, Sweden). Pyridoxal-5-phosphate monohydrate (PLP) was obtained from Acros Organics, Thermo Fisher Scientific (Waltham, MA, USA). Hexanal, hexylamine, soybean LOX-1, and L-lactate dehydrogenase (LDH) were supplied from Sigma Aldrich (St. Louis, MO, USA). Linoleic acid was obtained from Thermo Fisher Scientific (Waltham, MA, USA). β-Nicotine amide adenine dinucleotide disodium salt (NADH), isopropyl β-d-1-thiogalactopyranoside (IPTG), l-alanine, imidazole, ampicillin sodium salt, and kanamycin sulfate were purchased from Carl Roth (Karlsruhe, Germany). 13S-Hydroperoxy-9(Z),11(E)-octadecadienoic acid (13S-HPODE) was prepared from Linoleic acid by a peroxidation reaction with LOX-1 from Glycine max as described previously (Gala Marti et al. 2021 (link)). All other chemicals were from Sigma-Aldrich (St. Louis, MO, USA), Thermo Fisher Scientific (Waltham, MA, USA) or Carl Roth (Karlsruhe, Germany).
9
Lipid Membrane Fluidity Analysis
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Oxacillin sodium salt (catalog number: sc-224180B, Santa Cruz Biotechnology Inc., Dallas, TX, USA) was dissolved in distilled water. Ricinoleic acid (catalog number: R7257, Sigma-Aldrich Inc., Seoul, Republic of Korea), palmitic acid (catalog number: 129702500, Acros Organics, ThermoFisher Scientific Korea Ltd., Seoul, Republic of Korea), stearic acid (catalog number: S0163, Tokyo Chemical Industry Co., Ltd., Tokyo, Japan), linoleic acid (catalog number: L07949, ThermoFisher Scientific Korea), and oleic acid (catalog number: O0180, Tokyo Chemical Industry) were dissolved in ethanol (catalog number: 000E0243, Samchun Chemicals). Laurdan (6-Dodecanoyl-2-Dimethylaminonaphthalene, catalog number: D250) was purchased from Invitrogen (ThermoFisher Scientific Korea). Phosphate-buffered saline (PBS, catalog number: P5493-1L) was purchased from Sigma-Aldrich Inc.
10
In Vitro Hepatocyte and Gut-Liver Chip Assays
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Mycophenolate mofetil, mycophenolic acid and TRITON X 100 were obtained from Sigma-Aldrich (St. Louis, Missouri, US). mycophenolic acid β-D-glucuronide was obtained from Toronto Research Chemicals (Toronto, Ontario, Canada). PBS, cryopreserved hepatocyte recovery medium, William's E medium, primary hepatocyte plating supplements (solution of FBS, dexamethasone, cocktail-A having penicillinstreptomycin, human recombinant insulin, GlutaMAX™, and HEPES), primary hepatocyte maintenance supplements having dexamethasone and cocktail-B [penicillin-streptomycin, ITS+ (insulin, transferrin, selenium complex), bovine serum albumin (BSA), linoleic acid, GlutaMAX™, and HEPES, penicillin/streptomycin], Dubeccos modified eagle medium (DMEM) high glucose with glutamine, non-essential amino acids, Pierce™ BCA Protein Assay Kit, DAPI (4′,6-diamidino-2phenylindole) solutions, and phalloidin were purchased from Thermo Fisher Scientific (Waltham, Massachusetts, US). Human hepatocytes (lot: RAS) were purchased from BioIVT (Royston, United Kingdom). Caco2 cells co-cultured with HT29 cells were purchased from ReadyCells (Barcelona, Spain) as pre-seeded in 6.5 mm diameter transwells. All Physiomimix gut-liver on a chip components (controller, docking station and drivers) and consumables (TL-6 plates) were provided by CN Bio Innovations (Cambridge, UK).
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