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M chloroperoxybenzoic acid

Manufactured by Merck Group
Sourced in United States

M-chloroperoxybenzoic acid is a chemical compound used as an oxidizing agent in laboratory settings. It is a crystalline solid with a distinctive odor. The primary function of this compound is to serve as a source of peroxy groups, which can be employed in various chemical reactions and synthesis processes. A detailed description of its intended use or applications is not available.

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4 protocols using m chloroperoxybenzoic acid

1

Synthesis of Chromium Porphyrin and Corrole Complexes

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meso-Tetramesitylporphyrin was purchased from Mid-Century Chemicals. Chromium(ii) chloride (CrCl2), chromium hexacarbonyl, and m-chloroperoxybenzoic acid (mCPBA) were purchased from Sigma-Aldrich. Chloroform was distilled from P4O10, deacidified by passing through a two-layered column of dry K2CO3 and dry basic alumina (Activity I), and stored over activated 4 Å molecular sieves. meso-Tetraphenylporphyrin22 (link) and meso-triphenylcorrole23 (link) were prepared according to literature procedures. Chromium(iii) meso-tetramesitylporphyrin chloride,24 (link) CrIII[TMP]Cl, and chromium(iii) meso-tetraphenylporphyrin chloride,25 (link) CrIII[TPP]Cl (1), were prepared under aerobic conditions using protocols due to Adler et al.26 (link) Chromium(iv)-oxo meso-tetramesitylporphyrin, CrIV[TMP]O (2), was prepared as previously described,44 with the following modifications: CrIII[TMP]Cl and mCPBA (4 equiv.) were stirred in dry, deacidified CHCl3 under argon for 15 min. Dry K2CO3 was added to the solution and after stirring for 3 min, the suspension was placed on a basic alumina (Activity I) column and flash-chromatographed with dry, deacidified CHCl3 under argon, whereupon CrIV[TMP]O eluted as the first red band. Chromium(v)-oxo meso-triphenylcorrole was prepared as previously described using a method similar to that used for the tris(pentafluorophenyl)corrole analogue.27 (link)
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2

Synthesis and Purification of Sterol Epoxides

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The 5α,6α-epoxycholesterol acetate and 5α,6α-epoxyphytosterols acetate were synthetized, respectively, from cholesterol and sitosterol (Sigma-Aldrich, USA) by acetylation and subsequent oxidation with m-chloroperoxybenzoic acid (Sigma-Aldrich, USA) as described by McCarthy et al. [6 (link)]. Next, the oxidation mixture was purified by column chromatography on silica gel using chloroform-acetone (4:1, v/v) as a mobile phase. Fractions containing pure ester were controlled by TLC technique (silica gel plates, solvent as above), pooled, and dried under vacuum.
According to information from the manufacturer, “sitosterol” contained about 90% β-sitosterol and ca. 10% other phytosterols and phytostanols. Thus, its oxidation products are named as 5α,6α-epoxyphytosterols.
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3

Cytotoxicity Assay of Chemical Compounds

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4-Cyanobenzaldehyde, benzil, 4-bromobenzoic acid, bis(pinacolato)diboron, 1,1′-carbonyldiimidazole (CDI), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)dichloride (PdCl2 (dppf)), H2O2, potassium super-oxide (KO2), t-butyl hydroperoxide (TBHP), m-chloroperoxybenzoic acid (mCPBA), hypochlorous acid (HOCl), HEPES buffer solution, Whatman papers, Dulbecco's phosphate-buffered saline (DBS), Roswell Park Memorial Institute (RPMI) medium, fetal bovine serum (FBS), penicillin, streptomycin, and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Ammonium acetate, acetic acid, ethanol, hydroxylamine hydrochloride, sodium hydroxide, ethyl acetate, hexane, sodium bicarbonate, dimethylformamide (DMF), dimethyl sulfoxide (DMSO), 1,4-dioxane, and potassium acetate were purchased from Daejung Chemicals (Siheungsi, Kyunggido, Republic of Korea). Sodium nitrate (NaNO3), potassium perchlorate (KClO4), sodium sulfate (Na2SO4), sodium nitrite (NaNO2), and benzoyl peroxide (BPO) were obtained from AccuStandard (New Haven, CT, USA). The MCF-7 cells were purchased from the Korean Cell Line Bank (Seoul, Republic of Korea). All reagents were used as received without further purification.
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4

Synthesis of 5α,6α-Epoxycholesterol Acetate

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5α,6α-Epoxycholesterol acetate was synthetized from cholesterol acetate (Sigma-Aldrich, USA) by oxidation with m-chloroperoxybenzoic acid (Sigma-Aldrich, USA) as described by McCarthy [11 (link)]. Next, oxidation product mixture was purified by column chromatography on silica gel with the use of chloroform-acetone (4 : 1, v/v) as mobile phase. Fractions containing pure ester were controlled by TLC technique (silica gel plates, solvent as above), pooled, and dried under vacuum.
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