Lc msd sl

γ-Oryzanol was extracted and determined according to a previous report by Wongwaiwech et al.^{1 (link)} using LC–MS. Briefly, samples were extracted with a mixture of chloroform and methanol. A solution of 500 µL of supernatant was mixed with a solution of 500 µL of acetonitrile, methanol, and isopropanol, which was subsequently injected into the LC–MS.
γ-Oryzanol was separated on an Agilent Technologies 1100 with a diode array detector (DAD) chromatographic system equipped with an ultraviolet (UV) detector set at 298 and 325 nm. The sample was separated on an Agilent Zorbax Eclipse XDB-C18 column (4.6 m × 150 mm × 5 µm, U.S. A), and the column temperature was set at 40 °C. The mass spectrometer was an Agilent Technologies LC/MSD SL equipped with an electrospray ion source (ESI). The ESI–MS spectra were acquired in the positive ionization mode with a capillary voltage of 4000 V, nebulizer pressure of 50 psi, gas temperature of 350 °C, drying gas of 13.01 L/min and recorded on a mass range of m/z 200–800. A standard mixture of γ-oryzanol was used as an external standard to identify the peaks by Agilent Mass Hunter software based on their retention times.

γ-Oryzanol was extracted and determined according to a previous report by Wongwaiwech et al. [104 (link)] using LC–MS. In brief, the extracted oils were mixed with a solution of acetonitrile, methanol, and isopropanol then injected into the LC–MS. γ-oryzanol was identified by an Agilent Technologies 1100 with a diode array detector (DAD) equipped with a UV detector set at 298 and 325 nm. The analytical column was an Agilent Zorbax Eclipse XDB-C18 column (4.6 mm × 150 mm × 5 µm, Agilent Technologies, Santa Clara, CA, USA). The mobile phase was consisting of acetonitrile, methanol, and isopropanol (25:70:5 v/v) with a flow rate of 1 mL/min. The temperature of the column was kept at 40 °C. The mass spectrometer was an Agilent Technologies (Santa Clara, CA, USA) LC/MSD SL equipped with an electrospray ion source (ESI) using the following interface parameters: a drying gas flow of 13.01 L/min, nebulizer pressure of 50 psi, drying gas temperatures of 350 °C, a capillary voltage of 4000 V, and recorded on a mass range of m/z 200–800.

The concentration of BPA was analyzed on a Shimadzu LC-10A HPLC system with an Agilent HC-C18 column (5 μm, 250 mm × 4.6 mm). The mobile phase was a solution containing water-methanol (30/70, v/v) at a flow rate of 1.0 mL min⁻¹. The detector wavelength of bisphenol A was 278 nm. The LC-MS system used in the study was an Agilent LC/MSD SL ion trap mass spectrometer equipped with an ESI source in the negative ion mode. The mass spectral data were obtained in the positive ion mode between m/z 100–300. The settings were: capillary voltage, 3500 V; drying gas, 10 L/min; drying gas temperature, 350 °C; capillary exit, 150 V; skimmer, 40 V; octopole RF amplitude, 160 Vpp; ICC target, 100,000; trap drive, 60; maximum accumulation time, 100 ms.

All reagents and solvents were purchased from commercial suppliers and were used directly without further purification. Ciminalum was purchased from State Plant for Chemical Reagents STC of Institute for Single Crystals of the NAS of Ukraine. The elemental analyses (C, H, N) were performed using the Perkin–Elmer 2400 CHN analyzer (Perkin–Elmer, Norwalk, CT, USA). NMR spectra were determined with Varian Unity Plus 400 (400 MHz) and Bruker 170 Avance 500 (500 MHz) spectrometers, in DMSO-d₆ using tetramethylsilane (TMS) as an internal standard. Melting points were measured on a Kofler hot stage and are uncorrected. LC-MS was performed using a system with an Agilent 1100 Series HPLC equipped with the diode-array detector and Agilent LC\MSD SL mass-selective detector using chemical ionization at atmospheric pressure (APCI).

¹H, ¹³C, ³¹P NMR spectra were obtained on a Bruker AVANCE DRX‐500 or Varian Mercury (400, 125, 151, 162 MHz, respectively) spectrometer (TMS as internal reference or 85 % phosphoric acid as external reference) in DMSO‐d₆. IR spectra were recorded on a Vertex 70 spectrometer in KBr pellets. Mass spectra were recorded on an Agilent 1100 Series LC‐MS system equipped with a diode array detector Agilent LC\MSD SL (atmospheric pressure chemical ionization). Elemental analysis was carried out in the Analytical Laboratory of the Institute of Bioorganic and Petrochemistry of the National Academy of Sciences of Ukraine by manual methods. The carbon and hydrogen contents were determined using the Pregl gravimetric method, while nitrogen was determined using the Duma's gasometrical micromethod. Chlorine content was determined by the mercurometric method, phosphorus content was determined by the colorimetric method and sulfur content by the Scheininger titrimetric method. M. p. was determined on a Fisher–Johns apparatus and are uncorrected. All reagents and solvents were purchased from commercial sources were used.
1‐Acylamino‐2,2‐dichloroethenyltriphenylphosphonium chlorides I were synthesized according to the method described in the article.^[13]