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Acetophenone

Acetophenone is a widely used organic compound with the chemical formula C6H5COCH3.
It is a colorless liquid with a characteristic odor, commonly used as a precursor in the synthesis of various pharmaceutical and fragrance compounds.
Acetophenone has a variety of applications in the chemical industry, including its use as a solvent, an intermediate in the production of other chemicals, and a flavor and fragrance additive.
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Most cited protocols related to «Acetophenone»

1
Volatile Organic Compounds Profiling of Antirrhinum and Petunia Flowers
Cited 7 times
We used completely developed 3–4 days old flowers of the Antirrhinum majus inbred line 165E [8 (link), 24 (link)] in order to generate the raw data which were then used to compare semi-quantification methods. Additionally, a flower scent profile was generated for Petunia x hybrida line Mitchell. The sampling system consisted in flowers placed inside a beaker with 4 ml of 5% sucrose in distilled water, supported by a glass slide, and a stir bar was attached to the border of the beaker with a stainless-steel paperclip. The beaker was then placed in a 2-l desiccator (Fig. 1).

Sampling system for VOCs in HSSE

Flowers for CG-MS analysis were kept under conditions of 12 h light and 12 h dark at 23 °C and 18 °C, respectively, in a growth chamber (Sanyo MRL 350). In case of A. majus, stir bars sampled the floral volatiles of 3 flowers in 3 different desiccators during 12 h of light or 12 h of dark periods. In case of Petunia x hybrida, stir bars sampled floral volatiles for 4 or 24 h, sampling times applied in circadian rhythm studies [25 (link)]. The VOC profile of A. majus, is based on compounds which appeared unanimously in the day and night replicas (Table 1). Contaminants were identified and omitted in subsequent analyses.

Chromatographic parameters for A. majus VOCs analysed in column HP5 MSVi

Retention timeCompoundCASLRILRI bibliographyReference
2.23Methyl 2-methylbutanoate868-57-5805774[26 ]
5.58β-myrcene123-35-3996991[27 ]
6.62Ocimene6874-10-810441038[28 ]
7.19Acetophenone98-86-210711065[27 ]
7.77Methyl benzoate93-58-310991091[27 ]
7.96Nonanal124-19-611071104[29 (link)]
9.03Acetophenone, 2’-hydroxy118-93-411671160[26 ]
We used 10 mm long Twisters™ (Gerstel, Mülheim an der Ruhr, Germany) (stir bars), covered with a 0.5 mm film of polydimethylsiloxane (PDMS). We also tested dual-phase stir bars (ethylene glycol and silicone) (Gerstel, Mülheim an der Ruhr, Germany). Both types of stir bars were conditioned for adsorption according to manufacturer indications.
Compounds adsorbed by the stir bars were analysed by GC–MS in a gas chromatograph HP-6890N coupled to a 5975 mass spectrometer (Agilent Technologies, Palo Alto, USA) combined with a TDU and cooling injector system (CIS4) (Gerstel, Mülheim an der Ruhr, Germany).
Desorption was carried out by heating from an initial temperature of 40° to 250 °C at 100 °C min−1 with 5 min hold time on splitless mode. Desorbed compounds were captured in a cool trap at − 100 °C. This process was automated by using a multipurpose sampler MPS2XL (Gerstel, Mülheim an der Ruhr, Germany).
Chromatographic separation was done in a HP5MS-UI column (Agilent Technologies, Palo Alto, USA) with helium as gas carrier in constant pressure mode and split ratio 1:50. Initial temperature was 50 °C, increasing at a ratio of 5 °C min−1 until 70 °C held 1 min. In the next step, temperature was increased until 240 °C at 10 °C min−1 held for 15 min.
The mass spectrometer operated at 70 eV ionization voltage. Source and quadrupole temperatures were 230 and 150 °C, respectively. Mass range was 30.0 to 450.0 uma at 4 scan/s. MSD transfer line was maintained at 280 °C.
We used ChemStation software (version E.02.02 SP1, Agilent Technologies, Palo Alto, USA) to acquire chromatograms. Compounds were qualitatively identified by comparison with mass spectral database Willey10th-NIST11b (Agilent Technologies, Wilmington, USA), considering match qualities above 90%. We used ocimene, acetophenone, methyl benzoate and methyl cinnamate (Sigma-Aldrich, W353901, 42163, 18344 and 96410, respectively) as standards. Methanol was used as solvent for dilution of standards (Panreac, 361091). Linear retention indexes (LRI) were calculated as a parameter for identifying compounds by comparing with retention times (RT) of C8-C20 alkanes (Sigma Aldrich, 04070), analysed under the same chromatographic conditions (Table 1) [30 (link)].
Ruiz-Hernández V., Roca M.J., Egea-Cortines M, & Weiss J. (2018). A comparison of semi-quantitative methods suitable for establishing volatile profiles. Plant Methods, 14, 67.
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Publication 2018
2
Catalytic Hydrogenation of Acetophenone
Cited 4 times
Inside the glovebox, a stock solution of 3 (0.0125 M) was prepared in 0.875 mL dioxane, treated with 0.125 mL of 1 M KBHEt3 solution in THF and stirred for 0.5 h. A 1 mL syringe was loaded with complex 3 (500, 250, 100, and 50 μL) and KBHEt3 (62.5, 93.8, 112.5, and 118.8 μL) in dioxane (total volume 0.7 mL), and a 20 mL syringe was loaded with acetophenone (1.460 mL, 12.5 mmol) and dodecane (113.6 μL, 0.625 mmol) in 10 mL dioxane. Under N2 flow, the substrate syringe was first injected into high pressure stainless steel reactor, in which a glass liner was inserted in advance. The dissolved catalyst was then placed in an injection port and the system was purged with H2 (3 × 10 bar). The reactor was brought to at 120 °C at 50 bar H2 pressure with stirring at 500 r.p.m. and reaction was initiated by injecting the catalyst solution. The samples were withdrawn at given time intervals using an autosampler apparatus and analyzed with GC. Data plotted in Fig. 4 of the manuscript.
Yang W., Chernyshov I.Y., van Schendel R.K., Weber M., Müller C., Filonenko G.A, & Pidko E.A. (2021). Robust and efficient hydrogenation of carbonyl compounds catalysed by mixed donor Mn(I) pincer complexes. Nature Communications, 12, 12.
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Publication 2021
acetophenone Dental Cavity Liner Dioxanes n-dodecane Pressure Stainless Steel Syringes
3
α-Glucosidase Inhibitory Assay Protocol
Cited 4 times
The α-glucosidase inhibitory assay was performed according to a slightly modified method previously reported21 ,22 . In brief, a series of reaction solutions, including a fixed amount of α-glucosidase (10 unit/mL 3.75 µL), different concentrations of inhibitors (the tested compounds or positive controls, 37.5 µL), and sodium phosphate buffer (PBS, 596.75 µL, 0.1 M, pH 6.8), were incubated at 37 °C for 10 min. To initiate the reaction, 112.5 µL of pNPG (6.0 mM, as a substrate) was added into the pre-incubated mixtures, and the final volume of reaction system was kept at 750 µL. The p-nitrophenol released from pNPG substrate was used as the target substance to quantify the enzymatic activity. The absorbance of p-nitrophenol was monitored at 405 nm after incubation at 37 °C for 30 min. All samples were analyzed in triplicate, acarbose, and genistein were used as positive controls. The negative control was prepared by adding PBS instead of α-glucosidase, the blank was prepared by adding solvent instead of tested compounds, and the inhibition rate was calculated as the following Equation (1).
(ODcontrol−ODcontrol blank)−(ODtest−ODtest blank)ODcontrol−ODcontrol blank×100%
Equation (1). Inhibition rate calculation formula.
Dan W.J., Zhang Q., Zhang F., Wang W.W, & Gao J.M. (2019). Benzonate derivatives of acetophenone as potent α-glucosidase inhibitors: synthesis, structure–activity relationship and mechanism. Journal of Enzyme Inhibition and Medicinal Chemistry, 34(1), 937-945.
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Publication 2019
4-nitrophenol 4-nitrophenylgalactoside Acarbose alpha Glucosidase Biological Assay Buffers enzyme activity Genistein inhibitors Nitrophenols Psychological Inhibition sodium phosphate Solvents
4
Synthesis and Neuroprotective Evaluation of Sterubin
Cited 4 times

General: All reagents were bought from Sigma Aldrich, Munich, Germany, unless otherwise noted, and were used without further purification. Thin‐layer chromatography was performed using Merck Silica Gel 60 F254 plates. For column chromatography, Silica Gel 60 (particle size 0.040–0.063 mm) (Sigma Aldrich, Munich, Germany) was used. Nuclear magnetic resonance (NMR) spectra were recorded with a Bruker AV‐400 NMR instrument (Bruker, Karlsruhe, Germany) in CDCl3 or [D6]DMSO. Chemical shifts are expressed in ppm relative to CDCl3 (7.26 ppm for 1H and 77.16 ppm for 13C) or [D6]DMSO (2.50 ppm for 1H and 39.52 ppm for 13C). The purity of the synthetic products was determined by HPLC (Shimadzu, Duisburg, Germany), containing a DGU‐20A3R degassing unit, an LC‐20AB liquid chromatograph, and an SPD‐20A UV/Vis detector. UV detection was done at 254 nm. Mass spectra were obtained by an LCMS‐2020 device (Shimadzu, Duisburg, Germany). As a stationary phase, a Synergi 4U fusion‐RP column (150 mm x 4.6 mm) was used, and, as a mobile phase, a gradient of methanol/water with 0.1 % formic acid. Parameters: A=water, B=methanol, V(B)/[(V(A)+ V(B)]=from 5 % to 90 % over 10 min, V(B)/[(V(A)+V(B)]=90 % for 5 min, V(B)/[(V(A)+V(B)]=from 90 % to 5 % over 3 min. The method was performed with a flow rate of 1.0 mL min−1. Compounds were used for biological evaluation only if the purity was 95 % or higher.
For the preparation of acetophenone 7 and aldehyde 8, see the Supporting Information.
Chalcone 9: A mixture of acetophenone 7 (650 mg, 2.16 mmol) in EtOH (10 mL) and a saturated solution of KOH in EtOH (15 mL) was stirred at 4 °C for 15 min. A solution of 8 (490 mg, 2.16 mmol) in EtOH (5 mL) was added dropwise and the mixture was allowed to stir overnight (16 h) at room temperature. The reaction was quenched with water and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography using a mixture of cyclohexane and ethyl acetate (3/1). The product was obtained as a yellow solid in 85 % yield (1.11 g). The analytical data were consistent with those reported in the literature.311H NMR (400 MHz, CDCl3): δ 7.35 (s, 1 H, Ar‐H), 7.26 (d, 2J=16.0 Hz, 1 H, HC=CH), 7.13 (s, 2 H, Ar‐H), 6.86 (d, 2J=16.0 Hz, 1 H, HC=CH), 6.43 (s, 2 H, Ar‐H), 5.25 (s, 2 H, CH2OCH3), 5.22 (s, 2 H, CH2OCH3), 5.11 (s, 4 H, CH2OCH3), 3.82 (s, 3 H, OCH3), 3.51 (s, 3 H, CH2OCH3), 3.50 (s, 3 H, CH2OCH3), 3.39 ppm (s, 6 H, CH2OCH3); 13C NMR (100 MHz, CDCl3): δ 194.4 (Cq, C=O), 162.1 (Cq, Ar‐C), 156.0 (2x Cq, Ar‐C), 149.4 (Cq, Ar‐C), 147.5 (Cq, Ar‐C), 144.7 (+, HC=CH), 129.4 (Cq, Ar‐C), 128.1 (+, HC=CH), 123.8 (+, Ar‐C), 116.3 (+, Ar‐C), 116.0 (+, Ar‐C), 113.8 (Cq, Ar‐C), 95.6 (−, CH2OCH3), 95.2 (−, CH2OCH3), 95.1 (2× +, Ar‐C), 94.6 (2x, −, CH2OCH3), 56.5 (+, CH2OCH3), 56.4 (+, CH2OCH3), 56.3 (2© +, CH2OCH3), 55.6 ppm (+, OCH3); ESI‐MS: m/z calcd for C24H30O10+H+: 479.19; found 479.2.
Sterubin (1): A solution of chalcone 9 (1.10 g, 2.32 mmol) in 10 % methanolic HCl was stirred for 30 min at 50 °C. NaOAc (3.80 g, 46.4 mmol) was added and the mixture was heated to reflux for 3 h, cooled, then water was added and the mixture was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a mixture of dichloromethane and methanol (40/1) as the eluent. The product was obtained as a white solid in 55 % yield (391 mg). The analytical data were consistent with those reported in the literature.13a1H NMR (400 MHz, [D6]DMSO): δ 12.11 (s, 1 H, OH), 9.03 (m, 2 H, OH), 6.91–6.86 (m, 1 H, Ar‐H), 6.78–6.71 (m, 2 H, Ar‐H), 6.10 6.06 (m, 2 H, Ar‐H), 5.42 (dd, 3J=12.6, 3.0 Hz, 1 H), 3.79 (s, 3 H, OCH3), 3.24 (dd, 2J=17.2, 3J=12.6 Hz, 1 H), 2.72 (dd, 2J=17.2, 3J=3.1 Hz, 1 H); 13C NMR (100 MHz, [D6]DMSO): δ 196.9 (Cq, C=O), 167.4 (Cq, Ar‐C), 163.1 (Cq, Ar‐C), 162.8 (Cq, Ar‐C), 145.7 (Cq, Ar‐C), 145.1 (Cq, Ar‐C), 129.2 (Cq, Ar‐C), 117.9 (+, Ar‐C), 115.3 (+, Ar‐C), 114.3 (+, Ar‐C), 102.6 (Cq, Ar‐C), 94.5 (+, Ar‐C), 93.7 (+, Ar‐C), 78.6 (+, Ar‐C), 55.8 (+, CH3, OCH3), 42.1 (−, CH2). ESI‐MS: m/z calcd for C16H15O6+H+: 303.09; found 303.15.
For the preparation of 11, see the Supporting Information.
Tri‐O‐acetyldehydrosterubin: To a solution of tri‐O‐acetylsterubin (11) (160 mg, 0.374 mmol) and NBS (67 mg, 0.374 mmol) in chloroform (5 mL) benzoyl peroxide (6 mg, 26 μmol) was added and the reaction mixture was heated to reflux for 2 h. Further chloroform was added, and the mixture was washed with water and brine. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography using an eluent of cyclohexane and ethyl acetate (2:1 → pure ethyl acetate) and the product was obtained as a white solid in 63 % yield (100 mg). 1H NMR: (400 MHz, CDCl3): δ 7.73 (dd, 3J=8.5, 4J=2.2 Hz, 1 H, Ar‐H), 7.70 (d, 4J=2.1 Hz, 1 H, Ar‐H), 7.35 (d, 3J=8.5 Hz, 1 H, Ar‐H), 6.87 (d, 4J=2.5 Hz, 1 H, Ar‐H), 6.62 (d, 4J=2.4 Hz, 1 H, Ar‐H), 6.55 (s, 1 H, C=CH), 3.92 (s, 3 H, OCH3), 2.44 (s, 3 H, CH3COO), 2.35 (s, 3 H, CH3COO), 2.33 (s, 3 H, CH3COO); 13C NMR (100 MHz, CDCl3): δ 176.3 (Cq, C=O), 169.7 (Cq, CH3COO), 168.1 (Cq, CH3COO), 167.9 (Cq, CH3COO), 163.7 (Cq, Ar‐C), 160.3 (Cq, C=CH), 158.9 (Cq, Ar‐C), 150.7 (Cq, Ar‐C), 144.7 (Cq, Ar‐C), 142.7 (Cq, Ar‐C), 130.2 (Cq, Ar‐C), 124.5 (+, Ar‐C), 124.3 (+, Ar‐C), 121.6 (+, Ar‐C), 111.3 (Cq, Ar‐C), 109.0 (+, C=CH), 108.6 (+, Ar‐C), 99.2 (+, Ar‐C), 56.1 (+, OCH3), 21.2 (CH3COO), 20.8 (CH3COO), 20.7 (CH3COO); ESI‐MS: m/z calcd for C22H18O9+H+: 427.10; found 427.20.
Dehydrosterubin (12): A solution of tri‐O‐acetyldehydrosterubin (97 mg, 0.227 mmol) in acetonitrile (3 mL) and conc. aqueous HCl (3 mL) was heated to reflux for 1.5 h. Yellow precipitant was formed, which was filtered off, washed with water, and dried under vacuum. The product was obtained as a yellow solid in 50 % yield (34 mg). 1H NMR (400 MHz, [D6]DMSO): δ 12.97 (s, 1 H, OH), 9.96 (s, 1 H, OH), 9.37 (s, 1 H, OH), 7.44 (m, 2 H, Ar‐H), 6.90 (d, 3J=8.1 Hz, 1 H, Ar‐H), 6.72 (s, 1 H, C=CH), 6.71 (d, 4J=2.5 Hz, 1 H, Ar‐H), 6.37 (d, 4J=2.2 Hz, 1 H, Ar‐H), 3.87 (s, 3 H, OCH3); 13C NMR (100 MHz, [D6]DMSO): δ 181.7 (Cq, C=O), 165.0 (Cq, Ar‐C), 164.2 (Cq, Ar‐C), 161.1 (Cq, C=CH), 157.1 (Cq, Ar‐C), 149.8 (Cq, Ar‐C), 145.7 (Cq, Ar‐C), 121.3 (Cq, Ar‐C), 119.0 (+, Ar‐C), 115.9 (+, Ar‐C), 113.5 (+, Ar‐C), 104.6 (Cq, Ar‐C), 103.0 (+, C=CH), 97.9 (+, Ar‐C), 92.5 (+, Ar‐C), 56.0 (+, OCH3); ESI‐MS: m/z calcd for C16H12O6+H+: 301.07; found 301.15.
Plant material: Leaves of Eriodictyon californicum Hook. & Arn. (Boraginaceae) were collected by Ms. Kyra Bobine in May, 2019.
Plant extraction: Dried leaves of E. californicum (18.6 g) were soaked in ethyl acetate (3×100 mL), ultrasonicated for 30 min, then shaken overnight (≈16 h) at room temperature. The crude extract was filtered, and the filtrate was concentrated in vacuo. The obtained residue (2.0 g) was re‐dissolved in 90 % aqueous methanol. By addition of n‐hexane, chlorophyll and non‐polar residues were removed and sterubin (1) and related flavones were precipitated. After filtration, the precipitate (0.6 g) was dissolved in methanol and directly subjected to HPLC on a ChiralPak‐IA column.
Chiral resolution of racemic sterubin: An HPLC‐UV guided resolution of the enantiomers of 1 was performed on a Jasco system equipped with a DG‐2080 degassing unit, a PU‐1580 ternary pump, an MD‐2010 plus multiwavelength detector, and an AS‐2055 autosampler. Separation of the enantiomers was done on a ChiralPak IA® (10×25 mm, 5 μm, Daicel Chemical Industries) column using a gradient system with initial conditions 32 % B (B: 90 % MeCN in water + 0.05 % TFA) to 60 % B in 29 min. The (R)‐ and (S)‐enantiomers of sterubin, (R)‐1 and (S)‐1, had retention times of 17.8 min and 20.2 min, respectively.
Online LC‐ECD analysis of the sterubin enantiomers: ECD spectroscopic analysis was performed using a Jasco J‐715 spectropolarimeter. Measurements were done at room temperature and the spectra were processed using the SpecDis software.32Oxytosis assay: HT22 cells were grown in Dulbecco's Modified Eagle Medium (DMEM, Sigma Aldrich, Munich, Germany) supplemented with 10 % (v/v) fetal calf serum (FCS) and 1 % (v/v) penicillin‐streptomycin. 5×103 HT22 cells per well were seeded into sterile 96‐well plates and incubated overnight (≈16 h). Aqueous glutamate solution (5 mm) (monosodium‐l‐glutamate, Sigma Aldrich, Munich, Germany) together with 2.5, 5.0, 7.5, or 10 μm of the respective compound was added to the cells and incubated for 24 h. Quercetin (25 μm) (Sigma Aldrich, Munich, Germany) together with glutamate (5 mm) served as a positive control. After 24 h incubation cell viability was determined using a colorimetric 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide (MTT, Sigma Aldrich, Munich, Germany) assay. MTT solution (5 mg mL−1 in PBS) was diluted 1:10 with medium and added to the wells after removal of the old medium. Cells were incubated for 3 h and then lysis buffer (10 % SDS) was added. The next day, absorbance at 560 nm was determined with a multiwell plate photometer (Tecan, SpectraMax 250). Results are presented as percentage of untreated control cells. All data are expressed as means ± SEM of three independent experiments. Analysis was accomplished using GraphPad Prism 5 Software applying Oneway ANOVA followed by Dunnett's multiple comparison posttest. Levels of significance: * p<0.05; ** p<0.01; *** p<0.001.
Cellular uptake and racemization experiments: 2×106 BV2 cells were grown in sterile 100 mm dishes overnight and 4 mL 50 μm (S)‐1 or (R)‐1 diluted in cell culture medium were added. Cells were incubated for the indicated time periods, after which the supernatant was removed, and cells were washed twice with PBS. Further PBS (1 mL) was added, cells were scraped and transferred to Eppendorf tubes. The samples were centrifuged and resuspended in 200 μL of MeOH. The cells were frozen in liquid nitrogen and thawed at 37 °C (10 times). Cell debris was pelleted by centrifugation and the supernatant was collected for HPLC analysis.
Neuroprotection studies in vivo: The in vivo behavioral experiments were performed as established and published previously.15, 33 Neurotoxicity was induced by ICV injection of oligomerized Aβ25–35 peptide, and sterubin (1) was evaluated for its neuroprotective properties. Sterubin was dissolved in 60 % DMSO and 40 % saline (0.9 % NaCl in milliQ water) and was injected once per day IP on days 1–7 to give doses of 0.3, 1, and 3 mg kg−1. The oligomerized Aβ25–35 peptide was injected ICV on day 1 of the study. The behavior of the mice was evaluated on day 8 (YMT) and days 9 and 10 (STPA). On day 11, the mice were sacrificed, and the brains were collected. Samples were frozen at −80 °C for further biochemical analysis.
Animals: Male Swiss mice 6 weeks old, body weight 30–40 g, obtained from JANVIER (Saint Berthevin, France) were housed in the animal facility of the University of Montpellier (CECEMA, Office of Veterinary Services agreement #B‐34‐172‐23) with access to food and water ad libitum (except during behavioral tests). The humidity and temperature were controlled, and the mice were kept at a 12 h light/12 h dark cycle (lights off at 7:00 p.m.). All animal procedures were conducted in strict adherence to the European Union directives of September 22nd, 2010 (2010/63/UE) and to the ARRIVE guidelines. The project was authorized by the French National Ethics Committee (APAFIS #1485‐15 034). Animals were assigned to different treatment groups randomly.
Preparation of sterubin injections: Sterubin (1) was dissolved in 100 % DMSO at a concentration of 6 mg mL−1 to give a stock solution, which was diluted with saline (0.9 % NaCl in milliQ water) and DMSO to the final test concentration and a final percentage of 60 % DMSO. 60 % DMSO in saline served as the vehicle (V2). After compound injections, the behavior of the mice in their home cage was checked visually. Weight was examined once per day. As demonstrated in Figure S1, a tendency was observed that weight gain was facilitated with an increasing dose of 1. Nevertheless, the difference in weight gain remained insignificant compared to Aβ+V2 treated mice in Dunnett's multiple comparison test.
Amyloid peptide preparation and ICV injection: All experiments followed previously described protocols.15, 25, 32 The Aβ25–35 peptide was prepared according to Maurice et al.15 Mice were anesthetized with 2.5 % isoflurane. Then, oligomerized Aβ25–35 peptide (9 nmol in 3 μL/mouse) was injected ICV. Bidistilled water was used as a vehicle (V1).
Spontaneous alternation performance in a Y‐maze: On day 8 of the study, the spatial working memory of all mice was evaluated in the Y‐maze.15, 25, 32 The Y‐maze is made from grey polyvinylchloride and has three identical arms (length 40 cm, height 13 cm, bottom width 3 cm, top width 10 cm (walls converge at an equal angle). For evaluation of memory, every mouse was placed into one arm and was allowed to explore the maze for 8 min. All entries into an arm (including the return into the same arm) were counted and the number of alternations (mouse entered all three arms consecutively) was calculated as percentage of total number of arm entries [alternations/ (arm entries−2)×100].
Step‐through passive avoidance test: STPA was performed on day 9 and day 10 in a two‐compartment box [(width 10 cm, total length 20 cm (10 cm per compartment), height 20 cm] consisting of polyvinylchloride. One of the compartments was white and illuminated with a bulb (60 W, 40 cm above the center of the compartment), the second compartment was black, covered, and had a grid floor. A guillotine door separated the compartments. On day 9 (training), each animal was placed in the white compartment and was left to explore for 5 s. Then, the door was opened, which allowed the mouse to enter the black compartment. After it had entered, the door was closed, and a foot shock was delivered (0.3 mA) for 3 s generated by a scramble shock generator (Lafayette Instruments, Lafayette, USA). The step‐through latency (time the mouse spent in the white compartment after the door was opened) and the level of sensitivity (no sign=0, flinching reactions=1, vocalization=2) were recoded. Treatment with sterubin (1) did not affect the measured parameters. On the next day (day 10), each mouse was placed in the white compartment and was allowed to explore for 5 s. Then, the door was opened allowing the mouse to step over into the black compartment. The step‐through latency was measured for up to 300 s.
Sacrifice and brain collection: All animals were sacrificed on day 11. The brains were collected, hippocampus and cortex were isolated, and the samples were frozen at −80 °C.
Statistical analysis: Weight gain and results from the YMT were analyzed by the software GraphPad Prism 5.0 using one‐way ANOVA, followed by Dunnett's post‐hoc multiple comparison test. STPA had a maximum step‐through latency of 300 s. Therefore, a Gaussian distribution could not be assumed. The results were analyzed using a Kruskal‐Wallis non‐parametric ANOVA, followed by a Dunn's multiple comparison test. p<0.05 was considered significant.
Novel‐object recognition test: Male C57Bl/6J mice were used and the testing was done by Scripps Research. All mice were acclimated to the colony room for at least 2 weeks prior to testing and were tested at an average age of 8 weeks. Mice were randomly assigned across treatment groups with 11 mice in each group. For each dose tested, a solution of sterubin in corn oil was prepared. The vehicle was corn oil alone. All were administered orally 60 min prior to the training session at a volume of 10 mL kg−1 body weight. Rolipram was dissolved in 10 % DMSO and administered intraperitoneally at 0.1 mg kg−1 20 min prior to training. The test was performed as described previously.29 Briefly, on day 1 mice were habituated to a circular open field arena for one hour in cage groups of four. 24 h later, individual mice were placed back in the same arena which now contained two identical objects for a 15 min training trial. On day 3, vehicle‐, sterubin‐ or rolipram‐treated mice were individually placed back in the same arena in the presence of both the familiar object (i.e., previously explored) and a novel object. The spatial positions of the objects were counter‐balanced between subjects. Each animal's test trial was recorded and the first 10 min of each session were scored. Object recognition was computed using the formula: Time spent with novel object x 100)/Total time spent exploring both objects. Data were analyzed by a one‐way ANOVA followed by post‐hoc comparisons with Fisher's test.
Hofmann J., Fayez S., Scheiner M., Hoffmann M., Oerter S., Appelt‐Menzel A., Maher P., Maurice T., Bringmann G, & Decker M. (2020). Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo. Chemistry (Weinheim an Der Bergstrasse, Germany), 26(32), 7299-7308.
Publication 2020
5
Odor-Potentiated Startle Behavioral Assay
Cited 3 times
Mice were habituated to the startle chambers for 5–10 min on three separate days. On the day of testing, mice were first exposed to 15 startle-alone (105-dB noise burst) trials (leaders), before being presented with ten odor + startle trials randomly intermingled with ten startle-alone trials. The odor + startle trials consisted of a 10-s odor presentation co-terminating with a 50-ms, 105-dB noise burst. For each mouse, an OPS score was computed by subtracting the startle response in the first odor + startle trial from the startle response in the last startle-alone leader. This OPS score was then divided by the last startle-alone leader and multiplied by 100 to yield the percent OPS score (% OPS) reported in the results. Mice were exposed to the acetophenone-potentiated startle (acetophe-none + startle) and propanol-potentiated startle (propanol + startle) procedures on independent days in a counter-balanced fashion.
Dias B.G, & Ressler K.J. (2013). Parental olfactory experience influences behavior and neural structure in subsequent generations. Nature neuroscience, 17(1), 89-96.
Publication 2013
acetophenone Mus Odors Propanols Reflex, Startle

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1
Acetophenone-based Transaminase Assay
The activity of ATAs towards selected amino acceptors was measured using the acetophenone assay, which measures the rate of acetophenone generation by measuring the UV-absorbance of the assay mixture at 245 nm. Assay mixtures contained 50 mM HEPES buffer (pH 7.5), 5 mM (S)-1-PEA, 20 µM PLP, and 5 mM pyruvate or selected carbohydrates containing 5 mM galactose. When oxidized carbohydrates were used as the amino acceptor, 29.8 µg/mL FgrGaOx, 12.8 µg/mL catalase, and 1.8 µg/mL HRP were also added. The assay mixtures were pre-oxidized at 37 °C for an hour, and transamination reactions were carried out on a UV-compatible 96-well microtiter plate at 200 µL volumes. For each reaction, 30 µg ATA was added (300 ng when using pyruvate as the amino acceptor), and the plate was moved immediately to a plate reader operating at 37 °C without shaking. The absorbance readings were taken at 245 nm in 30-s intervals for 30 min, and linear portions of the absorbance-vs-time graphs were used to calculate the rates of acetophenone formation. All experiments were conducted in 4 replicates (n = 4).
Feng X., Hong S., Zhao H., Vuong T.V, & Master E.R. (2024). Biocatalytic cascade to polysaccharide amination. Biotechnology for Biofuels and Bioproducts, 17, 34.
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Publication 2024
2
Kinetics of Acetophenone Assay for ATAs
The kinetic parameters of ATAs were measured using the acetophenone assay and using pyruvate with concentrations from 0.001 to 0.1 mM as the amino acceptor. The reactions were performed in the same way as in the activity measurements except for using variable pyruvate concentration. Reactions (200 µL) were performed on a UV-compatible 96-well microtiter plate at 37 °C without shaking. The UV-absorbance of the assay mixtures was measured at 245 nm in 20-s intervals for 10 min, and the initial linear portion of absorbance-vs-time graphs was used to calculate the rate of acetophenone formation. The initial rates were plotted against pyruvate concentrations, and kinetic parameters were calculated using Prism 10 software.
Feng X., Hong S., Zhao H., Vuong T.V, & Master E.R. (2024). Biocatalytic cascade to polysaccharide amination. Biotechnology for Biofuels and Bioproducts, 17, 34.
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Publication 2024
3
Enantioselective Reduction of Acetophenone
A 1 mL vial, under inert atmosphere, was filled with NaOH (1.0 mg, 25 μmol), acetophenone (12 μL, 100 μmol), and a solution of ruthenium complex 9 (1.3 mg, 1 μmol) in iPrOH (0.125 mL, 1.63 mmol, around 16 equiv./ketone). The reaction mixture was heated for 1 h. The solution was diluted with 0.2 mL of CH2Cl2 and passed through a Millipore filter. An aliquot was analyzed by GC with a Chirasil-DEX CB column (25 m × 0.25 mm) (Agilent Technologies, Santa Clara, CA, USA) to determinate the enantiomeric excess. The remaining solution was concentrated under vacuum and the resulting crude solution was analyzed by 1H NMR spectroscopy to determinate the conversion.
Bauder C, & Sémeril D. (2024). Optically Pure Calixarenyl Phosphine via Stereospecific Alkylation on Evans’ Oxazolidinone Moiety. Molecules, 29(5), 1156.
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Publication 2024
4
Photocatalytic Hydrogenation of Acetophenone
The ruthenium catalyst solution used for the photocatalytic TH was prepared by dissolving the complexes 1, 4–7 (0.02 mmol) in 2-propanol (5 mL). The catalyst solution (250 μL, 1.0 μmol) and a 0.1 M solution of NaOiPr (200 μL, 20 μmol) in 2-propanol were added subsequently to the acetophenone solution (1.0 mmol) in 2-propanol or a 2-propanol/MeOH (1:1 v/v) mixture (final volume 10 mL). The resulting solutions were stirred in a thermostated water bath at 30 °C. Irradiation of the samples was carried out using a 300 W Xenon Arc Lamp (LSB530A, LOT-Oriel, Darmstadt, Germany), emitting in the range 200–2500 nm (solar simulator). Samples were purged with Ar at least 15 min before irradiation. The reaction was sampled by removing an aliquot of the reaction mixture, which was quenched by the addition of diethyl ether (1:1 v/v), filtered over a short silica pad and submitted to GC analysis. The base addition was considered as the start time of the reaction. The S/C molar ratio was 1000/1, whereas the base concentration was 2 mol% with respect to the ketone substrate (0.1 M).
Ballico M., Alessi D., Aneggi E., Busato M., Zuccaccia D., Allegri L., Damante G., Jandl C, & Baratta W. (2024). Cyclometalated and NNN Terpyridine Ruthenium Photocatalysts and Their Cytotoxic Activity. Molecules, 29(9), 2146.
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Publication 2024
5
Synthesis of nitrovinyl benzene derivatives
Pyridine, acetophenone, (E)-1-methyl-4-(2-nitrovinyl) benzene, and other raw materials were purchased from Bide Pharmatech Co., Ltd. (Shanghai, China) All commercially available organic and inorganic compounds were used directly without further purification.
Zhang X., Zhang J., Liu Z., Bi W., Shen J, & Li G. (2024). Efficient Solvent-Free Synthesis of Indolizines Using CuBr Catalyst from Pyridine, Acetophenone, and Electron-Deficient Alkenes. Molecules, 29(9), 2061.
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Publication 2024

Top products related to «Acetophenone»

1
Acetophenone by Merck Group
Sourced in United States, Germany, Belgium, India
Acetophenone is a chemical compound used as a common laboratory reagent and precursor in organic synthesis. It is a colorless liquid with a characteristic odor. Acetophenone is widely used in various chemical processes and research applications.
2
Benzaldehyde by Merck Group
Sourced in United States, Germany, China, India, United Kingdom, Canada, Italy, Spain, Belgium, Australia
Benzaldehyde is a clear, colorless liquid with a characteristic almond-like odor. It is a widely used organic compound that serves as a precursor and intermediate in the synthesis of various chemicals and pharmaceuticals.
3
Octanal by Merck Group
Sourced in United States, Germany, China, Spain
Octanal is a chemical compound used in laboratory settings. It is a colorless liquid with a characteristic pungent odor. Octanal serves as a reagent and an intermediate in organic synthesis reactions.
4
2 2 dimethoxy 2 phenylacetophenone by Merck Group
Sourced in United States, Germany, United Kingdom
2,2-dimethoxy-2-phenylacetophenone is a photoinitiator compound commonly used in the field of photochemistry and photopolymerization. It functions as a light-sensitive initiator, capable of generating free radicals upon exposure to UV or visible light. This property makes it useful in various applications involving light-induced chemical reactions and processes.
5
Ethyl butyrate by Merck Group
Sourced in United States, Germany, China
Ethyl butyrate is a colorless liquid compound with a sweet, fruity odor. It is used as a flavoring agent in various food and beverage products.
6
Acetophenone by Thermo Fisher Scientific
Sourced in United States
Acetophenone is a colorless liquid compound with a characteristic odor. It is commonly used as a solvent, an intermediate in organic synthesis, and as a raw material for the production of various chemicals. Acetophenone has a molecular formula of C6H5COCH3 and a molar mass of 120.15 g/mol.
7
Butyrophenone by Merck Group
Sourced in Belgium
Butyrophenone is a chemical compound that is commonly used as a starting material or intermediate in the synthesis of various pharmaceutical and agrochemical products. It has a molecular formula of C10H12O and a molecular weight of 148.20 g/mol. Butyrophenone is a colorless liquid with a characteristic odor. Its core function is to serve as a building block or precursor in the production of other more complex molecules.
8
Toluene by Merck Group
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Toluene is a colorless, flammable liquid with a distinctive aromatic odor. It is a common organic solvent used in various industrial and laboratory applications. Toluene has a chemical formula of C6H5CH3 and is derived from the distillation of petroleum.
9
Hexanoic acid by Merck Group
Sourced in United States, Germany, United Kingdom, China, Spain, Sao Tome and Principe, India
Hexanoic acid is a carboxylic acid with the chemical formula CH3(CH2)4COOH. It is a colorless liquid with a characteristic unpleasant odor. Hexanoic acid is used as a precursor in the synthesis of various organic compounds and as a component in certain industrial and laboratory applications.
10
Nonanal by Merck Group
Sourced in United States, Germany, China, United Kingdom, Mexico
Nonanal is a chemical compound commonly used in laboratory settings. It is a colorless liquid with a characteristic fatty, green, and floral aroma. Nonanal is a saturated aliphatic aldehyde with the molecular formula C9H18O.

More about "Acetophenone"

Acetophenone, also known as phenyl methyl ketone or benzoyl methane, is a versatile organic compound with the chemical formula C6H5COCH3.
This colorless liquid has a distinct, aromatic odor and is widely used as a precursor, solvent, and flavoring agent in various industries.
Acetophenone's applications extend beyond its primary use as a pharmaceutical and fragrance intermediate.
It is commonly employed as a solvent for resins, oils, and waxes, and finds use in the production of other chemicals, such as benzaldehyde, octanal, 2,2-dimethoxy-2-phenylacetophenone, ethyl butyrate, butyrophenone, and toluene.
Additionally, acetophenone serves as a flavoring agent, contributing its unique aroma and taste to a variety of products, including foods, beverages, and personal care items.
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