Structure of 4,4'-Sulfonyldiphenol
CAS No.: 80-09-1
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Search for reports by entering the product batch number.
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Search for reports by entering the product batch number.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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Askarniya, Zahra ; Rayaroth, Manoj P. ; Sun, Xun ; Wang, Zhaohui ; Boczkaj, Grzegorz ;
Abstract: Degradation of bisphenol S was studied using ozone activated by sodium percarbonate and the effectiveness of optimized process was compared with the peroxone process. The influence of several factors including sodium percarbonate concentration, ozone dose, pH, and water matrix were investigated. A synergetic coefficient of 3.84 was achieved for the combination of sodium percarbonate and ozone, confirming the effectiveness of this hybrid process. Scavenging tests revealed, that carbonate radicals, hydroxyl radicals, superoxide radicals, and singlet oxygen contributed to the degradation of bisphenol S. At the same operating condition, degradation effectiveness values of 99% and 81% were obtained by ozone combined with sodium percarbonate and hydrogen peroxide, resp., demonstrating the superiority of sodium percarbonate over hydrogen peroxide in combination with ozone for the degradation of bisphenol S. Low concentration of inorganic anions had a negligible effect on the degradation, while carbonate ions increased the first-order degradation rate constant by 56%.
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Keywords: Effluents ; Wastewater treatment ; Advanced oxidation processes ; Hybrid processes ; Radicals ; Chemical treatment
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Cytotoxic and genotoxic evaluation of bisphenol S on onion root tips by Allium cepa and comet tests
Muhammad Muddassir Ali ; Areej Fatima ; Sadia Nawaz ; Abdul Rehman ; Maryam Javed ; Asif Nadeem
Abstract: Bisphenol S (BPS) is an analog of bisphenol A, which is used as substitute of BPA in many products like airport luggage tags, baby bottles, plastics, and epoxy resins etc. Bisphenol S can cause toxic effects in different organisms, i.e., mice, rat, zebrafish, and C.elegans, etc. Bisphenol S is also known as “endocrine disruptor” due to its ability to mimic the endocrine receptors. So, the aim of this study was to evaluate the cytotoxic and genotoxic effects of bisphenol S on meristematic cells present in onion root tips through Allium cepa (A.cepa) and comet tests. Root growth inhibition was evaluated by root growth inhibition assay. Mitotic index (MI) and chromosomal aberrations (CAs) were assessed by A.cepa assay. DNA damage was evaluated by comet assay. Root growth of A.cepa was inhibited due to bisphenol S. LC50 value calculated by root growth inhibition assay for bisphenol S was (2.6±0.63, 50 μg/ml). Mitotic index was reduced, and chromosomal aberrations were observed, i.e., stickiness, polyploidy, and disturbed ana-telophase in anaphase and telophase stages of mitosis. In case of comet assay, DNA damage was increased in statistically significant manner (p ≤ 0.05). It was concluded that bisphenol S constitutes cytotoxic and genotoxic effects on A. cepa root meristematic cells. Moreover, it is suggested to explore more toxicity studies of bisphenol S at molecular level.
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Keywords: Bisphenol S ; Allium cepa assay ; Mitotic index ; DNA damage ; Chromosomal aberrations ; Endocrine recep
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CAS No. : | 80-09-1 |
Formula : | C12H10O4S |
M.W : | 250.27 |
SMILES Code : | O=S(C1=CC=C(O)C=C1)(C2=CC=C(O)C=C2)=O |
MDL No. : | MFCD00002350 |
InChI Key : | VPWNQTHUCYMVMZ-UHFFFAOYSA-N |
Pubchem ID : | 6626 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 62.43 |
TPSA ? Topological Polar Surface Area: Calculated from |
82.98 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.27 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.9 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.01 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.87 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.32 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.88 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.98 |
Solubility | 0.263 mg/ml ; 0.00105 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.27 |
Solubility | 0.136 mg/ml ; 0.000543 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.69 |
Solubility | 0.0505 mg/ml ; 0.000202 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.48 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.88 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.3% | With ammonia In water | EXAMPLE 2 Preparation of 4-amino-5-chloro-1-phenylpyridazin-6-one (chloridazon) using bis(4-hydroxyphenyl) sulfone as catalyst In a 1 l stirring autoclave, 300 parts of water, 210 parts (3.09 mol) of 25percent strength ammonia, 36 parts (0.15 mol) of 4,5-dichloro-1-phenylpyridazin-6-one (purity: 99.7percent) and 37.5 parts (0.15 mol) of bis(4-hydroxyphenyl)sulfone were stirred at 130° C. for 8 hours. The pressure rose steadily to about 5 bar. After stirring overnight, the autoclave was depressurized to atmospheric pressure, with the excess ammonia being stripped off. After cooling to room temperature, the precipitated solid was filtered off, washed with water and dried at 50° C. in a vacuum drying oven. This gave 30.7 parts of 4-amino-5-chloro-1-phenylpyridazin-6-one having a purity of 99.9percent; this corresponds to a yield of 92.3percent of theory. The pH of the filtrate was adjusted to 1.4 using 60percent strength sulfuric acid and the precipitated bis(4-hydroxyphenyl)sulfone was filtered off and washed with water. This gave 53.5 parts of bis(4-hydroxyphenyl)sulfone having a water content of 30percent. This corresponds to 99.8percent of the amount of catalyst used. |
90% | With ammonia In water | EXAMPLE 1 Preparation of 4-amino-5-chloro-1-phenylpyridazin-6-one (chloridazon) using bis(4-hydroxyphenyl)sulfone In a 250 ml stirring autoclave, 100 parts of water, 70 parts (1.03 mol) of 25percent strength ammonia, 12 parts (0.05 mol) of 4,5-dichloro-1-phenylpyridazin-6-one (purity: 99.7percent) and 12.5 parts (0.05 mol) of bis(4-hydroxyphenyl)sulfone were stirred at 130° C. for 8 hours. The pressure rose steadily to about 5 bar. After stirring overnight, the autoclave was depressurized to atmospheric pressure, with the excess ammonia being stripped off. After cooling to room temperature, the precipitated solid was filtered off, washed with water and dried at 50° C. in a vacuum drying oven. This gave 10.1 parts of 4-amino-5-chloro-1-phenylpyridazin-6-one having a purity of 98.8percent; this corresponds to a yield of 90percent of theory. The pH of the filtrate was adjusted to 1.5 using 60percent strength sulfuric acid and the precipitated bis(4-hydroxyphenyl)sulfone was filtered off, washed with water and dried. This gave 12.6 parts of bis(4-hydroxyphenyl)sulfone having a purity of 99.2percent; this corresponds to 100percent of the amount of catalyst used. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | With sodium hydroxide; In water; at 80.0℃; for 24.0h;Inert atmosphere; | General procedure: Bisphenol A (20mmol, 4.566g) was added to a 250mL round bottom flask containing NaOH aqueous solution (40mmol, 150mL, 1.599g). The reactor was then equipped with a reflux condenser and brought to 80C in a nitrogen environment with vigorous stirring via a Teflon-coated magnetic stir bar. Once completely dissolved, benzyl bromide (20mmol, 0.342g) was added via syringe. The mixture was allowed to stir for 2h at 80C in a nitrogen environment. After stirring was ceased, a beige precipitate settled out in a clear solution. While still hot, the supernatant was decanted and the crude product washed with water (ca. 80C). The crude product was then dissolved in chloroform, transferred to a separatory funnel, washed w/10% HCl (v/v), and then washed twice with DI H2O. The organic layer was then dried over magnesium sulfate, filtered into a tared receiver flask, and isolated under vacuum as an off-white solid. The compound was then recrystallized twice from hexanes/ethyl acetate to afford a white, crystalline solid (3.80g, 59.7% yield, mp (DSC)=109C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | With sodium hydroxide; In water; at 80.0℃; for 24.0h;Inert atmosphere; | Synthesis was analogous to compound 1 with an extended reaction time of 24 h. Significant amounts of di-benzyl protected side product was produced, requiring purification by column chromatography (silica/90:10 DCM:MeOH, Rf = 0.67) to afford awhite, crystalline solid (215 mg, 16% yield, mp (DSC) = 92.3 8C).ATR-FTIR (neat, cm1): 3570, 3380, 3100, 3070, 3040, 2950, 2900,2860, 2830, 1590, 1500, 1460, 1420, 1380, 1290, 1250, 1150, 1110,1080, 1030, 1010, 845, 829, 744, 727, 702, 665, 600, 553. 1H NMR(d, ppm, 500 MHz, acetone-d6): 5.27 (s, -CH2Ph, 2H), 7.09 (d, 2H,3JHH = 8.7 Hz), 7.25 (d, 2H, 3JHH = 8.9 Hz), 7.40-7.55 (m, 5H), 7.91(d, 2H, 3JHH = 8.7 Hz), 7.97 (d, 2H, 3JHH = 8.9 Hz), 9.45 (s, OH, 1H).13C (d, ppm, 125 MHz, acetone-d6): 70.9, 116.2, 116.7, 128.5, 128.9,129.3, 130.2, 130.6, 134.2, 135.8, 137.4, 162.3, 163.1. |
Tags: 80-09-1 synthesis path| 80-09-1 SDS| 80-09-1 COA| 80-09-1 purity| 80-09-1 application| 80-09-1 NMR| 80-09-1 COA| 80-09-1 structure
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