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[ CAS No. 101-80-4 ] {[proInfo.proName]}

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Chemical Structure| 101-80-4
Chemical Structure| 101-80-4
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Quality Control of [ 101-80-4 ]

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Product Citations

Product Citations      Expand+

James T.F. Wise ; David W. Hein ; DOI: PubMed ID:

Abstract: Waterpipe smoking is increasingly popular and understanding how chemicals found in hookah smoke may be harmful to human bronchial epithelial cells is of great importance. 4,4’-Oxydianiline (ODA), is an aromatic amine which is present at comparatively high levels in hookah smoke. The metabolism and the subsequent toxicity of ODA in human bronchial epithelial cells remains unknown. Given that ODA is an aromatic amine, we hypothesized that ODA is N-acetylated and induces DNA damage following exposure to immortalized human bronchial epithelial cells (BEP2D cells). We measured the N-acetylation of ODA to mono-acetyl-ODA and the Nacetylation of mono-acetyl-ODA to diacetyl-ODA by BEP2D cells following separation and quantitation by high performance liquid chromatography. For ODA, the apparent KM in cells was 12.4 ± 3.7 μM with a Vmax of 0.69 ± 0.03 nmol/min/1000000 cells, while for mono-acetyl-ODA, the apparent KM was 111.2 ± 48.3 μM with a Vmax of 17.8 ± 5.7 nmol/min/1000000 cells ODA exposure for 24 h resulted in DNA damage to BEP2D cells following concentrations as low as 0.1 μM as measured by yH2Ax protein expression These results demonstrate that ODA, the most prevalent aromatic amine identified in hookah smoke, is N-acetylated and induces DNA damage in human bronchial epithelial cells.

Keywords: 4,4'-Oxydianiline ; Human bronchial epithelial cells ; Hookah smoke ; N-acetylation ; DNA damage ; Waterpipe

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Boyao Zhang ; George-Eugen Maftei ; Bartosz Bartmanski , et al. DOI:

Abstract: Organic carcinogens, in particular DNA-reactive compounds, contribute to the irreversible initiation step of tumorigenesis through introduction of genomic instability. Although carcinogen bioactivation and detoxification by human enzymes has been extensively studied, carcinogen biotransformation by human-associated bacteria, the microbiota, has not yet been systematically investigated. We tested the biotransformation of 68 mutagenic carcinogens by 34 bacterial species representative for the upper and lower human gastrointestinal tract and found that the majority (41) of the tested carcinogens undergo bacterial biotransformation. To assess the functional consequences of microbial carcinogen metabolism, we developed a pipeline to couple gut bacterial carcinogen biotransformation assays with Ames mutagenicity testing and liver biotransformation experiments. This revealed a bidirectional crosstalk between gut microbiota and host carcinogen metabolism, which we validated in gnotobiotic mouse models. Overall, the systematic assessment of gut microbiota carcinogen biotransformation and its interplay with host metabolism highlights the gut microbiome as an important modulator of exposome-induced tumorigenesis.

Purchased from AmBeed: ; ; ; ; ; ; ; ; 62-44-2 ; ; ; ; ; ; ; ; ; ; ; 101-61-1 ; ; ; ; ; 90-94-8 ; ; ; ; ; ; ; ; ; ; ; ; ; 117-39-5 ; ; ; ; ; ; ; ; ;

Product Details of [ 101-80-4 ]

CAS No. :101-80-4 MDL No. :MFCD00007863
Formula : C12H12N2O Boiling Point : -
Linear Structure Formula :O((C6H4)NH2)2 InChI Key :HLBLWEWZXPIGSM-UHFFFAOYSA-N
M.W : 200.24 Pubchem ID :7579
Synonyms :

Safety of [ 101-80-4 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P201-P261-P273-P280-P301+P310-P311 UN#:2811
Hazard Statements:H301+H311+H331-H317-H340-H350-H361-H410 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 101-80-4 ]

* 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.

  • Downstream synthetic route of [ 101-80-4 ]

[ 101-80-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 39213-20-2 ]
  • [ 101-80-4 ]
  • bis-[4-(3,5-dibromo-benzenesulfonylamino)-phenyl]-ether [ No CAS ]
  • 2
  • [ 101-80-4 ]
  • [ 119389-05-8 ]
  • 4,4-(2,2,2-trifluoro-1-phenylethylidene)bis(phthalic anhydride) [ No CAS ]
  • polymer, Mn 5703 Da, Mw 11161 Da, PDI 1.96; monomer(s): 4,4\-(2,2,2-trifluoro-1-phenylethylidene)diphthalic anhydride; 4,4\-diaminodiphenyl ether; 4-(phenylethynyl)phthalic anhydride [ No CAS ]
  • 3
  • [ 2420-87-3 ]
  • [ 101-80-4 ]
  • [ 119389-05-8 ]
  • C128H82N8O28 [ No CAS ]
  • 4
  • [ 628-36-4 ]
  • [ 101-80-4 ]
  • 4-(4-(4-(4H-1,2,4-triazol-4-yl)phenoxy)phenyl)-4H-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% at 150℃; for 24h; The molar ratio of 4-(4-aminophenoxy)aniline: bisformylhydrazide was 1:4A 50 mL three-necked round bottom flask equipped with a magnetic stirrer, a reflux condenser and a thermometer was charged with 4-(4-aminophenoxy)aniline (1 mmol) and bisformylhydrazide (4 mmol). Start the stiring at 150 deg.C. React for 24 hours. After the completion of the reaction, the reaction solution was cooled to room temperature, and the resulting precipitate was added to 100 mL of hot methanol. After stirring, the solution was filtered and the filtrate was slowly evaporated to give a white solid in a yield of 85percent.
85% at 150℃; for 24h; The magneton, of the reflux condenser and a thermometer 50 ml three-port round bottom flask is added to 4 - (4-aminophenoxy) aniline (1mmol) and double-carbohydrazide (4mmol), are started to stir the 150oC, reaction 24 hours. After the reaction, the reaction liquid to room temperature, will be precipitated by adding 100 ml hot methanol, after stirring to dissolve, filtered, filtrate slowly volatilized to obtain white solid, yield 85percent;
85% at 150℃; for 24h; 4-(4-aminophenoxy)aniline : <strong>[628-36-4]N,N'-bisformylhydrazine</strong> molar ratio of 1:4In a 50 ml three-necked flask equipped with magnetic stirrer, reflux condenser and thermometer, add 4-(4-aminophenoxy)aniline (1mmol) and <strong>[628-36-4]N,N'-bisformylhydrazine</strong> (4mmol). Start stirring at 150 deg.C. React for 24 hours. After the reaction, the reaction liquid to room temperature, will be precipitated by adding 100 ml hot methanol, after stirring to dissolve, filtered, filtrate slowly volatilized to obtain white solid, yield 85percent;
85% at 150℃; for 24h; The molar ratio of bis-formylhydrazine was 1: 4,A reflux condenser and a thermometer, respectively, in a 50 mL three-neck round bottom flaskA solution of 4- (4-aminophenoxy) aniline (1 mmol) and bisformylhydrazide (4 mmol)Start stirring at 150oC,For 24 hours.After completion of the reaction,The reaction solution was cooled to room temperature,The resulting precipitate was added to 100 mL of hot methanol,After stirring and dissolving,filter,The filtrate was slowly evaporated to give a white solid in 85percent yield;
85% at 150℃; for 24h; 4 - (4-aminophenoxy) aniline: double-carbohydrazide molar ratio of 1:4The magneton, of the reflux condenser and a thermometer 50 ml three-port round bottom flask is added to 4 - (4-aminophenoxy) aniline (1mmol) and double-carbohydrazide (4mmol), are started to stir the 150oC, reaction 24 hours. After the reaction, the reaction liquid to room temperature, will be precipitated by adding 100 ml hot methanol, after stirring to dissolve, filtered, filtrate slowly volatilized to obtain white solid, yield 85percent;
85% at 150℃; for 24h; 4 - (4-aminophenoxy) aniline: double-carbohydrazide molar ratio of 1:4The magneton, of the reflux condenser and a thermometer 50 ml three-port round bottom flask is added to 4 - (4-aminophenoxy) aniline (1mmol) and double-carbohydrazide (4mmol), are started to stir the 150oC, reaction 24 hours. After the reaction, the reaction liquid to room temperature, will be precipitated by adding 100 ml hot methanol, after stirring to dissolve, filtered, filtrate volatilize slow to get purpled solid, yield 85percent;
85% at 150℃; for 24h;Reflux; In the sub equipped with a magnetic, reflux condenser, and thermometer three 50mL round-bottomed flask were added 4- (4-aminophenoxy) aniline (1 mmol of) formyl hydrazide and bis (4mmol), stirring was started at 150Othe C, For 24 hours.After completion of the reaction, the reaction solution was cooled to room temperature, and the resulting precipitate was added to 100 mL of hot methanol. After stirring, the solution was filtered and the filtrate was slowly evaporated to give a purple solid in a yield of 85percent.

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