Comparative hydrolysis of substituted ureas in a mixed alcoholic-water solution

Audu, A. A.; Heyn, Arno H.A.

doi:10.1016/0043-1354(88)90011-5

Cited by 8 publications

(13 citation statements)

References 6 publications

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“…Such proposal corroborates with Tarbin et al., who observed that DNC concentration decreased in aqueous solutions. This is a reasonable pathway for DNC breakdown because phenylurea analogues typically undergo hydrolysis to release the aniline derivatives. − Therefore, p -NA is expected as the major breakdown product. Considering that chicken meat pH is in the range of 5.0–6.0, some possible mechanisms described in the literature can illustrate the chemistry of DNC degradation (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Degradation of 4,4′-Dinitrocarbanilide in Chicken Breast by Thermal Processing

Bacila

Cunha

Weber

et al. 2018

J. Agric. Food Chem.

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Nicarbazin is one of the major anticoccidials used in broiler feeds. The compound 4,4'-dinitrocarbanilide (DNC) is the marker residue of concern left from nicarbazin in chicken meat. The effect of thermal processing on DNC content accumulated in chicken breast was assessed, and samples were analyzed by liquid chromatography-tandem mass spectrometry. Five conventional cooking methods were evaluated: boiling, grilling, microwaving, frying, and roasting. To ensure DNC in meat, broilers were fed nicarbazin without withdrawal period. All heating methods surpassed the 70 °C end point core temperature in chicken breast. Maximum DNC degradation was reached at 10 min for boiling, at 30 min for grilling, and at 2 min for microwaving, and no further reduction was observed for longer thermal processing time. Boiling was more efficient in reducing DNC (69%). Grilling, microwaving, and frying achieved on average 55% of degradation. The outcomes reported herein may be considered in decision-making regarding further review of maximum residue limits.

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Section: Resultsmentioning

confidence: 99%

Degradation of 4,4′-Dinitrocarbanilide in Chicken Breast by Thermal Processing

Bacila

Cunha

Weber

et al. 2018

J. Agric. Food Chem.

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“…Pseudo-first-order rate constants at 25°C for hydrolysis in basic (0.5 M NaOH), neutral (pH=6.7), or acidic solution (0.5 M HCl) are as low as 10 −9~1 0 −10 min −1 , yielding corresponding half-lives between 5 and 42 years, respectively (Audu and Heyn 1988). In our work, we found that the decrease of TCC concentration was negligible in dark control experiments.…”

Section: Effects Of Solution Ph and Initial Tcc Concentrationsmentioning

confidence: 89%

Influence of pH, inorganic anions, and dissolved organic matter on the photolysis of antimicrobial triclocarban in aqueous systems under simulated sunlight irradiation

Ding

Wang

Jiang

et al. 2014

Environ Sci Pollut Res

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The photolysis of the antimicrobial triclocarban (TCC) in aqueous systems under simulated sunlight irradiation was studied. The effects of several abiotic parameters, including solution pH, initial TCC concentration, presence of natural organic matter, and most common inorganic anions in surface waters, were investigated. The results show that the photolysis of TCC followed pseudo-first-order kinetics. The TCC photolysis rate constant increased with increasing solution pH and decreasing the initial TCC concentration. Compared with the TCC photolysis in pure water, the presence of aqueous bicarbonate, nitrate, humic acids, and its sodium salt decreased the TCC photolysis rate, but fulvic acid increased the TCC photolysis rate. The electron spin resonance and reactive oxygen species scavenging experiments indicated that TCC may undergo two different types of phototransformation reactions: direct photolysis and energy transfer to generate (1)O2. The main degradation products were tentatively identified by gas chromatography interfaced with mass spectrometry (GC-MS), and a possible degradation pathway was also proposed.

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“…The amount of the aromatic amine released from DNC hydrolysis was determined on the basis of the Bratton-Marshall diazotization according to a procedure adapted from previous studies. , Thus, after the reaction mixture was cooled, the following reagents were successively added into the tubes: 500 μL of 2 mol/L HCl, 50 μL of 2% (w/v) NaNO 2 (aq. ), 50 μL of 10% (w/v) sulfamic acid (aq.…”

Section: Experimental Sectionmentioning

confidence: 99%

Detection of p-Nitroaniline Released from Degradation of 4,4′-Dinitrocarbanilide in Chicken Breast during Thermal Processing

Bacila

Cunha

Gressler

et al. 2019

J. Agric. Food Chem.

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The diphenylurea 4,4′-dinitrocarbanilide (DNC) is the residue of concern left in edible tissues of broilers fed diets containing the anticoccidial nicarbazin. When chicken meat is submitted to thermal processing, p-nitroaniline (p-NA) is expected from DNC degradation. This work aimed at evaluating whether thermal processing of DNC-containing chicken meat induces p-NA appearance. First, a hydrolysis assay was performed in aqueous solutions at 100 °C in different pH, confirming that DNC cleavage yields p-NA. Then a novel LC-MS/MS method was used to detect traces of this aromatic amine in DNCcontaining chicken breast fillets subjected to cooking methods. Our evidence showed p-NA occurrence in such chicken meat samples, which corroborated results from hydrolysis assay. The p-NA appearance in fillets was rather discrete during boiling treatment, but its concentration became pronounced over time for grilling, frying, and roasting, achieving respectively 326.3, 640.0, and 456.9 μg/kg. As far as we are concerned, no other research identified degradation products from DNC residue in heat-processed chicken fillets. Therefore, this study leads to additional approaches to assess impacts on food safety.

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Comparative hydrolysis of substituted ureas in a mixed alcoholic-water solution

Cited by 8 publications

References 6 publications

Degradation of 4,4′-Dinitrocarbanilide in Chicken Breast by Thermal Processing

Degradation of 4,4′-Dinitrocarbanilide in Chicken Breast by Thermal Processing

Influence of pH, inorganic anions, and dissolved organic matter on the photolysis of antimicrobial triclocarban in aqueous systems under simulated sunlight irradiation

Detection of p-Nitroaniline Released from Degradation of 4,4′-Dinitrocarbanilide in Chicken Breast during Thermal Processing

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