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Environmental fate & pathways

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Description of key information

Hydrolysis

Hydrolysis of 4'-Cyanoacetophenone (CAS no. 1443 -80 -7) is predicted using OECD QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. The estimated half-life of 4'-Cyanoacetophenone was estimated to be 156.46 days, indicating that it is not hydrolysable.

Biodegradation in water

Estimation Programs Interface Suite (EPI suite, 2017) was run to predict the biodegradation potential of the test compound 4'-Cyanoacetophenone (CAS no. 1443 -80 -7) in the presence of mixed populations of environmental microorganisms. The biodegradability of the substance was calculated using seven different models such as Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI Linear Model, MITI Non-Linear Model and Anaerobic Model (called as Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical 4'-Cyanoacetophenone is expected to be readily biodegradable.

 

Biodegradation in water and sediment

Estimation Programs Interface (EPI Suite, 2017) prediction model was run to predict the half-life in water and sediment for the test compound 4'-Cyanoacetophenone

(CAS No. 1443 -80 -7). If released in to the environment, 25.3% of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of

4'-Cyanoacetophenone in water is estimated to be 15 days (360 hrs). The half-life (15 days estimated by EPI suite) indicates that the chemical is not persistent in water and the exposure risk to aquatic animals is moderate to low whereas the half-life period of 4'-Cyanoacetophenone in sediment is estimated to be 135 days (3240 hrs). However, as the percentage release of test chemical into the sediment is less than 1% (i.e, reported as 0.0822%), indicates that 4'-Cyanoacetophenone is not persistent in sediment.

Biodegradation in soil

The half-life period of 4'-Cyanoacetophenone (CAS No.1443 -80 -7) in soil was estimated using Level III Fugacity Model by EPI Suite version 4.1 estimation database (EPI suite, 2017). If released into the environment, 73.2% of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of 4'-Cyanoacetophenone in soil is estimated to be 30 days (720 hrs). Based on this half-life value of 4'-Cyanoacetophenone, it is concluded that the chemical is not persistent in the soil environment and the exposure risk to soil dwelling animals is moderate to low.

Bioaccumulation: aquatic / sediment

BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 4'-Cyanoacetophenone (CAS No. 1443 -80 -7). The bioconcentration factor (BCF) of 4'-Cyanoacetophenone was estimated to be 0.7706 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical 4'-Cyanoacetophenone is not expected to bioaccumulate in the food chain.

Adsorption / desorption

The adsorption coefficient Koc in soil and in sewage sludge of test chemical 4'-cyanoacetophenone (CAS No. 1443 -80 -7) was determined by the Reverse Phase High Performance Liquid Chromatographic method according to OECD Guideline No. 121 for testing of Chemicals (Sustainability Support Services (Europe) AB, Report no. UERL/PC/010-03, 2017). The solutions of the test substance and reference substances were prepared in appropriate solvents. A test item solution was prepared by accurately weighing 4 mg of test item and diluted with Acetonitrile up to 10 ml. Thus, the test solution concentration was 400 mg/l. The pH of test substance was 5.5. Each of the reference substance and test substance were analysed by HPLC at 210 nm. After equilibration of the HPLC system, Urea was injected first, the reference substances were injected in duplicate, followed by the test chemical solution in duplicate. Reference substances were injected again after test sample, no change in retention time of reference substances was observed. Retention time tR were measured, averaged and the decimal logarithms of the capacity factors k were calculated. The graph was plotted between log Koc versus log k(Annex - 2).The linear regression parameter of the relationship log Koc vs log k were also calculated from the data obtained with calibration samples and therewith, log Koc of the test substance was determined from its measured capacity factor. The reference substances were chosen according to functional similarity with the test substance and calibration graph prepared. The reference substances were 4 -chloroaniline, 4-methylaniline(p-Tolouidine), N-methylaniline, p-toluamide, Aniline, 2,5-Dichloroaniline, 4 -nitrophenol, 2 - nitrophenol, 2-nitrobenzamide, 3 -nitrobenzamide, Nitrobenzene, 4 -Nitrobenzamidel, 1 -naphthylamine, 1-naphtol, Direct Red 81, Benzoic acid methylester, Carbendazim, Benzoic acid phenylester, Xylene, Ethylbenzene, Toluene, Naphthalene, 1,2,3-trichlorobenzene, phenanthrene, Phenol, N,Ndimethylbenzamide, 3,5-dinitrobenzamide, N-methylbenzamide, Benzamide, Pentachlorophenol, DDT, Acetanilide having Koc value ranging from 1.25 to 5.63. The Log Koc value of test chemical 4'-cyanoacetophenone was determined to be 2.214 ± 0.001 at 25°C. This log Koc value indicates that the substance 4'-cyanoacetophenone has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

Additional information

Hydrolysis

Hydrolysis of 4'-Cyanoacetophenone (CAS no. 1443 -80 -7) is predicted using OECD QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. The estimated half-life of 4'-Cyanoacetophenone was estimated to be 156.46 days, indicating that it is not hydrolysable.

Biodegradation in water

Predicted data for the target compound 4'-Cyanoacetophenone (CAS No. 1443-80-7) and various supporting weight of evidence studies for its read across substance were reviewed for the biodegradation end point which are summarized as below:

 

In a prediction using the Estimation Programs Interface Suite (EPI suite, 2017), the biodegradation potential of the test compound 4'-Cyanoacetophenone(CAS No. 1443-80-7) in the presence of mixed populations of environmental microorganisms was estimated.The biodegradability of the substance was calculated using seven different models such as Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI Linear Model, MITI Non-Linear Model and Anaerobic Model (called as Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical4'-Cyanoacetophenoneis expected to be readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017) for the read across chemical 1-(4-methylphenyl)ethan-1-one (CAS no. 122-00-9),biodegradation experiment was conducted for 14 days for evaluating the percentage biodegradability of read across substance 1-(4-methylphenyl)ethan-1-one. Activated sludge was used as a test inoculums for the study. Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of substance 1-(4-methylphenyl)ethan-1-one was determined to be 77, 92 and 96% by BOD, TOC removal and HPLC parameter in 14 days. Thus, based on percentage degradation,1-(4-methylphenyl)ethan-1-one is considered to be readily biodegradable in nature.

 

For the read across chemical 1-phenylethan-1-one (CAS no. 98-86-2) from peer reviewed journal (Kohei Urano and Zenji Kato, 1986), biodegradation study was conducted with an electrolytic respirometer for 14 days for evaluating the percentage biodegradability of read across substance 1-phenylethan-1-one at a temperature of 20± 1°C and pH 7 ± 1. Activated sludge was used as a test inoculums for the study. Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. JIS inorganic medium (1ml/300 ml) was used as a test medium for the study. The measurements of the biochemical oxygen demand (BOD) curves and the concentrations of dissolved organic carbon (DOC) were repeated two or three times for the test compound, and the reproducibilities were confirmed. The percentage degradation of substance 1-phenylethan-1-one was determined to be ranges from 65 to 73% by BOD and ThOD parameter in 11 days. Thus, based on percentage degradation,1 -phenylethan-1-one is considered to be readily biodegradable in nature.

 

Another biodegradation study was conducted for 5 days for evaluating the percentage biodegradability of the same read across substance 1-phenylethan-1-one (CAS no. 98-86-2) (Dinesh D. Vaishnav et. al; 1987). The biodegradation was determined using the BOD technique. Acclimated microbial culture capable of degrading the test chemical as sole carbon and energy source was used as a test inoculum obtained from by a conventional enrichment technique. Mineral salts medium containing either 250 mg/ of the chemical was inoculated with domestic sewage, and incubated on a rotary shaker (120 rpm) at 21 + 3°C. These cultures were stored individually at 4 °C in 0.2 M phosphate buffer (pH 6.8) containing 100 mg/L of the enrichment substrate. Test chemical and 1 mL of acclimated seed were added to 20 mL of dilution water in 300-mL BOD bottles. The bottles were then filled to capacity with dilution water, sealed, and incubated for 5 d at 21 ± 3 °C. Initial concentrations of test chemical in the BOD bottles ranged from 0 to 3.2 mg/L. Initial and 5-day dissolved 02 (DO) concentrations were measured using a YSI 54 oxygen meter with a self-stirring probe. The DO concentrations in randomly selected bottles were determined by the azide modification of the iodometric titration method. Nonlinear and linear regression were performed using the NLIN and REG procedures, respectively, in the Statistical Analysis System (SAS), on the U.S. Environmental Protection Agency's VAX 11/780 computer at Research Triangle Park, N.C. The percentage degradation of substance 1-phenylethan-1-one was determined to be 59.1% by ThOD parameter in 5 days. Thus, based on percentage degradation,1-phenylethan-1-one is considered to be readily biodegradable in nature.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017 and EnviChem, 2014) for the read across chemical 1-phenylethan-1-one (CAS no. 98-86-2),biodegradation study was conducted for 14 days for evaluating the percentage biodegradability of read across substance 1-phenylethan-1-one. The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I).Activated sludge was used as a test inoculums for the study. Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of substance 1-phenylethan-1-one was determined to be 64.7, 80.9 and 90.7% by BOD, TOC removal and GC parameter in 14 days. Thus, based on percentage degradation,1-phenylethan-1-one is considered to be readily biodegradable in nature.

 

On the basis of above results for target chemical 4'-Cyanoacetophenone (from EPI suite, 2017) and for its read across substance (from peer reviewed journals and authoritative database J-CHECK & EnviChem), it can be concluded that the test substance 4'-Cyanoacetophenone can be expected to be readily biodegradable in nature.

Biodegradation in water and sediment

Estimation Programs Interface (EPI Suite, 2017) prediction model was run to predict the half-life in water and sediment for the test compound 4'-Cyanoacetophenone

(CAS No. 1443 -80 -7). If released in to the environment, 25.3% of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of

4'-Cyanoacetophenone in water is estimated to be 15 days (360 hrs). The half-life (15 days estimated by EPI suite) indicates that the chemical is not persistent in water and the exposure risk to aquatic animals is moderate to low whereas the half-life period of 4'-Cyanoacetophenone in sediment is estimated to be 135 days (3240 hrs). However, as the percentage release of test chemical into the sediment is less than 1% (i.e, reported as 0.0822%), indicates that 4'-Cyanoacetophenone is not persistent in sediment.

Biodegradation in soil

The half-life period of 4'-Cyanoacetophenone (CAS No.1443 -80 -7) in soil was estimated using Level III Fugacity Model by EPI Suite version 4.1 estimation database (EPI suite, 2017). If released into the environment, 73.2% of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of 4'-Cyanoacetophenone in soil is estimated to be 30 days (720 hrs). Based on this half-life value of 4'-Cyanoacetophenone, it is concluded that the chemical is not persistent in the soil environment and the exposure risk to soil dwelling animals is moderate to low.

On the basis of available information, the test substance4'-Cyanoacetophenone can be considered to be readily biodegradable in nature.

Bioaccumulation: aquatic / sediment

Various predicted data for the target compound 4'-Cyanoacetophenone (CAS No. 1443-80-7) and supporting weight of evidence study for its read across substance were reviewed for the bioaccumulation end point which are summarized as below:

 

In aprediction done using theBCFBAF Program(v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 4'-Cyanoacetophenone (CAS No. 1443 -80 -7). The bioconcentration factor (BCF) of 4'-Cyanoacetophenone was estimated to be 0.7706 L/kg whole body w.w (at 25 deg C).

 

In an another prediction done by using Bio-concentration Factor (v12.1.0.50374) moduleACD (Advanced Chemistry Development)/I-Lab predictive module, 2017), theBCF over the entire pH scale (pH 1 -14) of the test substance 4'-Cyanoacetophenone (CAS no. 1443 -80 -7) was estimated to be 4.98.

 

Bioconcentration Factor (BCF) of test chemical 4'-Cyanoacetophenone was estimated using Chemspider database(ChemSpider, 2017). The bioconcentration factor of test substance 4'-Cyanoacetophenone was estimated to be 6.35 at both pH 5.5 and 7.4, respectively.

 

Another predicted data was estimated usingSciFinder database (American Chemical Society (ACS), 2017) was used for predicting the bioconcentration factor (BCF) of test chemical 4'-Cyanoacetophenone (CAS No. 14423 -80 -7).The bioconcentration factor (BCF) of 4'-Cyanoacetophenone was estimated to be 4.98 (at 25 deg C).

 

From CompTox Chemistry Dashboard using OPERA (OPEn (quantitative) structure-activity Relationship Application)  V1.02 model in which calculation based on PaDEL descriptors (calculate molecular descriptors and fingerprints of chemical), the bioaccumulation i.e BCF for test substance 4'-Cyanoacetophenone was estimated to be 3.17 dimensionless . The predicted BCF result based on the 5 OECD principles.

 

In a supporting weight of evidence study from authoritative database (HSDB, 2017) for the read across chemical 1-phenylethan-1-one (CAS no. 98-86-2),bioaccumulation experiment was conducted for estimating the BCF (bioaccumulation factor) value of read across chemical 1-phenylethan-1-one. The bioaccumulation factor (BCF) value was calculated using a logKow of 1.58 and a regression-derived equation. The estimated BCF (bioaccumulation factor) value of 1 -phenylethan-1 -one was determined to be 0.5 dimensionless.

 

For the read across chemical Benzonitrile (CAS no. 100-47-0), bioaccumulation study in fish was conducted for estimating the BCF (bioaccumulation factor) value of read across chemical Benzonitrile (HSDB, 2017). The bioaccumulation factor (BCF) value was calculated using a measured logKow of 1.56 and a regression-derived equation. The estimated BCF (bioaccumulation factor) value of Benzonitrile was determined to be 5 dimensionless.

 

On the basis of above results for target chemical4'-Cyanoacetophenone(from EPI suite, ACD labs,ChemSpider and CompTox Chemistry Dashboard,  2017) and for its read across substance from authoritative database (HSDB, 2017), it can be concluded that the BCF value of test substance4'-Cyanoacetophenoneranges from 0.7706 – 6.35 which does not exceed the bioconcentration threshold of 2000, indicating that the chemical4'-Cyanoacetophenoneis not expected to bioaccumulate in the food chain.

Adsorption / desorption

Experimental study for the target compound 4'-Cyanoacetophenone(CAS No. 1443-80-7) and supporting study for its read across substance were reviewed for the adsorption end point which are summarized as below:

 

In an experimental key study from UERL study report (Sustainability Support Services (Europe) AB, Report no. UERL/PC/010-03, 2017), the adsorption coefficient Koc in soil and in sewage sludge of test chemical 4'-cyanoacetophenone (CAS No. 1443 -80 -7) was determined by the Reverse Phase High Performance Liquid Chromatographic method according to OECD Guideline No. 121 for testing of Chemicals. The solutions of the test substance and reference substances were prepared in appropriate solvents. A test item solution was prepared by accurately weighing 4 mg of test item and diluted with Acetonitrile up to 10 ml. Thus, the test solution concentration was 400 mg/l. The pH of test substance was 5.5. Each of the reference substance and test substance were analysed by HPLC at 210 nm. After equilibration of the HPLC system, Urea was injected first, the reference substances were injected in duplicate, followed by the test chemical solution in duplicate. Reference substances were injected again after test sample, no change in retention time of reference substances was observed. Retention time tR were measured, averaged and the decimal logarithms of the capacity factors k were calculated. The graph was plotted between log Koc versus log k(Annex - 2).The linear regression parameter of the relationship log Koc vs log k were also calculated from the data obtained with calibration samples and therewith, log Koc of the test substance was determined from its measured capacity factor. The reference substances were chosen according to functional similarity with the test substance and calibration graph prepared. The reference substances were 4 -chloroaniline, 4-methylaniline(p-Tolouidine), N-methylaniline, p-toluamide, Aniline, 2,5-Dichloroaniline, 4 -nitrophenol, 2 - nitrophenol, 2-nitrobenzamide, 3 -nitrobenzamide, Nitrobenzene, 4 -Nitrobenzamidel, 1 -naphthylamine, 1-naphtol, Direct Red 81, Benzoic acid methylester, Carbendazim, Benzoic acid phenylester, Xylene, Ethylbenzene, Toluene, Naphthalene, 1,2,3-trichlorobenzene, phenanthrene, Phenol, N,Ndimethylbenzamide, 3,5-dinitrobenzamide, N-methylbenzamide, Benzamide, Pentachlorophenol, DDT, Acetanilide having Koc value ranging from 1.25 to 5.63. The Log Koc value of test chemical 4'-cyanoacetophenone was determined to be 2.214 ± 0.001 at 25°C. This log Koc value indicates that the substance 4'-cyanoacetophenone has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

In a supporting study from authoritative database (HSDB, 2017) for the read across chemical Benzonitrile (CAS no. 100-47-0), adsorption experiment was conducted for estimating the adsorption coefficient (Koc) value of read across chemical Benzonitrile (CAS no. 100-47-0). The adsorption coefficient (Koc) value was calculated using a logKow of 1.56 and a regression derived equation. The adsorption coefficient (Koc) value of substance Benzonitrile was estimated to be 150 (Log Koc = 2.176). This Koc value indicates that the substance Benzonitrile has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

On the basis of above overall results for target chemical 4'-Cyanoacetophenone (from experimental study report) and for its read across substance from authoritative database (HSDB, 2017), it can be concluded that the log Koc value of test substance 4'-Cyanoacetophenone was determined to be 2.214, indicating that the test chemical 4'-Cyanoacetophenone has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.