1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxyanthraquinone

Endpoint summary

Description of key information

Biodegradation in water

Biodegradability of 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (CAS no. 28198 -05 -2) is predicted using OECD QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 0% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione was estimated to be not readily biodegradable in water.

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 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10-dione (CAS No.28198 -05 -2). If released in to the environment, 16.4 % of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of test chemical 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione in water is estimated to be 37.5 days (900 hrs). The half-life (37.5 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 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione in sediment is estimated to be 337.5 days (8100 hrs). Based on this half-life value, it indicates that 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione is persistent in sediment.

Biodegradation in soil

The half-life period of test chemical 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (CAS No. 28198 -05 -2) 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, 79.7 % of the chemical 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy- 9,10 -dihydroanthracene-9,10 -dione will partition into soil according to the Mackay fugacity model level III. The half-life period of test chemical in soil is estimated to be 75 days (1800 hrs). Based on this half-life value of 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione, 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

Using Bio-concentration Factor (v12.1.0.50374) module Bio-concentration Factor over the entire pH scale (pH 0 -14) of the test substance 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10-dione (CAS no. 28198 -05 -2) was estimated to be > 1000000.0,  4146662, 391974, 11176, 1181, 955, 941 and 940 at pH 0-6, 7, 8, 9, 10, 11, 12 and 13-14, respectivelyACD (Advanced Chemistry Development)/I-Lab predictive module, 2017). This value indicates that the test substance 1,4 -bis[(4 -butylphenyl)amino] -5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione was considered to be accumulative in aquatic organisms.

Adsorption/desorption

KOCWIN model (v2.00) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the soil adsorption coefficient i.e Koc value of test chemical 1,4 -bis[(4 -butylphenyl) amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10-dione (CAS No. 28198 -05 -2). The soil adsorption coefficient i.e Koc value of 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione was estimated to be 329700000 L/kg (log Koc=8.5181)  by means of MCI method (at 25 deg C). This Koc value indicates that the substance 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.

Additional information

Biodegradation in water

Various predicted data for the target compound 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (CAS No. 28198-05-2) and 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 done by SSS (2017) using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor, percentage biodegradability of test chemical 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione (CAS No. 28198-05-2) was estimated. Test substance undergoes 0% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione was estimated to be not readily biodegradable in water.

 

In another prediction using the Estimation Programs Interface Suite (EPI suite, 2017), the biodegradation potential of the test compound 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione(CAS No. 28198-05-2) 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 chemical 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione is expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017 and Envichem, 2014) for the read across chemical Bis(octylphenyl)amine (CAS no. 26603-23-6), biodegradation experiment was conducted for 14 days for evaluating the percentage biodegradability of read across substance Bis(octylphenyl)amine. 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 Bis(octylphenyl)amine was determined to be 0 and 5.2% by BOD and UV-Vis parameter in 14 days. Thus, based on percentage degradation, Bis(octylphenyl)amine is considered to be not readily biodegradable in nature.

 

For the read across chemical 4-octyl-N-(4-octylphenyl)aniline (CAS no. 101-67-7) from authoritative database (J-CHECK, 2017), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance 4 -octyl-N-(4 -octylphenyl)aniline. 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 4 -octyl-N-(4 -octylphenyl)aniline was determined to be 0 and 2% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation, 4 -octyl-N-(4 -octylphenyl)aniline is considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance 2,2'-methylenebis(6-tert-butyl-4-methylphenol) (CAS no119-47-1) (J-CHECK, HSDB, 2017 and Envichem, 2014). 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 2,2'-methylenebis(6 -tert-butyl-4 -methylphenol) was determined to be 0 and 1% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation, 2,2'-methylenebis(6 -tert-butyl-4 -methylphenol) is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione(from OECD QSAR toolbox version 3.3 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK, HSDB and Envichem), it can be concluded that the test substance 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione can be expected to be not 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 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10-dione (CAS No.28198 -05 -2). If released in to the environment, 16.4 % of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of test chemical 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione in water is estimated to be 37.5 days (900 hrs). The half-life (37.5 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 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione in sediment is estimated to be 337.5 days (8100 hrs). Based on this half-life value, it indicates that 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione is persistent in sediment.

Biodegradation in soil

The half-life period of test chemical 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (CAS No. 28198 -05 -2) 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, 79.7 % of the chemical 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy- 9,10 -dihydroanthracene-9,10 -dione will partition into soil according to the Mackay fugacity model level III. The half-life period of test chemical in soil is estimated to be 75 days (1800 hrs). Based on this half-life value of 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione, 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 substance 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione can be considered to be not readily biodegradable in nature.

Bioaccumulation: aquatic/sediment

Various predicted data for the target compound1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione(CAS No. 28198-05-2) were reviewed for the bioaccumulation end point which are summarized as below:

 

In a 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 0 -14) of the test substance 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10-dione (CAS no. 28198 -05 -2) was estimated to be > 1000000.0,  4146662, 391974, 11176, 1181, 955, 941 and 940 at pH 0-6, 7, 8, 9, 10, 11, 12 and 13-14, respectively.

 

Bioconcentration Factor (BCF) of test chemical 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (CAS no. 28198 -05 -2) was estimated using Chemspider database(ChemSpider, 2017). The bioconcentration factor of test substance 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione was estimated to be 1000000.00 and 289710.13 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 (1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione (CAS No. 28198 -05 -2). The bioconcentration factor (BCF) of 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydro anthracene-9,10 -dione was estimated to be 1000000.0, 222000.0 and 23500 at pH range 1-8, 9 and 10, respectively (at 25 deg C).

 

On the basis of above results for target chemical1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione(from ACD labs,ChemSpider and SciFinder database,  2017), it can be concluded that the BCF value of test substance1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione ranges from 940 –4146662which exceeds the bioconcentration threshold of 2000, indicating that the chemical 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione is expected to bioaccumulate in the food chain.

Adsorption/desorption

Various predicted data for the target compound 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (CAS No. 28198-05-2) and supporting weight of evidence study for its read across substance were reviewed for the adsorption end point which are summarized as below:

 

In aprediction done using theKOCWIN Program(v2.00) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the soil adsorption coefficient i.e Koc value of test chemical 1,4 -bis[(4 -butylphenyl) amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10-dione (CAS No. 28198 -05 -2). The soil adsorption coefficient i.e Koc value of 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione was estimated to be 329700000 L/kg (log Koc=8.5181)  by means of MCI method (at 25 deg C).

 

The Soil Adsorption Coefficient i.e Koc value of test substance 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (CAS no. 28198 -05 -2) was estimated using Adsorption Coefficient module (v12.1.0.50374) program as Koc 3986438, 4325568, 4362613, 4365545, 4357768, 4277912, 3611842, 1364302, 128964, 3677, 388, 314, 310 and 309 at pH range 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13-14 respectively (log Koc ranges from 2.5 ± 1.0 to 6.6 ± 1.0)(ACD (Advanced Chemistry Development)/I-Lab predictive module, 2017).

 

In an another prediction done by using ChemSpider Database (2017),the Soil Adsorption Coefficient i.e Koc value of test substance 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (CAS no. 28198 -05 -2) was estimated. The adsorption coefficient (Koc) value of test substance 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione was estimated to be 1066884.00 (Log Koc =6.028) and 162630.20 (Log Koc = 5.211) at pH 5.5 and pH 7.4, respectively.

 

Additional soil adsorption coefficient i.e Koc value of test chemical 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione(CAS No. 28198-05-2)was estimated using the SciFinder database (American Chemical Society (ACS), 2017).The soil adsorption coefficient i.e Koc value of 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione was estimated to be 10000000, 1000000, 31300 and 3300 at pH range 1 -7, 8, 9 and 10, respectively (log Koc ranges from 3.518 to 7) (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 adsorption coefficient i.e KOC for test substance 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione was estimated to be 89500 L/kg (log Koc = 4.95).The predicted KOC result based on the 5 OECD principles. This Koc value indicates that the substance 1,4 -bis[(4 -butyl phenyl)amino]- 5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 - dione has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.

 

In a supporting weight of evidence study from authoritative database (HSDB, 2017) for the read across chemical 1,4-bis[(4-methylphenyl)amino]-9,10-anthraquinone (CAS no. 128-80-3), adsorption experiment was conducted for estimating the adsorption coefficient (Koc) value of read across chemical 1,4 -bis[(4 -methylphenyl)amino]-9,10 -anthraquinone. The adsorption coefficient (Koc) value was calculated using a structure estimation method based on molecular connectivity indices. The adsorption coefficient (Koc) value of substance 1,4 -bis[(4 -methylphenyl)amino]-9,10 -anthraquinone was estimated to be 4800000 (Log Koc = 6.681).

 

On the basis of above overall results for target chemical1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione(from EPI suite, ACD labs,ChemSpider, SciFinder database and CompTox Chemistry Dashboard,2017) and for its read across substance (from authoritative database HSDB, 2017), it can be concluded that the Koc value of test substance1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione ranges from 309 –329700000 indicating that the test chemical 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.