4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid

Endpoint summary

Description of key information

Stability:

Hydrolysis:

The half life of hydrolysis of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS no. 70239 -77 -9) was estimated by using OECD QSAR tool box v3.3 and six closest read across chemicals with log Kow as primary descriptor. The half life of hydrolysis of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid was estimated to be 252.204 days. Based on this half life value it is concluded that this test chemical can show negligible hydrolysis that means it is not hydrolysable.

Biodegradation:

Biodegradation in water:

Biodegradability of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid was estimated by using OECD QSAR tool box v3.3 and using five closest read across chemical with log Kow as primary descriptor. Percent biodegradability of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid was  determined to be 2.43% by considering BOD as parameter  and microorganisms as inoculum in 28 days. Based on percent biodegrdability value it can be concluded that this test chemical is not 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-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS no.70239 -77 -9) . If released in to the environment, 11.3 % of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of test chemical in water is estimated to be 37.5 days (360 hrs). The half-life (37.5days estimated by EPI suite) indicates that the chemical is not persistent in water and the exposure risk to aquatic animals is low whereas the half-life period of test chemical ) 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid in sediment is estimated to be 337.5 days (8100 hrs). However, as the percentage release of test chemical into the sediment is less than 2% (i.e, reported as 1.43 %), indicates that test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid is not persistent in sediment as well.

Biodegradation in soil:

The half-life period of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS no.70239 -77 -9) 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, 87.3 % of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid in soil is estimated to be 75 days (1800 hrs). Based on this half-life value of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid , it is concluded that the chemical is not persistent in the soil environment and the exposure risk to soil dwelling animals is low .

Bioaccumulation:

Bioaccumulation:aquatic/sediments:

Using BCFBAF Program (v3.00) model of EPI suite 2017 the estimated bio concentration factor (BCF) for 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS No. 70239-77-9) is 3.162 L/kg wet-wt at 25 deg. c which does not exceed the bioconcentration threshold of 2000. Therefore it is concluded that test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid is non bioaccumulative in food chain.

Transport and Distribution:

Adsorption/desorption:

The Soil Adsorption Coefficient i.e. Koc value of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS No. 70239-77-9) was estimated using EPI suite KOCWIN Program (v2.00) as 2231 L/kg (log Koc= 3.3484) by means of MCI method at 25 deg. C. This log Koc value indicates that test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid has moderate sorption to soil and therefore have slow migration potential to ground water.

Additional information

Stability:

Hydrolysis:

The half life of hydrolysis of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS no. 70239 -77 -9) was estimated by using OECD QSAR tool box v3.3 and six closest read across chemicals with log Kow as primary descriptor. The half life of hydrolysis of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid was estimated to be 252.204 days. Based on this half life value it is concluded that this test chemical can show negligible hydrolysis that means it is not hydrolysable.

Biodegradation:

Biodegradation in water:

Two predicted data studies for target chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS no. 70239 -77 -9) and three experimental studies for its structurally similar read across chemicals are summarized below for biodegradation in water endpoint.

 

In first weight of evidence study the Biodegradability of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid was estimated by using OECD QSAR tool box v3.3 and using five closest read across chemical with log Kow as primary descriptor. Percent biodegradability of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid was  determined to be 2.43% by considering BOD as parameter  and microorganisms as inoculum in 28 days. Based on percent biodegrdability value it can be concluded that this test chemical is not readily biodegradable.

 

Another predicted data study was done by using Estimation Programs Interface Suite (EPI suite, 2017) to estimate the biodegradation potential of the test compound 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS no. 70239 -77 -9) 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-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid is expected to be not readily biodegradable.

 

Next weight of evidence study of read across chemical Acid Red 1 was done from Water Engineering Research Laboratory Cincinnati, OH 45268, July 1988 in this study the water soluble dye Acid Red 1 was dosed to the two experimental systems at target active ingredient doses of 1 and 5 mg/L of influent flow. The primary sludge was not sampled. The influent, primary effluent and sludge effluent were filtered and the filtrate was extracted. All the extracted samples were analysed by HPLC with an ultraviolet-visible detector. Total suspended solids (TSS) analyses were also performed on all the samples. All systems were operated for at least three times. All samples were 24 hour composites made up of 6 grab samples collected every 4 hour stored at 4 degrees Celsius. The pH of the influent was 2.0-8.0. The aeration of basin temperature was 21-25 degrees Celsius. Dissolved oxygen was 2-4 mg/L. Hydraulic retention time was 0.28 days. Solids retention time was 2.7 days. The possible removal mechanism for a dye compound in the ASP system includes adsorption, biodegradation, chemical transformation, photodegradation, chemicals photodegrading and air stripping. The recoveries for the 18 dues were generally very good and with relatively low standard deviations. No photodegrading was found in the laboratory study. The authors assumed that adsorption and biodegradation was the only removal mechanisms of the pilot-scale activated sludge system. If a compound was recovered near the target range of 80% to 120% then it was assumed that this compound was not biodegraded. Conversely, if the recovery was less than 20% to 30% then it was assumed that the compound was apparently biodegraded. Lastly, if the compound was recovered near 80 to 120% one investigated the percentage adsorbed data. If amount adsorbed was greater than 30% then it was concluded that such compound was removed by adsorption. Eleven of the 18 azo dyes passed through the pilot scale activated sludge plant untreated and one on these was Acid Red 1. Acid Red 1 was not removed via adsorption. The relatively high sulfonic acid substitution of these dyes may explain why they were unaffected by the sewage treatment process. By speculation, the position of the sulfonic acid functional groups and the molecular weight appeared to limit uptake by microorganisms. Acid Red 1 was based on this study not consider to be readily biodegraded in regular wastewater treatment plants.

 

Further, another experimental weight of evidence study was done from UERL laboratory (2017) in this study a 28-days closed bottle test following the OECD guideline 301D to determine the ready biodegradability of the same read across chemical Acid Red 1 (CAS No.3734 -67 -6) was performed. The test setup included in addition to Acid Red 1 separate bottles with negative control and positive control (reference substance was sodium benzoate). The tested chemical concentration was 32 mg/L. The inoculum concentration was 32 ml/L. The incubation temperature was 20 ± 1°C. The biological oxygen demand (BOD) was after 28 days of incubation with inoculums determined to be 0.475mg O2/mg. The theoretical oxygen demand (ThOD) was calculated to 1.194mg O2/mg. The % degradation of the read across chemical after 28 days of incubation at 20±1°C was calculated to 39.78%. The chemical could based on 40% degradation after 28 days neither be classified as readily degradable (60% degradation threshold in OECD 301 test) nor inherently degradable (approx. 50-55% degradation threshold in OECD 301 test). The chemical was therefore not considered to be biodegradable under the tested conditions.

 

The last experimental weight of evidence study was done by UERL laboratory (2016)of read across chemical disodium 3- [(2,4 -dimethyl-5 -sulphonatophenyl)azo]-4 -hydroxynaphthalene-1 -sulphonate, CAS No. 4548 -53 -2 in this study a 28-days Manometric respirometry testfollowing the OECD guideline 301F to determine the ready biodegradability of the read across chemical disodium 3- [(2,4 -dimethyl-5 -sulphonatophenyl)azo]-4 -hydroxynaphthalene-1 -sulphonate, CAS No. 4548 -53 -2. The test system included control, test item and reference item. The concentration of read across chemical and reference item ( Sodium Benzoate) chosen for both the study was 30 mg/L, while that of inoculum was 10 ml/l. ThOD (Theoretical oxygen demand) of test and reference item was determined by calculation. % Degradation was calculated using the values of BOD and ThOD for read across chemical and reference item. The BOD28 value of disodium 3-[(2,4-dimethyl-5-sulphonatophenyl)azo]-4-hydroxynaphthalene-1-sulphonate was observed to be mgO2sup>/mg. ThOD was calculated as mgO2/mg. Accordingly, the % degradation of the test item after 28 days of incubation at 20 ± 1°C according to manometric respirometry test was determined to be 12.807 %.Based on the results, the read across, under the test conditions, was considered to be not readily biodegradable at 20± 1°C over a period of 28 days.

 

On the basis of all the studies mentioned above it is concluded that target chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulfonic acid (CAS no.70239-77-9) can be considered as not 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-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS no.70239 -77 -9) . If released in to the environment, 11.3 % of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of test chemical in water is estimated to be 37.5 days (360 hrs). The half-life (37.5days estimated by EPI suite) indicates that the chemical is not persistent in water and the exposure risk to aquatic animals is low whereas the half-life period of test chemical ) 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid in sediment is estimated to be 337.5 days (8100 hrs). However, as the percentage release of test chemical into the sediment is less than 2% (i.e, reported as 1.43 %), indicates that test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid is not persistent in sediment as well.

Biodegradation in soil:

The half-life period of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS no.70239 -77 -9) 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, 87.3 % of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid in soil is estimated to be 75 days (1800 hrs). Based on this half-life value of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid , it is concluded that the chemical is not persistent in the soil environment and the exposure risk to soil dwelling animals is low.

Bioaccumulation:

Bioaccumulation:aquatic/sediments:

Different predicted data studies have been conducted for target chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulfonic acid (CAS no.70239-77-9) and their results are summarized below.

 

The first weight of evidence study was done by using BCFBAF Program (v3.00) model of Estimation Program Interface (EPI suite 2017) the estimated bio concentration factor (BCF) for 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS No. 70239-77-9) is 3.162 L/kg wet-wt at 25 deg. c which does not exceed the bioconcentration threshold of 2000.

 

Another weight of evidence study was done by using Bio-concentration Factor (v12.1.0.50374) module of Advanced Chemistry Development/I-lab predictive module in this study Bio-concentration Factor at range pH 1-14  of the chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS no.70239 -77 -9) estimated to be 1.00 dimensionless.

 

Next weight of evidence study was done by using SciFinder Database of American Chemical Society (ACS, 2017) in this study the Bioconcentration factor (BCF) for test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS No: 70239-77-9) was predicted in aquatic organisms at pH 1-10 and temperature 25 °C .The Bioconcentration factor (BCF) of test substance 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid at pH 1-10 and temperature 25 °C was estimated to be 1.00 dimensionless.  

 

Last weight of study was done by using  Chemspider- ACD/PhysChem Suite of Royal Society of Chemistry (RCS, 2017) in this study the Bioconcentration factor (BCF) for test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS No: 70239-77-9) was predicted in aquatic organisms at pH 5.5 and pH 7.4.The Bioconcentration factor (BCF) of test substance  at pH 5.5 and pH 7.4 was estimated to be 1.00 dimensionless. 

 

On the basis of all the studies mentioned above it is concluded that BCF value of the test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid  falls in range of 1-3.162 dimensionless and this test chemical is considered as non bioaccumulative in aquatic organisms as BCF value does not exceeds 2000 criteria.

Transport and Distribution:

Adsorption/desorption:

One predicted data study of target chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS No. 70239-77-9) and two experimental studies of its structurally similar red across chemical are summarized below for Adsorption endpoint.

 

In predicted data study the Soil Adsorption Coefficient i.e. Koc value of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS No. 70239-77-9) was estimated using Estimation Program Interface (EPI suite, 2017) KOCWIN Program (v2.00) as 2231 L/kg (log Koc= 3.3484) by means of MCI method at 25 deg. C.

 

Next weight of evidence study was experimental study done for read across chemical from journal of J. Environ. Eng. Manage., 17(1), 29-38 (2007) in this study the adsorption of Acid Red 1 on organoclay is dominated by ion exchange process. The Freundlich and Langmuir adsorption isotherm constants of Acid Red 1 on organoclay are as follows: Acid Red 1 adsorption on organoclay the coefficients for fitting are 0.995 < rL2 < 0.997 and 0.573 < rF2 < 0.751. It can be seen that the Langmuir model yields a much better fit than the Freundlich model when the r2 values are compared. The affinity parameter, KL, and its reciprocal indicate that the adsorption capacity of Acid Red 1 on organoclay is highly perceptible to changes in temperature. The Q max values indicate that Acid Red 1 possesses higher adsorption capacity at lower temperature.

 

Last weight of evidence study was also experimental study done for another read across chemical disodium 5-amino-4-hydroxy-3-(phenylazo)naphthalene-2,7-disulphonate (CAS No. 3567-66-6) from UERL laboratory (2016) in this study the adsorption coefficient Koc in soil and in sewage sludge disodium 5-amino-4-hydroxy-3-(phenylazo)naphthalene-2,7-disulphonate (CAS No. 3567-66-6) was determined by the Reverse Phase High Performance Liquid Chromatographic method. The reference substances were chosen according to estimated Koc range of the test substance and generalized calibration graph was prepared. The reference substances were Phenol, Aniline, Nitrobenzene, naphthalene, Phenanthrene and DDT were chosen having Koc value ranging from 1.32 to 5.63. The Log Koc value of read across chemical disodium 5-amino-4-hydroxy-3-(phenylazo)naphthalene-2,7-disulphonate was determined to be 3.679 dimensionless at 25°C. Based on the value of log Koc it is concluded that this read across chemical has strong sorption to soil and sediments and therefore has slow migration potential to ground water.

On the basis of all the study mentioned above it is concluded that test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS No. 70239-77-9) has moderate to strong sorption to soil and sediment therefore it has slow migration potential to ground water.