6-aminonaphthalene-1,3-disulphonic acid

Endpoint summary

Description of key information

Biodegradation in water

Biodegradation study was conducted for 9 days for evaluating the percentage biodegradability of test substance 6 -aminonaphthalene-1,3 -disulfonic acid

(J. Ruff et.al, 1999). Test chemical 6 -aminonaphthalene-1,3 -disulfonic acid was purchased from TCI (Tokyo) at the highest purity available.Glassware was cleaned thoroughly and care taken to exclude extraneous sulfur.Pseudomonas putidastrain S-313 was used as a test inoculum obtained from activated sludge from sewage treatment plants in Konstanz, Germany (largely communal) and Ludwigshafen, Germany (largely industrial).Initial experiments were done with the phosphate-buffered medium. The sulfur-free acetate-Tris-buffered salts medium gave the same products with negligible background growth, and thus used as a standard medium.Sulfur was provided at 50µM, except for disulfonates, where the initial sulfonate concentration was 30µM.Cultures were grown in screw-capped tubes on a roller at 30°C.Samples were taken at 3-day intervals for 9 days. Bacteria were removed by centrifugation and the protein content measured, and 100µl portions of the supernatant fluid were examined by HPLC. Substrates and products were determined by isocratic reversed-phase high-pressure liquid chromatography (HPLC) or by ion-pair chromatography. The apparatus included a diode array detector. Chromatograms were initially evaluated with wavelength settings of 245 nm for the amino-naphthalenedisulfonates. Protein was assayed by a Lowry-type method.The percentage degradation of test chemical 6 -aminonaphthalene-1,3 -disulfonic acid was determined to be 0% by usingPseudomonas putidastrain S-313 as an inoculum. Thus, based on percentage degradation, chemical 6 -aminonaphthalene-1,3 -disulfonic acid can be considered 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 6-aminonaphthalene-1,3-disulfonic acid (CAS No. 118 -33 -2). If released in to the environment, 11.7% of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of 6-aminonaphthalene-1,3-disulfonic acid 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 6-aminonaphthalene-1,3-disulfonic acid in sediment is estimated to be 337.5 days (8100 hrs). However, as the percentage release of 6-aminonaphthalene-1,3-disulfonic acid into the sediment is less than 1% (i.e, reported as 0.775%), indicates that 6-aminonaphthalene-1,3-disulfonic acid is not persistent in sediment.

Biodegradation in soil

The half-life period of 6-aminonaphthalene-1,3-disulfonic acid (CAS No. 118 -03 -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, 87.6% of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of 6-aminonaphthalene-1,3-disulfonic acid in soil is estimated to be 75 days (1800 hrs). Based on this half-life value of 6-aminonaphthalene-1,3-disulfonic acid, 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 6 -aminonaphthalene-1,3 -disulfonic acid (CAS No. 118 -33 -2). The bioconcentration factor (BCF) of 6 -aminonaphthalene-1,3 -disulfonic acid was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which does not exceed the bioconcentration threshold of 2000, indicating that the chemical  6-aminonaphthalene-1,3-disulfonic acid is not expected to bioaccumulate in the food chain.

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 6-aminonaphthalene- 1,3 -disulfonic acid (CAS No. 118 -33 -2). The soil adsorption coefficient i.e Koc value of 6-aminonaphthalene-1,3-disulfonic acid was estimated to be 1192 L/kg (log Koc=3.0764) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 6-aminonaphthalene-1,3-disulfonic acid has a moderate sorption to soil and sediment and therefore have slow migration potential to ground water

Additional information

Biodegradation in water

Various experimental key and supporting studies for the target compound 6 -aminonaphthalene-1,3 -disulfonic acid (CAS No. 118 -33 -2) and supporting study for its read across substance were reviewed for the biodegradation end point which are summarized as below:

 

In an experimental key study from peer reviewed journal (J. Ruff et.al, 1999), biodegradation experiment was conducted for 9 days for evaluating the percentage biodegradability of test substance 6 -aminonaphthalene-1,3 -disulfonic acid (CAS no. 118-33-2). Test chemical 6 -aminonaphthalene-1,3 -disulfonic acid was purchased from TCI (Tokyo) at the highest purity available.Glassware was cleaned thoroughly and care taken to exclude extraneous sulfur. Pseudomonas putida strain S-313 was used as a test inoculum obtained from activated sludge from sewage treatment plants in Konstanz, Germany (largely communal) and Ludwigshafen, Germany (largely industrial).Initial experiments were done with the phosphate-buffered medium. The sulfur-free acetate-Tris-buffered salts medium gave the same products with negligible background growth, and thus used as a standard medium.Sulfur was provided at 50µM, except for disulfonates, where the initial sulfonate concentration was 30µM.Cultures were grown in screw-capped tubes on a roller at 30°C.Samples were taken at 3-day intervals for 9 days. Bacteria were removed by centrifugation and the protein content measured, and 100µl portions of the supernatant fluid were examined by HPLC. Substrates and products were determined by isocratic reversed-phase high-pressure liquid chromatography (HPLC) or by ion-pair chromatography. The apparatus included a diode array detector. Chromatograms were initially evaluated with wavelength settings of 245 nm for the amino-naphthalenedisulfonates. Protein was assayed by a Lowry-type method.The percentage degradation of test chemical 6 -aminonaphthalene-1,3 -disulfonic acid was determined to be 0% by using Pseudomonas putida strain S-313 as an inoculum. Thus, based on percentage degradation, chemical 6 -aminonaphthalene-1,3 -disulfonic acid can be considered to be not readily biodegradable in nature.

 

In an supporting study from peer reviewed journal (GREIM H. et. al, 1994) and secondary source, biodegradation experiment was conducted for 30 days under aerobic conditions for evaluating the percentage biodegradability of test substance 6 -aminonaphthalene-1,3 -disulfonic acid (CAS no. 118 -33 -2). The study was performed according to OECD Guideline 301 D "Ready Biodegradability: Closed Bottle Test". Initial test substance conc. used in the study were 3, 10 and 30 mg/l, respectively. The percentage degradation of test substance 6 -aminonaphthalene-1,3 -disulfonic acid was determined to be 0% by BOD parameter in 30 days. Thus, based on percentage degradation, 6 -aminonaphthalene-1,3 -disulfonic acid is considered to be not readily biodegradable in nature.

 

Another biodegradability of test substance 6-aminonaphthalene-1,3-disulfonic acid was estimated using the BIODEG linear and non-linear model (E. Rorije et. al, 1997). The models have been applied are Quantitative Structure-Activity Relationships. Two models are fitted to the judgement of an evaluation of various different biodegradation rates of chemical. This include the one using linear regression and other using a form of non-linear fitting. These models used 36 fragments as descriptors with the molecular weight of the molecule as an added descriptor, and are fitted on the evaluated biodegradation data of a series of 295 compounds. The output of the models, x, is the number that should be interpreted as x < 0.5 (=0) (Chemical biodegrades slowly or not at all) or x > 0.5 (=1) (Chemical biodegrades fast), respectively. These tests typically produce ‘biodegradable’ (1) or ‘non-biodegradable’ (0) as a result. The application of the models has been automated, the BIODEG models are incorporated in the PC-based program. As the biodegradability prediction of chemical 6-aminonaphthalene-1,3-disulfonic acid by the BIODEG models comes out to be 0, test chemical 6-aminonaphthalene-1,3-disulfonic acid is estimated to be not readily biodegradable in nature.

 

For the read across chemical 2-aminonaphthalene-1,5-disulfonic acid (CAS no. 117-62-4), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance 2-aminonaphthalene-1,5-disulfonic acid (CAS no. 117-62-4). 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 -aminonaphthalene-1,5 -disulfonic acid was determined to be 1, 5 and 0% by BOD, TOC removal and HPLC parameter in 28 days. Thus, based on percentage degradation, 2 -aminonaphthalene-1,5 -disulfonic acid is considered to be not readily biodegradable in nature.

On the basis of above results for target chemical 6-aminonaphthalene-1,3-disulfonic acid (from peer reviewed journal and secondary source) and for its read across substance (from authoritative database J-CHECK), it can be concluded that the test substance 6 -aminonaphthalene-1,3 -disulfonic acid 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 6-aminonaphthalene-1,3-disulfonic acid (CAS No. 118 -33 -2). If released in to the environment, 11.7% of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of 6-aminonaphthalene-1,3-disulfonic acid 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 6-aminonaphthalene-1,3-disulfonic acid in sediment is estimated to be 337.5 days (8100 hrs). However, as the percentage release of 6-aminonaphthalene-1,3-disulfonic acid into the sediment is less than 1% (i.e, reported as 0.775%), indicates that 6-aminonaphthalene-1,3-disulfonic acid is not persistent in sediment.

Biodegradation in soil

The half-life period of 6-aminonaphthalene-1,3-disulfonic acid (CAS No. 118 -03 -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, 87.6% of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of 6-aminonaphthalene-1,3-disulfonic acid in soil is estimated to be 75 days (1800 hrs). Based on this half-life value of 6-aminonaphthalene-1,3-disulfonic acid, 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 6 -aminonaphthalene-1,3 -disulfonic acid can be considered to be not readily biodegradable in nature.

Bioaccumulation: aquatic/sediment

Various predicted data for the target compound 6-aminonaphthalene-1,3-disulfonic acid (CAS No. 118-33-2) and supporting weight of evidence study for its read across substance were reviewed for the bioaccumulation end point which are summarized as below:

 

In a prediction done using the BCFBAF Model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 6 -aminonaphthalene-1,3 -disulfonic acid (CAS No. 118 -33 -2). The bioconcentration factor (BCF) of 6 -aminonaphthalene-1,3 -disulfonic acid was estimated to be 3.162 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 0 -14) of the test substance 6-aminonaphthalene-1,3-disulfonic acid (CAS no. 118 -33 -2) was estimated to be 1.

 

Bioconcentration Factor (BCF) of test chemical 6-aminonaphthalene-1,3-disulfonic acid (CAS no. 118 -33 -2) was estimated using Chemspider database(ChemSpider, 2017). The bioconcentration factor of test substance 6-aminonaphthalene-1,3-disulfonic acid was estimated to be 1 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 6-aminonaphthalene-1,3-disulfonic acid (CAS No. 118 -33 -2). The bioconcentration factor (BCF) of 6-aminonaphthalene-1,3-disulfonic acid was estimated to be 1 (at 25 deg C).

 

From CompTox Chemistry Dashboard using OPERA (OPEn (qauantitative) 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 6-aminonaphthalene-1,3-disulfonic acid was estimated to be 2.46 dimensionless . The predicted BCF result based on the 5 OECD principles. Thus based on the result it is concluded that the test substance 6-aminonaphthalene-1,3-disulfonic acid is non-bioaccumulative in nature.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017) for the read across chemical 2-aminonaphthalene-1-sulfonic acid (CAS no. 81-16-3), bioaccumulation experiment was conducted on test organism Cyprinus carpio for 8 weeks for evaluating the bioconcentration factor (BCF value) of substance 2 -aminonaphthalene-1 -sulfonic acid (CAS no. 81 -16 -3) under static conditions. Test chemical nominal conc. used for the study were 5 mg/l and 0.5 mg/l (w/v), respectively. Range finding study involve the TLm (48 hr) 610 mg/l on Rice fish (Oryzias latipes). The bioconcentration factor (BCF value) of substance 2 -aminonaphthalene-1 -sulfonic acid on Cyprinus carpio was determined to be < 0.6 L/Kg at a conc. of 5 mg/l and < 6 L/Kg at a conc. of 0.5 mg/l, respectively, which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 2 -aminonaphthalene-1 -sulfonic acid is not expected to bioaccumulate in the food chain.

 

On the basis of above results for target chemical 6 -aminonaphthalene-1,3 -disulfonic acid (from EPI suite, ACD labs,ChemSpider, SciFinder database and CompTox Chemistry Dashboard,  2017) and for its read across substance (from authoritative database J-CHECK, 2017), it can be concluded that the BCF value of test substance 6 -aminonaphthalene-1,3 -disulfonic acid ranges from 1 – 3.162 which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 6 -aminonaphthalene-1,3 -disulfonic acid is not expected to bioaccumulate in the food chain.

Adsorption/desorption

Various predicted data for the target compound 6-aminonaphthalene-1,3-disulfonic acid (CAS No. 118-33-2) were reviewed for the adsorption end point which are summarized as below:

 

In a prediction done using theKOCWIN Program(v2.00) of Estimation Programs Interface (EPI Suite, 2017) the soil adsorption coefficient i.e Koc value of 6-aminonaphthalene-1,3-disulfonic acid was estimated to be 1192 L/kg (log Koc=3.0764) by means of MCI method (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 6-aminonaphthalene-1,3-disulfonic acid (CAS no. 118 -33 -2) was estimated to be 304 L/kg (log Koc = 2.482).The predicted KOC result based on the 5 OECD principles.

 

On the basis of above overall results for target chemical 6-aminonaphthalene-1,3-disulfonic acid(from EPI suiteand CompTox Chemistry Dashboard,2017), it can be concluded that the Koc value of test substance6-aminonaphthalene-1,3-disulfonic acid ranges from 304 –1192indicating that the test chemical 6-aminonaphthalene-1,3-disulfonic acidhas a moderate sorption to soil and sediment and therefore have slow migration potential to ground water.