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Environmental fate & pathways

Bioaccumulation: aquatic / sediment

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Reference
Endpoint:
bioaccumulation in aquatic species: fish
Type of information:
calculation (if not (Q)SAR)
Adequacy of study:
weight of evidence
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
accepted calculation method
Justification for type of information:
Data is from authoritative database.
Qualifier:
according to
Guideline:
other: Modelling database
Principles of method if other than guideline:
Prediction done using Bioconcentration factor (v12.1.0.50374).This particular module provides bioconcentration factor (BCF) values over the entire pH scale. Calculations are performed for both neutral and ionic species present at a given pH and utilize predicted values for LogP as well as pKa. The BCF and Koc values characterize the tendency for a compound to accumulate in aquatic organisms and soil respectively, putting these two values among the most important ones in the assessment of environmental fate of chemicals.
GLP compliance:
not specified
Specific details on test material used for the study:
- Name of the test material: N-(2-ethylhexyl)-1-[[2-methyl-4-[(4-methylphenyl)azo]phenyl]azo]naphthalen-2-amine
- Regulatory name: N-(2-ethylhexyl)-1-[[2-methyl-4-[(4-methylphenyl)azo]phenyl]azo]naphthalen-2-amine
- Molecular formula: C32H37N5
- Molecular weight: 491.6793 g/mol
- Smiles: CCCCC(CC)CNc1ccc2ccccc2c1/N=N/c3ccc(cc3C)/N=N/c4ccc(cc4)C
- InChI: 1S/C32H37N5/c1-5-7-10-25(6-2)22-33-31-19-15-26-11-8-9-12-29(26)32(31)37-36-30-20-18-28(21-24(30)4)35-34-27-16-13-23(3)14-17-27/h8-9,11-21,25,33H,5-7,10,22H2,1-4H3/b35-34+,37-36+
- Substance type: Organic
Physical form: Dark red clear liquid
Radiolabelling:
not specified
Vehicle:
not specified
Test organisms (species):
other: aquatic organisms
Route of exposure:
aqueous
Test type:
other: predicted
Water / sediment media type:
natural water: freshwater
Reference substance (positive control):
not specified
Key result
pH:
6
Type:
BCF
Value:
100 000 dimensionless
Basis:
whole body w.w.
Calculation basis:
steady state
Remarks on result:
other: at pH range 0-14
Key result
pH:
7
Type:
BCF
Value:
1 000 000 dimensionless
Basis:
whole body w.w.
Calculation basis:
other: no data
Remarks on result:
other: at pH range 0-14
Key result
pH:
8
Type:
BCF
Value:
1 000 000 dimensionless
Basis:
whole body w.w.
Calculation basis:
steady state
Remarks on result:
other: at pH range 0-14

Bioconcentration factor (BCF):

pH = 0.0 ; BCF = 130991 ; log(BCF) = 5.1 ± 1.0

pH = 1.0 ; BCF = 171995 ; log(BCF) = 5.2 ± 1.0

pH = 2.0 ; BCF = 577444 ; log(BCF) = 5.8 ± 1.0

pH = 3.0 ; BCF = 4219679 ; log(BCF) = 6.6 ± 1.0

pH = 4.0 ; BCF > 1000000.0

pH = 5.0 ; BCF > 1000000.0

pH = 6.0 ; BCF > 1000000.0

pH = 7.0 ; BCF > 1000000.0

pH = 8.0 ; BCF > 1000000.0

pH = 9.0 ; BCF > 1000000.0

pH = 10.0 ; BCF > 1000000.0

pH = 11.0 ; BCF > 1000000.0

pH = 12.0 ; BCF > 1000000.0

pH = 13.0 ; BCF > 1000000.0

pH = 14.0 ; BCF > 1000000.0

Validity criteria fulfilled:
not specified
Conclusions:
Using Bio-concentration Factor (v12.1.0.50374) module Bio-concentration Factor at range pH 1-14 of the chemical N-(2-ethylhexyl)-1-[[2-methyl-4-[ (4-methylphenyl) azo]phenyl]azo]naphthalen-2-amine estimated to be > 1000000.0 dimensionless.
Executive summary:

Using Bio-concentration Factor (v12.1.0.50374) module Bio-concentration Factor at range pH 1-14  of the chemical N-(2-ethylhexyl)-1-[[2-methyl-4-[ (4-methylphenyl) azo]phenyl]azo]naphthalen-2-amine (CAS no.93964 -07 -9) estimated to be > 1000000.0 dimensionless. This value indicates that the chemical N-(2-ethylhexyl)-1-[[2-methyl-4-[ (4-methylphenyl) azo]phenyl]azo]naphthalen-2-amine is very bioaccumulative in aquatic organisms as this value exceeded 2000 criteria.

Description of key information

Using Bio-concentration Factor (v12.1.0.50374) module Bio-concentration Factor at range pH 1-14  of the chemical N-(2-ethylhexyl)-1-[[2-methyl-4-[ (4-methylphenyl) azo]phenyl]azo]naphthalen-2-amine (CAS no.93964 -07 -9) estimated to be > 1000000.0 dimensionless. This value indicates that the chemical N-(2-ethylhexyl)-1-[[2-methyl-4-[ (4-methylphenyl) azo]phenyl]azo]naphthalen-2-amine is very bioaccumulative in aquatic organisms as this value exceeded 2000 criteria.

Key value for chemical safety assessment

BCF (aquatic species):
1 000 000 dimensionless

Additional information

Various predicted data for the target compound N-(2-ethylhexyl)-1-[[2-methyl-4-[(4-methylphenyl)azo]phenyl]azo]naphthalen-2-amine (CAS No. 93964-07-9) and supporting weight of evidence studies for its read across substance were reviewed for the bioaccumulation end point and their results are summarized as below:

 

Bioaccumulation potential of the test material was estimated using ACD (Advanced Chemistry Development)/I-Lab; Algorithm Version: v5.0.0.184

Using Bio-concentration Factor (v12.1.0.50374) module Bio-concentration Factor at range pH 1-14  of the chemical N-(2-ethylhexyl)-1-[[2-methyl-4-[ (4-methylphenyl) azo]phenyl]azo]naphthalen-2-amine (CAS no.93964 -07 -9) estimated to be > 1000000.0 dimensionless. This value indicates that the chemical N-(2-ethylhexyl)-1-[[2-methyl-4-[ (4-methylphenyl) azo]phenyl]azo]naphthalen-2-amine is very bioaccumulative in aquatic organisms as this value exceeded 2000 criteria.

 

The above prediction was further supported by another predicted data estimated by SciFinder, American Chemical Society (ACS); 2017

The Bioconcentration factor (BCF) for test chemical N-(2-ethylhexyl)-1-[[2-methyl-4-[(4-methylphenyl)azo]phenyl]azo]naphthalen-2-amine (CAS No: 93964-07-9) was predicted in aquatic organisms by Scifinder database at pH 1-10 and temperature 25 °C .The Bioconcentration factor (BCF) of test substance  N-(2-ethylhexyl)-1-[[2-methyl-4-[(4-methylphenyl)azo]phenyl]azo]naphthalen-2-amine at pH 1-10 and temperature 25 °C was estimated to be 1.00E6 dimensionless.  This BCF value at pH 1-10 and temperature 25 °C suggests that the test chemical N-(2-ethylhexyl)-1-[[2-methyl-4-[(4-methylphenyl)azo]phenyl]azo]naphthalen-2-amine is very bioaccumulative in aquatic organisms.

 

Another predicted data was estimated using ChemSpider- Free chemical Database, Royal Society of Chemistry, 2017) was used for predicting the bioconcentration factor (BCF) of test chemical N-(2-ethylhexyl)-1-[[2-methyl-4-[(4-methylphenyl)azo]phenyl]azo]naphthalen-2-amine.

The Bioconcentration factor (BCF) for test chemical N-(2-ethylhexyl)-1-[[2-methyl-4-[(4-methylphenyl)azo]phenyl]azo]naphthalen-2-amine (CAS No: 93964-07-8) was predicted in aquatic organisms by Chemspider- ACD/PhysChem Suite at pH 5.5 and pH 7.4.The Bioconcentration factor (BCF) of test substance N-(2-ethylhexyl)-1-[[2-methyl-4-[(4-methylphenyl)azo]phenyl]azo]naphthalen-2-amine at pH 5.5 and pH 7.4 was estimated to be 1000000.00 dimensionless. This BCF value suggests that the test chemical N-(2-ethylhexyl)-1-[[2-methyl-4-[(4-methylphenyl)azo]phenyl]azo]naphthalen-2-amine is very bioaccumulative in aquatic organisms.

 

The above prediction was further supported by experimental data summarized in HSDB (Hazardous Substances Data Bank); US national Library of Medicine reviewed by SRC, 2017 in this study the BCF of test chemical in aquatic organisms was reported as 290000 using a measured log Kow of 7.5 and a recommended regression-derived equation. This BCF value indicates that bioconcentration in aquatic organisms will be an important fate process.

On the basis of above results for target chemical N-(2-ethylhexyl)-1-[[2-methyl-4-[(4-methylphenyl)azo]phenyl]azo]naphthalen-2-amine(from ACD labs, ChemSpider, SciFinder database and CompTox Chemistry Dashboard,  2017) and for its read across substance (from authoritative database HSDB), it can be concluded that the BCF value of test substance N-(2-ethylhexyl)-1-[[2-methyl-4-[(4-methylphenyl)azo]phenyl]azo]naphthalen-2-amine ranges from 1000000.00 - 290000 which exceeds the bioconcentration threshold of 2000, indicating that the chemical N-(2-ethylhexyl)-1-[[2-methyl-4-[(4-methylphenyl)azo]phenyl]azo]naphthalen-2-amine is expected to be very bioaccumulate in the food chain.