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

Bioaccumulation: aquatic / sediment

Link to relevant study record(s)

Reference

Endpoint:

bioaccumulation in aquatic species, other

Remarks:

aquatic organisms

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 ACD/I-Labs Algorithm Version: v5.0.0.184

Qualifier:

according to guideline

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 test material: 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione
- Molecular formula: C34H34N2O4
- Molecular weight: 534.6526 g/mole
- Smiles notation: CCCCc1ccc(cc1)Nc2ccc(c3c2C(=O)c4c(ccc(c4C3=O)O)O)Nc5ccc(cc5)CCCC
-InChl: 1S/C34H34N2O4/c1-3-5-7-21-9-13-23(14-10-21)35-25-17-18-26(36-24-15-11-22(12-16-24)8-6-4-2)30-29(25)33(39)31-27(37)19-20-28(38)32(31)34(30)40/h9-20,35-38H,3-8H2,1-2H3
- Substance type: Organic

Radiolabelling:

not specified

Vehicle:

not specified

Test organisms (species):

other: aquatic organisms

Route of exposure:

aqueous

Test type:

not specified

Water / sediment media type:

natural water: freshwater

Reference substance (positive control):

not specified

Key result

Type:

BCF

Value:

> 1 000 000 dimensionless

Basis:

whole body w.w.

Calculation basis:

other: no data

Remarks on result:

other: BCF reported at pH range 0.0-6.0

Key result

pH:

7

Type:

BCF

Value:

4 146 662 dimensionless

Basis:

whole body w.w.

Calculation basis:

other: no data

Remarks on result:

other: log(BCF) = 6.6 ± 1.0

Key result

pH:

8

Type:

BCF

Value:

391 974 dimensionless

Basis:

whole body w.w.

Calculation basis:

other: no data

Remarks on result:

other: log(BCF) = 5.6 ± 1.0

Key result

pH:

9

Type:

BCF

Value:

11 176 dimensionless

Basis:

whole body w.w.

Calculation basis:

other: no data

Remarks on result:

other: log(BCF) = 4.0 ± 1.0

Key result

pH:

10

Type:

BCF

Value:

1 181 dimensionless

Basis:

whole body w.w.

Calculation basis:

other: no data

Remarks on result:

other: log(BCF) = 3.1 ± 1.0

Key result

pH:

11

Type:

BCF

Value:

955 dimensionless

Basis:

whole body w.w.

Calculation basis:

other: no data

Remarks on result:

other: log(BCF) = 3.0 ± 1.0

Key result

pH:

12

Type:

BCF

Value:

941 dimensionless

Basis:

whole body w.w.

Calculation basis:

other: no data

Remarks on result:

other: log(BCF) = 3.0 ± 1.0

Key result

Type:

BCF

Value:

940 dimensionless

Basis:

whole body w.w.

Calculation basis:

other: no data

Remarks on result:

other: log(BCF) = 3.0 ± 1.0, BCF reported at pH 13 and 14, respectively.

Validity criteria fulfilled:

not specified

Conclusions:

Using Bio-concentration Factor (v12.1.0.50374) module Bio-concentration Factor over the entire pH scale of the test substance 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydro anthracene-9,10-dione 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.

Executive summary:

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, respectively. 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.

Description of key information

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, respectively ACD (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.

Key value for chemical safety assessment

BCF (aquatic species):

4 146 662 dimensionless

Additional information

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.