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

Adsorption / desorption

Link to relevant study record(s)

Reference

Endpoint:

adsorption / desorption

Remarks:

adsorption

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:

Estimated data generated using the EPI Suite model developed by the USEPA.

Qualifier:

according to guideline

Guideline:

other: Modeling database

Principles of method if other than guideline:

Prediction done using KOCWIN Program (v2.00)

GLP compliance:

not specified

Type of method:

other: MCI Method

Media:

soil

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

Test temperature:

25 deg.C

Analytical monitoring:

not specified

Key result

Type:

Koc

Value:

329 700 000 L/kg

Temp.:

25 °C

Remarks on result:

other: log Koc = 8.5181 (estimated by MCI method)

Transformation products:

not specified

KOCWIN Program (v2.00) Results:

==============================

SMILES : O=C(c(c(c(Nc(ccc(c1)CCCC)c1)cc2)C(=O)c3c(O)ccc4O)c2Nc(ccc(c5)CCCC)c5)

c34

CHEM : 9,10-Anthracenedione, 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-

MOL FOR: C34 H34 N2 O4

MOL WT : 534.66

--------------------------- KOCWIN v2.00 Results ---------------------------

Koc Estimate from MCI:

---------------------

First Order Molecular Connectivity Index ........... : 19.405

Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 10.7158

Fragment Correction(s):

2 Nitrogen to non-fused aromatic ring ... : -1.0450

2 Ketone (-C-CO-C-) ................... : -2.2581

* Quinone (diketone) ring ............... : 1.2986

2 Aromatic Hydroxy (aromatic-OH) ....... : -0.1932

Corrected Log Koc .................................. : 8.5181

Estimated Koc: 3.297e+008 L/kg <===========

Validity criteria fulfilled:

not specified

Conclusions:

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.

Executive summary:

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.

Description of key information

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.

Key value for chemical safety assessment

Koc at 20 °C:

329 700 000

Additional information

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.

[LogKoc: 8.5181]