1,4-bis[(2-methylphenyl)amino]anthraquinone

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[(2-methylphenyl)amino]anthraquinone
- Molecular formula : C28H22N2O2
- Molecular weight : 418.494 g/mol
- Smiles notation : c1cc2C(=O)c3c(C(=O)c2cc1)c(Nc1ccccc1C)ccc3Nc1c(cccc1)C
- InChl : 1S/C28H22N2O2/c1-17-9-3-7-13-21(17)29-23-15-16-24(30-22-14-8-4-10-18(22)2)26-25(23)27(31)19-11-5-6-12-20(19)28(26)32/h3-16,29-30H,1-2H3
- Substance type : Organic
- Physical state : Solid

Radiolabelling:

not specified

Test temperature:

25 deg.C

Analytical monitoring:

not specified

Key result

Type:

Koc

Value:

4 979 000 L/kg

Temp.:

25 °C

Remarks on result:

other: Log Koc= 6.6972 (estimated by MCI method)

Transformation products:

not specified

KOCWIN Program (v2.00) Results:

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

SMILES : O=C(c(c(C(=O)c1c(Nc(c(ccc2)C)c2)ccc3Nc(c(ccc4)C)c4)ccc5)c5)c13

CHEM : 9,10-Anthracenedione, 1,4-bis (2-methylphenyl)amino -

MOL FOR: C28 H22 N2 O2

MOL WT : 418.50

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

Koc Estimate from MCI:

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

First Order Molecular Connectivity Index ........... : 15.542

Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 8.7017

Fragment Correction(s):

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

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

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

Corrected Log Koc .................................. : 6.6972

Estimated Koc: 4.979e+006 L/kg <===========

Validity criteria fulfilled:

not specified

Conclusions:

The soil adsorption coefficient i.e Koc value of 1,4-bis[(2-methylphenyl)amino]anthraquinone was estimated to be 4979000 L/kg (log Koc=6.6972) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 1,4-bis[(2-methylphenyl)amino]anthraquinone 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[(2 -methylphenyl)amino] anthraquinone (CAS No. 6737 -68 -4). The soil adsorption coefficient i.e Koc value of 1,4-bis[(2-methylphenyl)amino]anthraquinone was estimated to be 4979000 L/kg (log Koc=6.6972) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 1,4-bis[(2-methylphenyl)amino]anthraquinone 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[(2 -methylphenyl)amino] anthraquinone (CAS No. 6737 -68 -4). The soil adsorption coefficient i.e Koc value of 1,4-bis[(2-methylphenyl)amino]anthraquinone was estimated to be 4979000 L/kg (log Koc=6.6972) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 1,4-bis[(2-methylphenyl)amino]anthraquinone 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:

4 979 000

Additional information

Various predicted data for the target compound 1,4-bis[(2-methylphenyl)amino]anthraquinone (CAS No. 6737-68-4) and supporting weight of evidence study for its structurally similar 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[(2 -methylphenyl)amino] anthraquinone (CAS No. 6737 -68 -4). The soil adsorption coefficient i.e Koc value of 1,4-bis[(2-methylphenyl)amino]anthraquinone was estimated to be 4979000 L/kg (log Koc=6.6972) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 1,4-bis[(2-methylphenyl)amino]anthraquinone has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.

 

The Soil Adsorption Coefficient i.e Koc value of test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone (CAS no. 6737 -68 -4) was estimated using Adsorption Coefficient module (v12.1.0.50374) program as Koc 17087, 20360, 20758, 20798, 20802 and 20803 at pH range 0, 1, 2, 3, 4 and 5-14, respectively (log Koc ranges from 4.2 ± 1.0 to 4.3 ± 1.0)(ACD (Advanced Chemistry Development)/I-Lab predictive module, 2017). This Koc value indicates that the test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone has a strong sorption to soil and therefore have negligible to slow migration potential to groundwater.

 

In an another prediction done by using ChemSpider Database (2017),the Soil Adsorption Coefficient i.e Koc value of test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone (CAS no. 6737 -68 -4) was estimated. The adsorption coefficient (Koc) value of test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone was estimated to be 19034.94 (Log Koc = 4.279) at pH 5.5 and 19036.30 (Log Koc = 4.279) at 7.4, respectively. This Koc value indicates that the test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone has a strong sorption to soil and therefore have negligible to slow migration potential to groundwater.

 

Additional soil adsorption coefficient i.e Koc value of test chemical1,4 -bis[(2 -methylphenyl)amino] anthraquinone (CAS No. 6737 -68 -4)was estimated using the SciFinder database (American Chemical Society (ACS), 2017).The soil adsorption coefficient i.e Koc value of 1,4 -bis[(2 -methylphenyl)amino]anthraquinone was estimated to be 147000, 150000 and 151000 at pH range 1, 2 and 3-10, respectively (log Koc ranges from 5.167 to 5.178) (at 25 deg C). This Koc value indicates that the substance 1,4-bis[(2-methylphenyl)amino]anthraquinone has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.

 

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[(2-methylphenyl)amino]anthraquinone was estimated to be 69000 L/kg (log Koc = 4.838).The predicted KOC result based on the 5 OECD principles. This Koc value indicates that the substance 1,4 -bis[(2 -methylphenyl)amino]anthraquinone 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(p-tolylamino)anthraquinone (CAS no. 128-80-3), adsorption experiment was conducted for estimating the adsorption coefficient (Koc) value of read across chemical 1,4-Bis(p-tolylamino)anthraquinone. The adsorption coefficient (Koc) value was calculated using a structure estimation method based on molecular connectivity indices. The adsorption coefficient (Koc) value of test substance 1,4 -Bis(p-tolylamino)anthraquinone was estimated to be 4800000 (Log Koc = 6.681). This Koc value indicates that the substance 1,4 -Bis(p-tolylamino)anthraquinone has a very strong sorption tosoil and sediment and therefore have negligible migration potential to ground water.

 

For the read across chemical 1-N,4-N-diphenylbenzene-1,4-diamine (CAS no. 74-31-7), adsorption study was conducted for estimating the adsorption coefficient (Koc) value of read across chemical 1-N,4-N-diphenylbenzene-1,4-diamine (HSDB, 2017). 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 -N,4 -N-diphenyl benzene-1,4 -diaminewas estimated to be 130000 (Log Koc = 5.113). This Koc value indicates that the substance 1 -N,4 -N-diphenylbenzene-1,4 -diamine has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.

 

On the basis of above overall results for target chemical 1,4-bis[(2-methylphenyl)amino]anthraquinone (from EPI suite, ACD labs,ChemSpider, Scifinder 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[(2-methylphenyl)amino]anthraquinone ranges from 19036.30–4979000, indicating that the test chemical 1,4 -bis[(2 -methylphenyl)amino]anthraquinone has a strong to very strong sorption to soil and sediment and therefore have negligible to slow migration potential to ground water.

[LogKoc: 6.6972]