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Reference
Endpoint:
adsorption / desorption, other
Type of information:
(Q)SAR
Adequacy of study:
key study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
results derived from a valid (Q)SAR model and falling into its applicability domain, with adequate and reliable documentation / justification
Justification for type of information:
QSAR prediction from a well-known and acknowledged tool. See below under ''attached background material section' for methodology and QPRF.
Qualifier:
according to guideline
Guideline:
other: REACH guidance on QSARs: Chapter R.6. QSARs and grouping of chemicals
Principles of method if other than guideline:
The Bioconcentration factor (BCF) value was calculated for the test subsatnce using BCFBAF v3.02 program of EPI Suite v 4.11. Since the test substance is an UVCB, the BCF values were estimated for individual constituents using SMILES codes as the input parameter.
Key result
Phase system:
other: Estimated
Value:
1 519.1 L/kg
Remarks on result:
other: MCI based method (Log Koc: 3.18)
Key result
Phase system:
other: Estimated
Value:
1 161.1 L/kg
Remarks on result:
other: Kow based method (Log Kow: 3.06)

Predicted value

The estimated Koc values for the different constituents using MCI and log Kow methods were as follows:

Table 1: KOC predictions: MCI method

Constituents/Carbon chain length*

Mean/adjusted conc

Mole fraction Xi = (mi/Mi)/∑ (mi/Mi)

Log Koc

(MCI)

Koc (L/kg)
MCI

Koc x Xi
(MCI)

MCI

C8

1.5

0.02095072

1.329804522

21.37

0.447716883

MW (ID),

Structural fragment (ID)

C10

1.5

0.018220725

1.851135995

70.98

1.293307026

MW (ID),

Structural fragment (ID)

C12

52.5

0.564229338

2.372359583

235.7

132.9888549

MW (ID),

Structural fragment (ID)

C14

20

0.192725527

2.893706293

782.9

150.8848148

MW (ID),

Structural fragment (ID)

C16

10

0.087337803

3.414973348

2600

227.0782887

MW (ID),

Structural fragment (ID)

C18

1.5

0.011978419

3.936312634

8636

103.4456235

MW (ID),

Structural fragment (ID)

C18'

11

0.088386801

3.936312634

8636

763.3084165

MW (ID),

Structural fragment (ID)

C18''

2

0.016170668

3.936312634

8636

139.6498864

MW (ID),

Structural fragment (ID)

 

 

 

 

Koc=

1519.10

 

 

 

 

 

Log Koc=

3.18158548

 

* Glycerol or MEA residues have not been considered for QSAR predictions

Table 2: KOC predictions: Log Kow-based method

Constituents/Carbon chain length*

Mean/adjusted conc

Mole fraction Xi = (mi/Mi)/∑ (mi/Mi)

Log Koc (log Kow)

Koc (L/kg)
Log Kow

Koc x Xi
(Log Kow)

Log Kow

C8

1.5

0.02095072

1.196176185

15.71

0.329135809

MW (ID), log Kow (ID)

Structural fragment (ID)

C10

1.5

0.018220725

1.738146089

54.72

0.997038045

MW (ID), log Kow (ID)

Structural fragment (ID)

C12

52.5

0.564229338

2.280122896

190.6

107.5421118

MW (ID), log Kow (ID)

Structural fragment (ID)

C14

20

0.192725527

2.822298871

664.2

128.0082948

MW (ID), log Kow (ID)

Structural fragment (ID)

C16

10

0.087337803

3.369957607

2344

204.7198111

MW (ID), log Kow (ID)

Structural fragment (ID)

C18

1.5

0.011978419

3.911956189

8165

97.80378834

MW (ID), log Kow (ID)

Structural fragment (ID)

C18'

11

0.088386801

3.790285164

6170

545.3465644

MW (ID), log Kow (ID)

Structural fragment (ID)

C18''

2

0.016170668

3.674125983

4722

76.35789298

MW (ID), log Kow (ID)

Structural fragment (ID)

 

 

 

 

Koc=

1161.10

 

 

 

 

 

Log Koc=

3.06487136

 

* Glycerol or MEA residues have not been considered for QSAR predictions

Koc prediction results:

SMILES : CCCCCCCC(=O)NCCO

CHEM  : C8

MOL FOR: C10 H21 N1 O2

MOL WT : 187.28

--------------------------- KOCWIN v2.01 Results ---------------------------

 

 Koc Estimate from MCI:

 ---------------------

        First Order Molecular Connectivity Index ........... : 6.308

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 3.8882

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -1.0277

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.2127

                 1  Aliphatic Alcohol (-C-OH) ........... : -1.3179

        Corrected Log Koc .................................. : 1.3298

 

                        Estimated Koc: 21.37 L/kg  <===========

 

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow (Kowwin estimate) ......................... : 1.28

        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 1.6331

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -0.0038

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.0218

                 1  Aliphatic Alcohol (-C-OH) ........... : -0.4114

        Corrected Log Koc .................................. : 1.1961

 

                        Estimated Koc: 15.71 L/kg  <===========

 

 

SMILES : CCCCCCCCCC(=O)NCCO

CHEM  : C10

MOL FOR: C12 H25 N1 O2

MOL WT : 215.34

--------------------------- KOCWIN v2.01 Results ---------------------------

 

 Koc Estimate from MCI:

 ---------------------

        First Order Molecular Connectivity Index ........... : 7.308

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 4.4095

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -1.0277

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.2127

                 1  Aliphatic Alcohol (-C-OH) ........... : -1.3179

        Corrected Log Koc .................................. : 1.8511

 

                        Estimated Koc: 70.98 L/kg  <===========

 

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow (Kowwin estimate) ......................... : 2.26

        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 2.1752

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -0.0038

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.0218

                 1  Aliphatic Alcohol (-C-OH) ........... : -0.4114

        Corrected Log Koc .................................. : 1.7382

 

                        Estimated Koc: 54.72 L/kg  <===========

 

 

SMILES : CCCCCCCCCCCC(=O)NCCO

CHEM  : C12

MOL FOR: C14 H29 N1 O2

MOL WT : 243.39

--------------------------- KOCWIN v2.01 Results ---------------------------

 

 Koc Estimate from MCI:

 ---------------------

        First Order Molecular Connectivity Index ........... : 8.308

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 4.9308

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -1.0277

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.2127

                 1  Aliphatic Alcohol (-C-OH) ........... : -1.3179

        Corrected Log Koc .................................. : 2.3724

 

                        Estimated Koc: 235.7 L/kg  <===========

 

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow (Kowwin estimate) ......................... : 3.24

        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 2.7172

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -0.0038

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.0218

                 1  Aliphatic Alcohol (-C-OH) ........... : -0.4114

        Corrected Log Koc .................................. : 2.2802

 

                        Estimated Koc: 190.6 L/kg  <===========

 

 

SMILES : CCCCCCCCCCCCCC(=O)NCCO

CHEM  : C14

MOL FOR: C16 H33 N1 O2

MOL WT : 271.45

--------------------------- KOCWIN v2.01 Results ---------------------------

 

 Koc Estimate from MCI:

 ---------------------

        First Order Molecular Connectivity Index ........... : 9.308

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 5.4521

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -1.0277

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.2127

                 1  Aliphatic Alcohol (-C-OH) ........... : -1.3179

        Corrected Log Koc .................................. : 2.8937

 

                        Estimated Koc: 782.9 L/kg  <===========

 

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow (Kowwin estimate) ......................... : 4.22

        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 3.2593

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -0.0038

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.0218

                 1  Aliphatic Alcohol (-C-OH) ........... : -0.4114

        Corrected Log Koc .................................. : 2.8223

 

                        Estimated Koc: 664.2 L/kg  <===========

 

 

SMILES : CCCCCCCCCCCCCCCC(=O)NCCO

CHEM  : C16

MOL FOR: C18 H37 N1 O2

MOL WT : 299.50

--------------------------- KOCWIN v2.01 Results ---------------------------

 

 Koc Estimate from MCI:

 ---------------------

        First Order Molecular Connectivity Index ........... : 10.308

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 5.9734

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -1.0277

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.2127

                 1  Aliphatic Alcohol (-C-OH) ........... : -1.3179

        Corrected Log Koc .................................. : 3.4150

 

                        Estimated Koc: 2600 L/kg  <===========

 

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow (Kowwin estimate) ......................... : 5.21

        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 3.8069

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -0.0038

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.0218

                 1  Aliphatic Alcohol (-C-OH) ........... : -0.4114

        Corrected Log Koc .................................. : 3.3699

 

                        Estimated Koc: 2344 L/kg  <===========

 

 

SMILES : CCCCCCCCCCCCCCCCCC(=O)NCCO

CHEM  : C18

MOL FOR: C20 H41 N1 O2

MOL WT : 327.56

--------------------------- KOCWIN v2.01 Results ---------------------------

 

 Koc Estimate from MCI:

 ---------------------

        First Order Molecular Connectivity Index ........... : 11.308

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 6.4947

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -1.0277

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.2127

                 1  Aliphatic Alcohol (-C-OH) ........... : -1.3179

        Corrected Log Koc .................................. : 3.9363

 

                        Estimated Koc: 8636 L/kg  <===========

 

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow (Kowwin estimate) ......................... : 6.19

        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 4.3490

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -0.0038

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.0218

                 1  Aliphatic Alcohol (-C-OH) ........... : -0.4114

        Corrected Log Koc .................................. : 3.9120

 

                        Estimated Koc: 8165 L/kg  <===========

 

 

SMILES : CCCCCCCCC=CCCCCCCCC(=O)NCCO

CHEM  : C18'

MOL FOR: C20 H39 N1 O2

MOL WT : 325.54

--------------------------- KOCWIN v2.01 Results ---------------------------

 

 Koc Estimate from MCI:

 ---------------------

        First Order Molecular Connectivity Index ........... : 11.308

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 6.4947

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -1.0277

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.2127

                 1  Aliphatic Alcohol (-C-OH) ........... : -1.3179

        Corrected Log Koc .................................. : 3.9363

 

                        Estimated Koc: 8636 L/kg  <===========

 

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow (Kowwin estimate) ......................... : 5.97

        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 4.2273

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -0.0038

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.0218

                 1  Aliphatic Alcohol (-C-OH) ........... : -0.4114

        Corrected Log Koc .................................. : 3.7903

 

                        Estimated Koc: 6170 L/kg  <===========

 

 

SMILES : CCCCCC=CCC=CCCCCCCCC(=O)NCCO

CHEM  : C18''

MOL FOR: C20 H37 N1 O2

MOL WT : 323.52

--------------------------- KOCWIN v2.01 Results ---------------------------

 

 Koc Estimate from MCI:

 ---------------------

        First Order Molecular Connectivity Index ........... : 11.308

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 6.4947

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -1.0277

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.2127

                 1  Aliphatic Alcohol (-C-OH) ........... : -1.3179

        Corrected Log Koc .................................. : 3.9363

 

                        Estimated Koc: 8636 L/kg  <===========

 

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow (Kowwin estimate) ......................... : 5.76

        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 4.1111

        Fragment Correction(s):

                 1  N-CO-C (aliphatic carbon) ............ : -0.0038

                 1  Nitrogen to Carbon (aliphatic) (-N-C).. : -0.0218

                 1  Aliphatic Alcohol (-C-OH) ........... : -0.4114

        Corrected Log Koc .................................. : 3.6741

 

                        Estimated Koc: 4722 L/kg  <===========

Validity criteria fulfilled:
not applicable
Conclusions:
The Koc of the test substance was estimated using KOCWIN v 2.01 program (EPISuite v 4.11), to be 1519.10 L/kg (log Koc= 3.18) with MCI method and 1161.10 L/kg (log koc= 3.06) Log Kow method.
Executive summary:

The soil adsorption and desorption potential (Koc) of the test substance, C12-18 and C18-unsatd. MEA, was estimated using the Molecular Connectivity Index (MCI) and Log Kow of the KOCWIN v 2.01 program (EPISuite v 4.11). Since the test substance is an UVCB, the Koc values were estimated for individual constituents using SMILES codes as the input parameter. Using the MCI and log Kow methods, the predicted Koc values for all the constituents were estimated to range from 21.37 to 8636 L/kg and 15.71 to 8165 L/kg respectively. The corresponding log Koc values ranged from 1.32 to 3.93 and 1.19 to 3.91 (US EPA, 2019). This indicates a negligible to moderate adsorption potential (US EPA, 2012). Since not all constituents meet the MW and structural fragment molecular descriptor domain criteria as defined in KOCWIN v 2.01 user guide of EPI Suite TM, the Koc predictions were considered to be less accurate. Given that the constituents are structurally very similar and vary only in the carbon chain length, a weighted average value, which considers the percentage of each constituent in the substance, was calculated to dampen the errors in predictions. The weighted average Koc (log Koc) values were calculated as1519.10 L/kg (log Koc= 3.18)and1161.10 L/kg (log koc= 3.06), using the MCI and log Kow methods respectively. Based on the above information, the test substance is expected to have a moderate adsorption potential (US EPA, 2012) to soil and sediment, leading to slow migration to ground water. Overall, the KOC predictions for the test substance using the KOCWIN model of EPI Suite TM can be considered to be reliable with moderate confidence.

Description of key information

Key value for chemical safety assessment

Koc at 20 °C:
1 340

Additional information

The soil adsorption and desorption potential (Koc) of the test substance, C12-18 and C18-unsatd. MEA, was estimated using the Molecular Connectivity Index (MCI) and the Log Kow of the KOCWIN v 2.01 programs (EPISuite v 4.11). Since the test substance is an UVCB, the Koc values were estimated for individual constituents using SMILES codes as the input parameter. Using the MCI and log Kow methods, the predicted Koc values for all the constituents were estimated to range from 21.37 to 8636 L/kg and 15.71 to 8165 L/kg respectively. The corresponding log Koc values ranged from 1.32 to 3.93 and 1.19 to 3.91 (US EPA, 2019). This indicates a negligible to moderate adsorption potential (US EPA, 2012). Since not all constituents meet the MW and structural fragment molecular descriptor domain criteria as defined in KOCWIN v 2.01 user guide of EPI Suite TM, the Koc predictions were considered to be less accurate. Given that the constituents are structurally very similar and vary only in the carbon chain length, a weighted average value, which considers the percentage of each constituent in the substance, was calculated to dampen the errors in predictions. The weighted average Koc (log Koc) values were calculated as 1519.10 L/kg (log Koc= 3.18) and1161.10 L/kg (log koc= 3.06), using the MCI and log Kow methods, respectively. Based on the above information, the test substance is expected to have a moderate adsorption potential (US EPA, 2012) to soil and sediment, leading to slow migration to ground water. Overall, the KOC predictions for the test substance using the KOCWIN model of EPI Suite TM can be considered to be reliable with moderate confidence.

The average Koc value of 1340 was retained for risk assessment purposes.

Furthermore, after discussion with ECHA in the frame of a Dossier Improvement Action Plan (DIAP), Koc testing according to OECD Guideline 106 is planned with the read across substance C16 MEA in order to support the modelling results obtained with EPISuite across all MEA-FAA substances.