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Partition coefficient

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Endpoint:
partition coefficient
Type of information:
experimental study
Adequacy of study:
key study
Study period:
From August, 2010 to August, 2010
Reliability:
1 (reliable without restriction)
Rationale for reliability incl. deficiencies:
guideline study
Qualifier:
according to guideline
Guideline:
OECD Guideline 123 (Partition Coefficient (1-Octanol / Water), Slow-Stirring Method)
Deviations:
no
GLP compliance:
no
Type of method:
HPLC method
Partition coefficient type:
octanol-water
Analytical method:
high-performance liquid chromatography
Key result
Type:
log Pow
Partition coefficient:
4.2
Temp.:
25 °C
pH:
ca. 7.36 - ca. 7.44
Remarks on result:
other: RSD= 0.55 %
Details on results:
For details on the results, please refer to 'attached background material'

Annotation: According to the applied guideline the slow-stirring method is particularly suitable for the determination of substances with expected log Pow values of 5 and higher, for which the shake-flask method (generally applicable from log Pow = -2 to 4) is prone to yield erroneous results.

However, according to the REACH Guidance on information requirements and chemical safety assessment - Chapter R.7a: Endpoint specific guidance, the shake-flask method is not recommended for surfactants. Instead, the slow-stirring method is advised as the preferred test method in this case.

Conclusions:
Under the study conditions, the Pow and Log Pow were determined to be 15418 and 4.2, respectively at 25°C.
Executive summary:

A study was conducted to determine the partition coefficient of the test substance, C12-18 and C18-unsatd. DEA (purity not specified), using slow stirring method according to OECD Guideline 123. Under the study conditions, the Pow and Log Pow were determined to be15418 and 4.2, respectively at 25°C (Frischmann, 2010).

Endpoint:
partition coefficient
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, but not (completely) 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 QPRF containing methodology and domain evaluation details.
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 Partition Coefficient (Log Kow) value for the test substance were estimated using the efficient partiiton algorithm (EPA) associative neural network (ASNN) method of the ALOGPS v.2.1 program from the Virtual Computational Chemistry Laboratory. Since the test substance is a UVCB, the Log Kow values were predicted for the individual constituents using SMILES codes as the input parameter.
Type of method:
other: Efficient Partiiton Algorithm (EPA) Associative Neural Network (ASNN)
Partition coefficient type:
other: QSAR
Key result
Type:
log Pow
Partition coefficient:
ca. 1.47 - ca. 6.49
Remarks on result:
other: predicted for the main constituents
Remarks:
ALOGPS v.2.1
Key result
Type:
log Pow
Partition coefficient:
ca. 4.28
Remarks on result:
other: weighted average Log Kow
Remarks:
ALOGPS v.2.1

Predicted value:

The predicted partition coefficient (log Kow) values for the different constituents using the efficient partiiton algorithm (EPA) associative neural network (ASNN) method were as follows:

Table 1: Log Kow predictions: EPA and ASNN based method

Constituents/Carbon chain length*

Mean/adjusted conc

Mole fraction Xi = (mi/Mi)/∑ (mi/Mi)

Log Kow

Log Kow * xi

C8

1.5

0.01985008

1.47

0.029179617

C10

1.5

0.017703525

2.66

0.047091377

C12

52.5

0.559137624

3.67

2.052035078

C14

20

0.194067297

4.7

0.912116298

C16

10

0.089111093

5.64

0.502586567

C18

1.5

0.012357357

6.49

0.080199247

C18'

11

0.091115906

6.19

0.56400746

C18''

2

0.016657117

5.61

0.093446429

 

 

 

Log Kow=

4.28

*Glycerol or DEA residues have not been considered for the QSAR prediction

Conclusions:
Using the EPA and ASNN based regression equations from ALOGPS V.2.1, the weighted average Partition coefficient (Log Kow) value for test substance was predicted to be 4.28.
Executive summary:

The partition coefficent (log Kow) value for the test substance, C12-18 and C18-unsatd. DEA was predicted using the EPA and ASNN based regression equations from ALOGPS V.2.1. Since the test substance is a UVCB, the log Kow values were predicted for the individual constituents using SMILES codes as the input parameter. Using the Associative neural network method, the Log Kow values for the individual constituents of the test substance ranged from 1.47 to 6.49. All constituents meet the E-indices, molecular weight and number of non-hydrogen atoms descriptor domain criteria. Further, 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 the constituent in the substance, was considered to dampen the errors in predictions (if any). Overall, considering either the individual log Kow predictions for the constituents or the weighted average values, the test substance is expected to be less hydrophobic with a good absorption and low accumulation potential.Therefore the log Kow predictions for the test substance using ALOGPS v.2.1 can be considered to be reliable with moderate confidence.

Endpoint:
partition coefficient
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, but not (completely) 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 QPRF containing methodology and domain evaluation details.
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 Partition Coefficient (Log Kow) value for the test substance were estimated using the KOWWIN v.1.68. program in EPI SuiteTM v4.11. Since the test substance is a UVCB, the Log Kow values were predicted for the individual constituents using SMILES codes as the input parameter.
Type of method:
other: Fragment constant method
Partition coefficient type:
other: QSAR prediction
Key result
Type:
log Pow
Partition coefficient:
ca. 0.92 - ca. 5.83
Remarks on result:
other: predicted for the main constituents
Remarks:
KOWWIN v.1.68. EPI SuiteTM v4.11
Key result
Type:
log Pow
Partition coefficient:
ca. 3.39
Remarks on result:
other: weighted average Log Kow
Remarks:
KOWWIN v.1.68. EPI SuiteTM v4.11

Predicted value (model result):

The predicted log Kow values for the different constituents using the Fragment constant method were as follows:

Table 2: Log Kow prediction: Fragment constantmethod

Constituents/Carbon chain length*

Mean/ adjusted conc

Mole fraction Xi = (mi/Mi)/∑ (mi/Mi)

KOWWIN Log Kow

KOWWIN Log Kow x Xi

Domain evaluation

C8

1.5

0.01985008

0.92

0.018262073

MW (ID), Structural fragments (ID)

C10

1.5

0.017703525

1.9

0.033636698

MW (ID), Structural fragments (ID)

C12

52.5

0.559137624

2.89

1.615907732

MW (ID), Structural fragments (ID)

C14

20

0.194067297

3.87

0.751040441

MW (ID), Structural fragments (ID)

C16

10

0.089111093

4.85

0.432188803

MW (ID), Structural fragments (ID)

C18

1.5

0.012357357

5.83

0.072043391

MW (ID), Structural fragment (OD) - 1 out of 5 fragments (aliphatic carbon (-CH2-), exceeds by 2 instances)

C18'

11

0.091115906

5.62

0.512071393

MW (ID), Structural fragments (ID)

C18''

2

0.016657117

5.4

0.089948434

MW (ID), Structural fragments (ID)

 Log Kow=

3.53

 

*Glycerol or DEA residues have not been considered for the QSAR prediction

Log Kow prediction results:

                 Log Kow(version 1.69 estimate): 0.92

 

SMILES : CCCCCCCC(=O)N(CCO)CCO

CHEM  :

MOL FOR: C12 H25 N1 O3

MOL WT : 231.34

-------+-----+--------------------------------------------+---------+--------

 TYPE | NUM |       LOGKOW FRAGMENT DESCRIPTION        | COEFF | VALUE

-------+-----+--------------------------------------------+---------+--------

 Frag | 1 | -CH3   [aliphatic carbon]               | 0.5473 | 0.5473

 Frag | 10 | -CH2-  [aliphatic carbon]               | 0.4911 | 4.9110

 Frag | 2 | -OH    [hydroxy, aliphatic attach]      |-1.4086 | -2.8172

 Frag | 1 | -N<    [aliphatic attach]               |-1.8323 | -1.8323

 Frag | 1 | -C(=O)N [aliphatic attach]              |-0.5236 | -0.5236

 Factor| 1 | Multi-alcohol correction                 | 0.4064 | 0.4064

 Const |    | Equation Constant                        |        | 0.2290

-------+-----+--------------------------------------------+---------+--------

                                                        Log Kow  =  0.9206

 

                 Log Kow(version 1.69 estimate): 1.90

 

SMILES : CCCCCCCCCC(=O)N(CCO)CCO

CHEM  :

MOL FOR: C14 H29 N1 O3

MOL WT : 259.39

-------+-----+--------------------------------------------+---------+--------

 TYPE | NUM |       LOGKOW FRAGMENT DESCRIPTION        | COEFF | VALUE

-------+-----+--------------------------------------------+---------+--------

 Frag | 1 | -CH3   [aliphatic carbon]               | 0.5473 | 0.5473

 Frag | 12 | -CH2-  [aliphatic carbon]               | 0.4911 | 5.8932

 Frag | 2 | -OH    [hydroxy, aliphatic attach]      |-1.4086 | -2.8172

 Frag | 1 | -N<    [aliphatic attach]               |-1.8323 | -1.8323

 Frag | 1 | -C(=O)N [aliphatic attach]              |-0.5236 | -0.5236

 Factor| 1 | Multi-alcohol correction                 | 0.4064 | 0.4064

 Const |    | Equation Constant                        |        | 0.2290

-------+-----+--------------------------------------------+---------+--------

                                                        Log Kow  =  1.9028

                 Log Kow(version 1.69 estimate): 2.89

 

SMILES : CCCCCCCCCCCC(=O)N(CCO)CCO

CHEM  :

MOL FOR: C16 H33 N1 O3

MOL WT : 287.45

-------+-----+--------------------------------------------+---------+--------

 TYPE | NUM |       LOGKOW FRAGMENT DESCRIPTION        | COEFF | VALUE

-------+-----+--------------------------------------------+---------+--------

 Frag | 1 | -CH3   [aliphatic carbon]               | 0.5473 | 0.5473

 Frag | 14 | -CH2-  [aliphatic carbon]               | 0.4911 | 6.8754

 Frag | 2 | -OH    [hydroxy, aliphatic attach]      |-1.4086 | -2.8172

 Frag | 1 | -N<    [aliphatic attach]               |-1.8323 | -1.8323

 Frag | 1 | -C(=O)N [aliphatic attach]              |-0.5236 | -0.5236

 Factor| 1 | Multi-alcohol correction                 | 0.4064 | 0.4064

 Const |    | Equation Constant                        |        | 0.2290

-------+-----+--------------------------------------------+---------+--------

                                                        Log Kow  =  2.8850

 

                 Log Kow(version 1.69 estimate): 3.87

 

SMILES : CCCCCCCCCCCCCC(=O)N(CCO)CCO

CHEM  :

MOL FOR: C18 H37 N1 O3

MOL WT : 315.50

-------+-----+--------------------------------------------+---------+--------

 TYPE | NUM |       LOGKOW FRAGMENT DESCRIPTION        | COEFF | VALUE

-------+-----+--------------------------------------------+---------+--------

 Frag | 1 | -CH3   [aliphatic carbon]               | 0.5473 | 0.5473

 Frag | 16 | -CH2-  [aliphatic carbon]               | 0.4911 | 7.8576

 Frag | 2 | -OH    [hydroxy, aliphatic attach]      |-1.4086 | -2.8172

 Frag | 1 | -N<    [aliphatic attach]               |-1.8323 | -1.8323

 Frag | 1 | -C(=O)N [aliphatic attach]              |-0.5236 | -0.5236

 Factor| 1 | Multi-alcohol correction                 | 0.4064 | 0.4064

 Const |    | Equation Constant                        |        | 0.2290

-------+-----+--------------------------------------------+---------+--------

                                                        Log Kow  =  3.8672

 

                 Log Kow(version 1.69 estimate): 4.85

 

SMILES : CCCCCCCCCCCCCCCC(=O)N(CCO)CCO

CHEM  :

MOL FOR: C20 H41 N1 O3

MOL WT : 343.55

-------+-----+--------------------------------------------+---------+--------

 TYPE | NUM |       LOGKOW FRAGMENT DESCRIPTION        | COEFF | VALUE

-------+-----+--------------------------------------------+---------+--------

 Frag | 1 | -CH3   [aliphatic carbon]               | 0.5473 | 0.5473

 Frag | 18 | -CH2-  [aliphatic carbon]               | 0.4911 | 8.8398

 Frag | 2 | -OH    [hydroxy, aliphatic attach]      |-1.4086 | -2.8172

 Frag | 1 | -N<    [aliphatic attach]               |-1.8323 | -1.8323

 Frag | 1 | -C(=O)N [aliphatic attach]              |-0.5236 | -0.5236

 Factor| 1 | Multi-alcohol correction                 | 0.4064 | 0.4064

 Const |    | Equation Constant                        |        | 0.2290

-------+-----+--------------------------------------------+---------+--------

                                                        Log Kow  =  4.8494

 

                 Log Kow(version 1.69 estimate): 5.83

 

SMILES : CCCCCCCCCCCCCCCCCC(=O)N(CCO)CCO

CHEM  :

MOL FOR: C22 H45 N1 O3

MOL WT : 371.61

-------+-----+--------------------------------------------+---------+--------

 TYPE | NUM |       LOGKOW FRAGMENT DESCRIPTION        | COEFF | VALUE

-------+-----+--------------------------------------------+---------+--------

 Frag | 1 | -CH3   [aliphatic carbon]               | 0.5473 | 0.5473

 Frag | 20 | -CH2-  [aliphatic carbon]               | 0.4911 | 9.8220

 Frag | 2 | -OH    [hydroxy, aliphatic attach]      |-1.4086 | -2.8172

 Frag | 1 | -N<    [aliphatic attach]               |-1.8323 | -1.8323

 Frag | 1 | -C(=O)N [aliphatic attach]              |-0.5236 | -0.5236

 Factor| 1 | Multi-alcohol correction                 | 0.4064 | 0.4064

 Const |    | Equation Constant                        |        | 0.2290

-------+-----+--------------------------------------------+---------+--------

                                                        Log Kow  =  5.8316

 

                 Log Kow(version 1.69 estimate): 5.62

 

SMILES : CCCCCCCCC=CCCCCCCCC(=O)N(CCO)CCO

CHEM  :

MOL FOR: C22 H43 N1 O3

MOL WT : 369.59

-------+-----+--------------------------------------------+---------+--------

 TYPE | NUM |       LOGKOW FRAGMENT DESCRIPTION        | COEFF | VALUE

-------+-----+--------------------------------------------+---------+--------

 Frag | 1 | -CH3   [aliphatic carbon]               | 0.5473 | 0.5473

 Frag | 18 | -CH2-  [aliphatic carbon]               | 0.4911 | 8.8398

 Frag | 2 | =CH- or =C< [olefinc carbon]            | 0.3836 | 0.7672

 Frag | 2 | -OH    [hydroxy, aliphatic attach]      |-1.4086 | -2.8172

 Frag | 1 | -N<    [aliphatic attach]               |-1.8323 | -1.8323

 Frag | 1 | -C(=O)N [aliphatic attach]              |-0.5236 | -0.5236

 Factor| 1 | Multi-alcohol correction                 | 0.4064 | 0.4064

 Const |    | Equation Constant                        |        | 0.2290

-------+-----+--------------------------------------------+---------+--------

                                                        Log Kow  =  5.6166

 

                 Log Kow(version 1.69 estimate): 5.40

 

SMILES : CCCCCC=CCC=CCCCCCCCC(=O)N(CCO)CCO

CHEM  :

MOL FOR: C22 H41 N1 O3

MOL WT : 367.58

-------+-----+--------------------------------------------+---------+--------

 TYPE | NUM |       LOGKOW FRAGMENT DESCRIPTION        | COEFF | VALUE

-------+-----+--------------------------------------------+---------+--------

 Frag | 1 | -CH3   [aliphatic carbon]               | 0.5473 | 0.5473

 Frag | 16 | -CH2-  [aliphatic carbon]               | 0.4911 | 7.8576

 Frag | 4 | =CH- or =C< [olefinc carbon]            | 0.3836 | 1.5344

 Frag | 2 | -OH    [hydroxy, aliphatic attach]      |-1.4086 | -2.8172

 Frag | 1 | -N<    [aliphatic attach]               |-1.8323 | -1.8323

 Frag | 1 | -C(=O)N [aliphatic attach]              |-0.5236 | -0.5236

 Factor| 1 | Multi-alcohol correction                 | 0.4064 | 0.4064

 Const |    | Equation Constant                        |        | 0.2290

-------+-----+--------------------------------------------+---------+--------

                                                        Log Kow  =  5.4016

Conclusions:
Using the fragment constant method, of KOWWIN V.1.68 program of EPI SuiteTM, the weighted average partition coefficient (log Kow) value for test substance was predicted to be 3.53.
Executive summary:

The partition coefficient (log Kow) value for the test substance, C12-18 and C18-unsatd. DEA was predicted using the fragment constant method, of KOWWIN V.1.68 program. Since the test substance is a UVCB, the log Kow values were predicted for the individual constituents using SMILES codes as the input parameter. Using the fragment constant method, the log Kow values for the individual constituents of the test substance ranged from 0.92 to 5.83. All constituents meet the molecular weight and structural fragment descriptor domain criteria, except for one of the constituent which exceed the maximum number of instances of fragment. Further, 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 the constituent in the substance, was considered to dampen the errors in predictions (if any). Overall, considering either the individual log Kow predictions for the constituents or the weighted average values, the test substance is expected to be less hydrophobic with a good absorption and low accumulation potential. Therefore the log Kow predictions for the test substance using KOWWIN v1.69 can be considered to be reliable with moderate confidence.

Endpoint:
partition coefficient
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, but not (completely) 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 QPRF containing methodology and domain evaluation details.
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 partition coefficient (log Kow) value for the test substance were estimated using the group contributions methodology of Molinspiration (miLogP2.2 - November 2005). Since the test substance is a UVCB, the log Kow values were predicted for the individual constituents using SMILES codes as the input parameter.
Type of method:
other: Group contributions
Partition coefficient type:
other: QSAR prediction
Key result
Type:
log Pow
Partition coefficient:
ca. 1.86 - ca. 6.91
Remarks on result:
other: predicted for the main constituents
Remarks:
Molinspiration (miLogP2.2)
Key result
Type:
log Pow
Partition coefficient:
ca. 4.5
Remarks on result:
other: weighted average Log Kow
Remarks:
Molinspiration (miLogP2.2)

Predicted value:

Using the group contribution method of molinspiration model, the partition coefficient (log Kow) values for the different constituents were predicted as follows:

Table 1: Log Kow predictions: Group contribution method

Constituents/Carbon chain length*

Mean/adjusted conc

Mole fraction Xi = (mi/Mi)/∑ (mi/Mi)

Log Kow

Log Kow * xi

C8

1.5

0.01985008

1.86

3.69E-02

C10

1.5

0.017703525

2.87

5.08E-02

C12

52.5

0.559137624

3.88

2.17E+00

C14

20

0.194067297

4.89

9.49E-01

C16

10

0.089111093

5.9

5.26E-01

C18

1.5

0.012357357

6.91

8.54E-02

C18'

11

0.091115906

6.42

5.85E-01

C18''

2

0.016657117

5.7

9.49E-02

 

 

 

Log Kow=

4.50

*Glycerol or DEA residues have not been considered for the QSAR prediction

Conclusions:
Using the group contribution method, of Molinspiration (miLogP 2.2), the weighted average partition coefficient (log Kow) value for test substance was predicted to be 4.5.
Executive summary:

The partition coefficient (log Kow) value for the test substance, C12-18 and C18-unsatd. DEA was predicted using the group contribution method, of Molinspiration (miLogP 2.2) program. Since the test substance is a UVCB, the log Kow values were predicted for the individual constituents using SMILES codes as the input parameter. Using the group contribution method, the log Kow values for the individual constituents of the test substance ranged from 1.86 to 6.91. All constituents meet the molecular weight and log Kow descriptor domain criteria. Further, 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 the constituent in the substance, was considered to dampen the errors in predictions (if any). Therefore, the weighted average log Kow value was calculated as 4.5. Overall, considering either the individual log Kow predictions for the constituents or the weighted average values, the test substance is expected to be less hydrophobic with a good absorption and low accumulation potential. Therefore the log Kow predictions for the test substance using Molinspiration (miLogP 2.2), can be considered to be reliable with moderate confidence.

Description of key information

The partition coefficient was determined according to OECD Guideline 123 (slow-stirring method) (Frischmann, 2010).

Weighted average partition coefficient values for the substance were also modelled using the fragment constant method of the KOWWIN V.1.68 program of EPI Suite, the group contribution method of Molinspiration (miLogP 2.2) and the efficient partition algorithm and associative neural network-based regression equations from ALOGPS V.2.1.

Key value for chemical safety assessment

Log Kow (Log Pow):
4.2
at the temperature of:
25 °C

Additional information

The measured Log Kow was determined to be 4.2 at 25°C.

Using the fragment constant method, of the KOWWIN V.1.68 program of EPI Suite, the weighted average partition coefficient (log Kow) value for the test substance was predicted to be 3.53. Using the group contribution method of Molinspiration (miLogP 2.2), the weighted average partition coefficient (log Kow) value for the test substance was predicted to be 4.5. Using the EPA and ASNN based regression equations from ALOGPS V.2.1, the weighted average partition coefficient (Log Kow) value for test substance was predicted to be 4.28.