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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:
2012-11-06 to 2012-12-05
Reliability:
1 (reliable without restriction)
Rationale for reliability incl. deficiencies:
guideline study
Qualifier:
according to
Guideline:
EU Method A.8 (Partition Coefficient)
Qualifier:
according to
Guideline:
OECD Guideline 117 (Partition Coefficient (n-octanol / water), HPLC Method)
GLP compliance:
yes
Type of method:
HPLC method
Partition coefficient type:
octanol-water
Analytical method:
high-performance liquid chromatography
Type:
log Pow
Partition coefficient:
> 9.4
Temp.:
30 °C
pH:
6.3
Details on results:
The result from the preliminary test indicated that the HPLC method was the most suitable for determination of partition coefficient for this test item.
The mobile phase’s pH was unadjusted as the test item had no dissociation constants in the environmentally relevant pH range and so was tested in its non-ionized form.
The chromatography of the test item showed one sharp main peak with a well-defined and reproducible retention time. The HPLC method was therefore considered to be suitable for the purpose of the study. Based on the chromatographic data, the test item was considered to be stable during the test procedure.
Conclusions:
The partition coefficient of the test item has been determined to be >2.51E+09, log10 Pow > 9.4.
Executive summary:

Method

The determination was carried out using the HPLC Method designed to be compatible with Method A8 Partition Coefficient of Commission Regulation (EC) No 440/2008 of 30 May 2008 and Method 117 of the OECD Guidelines for Testing of Chemicals, 13 April 2004.

The test system consisted of a high performance liquid chromatograph with a suitable detector (UV/VIS, ELS). A reverse phase HPLC column with a very low percentage of polar groups was used (e.g. C8, C18). The mobile phase contained at least 25% aqueous phase.

Conclusion

The partition coefficient of the test item has been determined to be >2.51E+09, log10 Pow > 9.4.

Endpoint:
partition coefficient
Type of information:
experimental study
Adequacy of study:
supporting study
Reliability:
1 (reliable without restriction)
Rationale for reliability incl. deficiencies:
guideline study
Qualifier:
according to
Guideline:
OECD Guideline 107 (Partition Coefficient (n-octanol / water), Shake Flask Method)
GLP compliance:
yes
Type of method:
shake-flask method to: flask method
Partition coefficient type:
octanol-water
Analytical method:
gas chromatography
Type:
log Pow
Partition coefficient:
> 2.7
Temp.:
22 °C

No data available for pH.

No GC-FID peak for the test substance was observed in any of the aqueous phases, indicating that the concentrations of test substance in these phases were less than the LDC (lowest detectable concentration) of 0.3 µg/mL.

The test substance was observed in the octanol phases at concentrations listed in table 1 below. Based on those concentrations, the average observed percentage of the test substance which partitioned into the octanol phases was 99 ± 9% (n = 7; table 2), indicating that the mass balance was acceptable.

Because the observed concentrations of the test substance in the aqueous phases were all less than the detection limit, the resulting Kow values were minima, ranging from > 92 to > 460 (log Kow > 2.7) (table 1), the latter minimum being the reported Kow for the test substance at 22 °C.

Table 1:

ID

System

Octanol (mL)

Water (mL)

oct/aq (v:v)

Observed test substance

Conc. (µg/mL)

Kow

Log Kow

Aqueous phase

Octanol phase

%RSD

1a

System-1

12

12

1

< 0.3

64.00

0.1%

> 213

> 2.32

1b

System-1

12

12

1

< 0.3

64.10

> 213

> 2.32

2a

System-2

6

12

0.5

< 0.3

136.14

0.4%

> 460

> 2.66

2b

System-2

6

12

0.5

< 0.3

139.29

> 464

> 2.66

3a

System-3

24

12

2

< 0.3

27.74

0.6%

> 92

> 1.96

3b

System-3

24

12

2

< 0.3

27.42

>91

> 1.96

 

Average

0.4%

 

Table 2:

Octanol phase

Observed test substance

Conc. (µg/mL)

Test substance mass in octanol phase (µg)

Test substance mass in octanol phase; % of total

O1a

63.08

757

99%

O1a

64.00

768

101%

O1b

64.10

769

101%

O2a

138.14

829

109%

O2b

139.29

836

110%

O3a

27.74

666

87%

O3b

27.42

658

88%

 

Average

99%

 

SD

9%

Conclusions:
Because the observed concentrations of the test substance in the aqueous phases were all less than the detection limit, the resulting Kow values were minima, ranging from > 92 to > 460 (log Kow > 2.7) (table 1), the latter minimum being the reported Kow for the test substance at 22 °C.
The actual Log Kow for this substance has been calculated as being > 10.
Endpoint:
partition coefficient
Type of information:
(Q)SAR
Adequacy of study:
supporting study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Accepted calculation method, peer-reviewed.
Justification for type of information:
QSAR prediction: migrated from IUCLID 5.6
Principles of method if other than guideline:
Calculation based on KOWWIN programme v1.67, Estimation Programs Interface Suite™ for Microsoft® Windows v 4.00. US EPA, United States Environmental Protection Agency, Washington, DC, USA.
GLP compliance:
no
Remarks:
Calculation
Type of method:
other: estimated by calculation
Partition coefficient type:
octanol-water
Type:
log Pow
Partition coefficient:
10.64
Type:
log Pow
Partition coefficient:
13.59

Estimated values, no data given for temperature and pH.

The log Pow was calculated (QSAR) with KOWWIN. Due to the fact that this substance is long chain hydrocarbon which exceeds the applicability domain of KOWWIN the value for log Pow is reported with restricitions.

The applicability domain covers log Pow up to 10 (maximum) so these values should be given as log Pow > 10.

The concrete value is reported to show the high lipophilic nature of the substance.

KOWWIN Program (v1.67) Results:

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

 

Log Kow(version 1.67 estimate): 10.64

 

SMILES : CCCCCCCC(=O)(OCC(CC)(COC(=O)(CCCCCCC))COC(=O)(CCCCCCC))

MOL FOR: C30 H56 O6

MOL WT : 512.78

 

TYPE

NUM

LOGKOW FRAGMENT DESCRIPTION        

COEFF

VALUE

Frag

4

-CH3   [aliphatic carbon]               

0.5473

2.1892

Frag

22

-CH2-  [aliphatic carbon]               

0.4911

10.8042

Frag

3

-C(=O)O [ester, aliphatic attach]

-0.9505

-2.8515

Frag

1

-tert Carbon [3 or more carbon attach]  

0.2676

0.2676

Const

 

Equation Constant                        

 

0.2290

Log Kow  =  10.6385

 

 

KOWWIN Program (v1.67) Results:

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

 

Log Kow(version 1.67 estimate): 13.59

 

SMILES : O=C(OCC(CC)(COC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC)CCCCCCCCC

MOL FOR: C36 H68 O6

MOL WT : 596.94

 

TYPE

NUM

LOGKOW FRAGMENT DESCRIPTION        

COEFF

VALUE

Frag

4

-CH3   [aliphatic carbon]               

0.5473

2.1892

Frag

28

-CH2-  [aliphatic carbon]               

0.4911

13.7508

Frag

3

-C(=O)O [ester, aliphatic attach]

-0.9505

-2.8515

Frag

1

-tert Carbon [3 or more carbon attach]  

0.2676

0.2676

Const

 

Equation Constant                        

 

0.2290

Log Kow  =  13.5851

Endpoint:
partition coefficient
Type of information:
(Q)SAR
Adequacy of study:
supporting study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Accepted calculation method, peer-reviewed.
Justification for type of information:
QSAR prediction: migrated from IUCLID 5.6
Principles of method if other than guideline:
Calculation based on KOWWIN programme v1.67, Estimation Programs Interface Suite™ for Microsoft® Windows v 4.00. US EPA, United States Environmental Protection Agency, Washington, DC, USA.
GLP compliance:
no
Remarks:
Calculation
Type of method:
other: estimated by calculation
Partition coefficient type:
octanol-water
Type:
log Pow
Partition coefficient:
6.74
Type:
log Pow
Partition coefficient:
14.6

Estimated values, no data given for temperature and pH.

The log Pow was calculated (QSAR) with KOWWIN. Due to the fact that this substance is long chain hydrocarbon which exceeds the applicability domain of KOWWIN the value for log Pow is reported with restricitions.

The applicability domain covers log Pow up to 10 (maximum) so these values should be given as log Pow > 10.

The concrete value is reported to show the high lipophilic nature of the substance.

KOWWIN Program (v1.67) Results:

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

 

Log Kow(version 1.67 estimate): 6.74

 

SMILES : O=C(OCC(COC(=O)CCCC)(COC(=O)CCCC)COC(=O)CCCC)CCCC

MOL FOR: C25 H44 O8

MOL WT : 472.62

 

TYPE

NUM

LOGKOW FRAGMENT DESCRIPTION        

COEFF

VALUE

Frag

4

-CH3   [aliphatic carbon]               

0.5473

2.1892

Frag

16

-CH2-  [aliphatic carbon]               

0.4911

7.8576

Frag

4

-C(=O)O [ester, aliphatic attach]

-0.9505

-3.8020

Frag

1

-tert Carbon [3 or more carbon attach]  

0.2676

0.2676

Const

 

Equation Constant                        

 

0.2290

Log Kow  =  6.7414

 

KOWWIN Program (v1.67) Results:

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

Log Kow(version 1.67 estimate): 14.60

 

SMILES : O=C(OCC(COC(=O)CCCCCCCC)(COC(=O)CCCCCCCC)COC(=O)CCCCCCCC)CCCCCCCC

MOL FOR: C41 H76 O8

MOL WT : 697.06

 

TYPE 

NUM

LOGKOW FRAGMENT DESCRIPTION        

COEFF 

VALUE

Frag

4

-CH3   [aliphatic carbon]               

0.5473 

2.1892

Frag

32

-CH2-  [aliphatic carbon]               

0.4911 

15.7152

Frag

4

-C(=O)O [ester, aliphatic attach]       

-0.9505 

-3.8020

Frag

1

-tert Carbon [3 or more carbon attach]

0.2676

| 0.2676

Const

 

Equation Constant                        

0.2290

 

Log Kow  = 14.5990

 

Endpoint:
partition coefficient
Type of information:
(Q)SAR
Adequacy of study:
supporting study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Accepted calculation method, peer-reviewed.
Justification for type of information:
QSAR prediction: migrated from IUCLID 5.6
Principles of method if other than guideline:
Calculation based on KOWWIN programme v1.67, Estimation Programs Interface Suite™ for Microsoft® Windows v 4.00. US EPA, United States Environmental Protection Agency, Washington, DC, USA.
GLP compliance:
no
Remarks:
Calculation
Type of method:
other: estimated by calculation
Partition coefficient type:
octanol-water
Type:
log Pow
Partition coefficient:
11.558
Remarks on result:
other: QSAR calculation

KOWWIN Program (v1.68) Results:

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

 

Log Kow(version 1.68 estimate): 11.56

 

SMILES : C(CC)(COC(=O)CC(C)CC(C)(C)(C))(COC(=O)CC(C)CC(C)(C)(C))(COC(=O)CC(C)C

C(C)(C)(C))

CHEM  : Hexanoic acid, 3,5,5-trimethyl-, 1,1'-[2-ethyl-2-[[(3,5,5-trimethyl-1

-oxohexyl)oxy]methyl]-1,3-propanediyl] ester

MOL FOR: C33 H62 O6

MOL WT : 554.86

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

TYPE | NUM |       LOGKOW FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 13 | -CH3   [aliphatic carbon]               | 0.5473 | 7.1149

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

Frag | 3 | -CH    [aliphatic carbon]               | 0.3614 | 1.0842

Frag | 3 | -C(=O)O [ester, aliphatic attach]       |-0.9505 | -2.8515

Frag | 4 | -tert Carbon [3 or more carbon attach]  | 0.2676 | 1.0704

Const |    | Equation Constant                        |        | 0.2290

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

Log Kow  = 11.5580

Endpoint:
partition coefficient
Type of information:
read-across from supporting substance (structural analogue or surrogate)
Adequacy of study:
key study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: analogue substance
Justification for type of information:
Determination of partition coefficient is not required because available data indicate that structural variation does not influence test results or adverse effect profile (see read-across and category justifications attached in Section 13).
Reason / purpose:
read-across source
Key result
Type:
log Pow
Partition coefficient:
> 9.4
Temp.:
30 °C
pH:
6.3

Description of key information

The partition coefficient of the analogue substance has been determined to be >2.51E+09, Log10 Pow > 9.4.

Key value for chemical safety assessment

Additional information

The partition coefficient of the analogue substance has been determined to be >2.51E+09, Log10 Pow > 9.4.