2-hydroxy-3-(prop-2-enoyloxy)propyl 2-methyl-2-propylhexanoate

Adsorption / desorption

Link to relevant study record(s)

Reference

Endpoint:

adsorption / desorption

Remarks:

other: Adsorption estimated

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:

See below under 'Overall remarks, attachments' for applicability domain.

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:

Since the test substance is an UVCB with several constituents, the Koc values were estimated for the major constituents, (which constitute approx. 99% of the composition) using the Kow based approach of KOCWIN v2.00. program.

Specific details on test material used for the study:

Input data for the model: Representative SMILES of the major constituents:
1. Cardura acrylate isomers: C(=O)(C=C)OCC(O)COC(=O)CC(C)(CCC)CCC
2. Neo undecanoic acid, 1-ester with 1,2,3-propanetriol mono-2-propenoate: C(=O)(C=C)OCC(O)COC(=O)CC(C)(CCC)CCCC
3. Cardura diester: C(C)(C)CC(C)C(C)(C)C(=O)OCC(O)COC(=O)C(C)(C)C(C)CC(C)C

See under test material information for composition details.

Computational methods:

Since the test substance is an UVCB with several constituents and not all of its constituents are defined, the Koc values were estimated for the major constituents, (which constitute approx. 99% of the composition) using the Kow based approaches of KOCWIN v2.00. program.

Kow based estimation methodology:
The traditional method of estimating soil adsorption Koc involves correlations developed with log octanol-water partition coefficient (log Kow) (Doucette, 2000). Since an expanded experimental Koc database was available from the new MCI regression, it was decided to develop a log Kow estimation methodology that was potentially more accurate than existing log Kow QSARs for diverse structure datasets.
Effectively, the new log Kow methodology simply replaces the MCI descriptor with log Kow and derives similar equations. The derivation uses the same training and validation data sets. The training set is divided into the same non-polar (no correction factors) and correction factor sets. The same correction factors are also used.
Separate equations correlating log Koc with log Kow were derived for nonpolar and polar compounds because it was statistically more accurate to do so than to use the approach taken with the MCI-based method. The equation derived by the non-polar (no correction factor) regression is:
log Koc = 0.8679 Log Kow - 0.0004
(n = 68, r2 = 0.877, std dev = 0.478, avg dev = 0.371)
One non-polar compound was removed from the regression (hexabromobiphenyl) because it was the only compound without a recommended experimental log Kow and the accuracy of its estimated log Kow (9.10) is suspect. This equation is used for any compound having no correction factors.
For the multiple-linear regression using correction factors, log Kow was included as an individual descriptor. For compounds having correction factors, the equation is:
log Koc = 0.55313 Log Kow + 0.9251 + ΣPfN
where ΣPfN is the summation of the products of all applicable correction factor coefficients from Appendix D of the help manual multiplied by the number of times (N) that factor is counted for the structure.

Key result

Type:

Koc

Value:

>= 216.3 - <= 12 260 L/kg

Remarks on result:

other: estimated based on log Kow method of KOCWIN v.2.00 for major constituents

Key result

Type:

log Koc

Value:

>= 2.09 - <= 4.08 dimensionless

Remarks on result:

other: estimated based on log Kow method of KOCWIN v.2.00 for major constituents

Details on results:

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

CHEM : Cardura acrylate isomers                            

MOL FOR: C16 H28 O5

MOL WT : 300.40             

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

                Koc Estimate from MCI:

 ---------------------          

        First Order Molecular Connectivity Index ........... : 9.864

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 5.7417

        Fragment Correction(s):

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

                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -2.5939

        Corrected Log Koc .................................. : 1.8298

                               

                        Estimated Koc: 67.58 L/kg  <===========

                               

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow (Kowwin estimate) ......................... : 3.53

        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 2.8776

        Fragment Correction(s):

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

                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.1312

        Corrected Log Koc .................................. : 2.3350

                               

                        Estimated Koc: 216.3 L/kg  <===========

                               

                               

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

CHEM  : Neo undecanoic acid, 1-ester with 1,2,3-propanetriol mono-2-propenoate                        

MOL FOR: C17 H30 O5

MOL WT : 314.43             

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

                               

 Koc Estimate from MCI:

 ---------------------          

        First Order Molecular Connectivity Index ........... : 10.364

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 6.0023

        Fragment Correction(s):

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

                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -2.5939

        Corrected Log Koc .................................. : 2.0905

                               

                        Estimated Koc: 123.2 L/kg  <===========

                               

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow (Kowwin estimate) ......................... : 4.02

        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 3.1487

        Fragment Correction(s):

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

                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.1312

        Corrected Log Koc .................................. : 2.6061

                               

                        Estimated Koc: 403.7 L/kg  <===========

                               

                                                              

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

CHEM  : Cardura diester                              

MOL FOR: C23 H44 O5

MOL WT : 400.60             

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

                               

 Koc Estimate from MCI:

 ---------------------          

        First Order Molecular Connectivity Index ........... : 12.617

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 7.1770

        Fragment Correction(s):

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

                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -2.5939

        Corrected Log Koc .................................. : 3.2651

                               

                        Estimated Koc: 1841 L/kg  <===========

                               

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow (Kowwin estimate) ......................... : 6.70

        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 4.6311

        Fragment Correction(s):

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

                 2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.1312

        Corrected Log Koc .................................. : 4.0884

                               

                        Estimated Koc: 1.226e+004 L/kg  <===========

Validity criteria fulfilled:

not applicable

Conclusions:

Based on the estimated values for the major constituents using KOCWIN v2.00 program (EPISuite v 4.1), the Koc of the test substance can be considered to range from 216.3-12260 L/kg (log Koc = 2.09-4.08).

Executive summary:

The soil adsorption coefficient (Koc) value for the test substance was estimated using the log Kow methods of KOCWIN v2.00 program (EPISuite v4.1). Since the test substance is an UVCB and not all of its constituents are defined, the Koc values were estimated for all its identified constituents, which are present at >1% and approximately constitute 99% of the composition. Using SMILES codes as the input parameter for the 4 major constituents, the Koc values based on log Kow method were estimated as follows:

- Cardura acrylate isomers: 216.3 L/kg; log Koc = 2.09

- Neo undecanoic acid, 1-ester with 1,2,3-propanetriol mono-2-propenoate: 403.7 L/kg; log Koc = 2.6

- Cardura diester: 12260 L/kg; log Koc = 4.08

The domain applicability evaluation indicated that the estimates for all the 3 constituents are reliable and accurate. Overall, based on the estimated values for the identified constituents using KOCWIN v2.00 program (EPISuite v 4.1), the Koc of the test substance ranges from 216.3-12260 L/kg (log Koc = 2.09-4.08) (US EPA, 2016). This range of Koc indicates moderate to slight mobility in soil/sediment or moderate to high adsorption potential to organic matter (White, 2009). Although the Koc value of the major constituent (present at >90%) corresponds to 216.3 L/kg (i.e, log Koc = 2.09), the upper limit of the range has been taken forward for risk assessment.

Description of key information

Based on the estimated values for the identified constituents (present at >1%) using KOCWIN v2.00 program (EPISuite v 4.1), the Koc values of the test substance is considered to range from 216.3 -12260 L/kg (log Koc = 2.09-4.08). Although the Koc value of the major constituent (present at >95%) corresponds to 216.3 L/kg (i.e, log Koc = 2.09), the upper limit of the range has been taken forward for risk assessment as a conservative approach.

Key value for chemical safety assessment

Koc at 20 °C:

12 260

Additional information

The soil adsorption coefficient (Koc) value for the test substance was estimated using the log Kow methods of KOCWIN v2.00 program (EPISuite v4.1). Since the test substance is an UVCB and not all of its constituents are defined, the Koc values were estimated for all its identified constituents, which are present at >1% and approximately constitute 99% of the composition. Using SMILES codes as the input parameter for the 4 major constituents, the Koc values based on log Kow method were estimated as follows:

- Cardura acrylate isomers: 216.3 L/kg; log Koc = 2.09

- Neo undecanoic acid, 1-ester with 1,2,3-propanetriol mono-2-propenoate: 403.7 L/kg; log Koc = 2.6

- Cardura diester: 12260 L/kg; log Koc = 4.08

The domain applicability evaluation indicated that the estimates for all the 3 constituents are reliable and accurate. Overall, based on the estimated values for the identified constituents using KOCWIN v2.00 program (EPISuite v 4.1), the Koc of the test substance ranges from 216.3-12260 L/kg (log Koc = 2.09-4.08) (US EPA, 2016). This range of Koc indicates moderate to slight mobility in soil/sediment or moderate to high adsorption potential to organic matter (White, 2009). Although the Koc value of the major constituent (present at >95%) corresponds to 216.3 L/kg (i.e, log Koc = 2.09), the upper limit of the range has been taken forward for risk assessment.

[LogKoc: 4.08]