Reaction products of furan-2,5-dione and octadec-1-ene

Adsorption / desorption

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

adsorption / desorption: screening

Data waiving:

study scientifically not necessary / other information available

Justification for data waiving:

the study does not need to be conducted because the substance and its relevant degradation products decompose rapidly

Reason / purpose for cross-reference:

data waiving: supporting information

Reason / purpose for cross-reference:

data waiving: supporting information

Reference 2

Endpoint:

adsorption / desorption: screening

Type of information:

(Q)SAR

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: See Remark.

Remarks:

Adorptipon coefficient prediction by KOCWIN version 2.00, a validated QSAR model included in the United States Environmental Protection Agency's EPI Suite, a publicly-available modelling software contained in the OECD QSAR Toolbox; the modelling was conducted on the hydrolysis product of the substance, by read-across from an analogue substance.

Justification for type of information:

QSAR prediction: migrated from IUCLID 5.6

Principles of method if other than guideline:

KOCWIN (version 2) estimates Koc with two separate estimation methodologies: (1) estimation using first-order Molecular Connectivity Index (MCI); and (2) estimation using log Kow (octanol-water partition coefficient). Overall, the MCI methodology is somewhat more accurate than the log Kow methodology, although both methods yield good results.

GLP compliance:

no

Type:

Koc

Value:

338 900

Remarks on result:

other: predicted value from KOCWIN, based on Molecular Connectivity Index (MCI)

Type:

log Koc

Value:

5.53

Remarks on result:

other: predicted value from KOCWIN, based on Molecular Connectivity Index (MCI)

Type:

Koc

Value:

29 520

Remarks on result:

other: predicted value from KOCWIN, based on estimation from partition coefficient (log Kow)

Type:

log Koc

Value:

4.47

Remarks on result:

other: predicted value from KOCWIN, based estimation from partition coefficient (log Kow)

KOCWIN Program (v2.00) Results:

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

SMILES : OC(=O)C(CCCCCCCCC=CCCCCCCCC)CC(=O)O

CHEM  : Octadecenylsuccinic acid

MOL FOR: C22 H40 O4

                Koc may be sensitive to pH!

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

 

 Koc Estimate from MCI:

 ---------------------

        First Order Molecular Connectivity Index ........... : 12.575

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 7.1549

        Fragment Correction(s):

                 *  Organic Acid (-CO-OH) ............... : -1.6249

        Corrected Log Koc .................................. : 5.5301

 

                        Estimated Koc: 3.389e+005 L/kg  <===========

 

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow (Kowwin estimate) ......................... : 7.80

        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 5.2395

        Fragment Correction(s):

                 *  Organic Acid (-CO-OH) ............... : -0.7694

        Corrected Log Koc .................................. : 4.4701

 

                        Estimated Koc: 2.952e+004 L/kg  <===========

 

  ********************************************************************

  *                           NOTE:                                *

  * The Koc of this structure may be sensitive to pH! The estimated *

  * Koc represents a best-fit to the majority of experimental values *

  * however, the Koc may vary significantly with pH.                *

  ********************************************************************

 

Conclusions:

The adsorption coefficient was predicted by two methodologies: molecular connectivity index (MC)), and by estimation from Kow. The estimate based on MCI methodology was adopted as the key value, since the MCI methodology has been described as "somewhat more accurate than the log Kow methodology, although both methods yield good results", and since the log Kow value for the substance is a predicted (and not experimentally-determined) value. The log Koc for the substance (as estimated by MCI) was 5.5301, corresponding to a Koc of 338,900.

Reference 3

Endpoint:

adsorption / desorption: screening

Type of information:

read-across from supporting substance (structural analogue or surrogate)

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: See Remark.

Remarks:

Adorptipon coefficient prediction by KOCWIN version 2.00, a validated QSAR model included in the United States Environmental Protection Agency's EPI Suite, a publicly-available modelling software contained in the OECD QSAR Toolbox; the modelling was conducted on the hydrolysis product of the substance, by read-across from an analogue substance.

Justification for type of information:

QSAR prediction: migrated from IUCLID 5.6. This study was conducted on octadecenyl succinic acid (CAS 28299-29-8), an analogue substance used as the source of information for the assessment of the target substance through read-across. Therefore, this study is informative for evaluation of the environmental fate and toxicity of the target substance, Reaction products of furan-2,5-dione and octadec-1-ene (known here as n-ODSA EC 701-338-8; no CASRN available), and it is adequate for classification and risk assessment.

Reason / purpose for cross-reference:

read-across source

Principles of method if other than guideline:

KOCWIN (version 2) estimates Koc with two separate estimation methodologies: (1) estimation using first-order Molecular Connectivity Index (MCI); and (2) estimation using log Kow (octanol-water partition coefficient). Overall, the MCI methodology is somewhat more accurate than the log Kow methodology, although both methods yield good results.

GLP compliance:

no

Type:

Koc

Value:

338 900

Remarks on result:

other: predicted value from KOCWIN, based on Molecular Connectivity Index (MCI)

Type:

log Koc

Value:

5.53

Remarks on result:

other: predicted value from KOCWIN, based on Molecular Connectivity Index (MCI)

Type:

Koc

Value:

29 520

Remarks on result:

other: predicted value from KOCWIN, based on estimation from partition coefficient (log Kow)

Type:

log Koc

Value:

4.47

Remarks on result:

other: predicted value from KOCWIN, based estimation from partition coefficient (log Kow)

KOCWIN Program (v2.00) Results:

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

SMILES : OC(=O)C(CCCCCCCCC=CCCCCCCCC)CC(=O)O

CHEM  : Octadecenylsuccinic acid

MOL FOR: C22 H40 O4

                Koc may be sensitive to pH!

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

 

 Koc Estimate from MCI:

 ---------------------

        First Order Molecular Connectivity Index ........... : 12.575

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 7.1549

        Fragment Correction(s):

                 *  Organic Acid (-CO-OH) ............... : -1.6249

        Corrected Log Koc .................................. : 5.5301

 

                        Estimated Koc: 3.389e+005 L/kg  <===========

 

 Koc Estimate from Log Kow:

 -------------------------

        Log Kow (Kowwin estimate) ......................... : 7.80

        Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 5.2395

        Fragment Correction(s):

                 *  Organic Acid (-CO-OH) ............... : -0.7694

        Corrected Log Koc .................................. : 4.4701

 

                        Estimated Koc: 2.952e+004 L/kg  <===========

 

  ********************************************************************

  *                           NOTE:                                *

  * The Koc of this structure may be sensitive to pH! The estimated *

  * Koc represents a best-fit to the majority of experimental values *

  * however, the Koc may vary significantly with pH.                *

  ********************************************************************

 

Conclusions:

The adsorption coefficient was predicted by two methodologies: molecular connectivity index (MC)), and by estimation from Kow. The estimate based on MCI methodology was adopted as the key value, since the MCI methodology has been described as "somewhat more accurate than the log Kow methodology, although both methods yield good results", and since the log Kow value for the substance is a predicted (and not experimentally-determined) value. The log Koc for the substance (as estimated by MCI) was 5.5301, corresponding to a Koc of 338,900.

Description of key information

Adsorption/desorption testing was waived, in accordance with Regulation (EC) No.1907/2006, Annex VIII, Column 2.

Additional information

Adsorption/desorption testing of the substance need not be conducted if the substance and its degradation products decompose rapidly.  The substance is expected to degrade rapidly in the environment; the substance undergoes rapid hydrolysis in the presence of water, and has been shown to be readily biodegradable, but failing the 10-day window.  Therefore, adsorption/desorption testing is not indicated. 

In a supporting study, the adsorption coefficient (Koc) of octadecenyl succinic acid, the hydrolysis product of the substance, was predicted through QSAR modeling, by read-across from an analogue substance. Due to the potential for ionisation of the hydrolysis product, the estimated Koc may vary significantly with pH.  The predicted adsorption coefficient (Koc = 338,900 L/kg; or log Koc = 5.5301) of octadecenyl succinic acid, the hydrolysis product of the substance, indicates the potential to sorb strongly to soil and sediment.  However, the substance is not expected to partition substantially to the soil and sediment compartments due to degradation. 

This information is from the substance octadecenyl succinic acid (CAS 28299-29-8), an analogue substance used for the assessment of several endpoints through read-across. The hypothesis for read-across between the substance being registered (Reaction products of furan-2,5-dione and octadec-1-ene; known here as n-ODSA EC 701-338-8; no CASRN available), and the analogue substance is a common functional group. The common functional group is a 2,5-furandione, dihydro- structure (also known as a succinic anhydride) or its hydrolysed form of butanedioic acid (also known a s succinic acid), to which is attached a linear, 18-carbon alkenyl group. The anhydride moiety is quickly hydrolysed to the dioic acid form in the environment; thus, the analogue substance (octadecenyl succinic acid) is the hydrolysed form of the substance being registered (n-ODSA EC 701-338-8). The dioic acid form of the moiety is expected to be representative of the environmental fate properties and aquatic toxicity of the anhydride form of the moiety. For each endpoint study based upon read-across, the analogue approach is substantiated by an evaluation provided in the Analogue Approach Report Format (AARF) attached to the endpoint study summary file. The AARF allows the read-across information to fulfil the information requirements of the REACH Annexes VII-X, to be the basis for classification and labelling decisions, and for risk assessment.

The predicted adsorption coefficient (Koc = 338,900 L/kg) for of octadecenyl succinic acid was used for the derivation of Predicted No Effects Concentrations for freshwater sediments, marine sediments and soil, from the extrapolation of aquatic toxicity data for the substance to the sediment and soil compartments by means of equilibrium partitioning.