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

Bioaccumulation: aquatic / sediment

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

bioaccumulation in aquatic species: fish

Data waiving:

other justification

Justification for data waiving:

the study does not need to be conducted because direct and indirect exposure of the aquatic compartment to the substance is unlikely

Reason / purpose for cross-reference:

data waiving: supporting information

Reason / purpose for cross-reference:

data waiving: supporting information

Reason / purpose for cross-reference:

data waiving: supporting information

Reference 2

Endpoint:

bioaccumulation: aquatic / sediment

Type of information:

(Q)SAR

Adequacy of study:

supporting 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

Remarks:

Bioaccumulation prediction using BCFBAF, version 3.01, a validated QSAR model included as part of the United States Environmental Protection Agency's EPI Suite modeling program, a publicly-available modeling software contained within the OECD QSAR Toolbox.

Justification for type of information:

QSAR prediction: migrated from IUCLID 5.6

Principles of method if other than guideline:

Bioaccumulation prediction for the substance using BCFBAF, version 3.01, a validated QSAR model included as part of the United States Environmental Protection Agency's EPI Suite modeling program, a publicly-available modeling software contained within the OECD QSAR Toolbox.

Details on estimation of bioconcentration:

Equation Used to Make BCF estimate:
Log BCF = -0.49 log Kow + 7.554 + Correction

Correction(s): Value
Alkyl chains (8+ -CH2- groups) -0.596

BCFBAF Program (v3.01) Results:

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

SMILES : O=C(OC(=O)C1)C1CC=CCCCCCCCCCCCCCCC

CHEM  : 2,5-Furandione, dihydro-3-(2-octadecenyl)-

MOL FOR: C22 H38 O3

MOL WT : 350.55

--------------------------------- BCFBAF v3.01 --------------------------------

Summary Results:

 Log BCF (regression-based estimate): 2.37 (BCF = 235 L/kg wet-wt)

 Biotransformation Half-Life (days) : 24.5 (normalized to 10 g fish)

 Log BAF (Arnot-Gobas upper trophic): 4.06 (BAF = 1.15e+004 L/kg wet-wt)

 

Log Kow (experimental): not available from database

Log Kow used by BCF estimates: 9.36

 

Equation Used to Make BCF estimate:

  Log BCF = -0.49 log Kow + 7.554 + Correction

 

     Correction(s):                   Value

      Alkyl chains (8+ -CH2- groups) -0.596

 

  Estimated Log BCF = 2.370 (BCF = 234.6 L/kg wet-wt)

 

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

Whole Body Primary Biotransformation Rate Estimate for Fish:

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

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

 TYPE | NUM | LOG BIOTRANSFORMATION FRAGMENT DESCRIP | COEFF | VALUE 

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

 Frag | 1 | Linear C4 terminal chain [CCC-CH3]   | 0.0341 | 0.0341

 Frag | 1 | Methyl [-CH3]                        | 0.2451 | 0.2451

 Frag | 15 | -CH2- [linear]                       | 0.0242 | 0.3628

 Frag | 1 | -CH2- [cyclic]                       | 0.0963 | 0.0963

 Frag | 1 | -CH - [cyclic]                       | 0.0126 | 0.0126

 Frag | 2 | -C=CH [alkenyl hydrogen]             | 0.0988 | 0.1977

 Frag | 2 | -C=CH [alkenyl hydrogen]             | 0.0000 | 0.0000

 L Kow| * | Log Kow =  9.36 (KowWin estimate)    | 0.3073 | 2.8772

 MolWt| * | Molecular Weight Parameter            |         | -0.8989

 Const| * | Equation Constant                     |         | -1.5371

============+============================================+=========+=========

  RESULT  |       LOG Bio Half-Life (days)       |        | 1.3898

  RESULT  |           Bio Half-Life (days)       |        |  24.53

  NOTE    | Bio Half-Life Normalized to 10 g fish at 15 deg C  |

============+============================================+=========+=========

 

Biotransformation Rate Constant:

 kM (Rate Constant): 0.02825 /day (10 gram fish)

 kM (Rate Constant): 0.01589 /day (100 gram fish)

 kM (Rate Constant): 0.008934 /day (1 kg fish)

 kM (Rate Constant): 0.005024 /day (10 kg fish)

 

Arnot-Gobas BCF & BAF Methods (including biotransformation rate estimates):

  Estimated Log BCF (upper trophic) = 1.319 (BCF = 20.86 L/kg wet-wt)

  Estimated Log BAF (upper trophic) = 4.062 (BAF = 1.153e+004 L/kg wet-wt)

  Estimated Log BCF (mid trophic)  = 1.455 (BCF = 28.54 L/kg wet-wt)

  Estimated Log BAF (mid trophic)  = 4.094 (BAF = 1.242e+004 L/kg wet-wt)

  Estimated Log BCF (lower trophic) = 1.497 (BCF = 31.43 L/kg wet-wt)

  Estimated Log BAF (lower trophic) = 4.116 (BAF = 1.306e+004 L/kg wet-wt)

 

Arnot-Gobas BCF & BAF Methods (assuming a biotransformation rate of zero):

  Estimated Log BCF (upper trophic) = 2.535 (BCF = 343 L/kg wet-wt)

  Estimated Log BAF (upper trophic) = 6.233 (BAF = 1.709e+006 L/kg wet-wt)

Conclusions:

The BCF of the substance, was estimated to be 234.6 L/kg wet weight, based on the octanol-water partition coefficient (log Kow = 9.36). The substance was predicted to be non-bioaccumulative for purposes of classification (BCF < 500) and PBT evaluation (BCF < 2000). Although the predicted BCF exceeded the guideline for food chain exposures (BCF < 100), the substance exhibits mitigating factors (ready biodegradability and rapid hydrolysis).

Reference 3

Endpoint:

bioaccumulation: aquatic / sediment

Type of information:

(Q)SAR

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: see 'Remark'

Remarks:

Bioaccumulation prediction using BCFBAF, version 3.01, a validated QSAR model included as part of the United States Environmental Protection Agency's EPI Suite modeling program, a publicly-available modeling software contained within the OECD QSAR Toolbox; the modelling was conducted on the hydrolysis product of the substance, by read-across based on an analogue substance.

Justification for type of information:

QSAR prediction: migrated from IUCLID 5.6

Principles of method if other than guideline:

The BCFBAF program estimates BCF of an organic compound using the compound's octanol-water partition coefficient (Kow), based upon the separate regressions for non-ionic and ionic organic compounds, based on the methodology of Meylan, et al. (1997, 1999).

GLP compliance:

no

Details on estimation of bioconcentration:

Equation Used to Make BCF estimate:
Log BCF = 1.75 (Ionic; Log Kow dependent)

BCFBAF Program (v3.01) Results:

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

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

CHEM  : Octadecenylsuccinic acid

MOL FOR: C22 H40 O4

MOL WT : 368.56

--------------------------------- BCFBAF v3.01 --------------------------------

Summary Results:

 Log BCF (regression-based estimate): 1.75 (BCF = 56.2 L/kg wet-wt)

 Biotransformation Half-Life (days) : 22.3 (normalized to 10 g fish)

 Log BAF (Arnot-Gobas upper trophic): 5.26 (BAF = 1.81e+005 L/kg wet-wt)

 

Log Kow (experimental): not available from database

Log Kow used by BCF estimates: 7.80

 

Equation Used to Make BCF estimate:

  Log BCF = 1.75 (Ionic; Log Kow dependent)

 

 

  Estimated Log BCF = 1.750 (BCF = 56.23 L/kg wet-wt)

Conclusions:

The BCF of octadecenyl succinic acid, the hydrolysed form of the substance, was estimated to be 56.23 L/kg wet weight, based on the octanol-water partition coefficient (log Kow = 7.80) of the hydrolysis product. The hydrolysed form of the substance was predicted to be non-bioaccumulative with respect to food chain exposures (BCF < 100), classification (BCF < 500) and PBT evaluation (BCF < 2000).

Reference 4

Endpoint:

bioaccumulation: aquatic / sediment

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:

Bioaccumulation prediction using BCFBAF, version 3.01, a validated QSAR model included as part of the United States Environmental Protection Agency's EPI Suite modeling program, a publicly-available modeling software contained within the OECD QSAR Toolbox; the modelling was conducted on the hydrolysis product of the substance, by read-across based on 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:

The BCFBAF program estimates BCF of an organic compound using the compound's octanol-water partition coefficient (Kow), based upon the separate regressions for non-ionic and ionic organic compounds, based on the methodology of Meylan, et al. (1997, 1999).

GLP compliance:

no

Details on estimation of bioconcentration:

Equation Used to Make BCF estimate:
Log BCF = 1.75 (Ionic; Log Kow dependent)

BCFBAF Program (v3.01) Results:

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

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

CHEM  : Octadecenylsuccinic acid

MOL FOR: C22 H40 O4

MOL WT : 368.56

--------------------------------- BCFBAF v3.01 --------------------------------

Summary Results:

 Log BCF (regression-based estimate): 1.75 (BCF = 56.2 L/kg wet-wt)

 Biotransformation Half-Life (days) : 22.3 (normalized to 10 g fish)

 Log BAF (Arnot-Gobas upper trophic): 5.26 (BAF = 1.81e+005 L/kg wet-wt)

 

Log Kow (experimental): not available from database

Log Kow used by BCF estimates: 7.80

 

Equation Used to Make BCF estimate:

  Log BCF = 1.75 (Ionic; Log Kow dependent)

 

 

  Estimated Log BCF = 1.750 (BCF = 56.23 L/kg wet-wt)

Conclusions:

The BCF of octadecenyl succinic acid, the hydrolysed form of the substance, was estimated to be 56.23 L/kg wet weight, based on the octanol-water partition coefficient (log Kow = 7.80) of the hydrolysis product. The hydrolysed form of the substance was predicted to be non-bioaccumulative with respect to food chain exposures (BCF < 100), classification (BCF < 500) and PBT evaluation (BCF < 2000).

Description of key information

Bioaccumulation testing was waived, in accordance with Regulation (EC) No.1907/2006, Annex IX, Column 2.  

Additional information

Bioaccumulation testing of the substance in aquatic species need not be conducted if direct and indirect exposure of the substance is unlikely.  The substance is expected to undergo rapid hydrolysis and 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, bioaccumulation testing in aquatic species is not indicated.

In two supporting studies, the bioconcentration factor (BCF) was predicted through QSAR, by read-across based on a chemical analogue. The QSAR model, BCFBAF version 3.01, was included as part of the United States Environmental Protection Agency's EPI Suite modeling program, a publicly-available modeling software contained within the OECD QSAR Toolbox. 

 

In the first supporting study, the BCF of the substance was estimated as 236.4 L/kg, based on the octanol-water partition coefficient (log Kow= 9.36). The substance was predicted to be non-bioaccumulative for purposes of classification (BCF < 500) and PBT evaluation (BCF < 2000). Although the predicted BCF exceeded the guideline for food chain exposures (BCF < 100), the substance exhibits mitigating factors (ready biodegradability and rapid hydrolysis).

 

Due to the expected rapid hydrolysis of the substance, the predicted BCF for octadecenyl succinic acid, the hydrolysis product of the substance, was determined in the second supporting study. The BCF for octadecenyl succinic acid was estimated as 56.23 L/kg wet weight, based on the regression-based estimate. Thus, the hydrolysis product of the substance was shown to be non-bioaccumulative for purposes of food chain exposures (BCF < 100), environmental classification (BCF < 500) and PBT evaluation (BCF < 2000). 

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.

 

Therefore, the substance is characterised by properties that reduce concern for bioaccumulation potential: rapid hydrolysis to octadecenyl succinic acid, and rapid degradation in the environment. The hydrolysis product of the substance, octadecenyl succinic acid, was shown to be non-bioaccumulative. Therefore, the QSAR modeling conducted in the supporting studies show that bioaccumulation testing in aquatic species is not indicated.