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REACH

2-Propenoic acid, reaction products with dipentaerythritol

EC number: 800-838-4 | CAS number: 1384855-91-7

Life Cycle description
Uses advised against

Environmental fate & pathways

Bioaccumulation: aquatic / sediment

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Administrative data

Link to relevant study record(s)

Reference

Endpoint:: bioaccumulation in aquatic species: fish
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 QMRF and QPRF including domain evaluation.
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 ‘2-Propenoic acid, reaction products with dipentaerythritol’ is a UVCB, the bioaccumulation (BCF) values were estimated for the individual substances representative of the major components. Considering the structures of test substance, the regression-based equations as well as the Arnot-Gobas BAF-BCF methodology were used for the BCF predictions.
Details on estimation of bioconcentration:: Since the test substance ‘2-Propenoic acid, reaction products with dipentaerythritol’ is a UVCB, the bioaccumulation (BCF) values were estimated for the individual substances representative of the major components. Considering the structures of test substance, the regression-based equations as well as the Arnot-Gobas BAF-BCF methodology were used for the BCF predictions.
Type:: other: BCF - weighted average value estimated from regression-based method
Value:: ca. 138.44 other: L/kg w/w
Basis:: whole body w.w.
Calculation basis:: other: calculated based on estimated log Kow for individual components
Remarks on result:: other: Log BCF 2.14
: Key result
Type:: other: BCF - weighted average value estimated from Arnot-Gobas method
Value:: ca. 5.56 other: L/kg w/w
Basis:: whole body w.w.
Calculation basis:: other: calculated based on estimated log Kow for individual components (including biotransformation rate estimates)
Remarks on result:: other: Log BCF 0.75
Validity criteria fulfilled:: not applicable
Conclusions:: The BCF range for the constituents of test substance were from 3.16 to 836 L/kg ww with the weighted average BCF value of 138.44 L/kg ww using regression-based method and from 1.018 to 12.51 L/kg ww with the weighted average BCF value of 5.56 L/kg ww using Arnot Gobus method, which overall indicates low bioaccumulation potential.
Executive summary:: The bioaccumulation factor (BCF) value for the test substance, 2-Propenoic acid, reaction products with dipentaerythritol were estimated using the regression-based and/or Arnot-Gobas BAF-BCF methodology of the BCFBAF v3.01 program (EPI SuiteTM v4.11). Since the test substance is a UVCB with similar constituents varying mainly in carbon chain lengths, the BCF values were estimated for the individual components followed by the determination of an overall weighted-average value using the mole fractions of all the individual components. SMILES codes were used as the input parameter for the BCF value estimation for the individual constituents. The BCF range for the constituents of test substance were from 3.16 to 836 L/kg ww with the weighted average BCF value of 138.44 L/kg ww using regression-based method and from 1.018 to 12.51 L/kg ww with the weighted average BCF value of 5.56 L/kg ww using Arnot Gobas method (US EPA, 2020). Considering that the BCF predictions for the non-ionic constituents from Arnot-Gobas method takes into account mitigating factors, like growth dilution and metabolic biotransformations, the BCF value from this model has been taken into consideration for the risk assessment. Overall, taking into consideration that the BCF prediction for not all the constituents of test substance using BCFBAF model of EPI SuiteTM are within domain, the model’s training set, validation set statistics and the fact that the training set only contains 61 ionic compounds, the BCF predictions for the individual constituents are considered to be reliable with moderate confidence. Therefore, the BCF value for the overall test substance is predicted to range from 1.018 to 12.51 L/kg ww.

Description of key information

The BCF range for the constituents of DPHA was 1.018 to 12.51 L/kg ww using Arnot Gobas method, which overall indicates low bioaccumulation potential.

Key value for chemical safety assessment

BCF (aquatic species):: 12.51 L/kg ww

Additional information

The bioaccumulation factor (BCF) value for the test substance, 2-Propenoic acid, reaction products with dipentaerythritol were estimated using the regression-based and/or Arnot-Gobas BAF-BCF methodology of the BCFBAF v3.01 program (EPI SuiteTM v4.11). Since the test substance is a UVCB with similar constituents varying mainly in carbon chain lengths, the BCF values were estimated for the individual components followed by the determination of an overall weighted-average value using the mole fractions of all the individual components. SMILES codes were used as the input parameter for the BCF value estimation for the individual constituents. The BCF range for the constituents of test substance were from 3.16 to 836 L/kg ww with the weighted average BCF value of 138.44 L/kg ww using regression-based method and from 1.018 to 12.51 L/kg ww with the weighted average BCF value of 5.56 L/kg ww using Arnot Gobas method (US EPA, 2020). Considering that the BCF predictions for the non-ionic constituents from Arnot-Gobas method takes into account mitigating factors, like growth dilution and metabolic biotransformations, the BCF value from this model has been taken into consideration for the risk assessment. Overall, taking into consideration that the BCF prediction for not all the constituents of test substance using BCFBAF model of EPI SuiteTM are within domain, the model’s training set, validation set statistics and the fact that the training set only contains 61 ionic compounds, the BCF predictions for the individual constituents are considered to be reliable with moderate confidence. Therefore, the BCF value for the overall test substance is predicted to range from 1.018 to 12.51 L/kg ww.

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Chemical constituents	SMILES	Adjusted composition for QSAR	Mole fraction Xi = (mi/Mi)/∑ (mi/Mi)	BCF (regression based)	*BCF (regression based)xi**	Domain evaluation
Dipentaerythritol hexaacrylate (DPHA)	C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C	30	3.39E-01	55.3	18.73	ID - MW, Log kow
Michaël addition of acrylic acid on dipentaerythritol hexaacrylate (DPHA-(AA)n)	C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)CCOC(=O)C=C	9	9.04E-02	58	5.24	ID - MW, Log kow
Dipentaerythritol pentaacrylate (DPPA)	O=C(OCC(COC(=O)C=C)(COC(=O)C=C)COCC(CO)(COC(=O)C=C)COC(=O)C=C)C=C	21	2.62E-01	7	1.83	ID - MW, Log kow
Michaël addition of acrylic acid on dipentaerythritol pentaacrylate (DPPA-AA)	O=C(OCC(COC(=O)C=C)(COC(=O)CCOC(=O)C=C)COCC(CO)(COC(=O)C=C)COC(=O)C=C)C=C	4	4.38E-02	7.34	0.32	ID - MW, Log kow
Tripentaerythritol octaacrylate (TPOA)	C=CC(=O)OCC(COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)(COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)COC(=O)C=C	0.5	4.05E-03	210	0.85	ID - MW, Log kow
Michaël addition of acrylic acid on tripentaerythritol octaacrylate (TPOA-AA)	C=CC(=O)OCC(COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)(COCC(COC(=O)C=C)(COC(=O)CCOC(=O)C=C)COC(=O)C=C)COC(=O)C=C	7.5	5.58E-02	220	12.28	ID - MW, Log kow
Dipentaerythritol tetraacrylate (DPTTA)	O=C(C=C)OCC(COC(=O)C=C)(COCC(COC(=O)C=C)(COC(=O)C=C)CO)CO	5	6.94E-02	3.16	0.22	ID - MW, Log kow
Michaël adduct of acrylic acid on dipentaerythritol tetraacrylate (DPTTA-AA)	O=C(C=C)OCC(COC(=O)C=C)(COCC(COC(=O)CCOC(=O)C=C)(COC(=O)C=C)CO)CO	1.5	1.81E-02	3.16	0.06	ID - MW, Log kow
Sum of several dimers corresponding to Michaël addition of OH function from dipentaerythritol pentaacrylate (DPPA) with acrylic double bonds from e.g. DPPA, DPHA, DPPA-AA, DPHA-AA and DPTA	C=CC(=O)OCC(COCCC(=O)OCC(COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)(COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)COC(=O)C=C	20	1.18E-01	836	98.92	OD - MW, ID - Log kow
Other constituents	-	1.5	-			-
				Weighted average BCF	138.44
				Weighted average log BCF	2.14

Chemical constituents	SMILES	Adjusted composition for QSAR	Mole fraction Xi = (mi/Mi)/∑ (mi/Mi)	BCF (Arnot Gobas)	*BCF (Arnot Gobas)xi**	Domain evaluation
Dipentaerythritol hexaacrylate (DPHA)	C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C	30	3.39E-01	6.23	2.11	ID - MW, Log kow
Michaël addition of acrylic acid on dipentaerythritol hexaacrylate (DPHA-(AA)n)	C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)CCOC(=O)C=C	9	9.04E-02	6.268	0.57	ID - MW, Log kow
Dipentaerythritol pentaacrylate (DPPA)	O=C(OCC(COC(=O)C=C)(COC(=O)C=C)COCC(CO)(COC(=O)C=C)COC(=O)C=C)C=C	21	2.62E-01	1.852	0.48	ID - MW, Log kow
Michaël addition of acrylic acid on dipentaerythritol pentaacrylate (DPPA-AA)	O=C(OCC(COC(=O)C=C)(COC(=O)CCOC(=O)C=C)COCC(CO)(COC(=O)C=C)COC(=O)C=C)C=C	4	4.38E-02	1.9	0.08	ID - MW, Log kow
Tripentaerythritol octaacrylate (TPOA)	C=CC(=O)OCC(COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)(COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)COC(=O)C=C	0.5	4.05E-03	12.5	0.05	ID - MW, Log kow
Michaël addition of acrylic acid on tripentaerythritol octaacrylate (TPOA-AA)	C=CC(=O)OCC(COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)(COCC(COC(=O)C=C)(COC(=O)CCOC(=O)C=C)COC(=O)C=C)COC(=O)C=C	7.5	5.58E-02	12.51	0.70	ID - MW, Log kow
Dipentaerythritol tetraacrylate (DPTTA)	O=C(C=C)OCC(COC(=O)C=C)(COCC(COC(=O)C=C)(COC(=O)C=C)CO)CO	5	6.94E-02	1.018	0.07	ID - MW, Log kow
Michaël adduct of acrylic acid on dipentaerythritol tetraacrylate (DPTTA-AA)	O=C(C=C)OCC(COC(=O)C=C)(COCC(COC(=O)CCOC(=O)C=C)(COC(=O)C=C)CO)CO	1.5	1.81E-02	1.027	0.02	ID - MW, Log kow
Sum of several dimers corresponding to Michaël addition of OH function from dipentaerythritol pentaacrylate (DPPA) with acrylic double bonds from e.g. DPPA, DPHA, DPPA-AA, DPHA-AA and DPTA	C=CC(=O)OCC(COCCC(=O)OCC(COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)(COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)COC(=O)C=C	20	1.18E-01	12.51	1.48	OD - MW, ID - Log kow
Other constituents	-	1.5	-			-
				Weighted average BCF	5.56
				Weighted average log BCF	0.75

BCF - QSAR predictions
SMILES : C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O
)C=C
CHEM :
MOL FOR: C28 H34 O13	Domain evaluation	MW (Training set)
MOL WT : 578.58	ID	959.17
--------------------------------- BCFBAF v3.01 --------------------------------
Summary Results:
Log BCF (regression-based estimate): 1.74 (BCF = 55.3 L/kg wet-wt)
Biotransformation Half-Life (days) : 5.44e-006 (normalized to 10 g fish)
Log BAF (Arnot-Gobas upper trophic): 0.79 (BAF = 6.23 L/kg wet-wt)

=============================
BCF (Bioconcentration Factor):
=============================
Log Kow (estimated) : 3.15
Log Kow (experimental): not available from database
Log Kow used by BCF estimates: 3.15	ID	min: -1.37 (non-ionic) max: 11.26

Equation Used to Make BCF estimate:
Log BCF = 0.6598 log Kow - 0.333 + Correction

Correction(s): Value
No Applicable Correction Factors

Estimated Log BCF = 1.742 (BCF = 55.25 L/kg wet-wt)

===========================================================
Whole Body Primary Biotransformation Rate Estimate for Fish:
===========================================================
------+-----+--------------------------------------------+---------+---------
TYPE \| NUM \| LOG BIOTRANSFORMATION FRAGMENT DESCRIPTION \| COEFF \| VALUE
------+-----+--------------------------------------------+---------+---------
Frag \| 6 \| Ester [-C(=O)-O-C] \| -0.7605 \| -4.5632
Frag \| 2 \| Carbon with 4 single bonds & no hydrogens \| -0.2984 \| -0.5969
Frag \| 1 \| Aliphatic ether [C-O-C] \| -0.0232 \| -0.0232
Frag \| 8 \| -CH2- [linear] \| 0.0242 \| 0.1935
Frag \| 18 \| -C=CH [alkenyl hydrogen] \| 0.0988 \| 1.7793
Frag \| 18 \| -C=CH [alkenyl hydrogen] \| 0.0000 \| 0.0000
L Kow\| * \| Log Kow = 3.15 (KowWin estimate) \| 0.3073 \| 0.9667