4-hydroxybutyl acrylate

Bioaccumulation: aquatic / sediment

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

bioaccumulation in aquatic species: fish

Type of information:

calculation (if not (Q)SAR)

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Principles of method if other than guideline:

Method: Calculation

GLP compliance:

no

Specific details on test material used for the study:

CAS No.: 2478-10-6

Test organisms (species):

other: aquatic organisms

Test temperature:

25 °C

Type:

BCF

Value:

2.3 L/kg

Remarks on result:

other: calculation

Reference 2

Endpoint:

bioaccumulation in aquatic species: fish

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

Justification for type of information:

- QMRF: see 'Overall remarks, attachments'.
- QPRF: see 'Executive summary'.

Qualifier:

no guideline followed

Principles of method if other than guideline:

Calculation using BCFBAF (v3.01)

GLP compliance:

no

Specific details on test material used for the study:

- SMILES code: O=C(OCCCCO)C=C

Details on estimation of bioconcentration:

BASIS FOR CALCULATION OF BCF
- Estimation software: EPISuite-BCFBAF (version 3.01)
- Result based on measured log Pow of: 0.77

Type:

BCF

Value:

3.16 L/kg

Basis:

whole body w.w.

Remarks on result:

other: Regression-based estimate; Log BCF: 0.50

Type:

BCF

Value:

1.039 L/kg

Basis:

whole body w.w.

Remarks on result:

other: Arnot-Gobas upper trophic, incl. biotransformation estimates; Log BCF: 0.016

Summary Results:

Log BCF (regression-based estimate): 0.50 (BCF = 3.16 L/kg wet-wt)

Biotransformation Half-Life (days) : 0.00796 (normalized to 10 g fish)

Log BAF (Arnot-Gobas upper trophic): 0.02 (BAF = 1.04 L/kg wet-wt)

Log Kow (experimental): not available from database

Log Kow used by BCF estimates: 0.77 (user entered)

Equation Used to Make BCF estimate:

Log BCF = 0.50

Correction(s): Value

Correction Factors Not Used for Log Kow < 1

Estimated Log BCF = 0.500 (BCF = 3.162 L/kg wet-wt)

 

Whole Body Primary Biotransformation Rate Estimate for Fish:

TYPE	NUM	LOG BIODEGRADATION FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	1	Aliphatic alcohol [-OH]	-0.0616	-0.0616
Frag	1	Ester [-C(=O)-O-C]	-0.7605	-0.7605
Frag	4	-CH2- [linear]	0.0242	0.0967
Frag	3	-C=CH [alkenyl hydrogen]	0.0988	0.2965
Frag	3	-C=CH [alkenyl hydrogen]	0.0000	0.0000
L Kow	*	Log Kow = 0.77 (user-entered)	0.3073	0.2367
MolWt	*	Molecular Weight Parameter		-0.3697
Const	*	Equation Constant		-1.5371
Result	LOG Bio Half-Life (days)			-2.0989
Result	Bio Half-life (days)			0.007963

 

Biotransformation Rate Constant:

kM (Rate Constant): 87.04 /day (10 gram fish)

kM (Rate Constant): 48.95 /day (100 gram fish)

kM (Rate Constant): 27.53 /day (1 kg fish)

kM (Rate Constant): 15.48 /day (10 kg fish)

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

Estimated Log BCF (upper trophic) = 0.016 (BCF = 1.039 L/kg wet-wt)

Estimated Log BAF (upper trophic) = 0.016 (BAF = 1.039 L/kg wet-wt)

Estimated Log BCF (mid trophic) = 0.037 (BCF = 1.09 L/kg wet-wt)

Estimated Log BAF (mid trophic) = 0.037 (BAF = 1.09 L/kg wet-wt)

Estimated Log BCF (lower trophic) = 0.041 (BCF = 1.098 L/kg wet-wt)

Estimated Log BAF (lower trophic) = 0.041 (BAF = 1.098 L/kg wet-wt)

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

Estimated Log BCF (upper trophic) = 0.183 (BCF = 1.523 L/kg wet-wt)

Estimated Log BAF (upper trophic) = 0.185 (BAF = 1.531 L/kg wet-wt)

Executive summary:

QPRF: BCFBAF v3.01 

1.	Substance	See “Test material identity”
2.	General information
2.1	Date of QPRF	See “Data Source (Reference)”
2.2	QPRF author and contact details	See “Data Source (Reference)”
3.	Prediction
3.1	Endpoint (OECD Principle 1)	Endpoint	Bioaccumulation (aquatic)
		Dependent variable	- Bioconcentration factor (BCF) - Bioaccumulation factor (BAF; 15 °C) - Biotransformation rate (kM) and half-life
3.2	Algorithm (OECD Principle 2)	Model or submodel name	BCFBAF Submodels: 1) Bioconcentration factor (BCF; Meylan et al., 1997/1999) 2) Biotransformation rate in fish (kM; Arnot et al., 2008a/b) 3) Arnot & Gobas BAF and steady-state BCF Arnot & Gobas, 2003)
		Model version	v. 3.01
		Reference to QMRF	Estimation of Bioconcentration, bioaccumulation and biotransformation in fish using BCFBAF v3.01 (EPI Suite v4.11)
		Predicted value (model result)	See “Results and discussion”
		Input for prediction	Chemical structure via CAS number or SMILES; log Kow (optional)
		Descriptor values	- SMILES: structure of the compound as SMILES notation - log Kow - Molecular weight
3.3	Applicability domain (OECD principle 3)	Domains:
		1) Bioconcentration factor (BCF; Meylan et al., 1997/1999)
		a) Ionic/non-Ionic	The substance is non-ionic.
		b) Molecular weight (range of test data set): - Ionic: 68.08 to 991.80 - Non-ionic: 68.08 to 959.17 (On-Line BCFBAF Help File, Ch. 7.1.3 Estimation Domain and Appendix G)	The substance is within range (144.17 g/mol).
		c) log Kow (range of test data set): - Ionic: -6.50 to 11.26 - Non-ionic: -1.37 to 11.26 (On-Line BCFBAF Help File, Ch. 7.1.3 Estimation Domain and Appendix G)	The substance is within range (0.77).
		d) Maximum number of instances of correction factor in any of the training set compounds (On-Line BCFBAF Help File, Appendix E)	Not applicable as correction factors were not used.
		2) Biotransformation rate in fish (kM; Arnot et al., 2008a/b)
		a) The substance does not appreciably ionize at physiological pH. (On-Line BCFBAF Help File, Ch. 7.2.3)	Fulfilled
		b) Molecular weight (range of test data set): 68.08 to 959.17 (On-Line BCFBAF Help File, Ch. 7.2.3)	The substance is within range (144.17 g/mol).
		c) The molecular weight is ≤ 600 g/mol. (On-Line BCFBAF Help File, Ch. 7.2.3)	Fulfilled
		d) Log Kow: 0.31 to 8.70 (On-Line BCFBAF Help File, Ch. 7.2.3)	The substance is within range (0.77).
		e) The substance is no metal or organometal, pigment or dye, or a perfluorinated substance. (On-Line BCFBAF Help File, Ch. 7.2.3)	Fulfilled
		f) Maximum number of instances of biotransformation fragments in any of the training set compounds (On-Line BCFBAF Help File, Appendix F)	Not exceeded.
		3) Arnot & Gobas BAF and steady-state BCF Arnot & Gobas, 2003)
		a) Log Kow ≤ 9 (On-Line BCFBAF Help File, Ch. 7.3.1)	Fulfilled
		b) The substance does not appreciably ionize. (On-Line BCFBAF Help File, Ch. 7.3.1)	Fulfilled
		c) The substance is no pigment, dye, or perfluorinated substance. (On-Line BCFBAF Help File, Ch. 7.3.1)	Fulfilled
3.4	The uncertainty of the prediction (OECD principle 4)	1. Bioconcentration factor (BCF; Meylan et al., 1997/1999) Statistical accuracy of the training data set (non-ionic plus ionic data): - Correlation coefficient (r^2) = 0.833 - Standard deviation = 0.502 log units - Absolute mean error = 0.382 log units   2. Biotransformation Rate in Fish (kM) Statistical accuracy (training set): - Correlation coefficient (r^2) = 0.821 - Correlation coefficient (Q^2) = 0.753 - Standard deviation = 0.494 log units - Absolute mean error = 0.383 log units   3. Arnot-Gobas BAF/BCF model No information on the statistical accuracy given in the documentation.
3.5	The chemical mechanisms according to the model underpinning the predicted result (OECD principle 5)	1. The BCF model is mainly based on the relationship between bioconcentration and hydrophobicity. The model also takes into account the chemical structure and the ionic/non-ionic character of the substance.   2. Bioaccumulation is the net result of relative rates of chemical inputs to an organism from multimedia exposures (e.g., air, food, and water) and chemical outputs (or elimination) from the organism.   3. The model includes mechanistic processes for bioconcentration and bioaccumulation such as chemical uptake from the water at the gill surface (BCFs and BAFs) and the diet (BAFs only), and chemical elimination at the gill surface, fecal egestion, growth dilution and metabolic biotransformation (Arnot and Gobas 2003). Other processes included in the calculations are bioavailability in the water column (only the freely dissolved fraction can bioconcentrate) and absorption efficiencies at the gill and in the gastrointestinal tract.

References

- Arnot JA, Gobas FAPC. 2003. A generic QSAR for assessing the bioaccumulation potential of organic chemicals in aquatic food webs. QSAR and Combinatorial Science 22: 337-345.

- Arnot JA, Mackay D, Parkerton TF, Bonnell M. 2008a. A database of fish biotransformation rates for organic chemicals. Environmental Toxicology and Chemistry 27(11), 2263-2270.

- Arnot JA, Mackay D, Bonnell M. 2008b. Estimating metabolic biotransformation rates in fish from laboratory data. Environmental Toxicology and Chemistry 27: 341-351.

- Meylan, W.M., Howard, P.H, Aronson, D., Printup, H. and S. Gouchie. 1997. "Improved Method for Estimating Bioconcentration Factor (BCF) from Octanol-Water Partition Coefficient", SRC TR-97-006 (2nd Update), July 22, 1997; prepared for: Robert S. Boethling, EPA-OPPT, Washington, DC; Contract No. 68-D5-0012; prepared by: ; Syracuse Research Corp., Environmental Science Center, 6225 Running Ridge Road, North Syracuse, NY 13212.

- Meylan, WM, Howard, PH, Boethling, RS et al. 1999. Improved Method for Estimating Bioconcentration / Bioaccumulation Factor from Octanol/Water Partition Coefficient. Environ. Toxicol. Chem. 18(4): 664-672 (1999). 

- US EPA (2012). On-Line BCFBAF Help File. .

Identified Correction Factors (Appendix E)

Correction Factors: Not used for Log Kow < 1.

 

Biotransformation Fragments and Coefficient values (Appendix F)  

Fragment Description	Coefficient value	No. compounds containing fragment in total training set	Maximum number of each fragment in any individual compound	No. of instances of each fragment for the current substance
Aliphatic alcohol  [-OH]	-0.06155701	7	3	1
Ester   [-C(=O)-O-C]	-0.76052851	15	2	1
-CH2-  [linear]	0.02418707	109	28	4
-C=CH  [alkenyl hydrogen]	0.09884729	34	6	3

 

Assessment of Applicability Domain Based on Molecular Weight and log Kow

 

1. Bioconcentration Factor (BCF; Meylan et al., 1997/1999)

Training set: Molecular weights	Ionic	Non-ionic
Minimum	68.08	68.08
Maximum	991.8	959.17
Average	244	244
Assessment of molecular weight	Molecular weight within range of training set
Training set: Log Kow	Ionic	Non-ionic
Minimum	-6.5	-1.37
Maximum	11.26	11.26
Assessment of log Kow	Log Kow within range of training set.

2. Biotransformation Rate in Fish (kM; Arnot et al., 2008a/b)

Training set: Molecular weights
Minimum	68.08
Maximum	959.17
Average	259.75
Assessment of molecular weight	Molecular weight within range of training set
Training set: Log Kow
Minimum	0.31
Maximum	8.7
Assessment of log Kow	Log Kow within range of training set.

                                  

3. Arnot-Gobas BAF/BCF (Arnot & Gobas, 2003)

Assessment of log Kow: Log Kow within acceptable range (log Kow ≤ 9).

Description of key information

The test substance has a low potential for bioaccumulation based on its measured log Pow of 0.77. This is supported by calculated BCF values of 2.3 L/kg (Bysshe, 1990) and 3.16 L/kg (BCFBAF v3.01; BASF, 2018).

Additional information

QSAR-disclaimer

In Article 13 of Regulation (EC) No 1907/2006, it is laid down that information on intrinsic properties of substances may be generated by means other than tests, provided that the conditions set out in Annex XI (of the same Regulation) are met. Furthermore according to Article 25 of the same Regulation testing on vertebrate animals shall be undertaken only as a last resort.

 

According to Annex XI of Regulation (EC) No 1907/2006 (Q)SAR results can be used if (1) the scientific validity of the (Q)SAR model has been established, (2) the substance falls within the applicability domain of the (Q)SAR model, (3) the results are adequate for the purpose of classification and labeling and/or risk assessment and (4) adequate and reliable documentation of the applied method is provided.

 

For the assessment of the substance 4-hydroxybutyl acrylate (Q)SAR results were used for assessment of bioaccumulation.The criteria listed in Annex XI of Regulation (EC) No 1907/2006 are considered to be adequately fulfilled and therefore the endpoint(s) sufficiently covered and suitable for risk assessment.

 

Furthermore, as the substance has a low potential for bioaccumulation based on a log Kow <3, further experimental studies on bioaccumulation are not provided.