2-Propenoic acid, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl ester

Adsorption / desorption

Administrative data

Endpoint:

adsorption / desorption, other

Remarks:

adsorption

Type of information:

(Q)SAR

Adequacy of study:

key study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Accepted calculation method, substance within applicability domain (or: Accepted calculation method, but substance not within applicability domain of model)

Justification for type of information:

1. SOFTWARE
Estimation Programs Interface (EPI) Suite for Microsoft Windows, v4.11 (US EPA, 2012)

2. MODEL (incl. version number)
KOCWIN v2.00

3. SMILES OR OTHER IDENTIFIERS USED AS INPUT FOR THE MODEL
See section 'Test Material'.

4. SCIENTIFIC VALIDITY OF THE (Q)SAR MODEL
See section "overall remarks, attachements" for QMRF

5. APPLICABILITY DOMAIN
See field "Executive summary" for QPRF

6. ADEQUACY OF THE RESULT
- The model is scientifically valid (see QMRF).
- The model estimates the KOC for the uncharged molecule at 25 °C; screening information on adsorption (and desorption) is required for substances manufactured or imported in quantities of 10 t/y or more (see also QPRF).
- See QPRF for reliability assessment.

Data source

Reference

Reference 1

Reference Type:

other: EPIWIN calculation

Title:

Unnamed

Year:

2019

Report date:

2019

Reference 2

Reference Type:

other: Estimation software

Title:

Estimation Programs Interface Suite for Microsoft Windows, v4.11

Author:

US-EPA

Year:

2012

Bibliographic source:

United States Environmental Protection Agency, Washington, DC, USA

Materials and methods

Principles of method if other than guideline:

KOCWIN (v2.00): estimation using first-order Molecular Connectivity Index (MCI)

GLP compliance:

no

Type of method:

other: QSAR estimation: KOCWIN v2.00: Koc estimate from MCI

Test material

Test material information

Constituent 1

Reference substance name:

(2,2-dimethyl-1,3-dioxolan-4-yl)methyl prop-2-enoate

EC Number:

814-155-4

Cas Number:

13188-82-4

Molecular formula:

C9H14O4

IUPAC Name:

(2,2-dimethyl-1,3-dioxolan-4-yl)methyl prop-2-enoate

Test material form:

liquid

Study design

Test temperature:

25 °C

Results and discussion

Adsorption coefficient

Adsorption coefficient 1

Type:

Koc

Value:

10

Temp.:

25 °C

Adsorption coefficient 2

Type:

log Koc

Value:

0.7

Temp.:

25 °C

Any other information on results incl. tables

Copy & paste table with detailed results from KOCWIN output.

Applicant's summary and conclusion

Executive summary:

 

QPRF: KOCWIN v2.00 (18 Nov. 2013)

 

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	Adsorption to solid phase of soils etc.
		Dependent variable	Organic carbon normalised adsorption coefficient (Koc)
3.2	Algorithm (OECD Principle 2)	Model or submodel name	KOCWIN
		Model version	v. 2.00
		Reference to QMRF	QMRF: Estimation of Soil Adsorption Coefficient using KOCWIN v2.00 (EPI Suite v4.11): MCI methodology
		Predicted value (model result)	See “Results and discussion”
		Input for prediction	- Chemical structure via CAS number or SMILES
		Descriptor values	- MCI (first order molecular connectivity index) - Correction factors
3.3	Applicability domain (OECD principle 3)	Domains:
		1) Molecular weight (range of test data set: 32.04 to 665.02 g/mol; On-Line KOCWIN User’s Guide, Ch. 6.2.4 Domain)	Substance within range (186.21 g/mol)
		2) Correction factors: Number of instances of the identified correction factor does not exceed the maximum number as listed in Appendix D (On-Line KOCWIN User’s Guide)	Fulfilled.
3.4	The uncertainty of the prediction (OECD principle 4)	Statistical accuracy for training dataset: n = 516, r² = 0.916, std. dev. = 0.330, average dev. = 0.263
3.5	The chemical mechanisms according to the model underpinning the predicted result (OECD principle 5)	Adsorption is caused by temporary (reversible) or permanent bonding between the substance and a surface (e.g. due to van der Waals interactions, hydrogen bonding to hydroxyl groups, ionic interactions, covalent bonding, etc.). The organic carbon normalized adsorption coefficient (Koc) is the ratio of a substance concentration sorbed in the organic matter component of soil or sediment to that in the aqueous phase at equilibrium. MCI methodology: The first-order molecular connectivity index is a measure to describe a variety of properties of chemicals. According to Sabljic (1984; cited in Meylan et al., 1992), the soil sorption potential is highly correlated with the first order MCI. Therefore, it has been used to derive the adsorption coefficient.

 

References

- US EPA (2012). On-Line KOCWIN User’s Guide.

- Meylan, W., P.H. Howard and R.S. Boethling. 1992. Molecular topology/fragment contribution method for predicting soil sorption coefficients. Environ. Sci. Technol. 26: 1560-1567.

 

 

Assessment of estimation domain (molecular weight, fragments, correction factors):

 

Model:	KOCWIN v2.00	MCI & Log Kow method
Substance:	2-Propenoic acid, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl ester
CAS-#:	13188-82-4
SMILES:	CC1(C)OCC(COC(=O)C=C)O1
Molecular weight (g/mol):	186
Log Kow (experimental data):	1,5	Reference:
	Molecular weight (g/mol)				log Kow
	Minimum	Maximum	Average		Minimum	Maximum
Training set	32,04	665,02	224,4		-2,11	8,12
Validation set	73,14	504,12	277,8		-5,98	8,68
Assessment of molecular weight	Molecular weight within range of training and validation set.
Assessment of log Kow (only relevant for log Kow method)	Log Kow within range of training and validation set.
Appendix D. MCI & Log Kow Correction Factors for 447 Compound Training Set
Correction Factor Descriptor	Coefficient for Molecular Connectivity Index (MCI) Regression Methodology		Coefficient for log Kow Regression Methodology	Occurrence		No. of instances of each bond found for the current substance
	(new model)	Remark		(number of compounds	(max per structure)
Ether, aliphatic (-C-O-C-)	-0,871597		-0,090599	20	2	2
Ester (-C-CO-O-C-) or (HCO-O-C)	-1,296957	(a)	-0,065594	50	2	1
						.
(a) Counted up to twice per structure, regardless of number of occurrences.						.
(b) Either one or both carbons aromatic; if both carbons aromatic, can not be cyclic.						.
(c) Any nitrogen attached to double bond is not counted; also, carbonyl and thiocarbonyl are not counted as carbons.						.
(d) This is the only fragment counted, even if other fragments occur.						.
(e) Not included in regression derivation; estimated from other carbonyl fragments.						.
(f) Counted only once per structure, regardless of number of occurrences.						.