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EC number: 204-210-5 | CAS number: 117-80-6
Adsorption / desorption
Administrative data
Link to relevant study record(s)
- Endpoint:
- adsorption / desorption
- Remarks:
- adsorption
- Type of information:
- (Q)SAR
- Adequacy of study:
- weight of evidence
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- other: Accepted calculation method. Molecular weight within range of training and validation set. LogKow within range of training and validation set. The number of instances of each bond found for the current substance was exceeded in one case.
- Justification for type of information:
- QSAR prediction: migrated from IUCLID 5.6
- Principles of method if other than guideline:
- KOCWIN (v2.00): estimation using estimated or experimentally derived log Kow
- GLP compliance:
- no
- Type of method:
- other: QSAR estimation: KOCWIN v2.00: Koc estimate from log Kow
- Test temperature:
- 25 °C
- Computational methods:
- - Other: log Kow used for estimation: 2.65 (estimated by KOCWIN)
- Type:
- Koc
- Value:
- 1 953
- Temp.:
- 25 °C
- Remarks on result:
- other: Molecular weight within range of training and validation set. LogKow within range of training and validation set. The number of instances of each bond found for the current substance was exceeded in one case.
- Type:
- log Koc
- Value:
- 3.291
- Temp.:
- 25 °C
- Remarks on result:
- other: Molecular weight within range of training and validation set. LogKow within range of training and validation set. The number of instances of each bond found for the current substance was exceeded in one case.
- 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): Estimation using log Kow
Predicted value (model result)
See “Results and discussion”
Input for prediction
- Chemical structure via CAS number or SMILES
- log Kow (for log Kow method; optional)
Descriptor values
- Chemical structure
- 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 (227.05 g/mol)
2) log Kow (range of test data set: -2.11 to 8.12; On-Line KOCWIN User’s Guide, Appendices E & F)
Substance within range (2.65)
3) 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)
Not fulfilled.
3.4
The uncertainty of the prediction
(OECD principle 4)Nonpolar compounds: n = 68; r2=0.478, average dev. = 0.371
Polar compounds: n = 447, r²=0.855, std. dev. = 0.396, average dev. = 0.307
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.
Estimation using log Kow: The model is based on the high correlation of log Kow and the adsorption potential.
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):
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) Ketone (-C-CO-C-) -1.129027 (a) 0.195596 7 1 2 . (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 isnotcounted; also, carbonyl and thiocarbonyl arenotcounted as carbons. . (d) This is theonlyfragment 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. . - Endpoint:
- adsorption / desorption
- Remarks:
- adsorption
- Type of information:
- (Q)SAR
- Adequacy of study:
- weight of evidence
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- other: Accepted calculation method. Molecular weight of the compound within range of training and validation set. The number of instances of each bond found for the current substance was exceeded in one case.
- Justification for type of information:
- QSAR prediction: migrated from IUCLID 5.6
- 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 temperature:
- 25 °C
- Type:
- Koc
- Value:
- 1 243
- Temp.:
- 25 °C
- Remarks on result:
- other: Molecular weight of the compound within range of training and validation set. The number of instances of each bond found for the current substance was exceeded in one case.
- Type:
- log Koc
- Value:
- 3.094
- Temp.:
- 25 °C
- Remarks on result:
- other: Molecular weight of the compound within range of training and validation set. The number of instances of each bond found for the current substance was exceeded in one case.
- 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 (227.05 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)
Not 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):
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. 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) Ketone (-C-CO-C-) -1.129027 (a) 0.195596 7 1 2 . (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 isnotcounted; also, carbonyl and thiocarbonyl arenotcounted as carbons. . (d) This is theonlyfragment 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. .
Referenceopen allclose all
KOCWIN Program (v2.00) Results:
==============================
SMILES : c1ccc2C(=O)C(CL)=C(CL)C(=O)c2c1
CHEM : 1,4-Naphthalenedione, 2,3-dichloro-
MOL FOR: C10 H4 CL2 O2
MOL WT : 227.05
--------------------------- KOCWIN v2.00 Results ---------------------------
Koc Estimate from Log Kow:
-------------------------
Log Kow (Kowwin estimate) ......................... : 2.65
Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 2.3909
Fragment Correction(s):
2 Ketone (-C-CO-C-) ................... : 0.3912
* Quinone (diketone) ring ............... : 0.5086
Corrected Log Koc .................................. : 3.2907
Estimated Koc: 1953 L/kg <===========
KOCWIN Program (v2.00) Results:
==============================
SMILES : c1ccc2C(=O)C(CL)=C(CL)C(=O)c2c1
CHEM : 1,4-Naphthalenedione, 2,3-dichloro-
MOL FOR: C10 H4 CL2 O2
MOL WT : 227.05
--------------------------- KOCWIN v2.00 Results ---------------------------
Koc Estimate from MCI:
---------------------
First Order Molecular Connectivity Index ........... : 6.626
Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 4.0539
Fragment Correction(s):
2 Ketone (-C-CO-C-) ................... : -2.2581
* Quinone (diketone) ring ............... : 1.2986
Corrected Log Koc .................................. : 3.0944
Estimated Koc: 1243 L/kg <===========
Description of key information
Adsorption to solid soil phase is expected.
Key value for chemical safety assessment
Additional information
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 CAS 117 -80 -6 (Q)SAR results were used for adsorption/desorption.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.
Therefore, further experimental studies on adsorption/desorption are not provided.
The adsorption/desortpion potential of the substance was assessed with two QSAR calculation methods integrated in the EPISuite v4.11 (KOCWIN v2.00; MCI and logKow-method). Both the molecular weight and the logKow of the substance are within the respective training set ranges. The number of instances of each bond found for the current substance was exceeded in one case. However, this is not expected to have a significant influence on the result. In conclusion, the QSAR calculations are regarded as reliable. The MCI method determined a logKoc of 3.0944 and the estimate from the logKow a logKoc of 3.2907. Adsosorption to the solid soil phase is expected.
Information on Registered Substances comes from registration dossiers which have been assigned a registration number. The assignment of a registration number does however not guarantee that the information in the dossier is correct or that the dossier is compliant with Regulation (EC) No 1907/2006 (the REACH Regulation). This information has not been reviewed or verified by the Agency or any other authority. The content is subject to change without prior notice.
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