1,5-Pentanediamine, 2-methyl-, reaction products with 2-ethyl-1,4-butanediamine and glycidyl tolyl ether

Adsorption / desorption

Administrative data

Endpoint:

adsorption / desorption, other

Type of information:

(Q)SAR

Adequacy of study:

key study

Study period:

December 2017

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:

1. SOFTWARE
Model: KOCWIN (a module of EPI Suite (U.S. Environmental Protection Agency, 2012)
Submodel: soil adsorption coefficient (Koc), v2.00, U.S. EPA, 2010

2. SMILES OR OTHER IDENTIFIERS USED AS INPUT FOR THE MODEL
- 1CGE-1MPMD adduct CC(CN)CCCNCC(O)COc1ccccc1C
- 2CGE-1MPDA adduct isomer Cc1ccccc1OCC(O)CNCCCC(C)CNCC(O)COc1ccccc1C
- 3CGE-1MPMD Cc1ccccc1OCC(O)CNCC(C)CCCN(CC(O)COc1ccccc1C)C(O)COc1ccccc1C
- mephenesin Cc1ccccc1OCC(O)CO
- di-CGE Cc1ccccc1OCC(O)COc1ccccc1C
- MPMD CC(CN)CCCN

3. SCIENTIFIC VALIDITY OF THE (Q)SAR MODEL
The Koc describes the partitioning equilibrium for a substance between water and the organic carbon contained in soil or sediment.

4. APPLICABILITY DOMAIN
Not specified by developer. For both MCI and Kow methods, the minimum to maximum of molecular mass in the training data: 32 < MW < 665 [g/mol]. MW of the components of CGE-PMDA range from 116 to 595 g/mol.

5. ADEQUACY OF THE RESULT
The predications are considered reliable because the estimated Koc values for the analogues are consistent with the experimental data.

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

2017

Report date:

2017

Materials and methods

Test guideline

Guideline:

other: Guidelines not applicable

Version / remarks:

QSAR prediction

GLP compliance:

no

Remarks:

Not applicable for QSAR

Test material

Test material information

Constituent 1

Reference substance name:

1-[(5-amino-4-methylpentyl)amino]-3-(2-methylphenoxy)-propan-2-ol

Cas Number:

1617528-43-4

Molecular formula:

C16H28N2O2

IUPAC Name:

1-[(5-amino-4-methylpentyl)amino]-3-(2-methylphenoxy)-propan-2-ol

Constituent 2

Reference substance name:

1,1'-[(2-Methyl-1,5-pentanediyl)diimino]bis[3-(2-methylphenoxy)-propan-2-ol]

Cas Number:

1617528-45-6

Molecular formula:

C26H40N2O4

IUPAC Name:

1,1'-[(2-Methyl-1,5-pentanediyl)diimino]bis[3-(2-methylphenoxy)-propan-2-ol]

impurity 1

Reference substance name:

Mephenesin

EC Number:

200-427-4

EC Name:

Mephenesin

Cas Number:

59-47-2

Molecular formula:

C10H14O3

IUPAC Name:

3-(2-methylphenoxy)propane-1,2-diol

impurity 2

Reference substance name:

1,3-bis(2-methylphenoxy)propan-2-ol

Cas Number:

17181-49-6

Molecular formula:

C17H20O3

IUPAC Name:

1,3-bis(2-methylphenoxy)propan-2-ol

impurity 3

Reference substance name:

2-methylpentane-1,5-diamine

EC Number:

239-556-6

EC Name:

2-methylpentane-1,5-diamine

Cas Number:

15520-10-2

Molecular formula:

C6H16N2

IUPAC Name:

2-methylpentane-1,5-diamine

impurity 4

Reference substance name:

3,3’-(5-(2-hydroxy-3-(o-tolyloxy)propylamino)-4-methylpentylazanediyl)bis(1-(o-tolyloxy)propan-2-ol)

Molecular formula:

C36H52N2O6

IUPAC Name:

3,3’-(5-(2-hydroxy-3-(o-tolyloxy)propylamino)-4-methylpentylazanediyl)bis(1-(o-tolyloxy)propan-2-ol)

Details on test material:

used for QSAR; similar to the boundary composition; no particular lot identified

Results and discussion

Adsorption coefficient

Key result

Type:

log Koc

Remarks:

MCI method, geometric mean

Value:

2.78 dimensionless

Any other information on results incl. tables

Table 1: Soil Adsorption Coefficent Koc, estimated from molecular connectivity index (MCI).

Koc Estimate from MCI	1 CGE-1MPMD adduct	2 CGE-1MPMD adduct isomer	3 CGE-1MPMD	mephenesin	di-CGE	MPMD
1^stOrder Molecular Connectivity Index	9.63	15.452	20.723	6.236	9.665	3.808
Non-Corrected Log Koc (0.5213 MCI + 0.60)	5.62	8.6551	11.4028	3.8508	5.6380	2.5849
Fragment Corrections
Ether, aromatic (-C-O-C)	-0.6791	-1.3582	-1.3582	-0.6791	-1.3582	--
Nitrogen to Carbon (aliphatic) (-N-C)	-0.6382	-0.8509	-1.0637	--	--	-0.4255
Aliphatic Alcohol (-C-OH)	-1.3179	-2.6358	-2.6358	-2.6358	-1.3179	--
Corrected Log Koc	2.9848	3.8102	6.3452	1.0*	2.9619	2.1595
Estimated Koc	965.7 l·kg^-1	6460 l·kg^-1	2.24·10^6l·kg^-1	10 l·kg^-1	916.1 l·kg^-1	144.4 l·kg^-1

 

Table 2: Soil Adsorption Coefficent Koc, was estimated from n-octanol/water partition coefficient (Kow)

Koc Estimate from log Kow	1CGE-1MPMD adduct	2CGE-1MPMD adduct isomer	3CGE-1MPMD	mephenesin	di-CGE	MPMD
log Kow (Kowwin estimate)	1.97	4.08	5.03	1.41	3.85	0.27
Non-Corrected Log Koc (0.5213 MCI + 0.60)	2.0148	3.1819	3.7073	1.7050	3.0547	1.0744
Fragment Corrections
Ether, aromatic (-C-O-C)	0.0559	0.1118	0.1118	0.0559	0.1118	--
Nitrogen to Carbon (aliphatic) (-N-C)	-0.0654	-0.0871	-0.1089	--	--	-0.0436
Aliphatic Alcohol (-C-OH)	-0.4114	-0.8229	-0.8229	-0.8229	-0.4114	--
Corrected Log Koc	1.5939	2.3837	2.8874	0.9380	2.7550	1.0309
Estimated Koc	39.25 l·kg^-1	241.9 l·kg^-1	771.5 l·kg^-1	8.671 l·kg^-1	568.9 l·kg^-1	10.74 l·kg^-1

Applicant's summary and conclusion

Conclusions:

The Soil Adsorption Coefficient (Koc) for CGE-PMDA adduct log Koc 2.78 indicates a low risk potential.