Amines, N-C12–14 (even numbered)-alkyltrimethylenedi-, reaction products with chloroacetic acid and diethylenetriamine, N-C12–14 (even numbered)-alkyl derivs.

Hydrolysis

Link to relevant study record(s)

Reference

Endpoint:

hydrolysis

Type of information:

read-across from supporting substance (structural analogue or surrogate)

Adequacy of study:

key study

Justification for type of information:

REPORTING FORMAT FOR THE ANALOGUE APPROACH

1. HYPOTHESIS FOR THE ANALOGUE APPROACH
This read-across is based on the hypothesis that source and target substances have similar toxicological properties because
- they are manufactured from similar or identical precursors under similar conditions
- they share structural similarities with common functional groups (corresponding to scenario 2 of the read-across assessment framework): both, the target and source substance, are aliphatic amines with C8-18 alkyl chains and acetate functions
- Two thirds (w/w) of the target substance Reaction product of lauryl-PDA/lauryl-DETA with chloroacetic acid (excluding the solvent water) are composed of the source substance DOPA-Glycinate. The remaining third of Reaction product of lauryl-PDA/lauryl-DETA with chloroacetic acid consists of other aliphatic amines and derivatives which are considered as structural analogues to those constituting the source substance DOPA-Glycinate and may therefore be expected to elicit comparable (eco)toxicological effects.

The read-across hypothesis is based on structural similarity of target and source substances. Based on available experimental data, including key physicochemical properties and data from acute toxicity, repeated dose toxicity, genotoxicity and short term ecotoxicity studies, the read-across hypothesis is supported by a quite similar toxicological profile of both substances.

(Eco)toxicological, physicochemical and environmental fate data are summarised in the data matrix; robust study summaries are included in the Technical Dossier in the respective sections.

Therefore, read-across from the existing ecotoxicity, environmental fate and toxicity studies conducted with the source substances is considered as an appropriate adaptation to the standard information requirements of the REACH Regulation for the target substance, in accordance with the provisions of Annex XI, 1.5 of the REACH Regulation.

Further details are attached to IUCLID section 13.

2. SOURCE AND TARGET CHEMICAL(S) (INCLUDING INFORMATION ON PURITY AND IMPURITIES)
For further details refer to IUCLID section 13.

3. ANALOGUE APPROACH JUSTIFICATION
For further details refer to IUCLID section 13.

4. DATA MATRIX
For further details refer to IUCLID section 13.

Reason / purpose for cross-reference:

read-across: supporting information

Reason / purpose for cross-reference:

read-across source

Duration:

5 d

Initial conc. measured:

>= 26.45 - <= 27.18 mg/L

Preliminary study:

Recoveries of 14C from the test solutions decreased to 59.3 % (for pH 7) and 58.6 % (for pH 9) at day 5 of the experiment respectively, whereas at pH 4, 105.6 % could be recovered. Low recoveries at pH 7 and 9 were explained by adsorption of the test substance onto the walls of the glass vials. Rinsing of the vial walls with 1 ml acetonitrile/water (3:7, v/v) and sonification resulted in improved recoveries of close to 100 % (see Table A7.1.1.1.1- 7).
Significant chromatographic peaks other than those attributable to the lead components of the test item were not detected: Any other signals accounted for less than 2.5 % ITR at any sampling time.

Since less than 10 % of the test item hydrolysed at 50 °C at pH 4, 7, and 9 within 5 days, corresponding to a DT50 (25°C) > 1 year (tier 1), no further hydrolysis testing was considered to be necessary (see below).

Transformation products:

not measured

Details on hydrolysis and appearance of transformation product(s):

Not applicable because the preliminary test results indicate that the substance is hydrolytically stable.

% Recovery:

>= 103.91 - <= 107.2

pH:

4

Temp.:

50 °C

Duration:

120 h

% Recovery:

>= 97.1 - <= 97.8

pH:

7

Temp.:

50 °C

Duration:

120 h

% Recovery:

> 92.9 - <= 93.3

pH:

9

Temp.:

50 °C

Duration:

120 h

pH:

4

Temp.:

25 °C

DT50:

> 1 yr

pH:

7

Temp.:

25 °C

DT50:

> 1 yr

pH:

9

Temp.:

25 °C

DT50:

> 1 yr

Conclusions:

The target substance is hydrolytically stable (half-life periods at pH 4, 7 and 9 can be expected to exceed one year at 25°C).

Description of key information

hydrolytically stable; half-life periods at pH 4, 7 and 9 > 1 year at 25°C (OECD guideline 111, GLP); read-across from DOPA-Glycinate

Key value for chemical safety assessment

Half-life for hydrolysis:

1 yr

at the temperature of:

25 °C

Additional information

No experimental data are available for the target substance Reaction product of lauryl-PDA/lauryl-DETA with chloroacetic acid. However, a hydrolysis study was conducted with the closely related source substance DOPA-Glycinate. A justification for read-across is attached to IUCLID section 13.

Dodecyl-1-¹⁴C-labelled DOPA-Glycinate was tested for hydrolysis according to OECD guideline 111 (2002). The test item was dissolved in buffered aqueous media of defined pH-values (pH 4, 7, or 9) and maintained at constant temperature (50 °C) in the darkness. The concentrations of the lead compounds of the test item were measured as a function of time. At 0, 1, 3 and 5 days radioactivity as well as the identity of the components of the test item and potential hydrolysis products were verified by HPLC-MS/MS.

The results of the preliminary test indicated no need for further testing. From day 1 to day 5 of the experiment, recoveries of¹⁴C in the test solution decreased from approx. 100 % to 59.3 % (at pH 7) and 58.6 % (at pH 9), respectively, whereas at pH 4 105.6 % of the radioactivity were recovered on day 5. It was clearly demonstrated that the test material had adsorbed onto the walls of the glass vials at pH 7 and 9, but was removable by rinsing the vial walls with acetonitrile/water, leading to total recovery rates of 92.9 and 102% as the sum of the test item solutions and the rinsing solutions. Less than 10 % of the test item hydrolysed in the preliminary test during five days at 50 ± 5 °C. Hence, k_H and DT₅₀ or DT₉₀ values could not be established.

In conclusion, DOPA-Glycinate is considered to be hydrolytically stable. The half-life periods at pH 4, 7 and 9 can be expected to exceed one year at 25 °C.