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EC number: - | CAS number: -
- Life Cycle description
- Uses advised against
- Endpoint summary
- Appearance / physical state / colour
- Melting point / freezing point
- Boiling point
- Density
- Particle size distribution (Granulometry)
- Vapour pressure
- Partition coefficient
- Water solubility
- Solubility in organic solvents / fat solubility
- Surface tension
- Flash point
- Auto flammability
- Flammability
- Explosiveness
- Oxidising properties
- Oxidation reduction potential
- Stability in organic solvents and identity of relevant degradation products
- Storage stability and reactivity towards container material
- Stability: thermal, sunlight, metals
- pH
- Dissociation constant
- Viscosity
- Additional physico-chemical information
- Additional physico-chemical properties of nanomaterials
- Nanomaterial agglomeration / aggregation
- Nanomaterial crystalline phase
- Nanomaterial crystallite and grain size
- Nanomaterial aspect ratio / shape
- Nanomaterial specific surface area
- Nanomaterial Zeta potential
- Nanomaterial surface chemistry
- Nanomaterial dustiness
- Nanomaterial porosity
- Nanomaterial pour density
- Nanomaterial photocatalytic activity
- Nanomaterial radical formation potential
- Nanomaterial catalytic activity
- Endpoint summary
- Stability
- Biodegradation
- Bioaccumulation
- Transport and distribution
- Environmental data
- Additional information on environmental fate and behaviour
- Ecotoxicological Summary
- Aquatic toxicity
- Endpoint summary
- Short-term toxicity to fish
- Long-term toxicity to fish
- Short-term toxicity to aquatic invertebrates
- Long-term toxicity to aquatic invertebrates
- Toxicity to aquatic algae and cyanobacteria
- Toxicity to aquatic plants other than algae
- Toxicity to microorganisms
- Endocrine disrupter testing in aquatic vertebrates – in vivo
- Toxicity to other aquatic organisms
- Sediment toxicity
- Terrestrial toxicity
- Biological effects monitoring
- Biotransformation and kinetics
- Additional ecotoxological information
- Toxicological Summary
- Toxicokinetics, metabolism and distribution
- Acute Toxicity
- Irritation / corrosion
- Sensitisation
- Repeated dose toxicity
- Genetic toxicity
- Carcinogenicity
- Toxicity to reproduction
- Specific investigations
- Exposure related observations in humans
- Toxic effects on livestock and pets
- Additional toxicological data
Hydrolysis
Administrative data
- Endpoint:
- hydrolysis
- Type of information:
- experimental study
- Adequacy of study:
- key study
- Study period:
- 6th August 2020 to 2nd February 2021
- Reliability:
- 1 (reliable without restriction)
- Rationale for reliability incl. deficiencies:
- guideline study
Data source
Reference
- Reference Type:
- study report
- Title:
- Unnamed
- Year:
- 2 021
- Report date:
- 2021
Materials and methods
Test guidelineopen allclose all
- Qualifier:
- according to guideline
- Guideline:
- OECD Guideline 111 (Hydrolysis as a Function of pH)
- Deviations:
- no
- Qualifier:
- according to guideline
- Guideline:
- EU Method C.7 (Degradation: Abiotic Degradation: Hydrolysis as a Function of pH)
- Deviations:
- no
- GLP compliance:
- yes (incl. QA statement)
Test material
- Reference substance name:
- Reaction mass of 2(R/S)‐1‐{[(1R,2S,5R,8S)‐4,4,8‐trimethyltricyclo[6.3.1.0~2,5~]dodecan‐1‐yl]oxy}pentan‐2‐o and 2(R/S)‐1‐{[(1S,2S,5R,8R)‐1,4,4‐trimethyltricyclo[6.3.1.0~2,5~]dodecan‐8‐yl]oxy}pentan‐2‐ol
- Molecular formula:
- C20H36O2
- IUPAC Name:
- Reaction mass of 2(R/S)‐1‐{[(1R,2S,5R,8S)‐4,4,8‐trimethyltricyclo[6.3.1.0~2,5~]dodecan‐1‐yl]oxy}pentan‐2‐o and 2(R/S)‐1‐{[(1S,2S,5R,8R)‐1,4,4‐trimethyltricyclo[6.3.1.0~2,5~]dodecan‐8‐yl]oxy}pentan‐2‐ol
- Test material form:
- liquid: viscous
- Details on test material:
- Chemical name: 1‐[(4,4,8‐trimethyltricyclo[6.3.1.02,5]dodecan‐1‐yl)oxy]pentan‐2‐ol and 1‐[(1,4,4‐trimethyltricyclo[6.3.1.02,5]dodecan‐8‐yl)oxy]pentan‐2‐ol and isomers
Constituent 1
- Specific details on test material used for the study:
- Test Item
Identification: FRET 18-0091
Chemical name: 1‐[(4,4,8‐trimethyltricyclo[6.3.1.02,5]dodecan‐1‐yl)oxy]pentan‐2‐ol and 1‐[(1,4,4‐trimethyltricyclo[6.3.1.02,5]dodecan‐8‐yl)oxy]pentan‐2‐ol and isomers
Appearance: light yellow viscous liquid
Batch: RDEA571-42
Purity: 92.0%
Expiry date: 01 December 2021
Storage conditions: room temperature, in the dark - Radiolabelling:
- no
Study design
- Analytical monitoring:
- yes
- Remarks:
- The concentration of test item in the sample solutions was determined by gas chromatography (GC).
- Details on sampling:
- Duplicate sample solutions were taken initially and from the waterbath at various time points. The pH of each solution was recorded.
Duplicate standard solutions of test item were prepared in hexane at a nominal concentration of 5 mg/L. - Buffers:
- The test system consisted of buffer solutions at pH’s 4, 7 and 9, detailed in the following table: (Please see 'Any other information on materials and methods incl. tables')
The buffer solutions were passed through a 0.2 µm membrane filter to sterilize and subjected to ultrasonication and degassing with nitrogen to minimize dissolved oxygen. - Details on test conditions:
- Preliminary Test/Tier 1
A spiking solution was prepared at a nominal 50 mg/L in methanol. This was used to prepare stock solutions of test item at a nominal 0.5 mg/L in the three buffer solutions containing 1% of the acetonitrile as a co-solvent. The stock solutions were split into individual glass vessels, sealed with no headspace, for each data point. These sample solutions were shielded from light whilst maintained at the test temperature. The sample solutions were maintained at 50.0 ± 0.5 °C for a period of 5 days.
Preliminary Test/Tier 1 – Repeat
A spiking solution was prepared at a nominal 10 mg/L in acetone. This was used to prepare stock solutions of test item at a nominal 0.5 mg/L in the three buffer solutions containing 5% of the acetone as a co-solvent. The stock solutions were split into individual glass vessels, sealed with minimal headspace (nitrogen filled), for each data point. These sample solutions were shielded from light whilst maintained at the test temperature. The sample solutions were maintained at 50.0 ± 0.5 °C for a period of 5 days.
Tier 2
A spiking solution was prepared at a nominal 10 mg/L in acetone. This was used to prepare stock solutions of test item at a nominal 0.5 mg/L in the three buffer solutions containing 5% of the acetone as a co-solvent. The stock solutions were split into individual glass vessels, sealed with minimal headspace (nitrogen filled), for each data point. These sample solutions were shielded from light whilst maintained at the test temperature. The sample solutions were maintained at 25.0 ± 0.5 °C for a period of 28 days.
Duration of testopen allclose all
- Duration:
- 120 h
- pH:
- 9
- Temp.:
- 25 °C
- Initial conc. measured:
- 0.408 - < 0.444 mg/L
- Duration:
- 120 h
- pH:
- 7
- Temp.:
- 25 °C
- Initial conc. measured:
- 0.353 - < 0.404 mg/L
- Remarks:
- Tier 2
- Duration:
- 120 h
- pH:
- 4
- Temp.:
- 25 °C
- Initial conc. measured:
- 0.409 - < 0.415 mg/L
- Remarks:
- Tier 2
- Number of replicates:
- Due to an unexpected significant reduction in the concentration of the test item at all pHs, preliminary/tier 1 was repeated to investigate the possible loss of test item due to volatilizing and absorption to the vessel lid.
6 replicates per pH test (3 of sample A, 3 of sample B) - Positive controls:
- no
- Negative controls:
- no
Results and discussion
- Preliminary study:
- Due to the nature/quantity of this information please see 'Any other information on results and discussion incl. tables'
- Transformation products:
- no
Total recovery of test substance (in %)open allclose all
- % Recovery:
- 94.9 - < 101
- pH:
- 9
- Temp.:
- 50 °C
- Duration:
- 120 h
- % Recovery:
- 94.4 - < 100
- pH:
- 7
- Temp.:
- 50 °C
- Duration:
- 120 h
- % Recovery:
- 91.4 - < 98.6
- pH:
- 4
- Temp.:
- 50 °C
- Duration:
- 120 h
Dissipation DT50 of parent compoundopen allclose all
- Key result
- pH:
- 9
- Temp.:
- 25 °C
- Hydrolysis rate constant:
- 0 h-1
- Key result
- pH:
- 7
- Temp.:
- 25 °C
- Hydrolysis rate constant:
- 0 h-1
- Key result
- pH:
- 4
- Temp.:
- 25 °C
- Hydrolysis rate constant:
- ca. 0 h-1
Any other information on results incl. tables
Preliminary Test/Tier 1
The mean peak areas relating to the standard and sample solutions are shown in the following table:
Table 2
Solution | Mean Peak Area |
Standard 5.01 mg/L | 2.6082 x 105 |
Standard 5.21 mg/L | 2.7291 x 105 |
Initial Sample A, pH 4 | 2.2304 x 105 |
Initial Sample B, pH 4 | 2.1103 x 105 |
Initial Sample A, pH 7 | 2.2903 x 105 |
Initial Sample B, pH 7 | 2.4362 x 105 |
Initial Sample A, pH 9 | 2.3389 x 105 |
Initial Sample B, pH 9 | 2.3411 x 105 |
Standard 5.09 mg/L | 3.6136 x 105 |
Standard 5.18 mg/L | 3.6471 x 105 |
24 Hour Sample A, pH 4 | 8.7901 x 104 |
24 Hour Sample B, pH 4 | 8.1342 x 104 |
24 Hour Sample A, pH 7 | 9.8240 x 104 |
24 Hour Sample B, pH 7 | 1.3558 x 105 |
24 Hour Sample A, pH 9 | 1.1140 x 105 |
24 Hour Sample B, pH 9 | 1.0598 x 105 |
Standard 5.09 mg/L | 3.3106 x 105 |
Standard 5.20 mg/L | 3.4475 x 105 |
120 Hour Sample A, pH 4 | 1.9267 x 104 |
120 Hour Sample B, pH 4 | 1.9738 x 104 |
120 Hour Sample A, pH 7 | 2.1009 x 104 |
120 Hour Sample B, pH 7 | 2.3731 x 104 |
120 Hour Sample A, pH 9 | 2.1988 x 104 |
120 Hour Sample B, pH 9 | 2.5429 x 104 |
The test item concentrations at the given time points are shown in the following tables:
Table 3 pH 4 at 50 ºC
Time (Hours) | Concentration (mg/L) | % of Mean Initial Concentration | ||
A | B | A | B | |
0 | 0.427 | 0.404 | 103 | 97.2 |
24 | 0.124 | 0.115 | 29.9 | 27.7 |
120 | 0.029 | 0.030 | 7.06 | 7.24 |
Table 4 pH 7 at 50 ºC
Time (Hours) | Concentration (mg/L) | % of Mean Initial Concentration | ||
A | B | A | B | |
0 | 0.438 | 0.466 | 96.9 | 103 |
24 | 0.139 | 0.192 | 30.7 | 42.4 |
120 | 0.032 | 0.036 | 7.07 | 7.99 |
Table 5 pH 9 at 50 ºC
Time (Hours) | Concentration (mg/L) | % of Mean Initial Concentration | ||
A | B | A | B | |
0 | 0.448 | 0.448 | 100 | 100 |
24 | 0.157 | 0.150 | 35.2 | 33.5 |
120 | 0.033 | 0.039 | 7.48 | 8.65 |
Due to an unexpected significant reduction in the concentration of the test item at all pHs, preliminary/tier 1 was repeated to investigate the possible loss of test item due to volatilizing and absorption to the vessel lids.
Preliminary Test/Tier 1 - Repeat
The mean peak areas relating to the standard and sample solutions are shown in the following table:
Table 6
Solution | Mean Peak Area |
Standard 5.16 mg/L | 2.8948 x 105 |
Standard 5.23 mg/L | 2.9375 x 105 |
Initial Sample A, pH 4 | 2.3036 x 105 |
Initial Sample B, pH 4 | 2.4192 x 105 |
Initial Sample A, pH 7 | 2.3012 x 105 |
Initial Sample B, pH 7 | 2.4165 x 105 |
Initial Sample A, pH 9 | 2.4485 x 105 |
Initial Sample B, pH 9 | 2.5148 x 105 |
Standard 5.05 mg/L | 2.7356 x 105 |
Standard 5.08 mg/L | 2.7197 x 105 |
24 Hour Sample A, pH 4 | 1.4390 x 105 |
24 Hour Sample B, pH 4 | 1.5784 x 105 |
24 Hour Sample A, pH 7 | 1.5351 x 105 |
24 Hour Sample B, pH 7 | 1.5077 x 105 |
24 Hour Sample A, pH 9 | 1.4605 x 105 |
24 Hour Sample B, pH 9 | 1.5960 x 105 |
Standard 5.04 mg/L | 2.5525 x 105 |
Standard 5.05 mg/L | 2.5005 x 105 |
120 Hour Sample A, pH 4 | 5.0678 x 104 |
120 Hour Sample B, pH 4 | 3.6511 x 104 |
120 Hour Sample A, pH 7 | 4.6874 x 104 |
120 Hour Sample B, pH 7 | 4.5374 x 104 |
120 Hour Sample A, pH 9 | 3.8071 x 104 |
120 Hour Sample B, pH 9 | 4.7657 x 104 |
The test item concentrations at the given time points are shown in the following tables:
Table 7 pH 4 at 50 ºC - Repeat
Time (Hours) | Concentration (mg/L) | % of Mean Initial Concentration | ||
A | B | A | B | |
0 | 0.410 | 0.431 | 97.6 | 102 |
24 | 0.267 | 0.293 | 63.5 | 69.6 |
120 | 0.101 | 0.073 | 24.0 | 17.3 |
Table 8 pH 7 at 50 ºC - Repeat
Time (Hours) | Concentration (mg/L) | % of Mean Initial Concentration | ||
A | B | A | B | |
0 | 0.410 | 0.430 | 97.6 | 102 |
24 | 0.285 | 0.280 | 67.8 | 66.6 |
120 | 0.094 | 0.091 | 22.3 | 21.6 |
Table 9 pH 9 at 50 ºC - Repeat
Time (Hours) | Concentration (mg/L) | % of Mean Initial Concentration | ||
A | B | A | B | |
0 | 0.436 | 0.448 | 98.7 | 101 |
24 | 0.271 | 0.296 | 61.3 | 67.0 |
120 | 0.076 | 0.095 | 17.2 | 21.5 |
This test had a higher concentration of test item remaining at 24 and 120 hours. This suggested that the higher percentage of organic solvent used as a co-solvent aided retention of the test item in solution. As a significant amount of test item was still lost at each pH, it suggested that adsorption to the vessel caps was not a major contribution to reduction in concentration in solution. It was considered that at 50 °C the test item was appreciably volatile, and this was the major contributor to loss of test item from solution. Therefore, it was decided to perform a tier 2 test directly at 25 °C for a period of 28 days.
Discussion
The preliminary/tier 1 test was initially performed using liquid chromatography mass spectrometry (LC-MS) for the sample analysis. The method had been shown to be acceptably linear from nominally 5 x 10-3 to 0.1 mg/L for the appropriate matrices. Timepoints were taken at 0, 24 and 120 hours also. However, instrument response was variable at times, and it was considered not reliable enough for accurate quantitation. It was probably that the method was sensitive to matrix variation even when solutions were matrix matched. Additionally, a significant peak at the retention time of the test item was observed in all matrix blanks. As a GC method had already been developed for the test item and considered reliable, it was decided to repeat the preliminary/tier 1 test using this analytical method. As the GC method was significantly less sensitive than the LC-MS, a sample extraction procedure had to be developed and validated. The results from the LC-MS analyses did indicate a loss in test item of similar magnitude as observed in the subsequent preliminary/tier 1 test.
The sample recovery procedure was performed for the sample preparation with 1% acetonitrile co-solvent only. A separate procedure for the 5% acetone co-solvent was not performed. However, it was considered that the procedure validated was adequately similar. This is because some of the acetone would partition into the extracting hexane and the ionic nature of the sodium chloride would enhance partitioning of the test item and acetone into the hexane. Also, as the test item has a high partition coefficient it would naturally favour the organic environment of the hexane solvent.
Various small peaks and baseline noise integration occurred in many of the GC chromatograms of the various matrix blanks. The areas of these have not been reported. As the peaks were often single entities and did not have a profile that matched that of the multi-component test item, they were considered to not represent the test item. The matrix blanks were not subtracted from the standards or samples.
The repeated Preliminary/Tier 1 test used a higher percentage of co-solvent and that was less polar but still water soluble to investigate if this helped retain the test item in solution. It had been considered that as the test item had a low water solubility, it could have been coming out of solution even though the test concentration was below the water solubility of the test item. This would be more likely as the test solutions are prepared in buffers rather than purified water. However, this process would have been expected to occur quickly rather than the gradual decrease over time. The test temperature of 50 °C should also have enhanced solubility of the test item.
Alternatively, it was considered that the test item may have been volatizing from solution even though initially testing avoided a headspace above the sample in the test vessel. Volatization would have been enhanced by the 50 °C test temperature and not unreasonable to occur gradually as this temperature is below the boiling point of the test item. The 5% acetone co-solvent was also to try to minimize volatization, if lack of solubilization in the aqueous media was contributing to the issue. Although the results for the repeated Preliminary/Tier 1 test still demonstrated a reduction in test item concentration for all three pHs, the loss was less than occurred using 1% acetonitrile co-solvent.
The decision for definitive testing was to perform the test directly at 25 °C. This should then significantly reduce volatization and demonstrate what may happen in the environment even though the 5% acetone co-solvent was retained. The test was conducted over a 28-day period to allow any changes to be distinctly observed and has been recommended by regulatory authorities previously.
One data point was removed from the correlation of the data points for both the pH 7 and pH 9 tests at 25 °C. This was because they were considered inconsistent and to have a significant effect on the correlation. They are plotted, colored red, on the graphical representation in Appendix 2 for reference.
The test item has no functional groups expected to be hydrolytically unstable at environmentally relevant temperatures and pH; therefore, the reduction in test item concentration in the samples was considered to be more likely due to a physical loss rather than degradation. Degradation results have been reported for information.
After 28 days, the estimated rate constant and half-life at 25 °C of the test item are shown in the following table:
Table 15
pH | Estimated Rate Constant at 25 °C (hr-1) | Estimated Half-Life | Most Test Item Lost from a Single Sample (%) |
4 | 4.48 x 10-4 | 64.5 | 36.6 |
7 | 3.42 x 10-4 | 84.4 | 21.4 |
9 | 4.30 x 10-4 | 67.2 | 28.8 |
Applicant's summary and conclusion
- Validity criteria fulfilled:
- yes
- Conclusions:
- The hydrolytic stability of the test item was assessed. Although the test item had no functional groups expected to be hydrolytically unstable at environmentally relevant temperatures and pH, the concentration of test item in solution decreased over time; this was considered to be predominantly due to volatilization.
- Executive summary:
Summary
The determination was carried out using a procedure designed to be compatible with Method C.7 Abiotic Degradation, Hydrolysis as a Function of pH of Commission Regulation (EC) No 440/2008 of 30 May 2008 and Method 111 of the OECD Guidelines for Testing of Chemicals, 13 April 2004
Results/Conclusion
The hydrolytic stability of the test item was assessed. Although the test item had no functional groups expected to be hydrolytically unstable at environmentally relevant temperatures and pH, the concentration of test item in solution decreased over time; this was considered to be predominantly due to volatilization. After 28 days, the estimated rate constant and half-life at 25 °C of the test item are shown in the following table:
Table 15
pH
Estimated Rate Constant at 25 °C (hr-1)
Estimated Half-Life
at 25 °C (days)Most Test Item Lost from a Single Sample (%)
4
4.48 x 10-4
64.5
36.6
7
3.42 x 10-4
84.4
21.4
9
4.30 x 10-4
67.2
28.8
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