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EC number: 604-569-1 | CAS number: 147126-62-3
- 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
Adsorption / desorption
Administrative data
- Endpoint:
- adsorption / desorption: screening
- Type of information:
- experimental study
- Adequacy of study:
- supporting study
- Study period:
- 17.08.2004 to 07.12.2004
- Reliability:
- 1 (reliable without restriction)
- Rationale for reliability incl. deficiencies:
- other: GLP study performed
Data source
Reference
- Reference Type:
- study report
- Title:
- Unnamed
- Year:
- 2 004
- Report date:
- 2004
Materials and methods
Test guideline
- Qualifier:
- according to guideline
- Guideline:
- OECD Guideline 106 (Adsorption - Desorption Using a Batch Equilibrium Method)
- Deviations:
- yes
- Principles of method if other than guideline:
- OECD 107 (Octanol/water partition coefficient) could not be completed because the test substance was unstable in water. As an alternative, OECD 105 (Octanol Solubility) was completed to allow for the calculation of the partition coefficient.
OECD 106 (Soil adsorption/desorption) was similarly not performed due to the instability of the test substance in water.
Each test method is described in its ·own section below which details materials, methods
and test results. - GLP compliance:
- yes (incl. QA statement)
Test material
- Reference substance name:
- (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylate
- EC Number:
- 604-569-1
- Cas Number:
- 147126-62-3
- Molecular formula:
- C14H24O4S
- IUPAC Name:
- (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylate
- Test material form:
- solid: particulate/powder
- Remarks:
- migrated information: powder
Constituent 1
- Radiolabelling:
- no
Study design
- Test temperature:
- 20.1 °C+- 0.2 °C
HPLC method
- Details on study design: HPLC method:
- In order to measure the amount of OSME in water in the presence of soil, it was necessary to develop an HPLC method capable of detecting OSME in the presence of organics present in soil. During the course of the method validation, it became clear that the test substance degrades rapidly in the presence of water.
We characterized OSME in acetonitrile, water, and various acetonitrile water mixtures
by HPLC under the following conditions:
HPLC under the following conditions:
• Flow isocratic at 1 ml/min
• Mobile phase: acetonitrile:buffer ( 0.0425% H3P04), 80:20
• Column: Supelcosil LC-18-S, 25 cm, 5 µm pore size
• Injection volume: 20 µL
• UV detector: 220 nm, Equipment Information: UV detector: Gilson Model 111 B
Chromatograms comparing OSME in acetonitrile and in water are shown in the report.
Batch equilibrium or other method
- Analytical monitoring:
- yes
- Details on sampling:
- The chromatogram on· the above left is OSME analyzed immediately after dissolution in water. The chromatogram shows a small peak of residual OSME at a retention time of 5.25 minutes. A large group of poorly resolved peaks consisting of OSME breakdown products can be seen between 2 and 3 minutes retention time. OSME was observed to immediately breaks down in water. Based on our dissociation constant measurements (see Section 16 of this report) and other observations we concluded that the test substance in water contains a single weakly acidic group with a pKa of 7.36 ± 0.05. A pKa of this magnitude rules out the presence of a carboxylic acid group in the breakdown products present in water. Such a strongly acidic group would be expected to display a pKa iiJ the range of 4. This suggested that the hydrolysis in water does not involve hydrolysis at the ester group but rather opening of the oxathiolane ring. Such a ring opening would be predicted to give rise to an enolizeable keto group. Such a group would be expected to display a pKa in the range of 7 or 8.
The enolizeable keto groups in, for example, acetoacetone, display a pKa of 8.2, while diacetyl acetone, displays a pKa of 7.4. The keto groups themselves are not acidic (Albert and Serjeant, 1962).
The HPLC chromatograms showed that a complex mixture of several breakdown products form when OSME was dissolved in water, almost immediately on contact. Our attempts to quench the hydrolysis were unsuccessful although it was possible to slow the rate of degradation by dilution in acetonitrile.
- Details on matrix:
- water and acetonitrile
- Details on test conditions:
- Evidence of chemical instability of substance during the test? Yes
Results and discussion
Applicant's summary and conclusion
- Validity criteria fulfilled:
- not applicable
- Conclusions:
- Our experiments demonstrated that OSME rapidly degraded in water giving rise to an unidentified series of products. Given the difficulty in isolating and quantifying the individual breakdown products, as would be required in order to conduct a soil adsorption/desorption study, we concluded that it was not possible to conduct an OECD Method 106 analysis within the present scope of work.
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