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EC number: 208-594-5 | CAS number: 534-22-5
- 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
Basic toxicokinetics
Administrative data
- Endpoint:
- basic toxicokinetics in vitro / ex vivo
- Type of information:
- experimental study
- Adequacy of study:
- supporting study
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- study well documented, meets generally accepted scientific principles, acceptable for assessment
Data source
Reference
- Reference Type:
- publication
- Title:
- Reactive metabolites from the bioactivation of toxic methylfurans
- Author:
- V. Ravindranath et al.
- Year:
- 1 984
- Bibliographic source:
- Science, Vol. 224, p. 884-6, 1984
Materials and methods
- Objective of study:
- metabolism
Test guideline
- Qualifier:
- no guideline followed
- Principles of method if other than guideline:
- Goal: to determine whether intermediates such as unsaturated dialdehydes (which have reactive functionality) are formed from 2-methylfuran and to assess to what extend they could be involved in the covalent binding and toxicity of 2-methylfuran.
- GLP compliance:
- no
Test material
- Reference substance name:
- 2-methylfuran
- EC Number:
- 208-594-5
- EC Name:
- 2-methylfuran
- Cas Number:
- 534-22-5
- Molecular formula:
- C5H6O
- IUPAC Name:
- 2-methylfuran
Constituent 1
- Specific details on test material used for the study:
- not available
- Radiolabelling:
- no
Test animals
- Species:
- rat
- Strain:
- not specified
- Remarks:
- liver microsomal preparations were used
- Details on species / strain selection:
- not applicable
- Sex:
- not specified
- Details on test animals or test system and environmental conditions:
- not applicable
Administration / exposure
- Route of administration:
- intraperitoneal
- Details on exposure:
- not applicable
- Duration and frequency of treatment / exposure:
- not applicable
- No. of animals per sex per dose / concentration:
- not applicable
- Positive control reference chemical:
- not applicable
- Details on study design:
- Experiment 1:
Rat hepatic microsomal incubations were performed in the presence and absence of NADPH, semicarbazide, and 2-methylfuran.
HPLC analyses of extracts from incubations with 2-methylfuran showed peaks corresponding to the synthetic acetylacrolein. When NADPH or semicarbazide or both were deleted, no such peaks were observed.
Subsequent preparative HPLC, purification by gel permeation chromatography and further comparisons by mass spectroscopy with acetylacrolein standards confirmed the identity. It appears that the aldehyde is the principal binding species.
Experiment 2:
To investigate the possibility that the unsaturated aldehyde might require further activation before it was bound.
Synthetic acetylacrolein was shown to be bound quickly in microsomal incubations and there was no further enhancement by the presence of NADPH. - Details on dosing and sampling:
- not specified
- Statistics:
- not applicable
Results and discussion
Toxicokinetic / pharmacokinetic studies
- Details on absorption:
- not applicable
- Details on distribution in tissues:
- not applicable
- Details on excretion:
- not applicable
Any other information on results incl. tables
Results experiment 1:
HPLC analyses of extracts from incubations with 2-methylfuran showed peaks corresponding to the synthetic acetylacrolein. When NADPH or semicarbazide or both were deleted, no such peaks were observed.
Subsequent preparative HPLC, purification by gel permeation chromatography and further comparisons by mass spectroscopy with acetylacrolein standards confirmed the identity. It appears that the aldehyde is the principal binding species.
Results experiment 2:
Synthetic acetylacrolein was shown to be bound quickly in microsomal incubations and there was no further enhancement by the presence of NADPH.
Applicant's summary and conclusion
- Conclusions:
- The unsaturated aldehyde acetylacrolein has been identified as the principal reactive intermediate of 2-methylfuran, that is produced and bound covalently to tissue macromolecules in hepatic and pulmonary microsomal systems in vitro
- Executive summary:
This study investigated the mechanism of toxicity of furans after cytochrome P-450 monooxygenase-catalyzed bioactivation of the test compound in situ directly within the target tissue to highly reactive electophilic products.
The results of the study provides new insight into the metabolic activation of toxic furans. At least in the case of alkylfurans, the unsaturated aldehyde intermediates are the products of microsomal metabolism. Therefore, these reactive compounds may be the ultimate toxic metabolites responsible for target tissue alkylation and for toxicity produced by the parent furans in vivo. Epoxides, even if formed transiently, appear not to play a major role in the covalent binding nor in the toxicity of the simple furan.
HPLC analyses of extracts from incubations with 2-methylfuran showed peaks corresponding to the synthetic acetylacrolein. When NADPH or semicarbazide or both were deleted, no such peaks were observed.
Synthetic acetylacrolein was shown to be bound quickly in microsomal incubations and there was no further enhancement by the presence of NADPH.
The unsaturated aldehyde acetylacrolein has been identified as the principal reactive intermediate of 2-methylfuran, that is
produced and bound covalently to tissue macromolecules in hepatic and pulmonary microsomal systems in vitro
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