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EC number: 214-804-6 | CAS number: 1195-79-5
- 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
Biodegradation in water: screening tests
Administrative data
Link to relevant study record(s)
- Endpoint:
- biodegradation in water: ready biodegradability
- Type of information:
- experimental study
- Adequacy of study:
- key study
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- other: Data is from peer reviewed journal
- Justification for type of information:
- Data is from peer reviewed journal
- Qualifier:
- according to guideline
- Guideline:
- other: as mentioned below
- Principles of method if other than guideline:
- Biodegradation study was conducted for evaluating the percentage biodegradability of test substance 3,3-Dimethyl-8,9-dinorbornan-2-one.
- GLP compliance:
- not specified
- Specific details on test material used for the study:
- - Name of test material (IUPAC name): 3,3-Dimethyl-8,9-dinorbornan-2-one
- Common name: 1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
- Molecular formula: C10H16O
- Molecular weight: 152.2354 g/mol
- Smiles notation: C[C@@]12CC[C@@H](C1)C(C)(C)C2=O
- InChl: 1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m0/s1
- Substance type: Organic
- Physical state: Liquid
- Other: d-,1-Fenchone was distilled through a 24 inch Vigreux column at 190-191.5° and chromatographed on Florisil. - Oxygen conditions:
- not specified
- Inoculum or test system:
- other: Corynebacterium spp. (Bacteria)
- Details on inoculum:
- - Method of cultivation: Corynebacterium sp., strain T1, was inoculated from stock culture slants into 100 ml sterile nutrient broth (Difco; 8.0 g/liter) and grown at 30°C with shaking for 24 hours. Then, 10 ml portions were used to inoculate the test vessel containing the test chemical fenchone.
- Duration of test (contact time):
- 48 h
- Initial conc.:
- 250 000 mg/L
- Based on:
- test mat.
- Parameter followed for biodegradation estimation:
- other: Thin Layer Chromatography (TLC) and Gas Chromatography (GC)
- Details on study design:
- TEST CONDITIONS
- Test temperature: 30°C
TEST SYSTEM
- Culturing apparatus: Erlenmeyer flasks were used as a test vessel for the study.
- Number of culture flasks/concentration: 6 repilcates - Key result
- Parameter:
- other: Thin Layer Chromatography (TLC) and Gas Chromatography (GC)
- Sampling time:
- 48 h
- Remarks on result:
- other: %degradation value of chemical was not known, but chemical fenchone undergoes degradation by Corynebacterium spp. giving rise to 1,2- and 2,3-fencholides, respectively.
- Details on results:
- A mixture of authentic 1,2- and 2,3-fencholides, obtained by the Baeyer-Villiger oxidation of fenchone with peracetic acid, showed essentially the same chromatographic properties as the biologically derived material. It will be noted that the major component corresponds to the 1,2-fencholide.
- Validity criteria fulfilled:
- not specified
- Interpretation of results:
- other: biodegradable
- Conclusions:
- A mixture of authentic 1,2- and 2,3-fencholides, obtained by the Baeyer-Villiger oxidation of 3,3-Dimethyl-8,9-dinorbornan-2-one (fenchone) with peracetic acid, showed essentially the same chromatographic properties as the biologically derived material. It will be noted that the major component corresponds to the 1,2-fencholide. Thus, based on this, 3,3-Dimethyl-8,9-dinorbornan-2-one is considered to be biodegradable in water.
- Executive summary:
Biodegradation study was conducted for evaluating the percentage biodegradability of test substance 3,3-Dimethyl-8,9-dinorbornan-2-one (CAS no. 1195-79-5).Corynebacterium spp. (Bacteria), an organism which grows at the expense of either (+)- or (-)- camphor was used as a test inoculum for the study. Corynebacterium sp., strain T1, was inoculated from stock culture slants into 100 ml sterile nutrient broth (Difco; 8.0 g/liter) and grown at 30°C with shaking for 24 hours. Then, 10 ml portions were used to inoculate the test vessel containing the test chemical 3,3-Dimethyl-8,9-dinorbornan-2-one. Ten ml portions were used to inoculate six 2 liter Erlenmeyer flasks each containing 400 ml of sterile broth. After 24 hours incubation 2.4 g3,3-Dimethyl-8,9-dinorbornan-2-onein N,N,-dimethyl formamide (0.25 g/ml) was equally divided among all six flasks and incubation continued for a further 24 hours. The cells were then centrifuged and the clear neutral supernatant extracted 3 times with 0.5 vol. diethyl ether. The ether solution, after drying over anhydrous Na2SO4, was taken to dryness and 1.12 g of pale yellow crystalline solid obtained. When crystallized from light petroleum (b.p. range 60-68°C) at -72°C, the material had m.p. 73-75°C, λCHCl3max 5.48µ (Found: C, 70.82; H 9.49. C10H16O2 requires C, 71.4; H, 9.52). Thin layer chromatography on silica gel G Drinkmann with ether-light petroleum (40:60, v/v) as solvent, revealed a single component reacting with alkaline hydroxylamine and detectable as its purple ferric hydroxamate. Gas chromatography on a stationary phase of 5% silicone gum rubber SE-30 at 150°C gave only a single peak but on 5% butanediol succinate polyester at 150°C a second component, approximately 10% of the total peak area, was distinguishable. A mixture of authentic 1,2- and 2,3-fencholides, obtained by the Baeyer-Villiger oxidation of 3,3-Dimethyl-8,9-dinorbornan-2-one (fenchone) with peracetic acid, showed essentially the same chromatographic properties as the biologically derived material. It will be noted that the major component corresponds to the 1,2-fencholide.Thus, based on this, 3,3-Dimethyl-8,9-dinorbornan-2-one is considered to be biodegradable in nature.
Reference
Table: Chromatographic Properties of Fenchone and Related Compounds.
Compound
|
Rf*
|
Retention time+ on |
|
SE-30 |
Butanediol succinate polyester |
||
Fenchone (3,3-Dimethyl-8,9-dinorbornan-2-one) |
- |
0.72
|
-
|
Where,
* =Thin layer chromatography on silica gel plates activated at 110°C for 30 minutes and developed with ether-light petroleum (40:60 v/v).
+ =Vapor phase chromatography retention times in minutes after emergence of solvent. Both SE-30 and butanediol succinate polyester were maintained at 150°.
Description of key information
Biodegradation study was conducted for evaluating the percentage biodegradability of test substance 3,3-Dimethyl-8,9-dinorbornan-2-one (CAS no. 1195-79-5) (P. J. Chapman, et. al; 1965). Corynebacterium spp. (Bacteria), an organism which grows at the expense of either (+)- or (-)- camphor was used as a test inoculum for the study. Corynebacterium sp., strain T1, was inoculated from stock culture slants into 100 ml sterile nutrient broth (Difco; 8.0 g/liter) and grown at 30°C with shaking for 24 hours. Then, 10 ml portions were used to inoculate the test vessel containing the test chemical 3,3-Dimethyl-8,9-dinorbornan-2-one. Ten ml portions were used to inoculate six 2 liter Erlenmeyer flasks each containing 400 ml of sterile broth. After 24 hours incubation 2.4 g3,3-Dimethyl-8,9-dinorbornan-2-onein N,N,-dimethyl formamide (0.25 g/ml) was equally divided among all six flasks and incubation continued for a further 24 hours. The cells were then centrifuged and the clear neutral supernatant extracted 3 times with 0.5 vol. diethyl ether. The ether solution, after drying over anhydrous Na2SO4, was taken to dryness and 1.12 g of pale yellow crystalline solid obtained. When crystallized from light petroleum (b.p. range 60-68°C) at -72°C, the material had m.p. 73-75°C, λCHCl3max 5.48µ (Found: C, 70.82; H 9.49. C10H16O2 requires C, 71.4; H, 9.52). Thin layer chromatography on silica gel G Drinkmann with ether-light petroleum (40:60, v/v) as solvent, revealed a single component reacting with alkaline hydroxylamine and detectable as its purple ferric hydroxamate. Gas chromatography on a stationary phase of 5% silicone gum rubber SE-30 at 150°C gave only a single peak but on 5% butanediol succinate polyester at 150°C a second component, approximately 10% of the total peak area, was distinguishable. A mixture of authentic 1,2- and 2,3-fencholides, obtained by the Baeyer-Villiger oxidation of 3,3-Dimethyl-8,9-dinorbornan-2-one (fenchone) with peracetic acid, showed essentially the same chromatographic properties as the biologically derived material. It will be noted that the major component corresponds to the 1,2-fencholide.Thus, based on this, 3,3-Dimethyl-8,9-dinorbornan-2-one is considered to be biodegradable in nature.
Key value for chemical safety assessment
- Biodegradation in water:
- readily biodegradable
Additional information
Experimental key study and supporting data for the target compound 3,3-Dimethyl-8,9-dinorbornan-2-one (CAS No. 1195-79-5) and supporting study for its structurally similar read across substance were reviewed for the biodegradation end point which are summarized as below:
In an experimental key study from peer reviewed journal (P. J. Chapman, et. al; 1965),biodegradation study was conducted for evaluating the percentage biodegradability of test substance 3,3-Dimethyl-8,9-dinorbornan-2-one (CAS no. 1195-79-5).Corynebacterium spp. (Bacteria), an organism which grows at the expense of either (+)- or (-)- camphor was used as a test inoculum for the study. Corynebacterium sp., strain T1, was inoculated from stock culture slants into 100 ml sterile nutrient broth (Difco; 8.0 g/liter) and grown at 30°C with shaking for 24 hours. Then, 10 ml portions were used to inoculate the test vessel containing the test chemical 3,3-Dimethyl-8,9-dinorbornan-2-one. Ten ml portions were used to inoculate six 2 liter Erlenmeyer flasks each containing 400 ml of sterile broth. After 24 hours incubation 2.4 g3,3-Dimethyl-8,9-dinorbornan-2-onein N,N,-dimethyl formamide (0.25 g/ml) was equally divided among all six flasks and incubation continued for a further 24 hours. The cells were then centrifuged and the clear neutral supernatant extracted 3 times with 0.5 vol. diethyl ether. The ether solution, after drying over anhydrous Na2SO4, was taken to dryness and 1.12 g of pale yellow crystalline solid obtained. When crystallized from light petroleum (b.p. range 60-68°C) at -72°C, the material had m.p. 73-75°C, λCHCl3max 5.48µ (Found: C, 70.82; H 9.49. C10H16O2 requires C, 71.4; H, 9.52). Thin layer chromatography on silica gel G Drinkmann with ether-light petroleum (40:60, v/v) as solvent, revealed a single component reacting with alkaline hydroxylamine and detectable as its purple ferric hydroxamate. Gas chromatography on a stationary phase of 5% silicone gum rubber SE-30 at 150°C gave only a single peak but on 5% butanediol succinate polyester at 150°C a second component, approximately 10% of the total peak area, was distinguishable. A mixture of authentic 1,2- and 2,3-fencholides, obtained by the Baeyer-Villiger oxidation of 3,3-Dimethyl-8,9-dinorbornan-2-one (fenchone) with peracetic acid, showed essentially the same chromatographic properties as the biologically derived material. It will be noted that the major component corresponds to the 1,2-fencholide.Thus, based on this, 3,3-Dimethyl-8,9-dinorbornan-2-one is considered to be biodegradable in nature.
In a supporting study from peer reviewed journal (B. C. J. Zoeteman, et. al; 1981), persistence of the test chemical 3,3-Dimethyl-8,9-dinorbornan-2-one (CAS no. 1195-79-5) was determined in groundwater at Netherlands and Noordwijk, respectively .The estimated half-life value of chemical in groundwater at Netherlands and Noordwijk was determined to be 109.5 and 219 days, respectively. Thus, based on this, 3,3 -Dimethyl-8,9 -dinorbornan-2 -one is considered as persistent in water and can be evaluated to be not readily biodegradable in nature.
For the read across chemical (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (CAS no. 76-22-2) from authoritative database (J-CHECK and HSDB, 2017), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of the read across substance(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one(CAS no. 76-22-2). The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I) under aerobic conditions. Activated sludge was used as a test inoculums for the study. Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of test substance (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one was determined to be 94% and 100% by BOD and GC parameter in 28 days. Thus, based on percentage degradation, (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one is considered to be readily biodegradable in nature.
Although the supporting estimated data for the target chemical 3,3-Dimethyl-8,9-dinorbornan-2-one indicates that the chemical is not readily biodegradable, but based onthe experimental key study (from peer reviewed journal) which indicates that the target chemical 3,3-Dimethyl-8,9-dinorbornan-2-one is biodegradable in 48 hrs resulting in the biodegradable products as 1,2- and 2,3-fencholides, respectively, it can be considered that the chemical is expected to be readily biodegradable in 28 days and for its read across substance (from authoritative database J-CHECK and HSDB), it can be concluded that the test substance 3,3-Dimethyl-8,9-dinorbornan-2-one can be expected to be readily biodegradable in nature.
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