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EC number: 229-551-7 | CAS number: 6606-59-3
- 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
Basic toxicokinetics
Administrative data
- Endpoint:
- basic toxicokinetics, other
- Remarks:
- (Q)SAR
- Type of information:
- (Q)SAR
- Adequacy of study:
- supporting study
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- accepted calculation method
- Justification for type of information:
- QSAR prediction
Data source
Reference
- Reference Type:
- study report
- Title:
- Unnamed
- Year:
- 2 012
- Report date:
- 2012
Materials and methods
- Principles of method if other than guideline:
- Protein/GSH reactivity modelling with OECD Toolbox
- GLP compliance:
- no
Test material
- Reference substance name:
- 1,6-hexanediyl bismethacrylate
- EC Number:
- 229-551-7
- EC Name:
- 1,6-hexanediyl bismethacrylate
- Cas Number:
- 6606-59-3
- Molecular formula:
- C14H22O4
- IUPAC Name:
- 6-[(2-methylprop-2-enoyl)oxy]hexyl 2-methylprop-2-enoate
Constituent 1
Results and discussion
Any other information on results incl. tables
The algorithm of the OECD toolbox has been used to predict GSH/protein reactiviry.
Test Chemical / Compound Identity |
Acronym |
SMILES |
Molecular Weight |
Protein Binding Potency |
2-ethylhexyl methacrylate |
EHMA |
O=C(OCC(CCCC)CC)\C(=C)C |
198.3 |
Slightly reactive (GSH) >> Methacrylates (MA) |
ethyl methacrylate |
EMA |
CCOC(=O)C(=C)C |
114.14 |
Slightly reactive (GSH) >> Methacrylates (MA) |
isobutyl methacrylate |
iBMA |
CC(C)COC(=O)C(=C)C |
142.2 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Methacrylic acid |
MAA |
CC(=C)C(=O)O |
100.12 |
No alert found |
Methyl methacrylate |
MMA |
CC(=C)C(=O)OC |
100.12 |
Slightly reactive (GSH) >> Methacrylates (MA) |
n-butyl methacrylate |
nBMA |
CCCCOC(=O)C(=C)C |
142.2 |
Slightly reactive (GSH) >> Methacrylates (MA) |
n-Hexyl methacrylate |
n-HMA |
CCCCCCOC(=O)C(=C)C |
170.25 |
Slightly reactive (GSH) >> Methacrylates (MA) |
ter-Butyl Methacrylate |
tBMA |
CC(=C)C(=O)OC(C)(C)C |
142.2 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Diethylaminoethyl methacrylate |
DEAEMA |
O=C(OCCN(CC)CC)C(=C)C |
185.263 |
Slightly reactive (GSH) >> Methacrylates (MA) |
2-tert-Butylaminoethyl methacrylate |
TBAEMA |
O=C(OCCNC(C)(C)C)C(=C)C |
185.26 |
Slightly reactive (GSH) >> Methacrylates (MA) |
2-Dimethylaminoethyl methacrylate |
MADAME |
CC(=C)C(=O)OCCN(C)C |
157.22 |
Slightly reactive (GSH) >> Methacrylates (MA) |
2-(2-Butoxyethoxy) ethyl methacrylate, Butyldiglycol methacrylate |
BDGMA |
CCCCOCCOCCOC(=O)C(=C)C |
230.3 |
Slightly reactive (GSH) >> Methacrylates (MA) |
2-(2-(2-Ethoxy ethoxy)-thoxyethyl methacrylate |
ET3EGMA |
O=C(OCCOCCOCCOCC)C(=C)C |
246.3 |
Slightly reactive (GSH) >> Methacrylates (MA) |
2-Methoxyethyl methacrylate |
MTMA |
CC(=C)C(=O)OCCOC |
144.08 |
Slightly reactive (GSH) >> Methacrylates (MA) |
2-Ethoxyethyl methacrylate |
ETMA |
CCOCCOC(=O)C(=C)C |
158.09 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Phenoxyethyl Methacrylate |
PTMA |
CC(=C)C(=O)OCCOC1=CC=CC=C1 |
206.24 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Allyl methacrylate |
AMA |
CC(=C)C(=O)OCC=C |
126.15 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Benzyl methacrylate |
BNMA |
CC(=C)C(=O)OCC1=CC=CC=C1 |
176.21 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Cyclohexyl methacrylate |
c-HMA |
O=C(OC(CCCC1)C1)C(=C)C |
168.23 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Isobornyl methacrylate |
IBOMA |
CC(=C)C(=O)OC1CC2CCC1(C2(C)C)C |
222.32 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Phenyethyl methacrylate |
Phenylethyl MA |
CC(=C)C(=O)OCCC1=CC=CC=C1 |
190.24 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Phenyl methacrylate |
PHMA |
CC(=C)C(=O)OC1=CC=CC=C1 |
162.19 |
Slightly reactive (GSH) >> Methacrylates (MA) |
3,3,5-Trimethylcyclohexyl methacrylate |
TMCHMA |
CC1CC(CC(C1)(C)C)OC(=O)C(=C)C |
210.31 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Tridecyl methacrylate |
TDMA C13MA |
CCCCCCCCCCCCCOC(=O)C(=C)C |
268.43 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Isodecyl methacrylate |
IDMA |
CC(C)CCCCCCCOC(=O)C(=C)C |
226.36 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Dodecyl methacrylate |
LMA |
CCCCCCCCCCCCOC(=O)C(=C)C |
254.41 |
Slightly reactive (GSH) >> Methacrylates (MA) |
n-Octyl methacrylate |
n-OMA |
CCCCCCCCOC(=O)C(=C)C |
198.3 |
Slightly reactive (GSH) >> Methacrylates (MA) |
2-Hydroxyethyl methacrylate |
HEMA |
CC(=C)C(=O)OCCO |
130.1 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Hydroxypropyl methacrylate |
HPMA |
CC(COC(=O)C(=C)C)O |
144.17 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Hydroxypropyl methacrylate |
HPMA |
CC(CO)OC(=O)C(=C)C |
144.17 |
Slightly reactive (GSH) >> Methacrylates (MA) |
N-butoxymethyl methacrylamide |
N-BMMA |
CCCCOCNC(=O)C(=C)C |
157.21 |
Moderately reactive (GSH) >> 2-Vinyl carboxamides (MA) |
N-Methylol methacrylamide |
N-MMAA |
CC(=C)C(=O)NCO |
115.13 |
Moderately reactive (GSH) >> 2-Vinyl carboxamides (MA) |
N,N'-methylenbis(methacrylamide) |
|
O=C(NCNC(=O)\C(=C)C)\C(=C)C |
154.19 |
Moderately reactive (GSH) >> 2-Vinyl carboxamides (MA) |
N-Dimethylaminopropyl methacrylamide |
DMAPMA |
CC(=C)C(=O)NCCCN(C)C |
170.25 |
Moderately reactive (GSH) >> 2-Vinyl carboxamides (MA) |
Methacrylamide |
MAA |
CC(=C)C(=O)N |
85.1 |
Moderately reactive (GSH) >> 2-Vinyl carboxamides (MA) |
1,12-Dodecanediol dimethacrylate |
1,12 DDDMA |
O=C(OCCCCCCCCCCCCOC(=O)\C(=C)C)\C(=C)C |
338.48 |
Slightly reactive (GSH) >> Methacrylates (MA) |
1,3-Butandiol dimethacrylate |
1,3-BDDMA |
CC(CCOC(=O)C(=C)C)OC(=O)C(=C)C |
226.27 |
Slightly reactive (GSH) >> Methacrylates (MA) |
1,4-Butandiol dimethacrylate |
1,4-BDDMA |
CC(=C)C(=O)OCCCCOC(=O)C(=C)C |
226.27 |
Slightly reactive (GSH) >> Methacrylates (MA) |
1,6-Hexanediol dimethacrylate |
1,6 HDDMA |
O=C(OCCCCCCOC(=O)\C(=C)C)\C(=C)C |
254.32 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Ethylene glycol dimethacrylate |
EGDMA |
CC(=C)C(=O)OCCOC(=O)C(=C)C |
198.22 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Trimethylpropane trimethacrylate |
TMPTMA |
CCC(COC(=O)C(=C)C)(COC(=O)C(=C)C)COC(=O)C(=C)C |
338.4 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Ethoxylated bisphenol A dimethacrylate |
2EBADMA |
CC(C)(C1=CC=C(C=C1)O)C2=CC=C(C=C2)O.C=CC(=O)O.C(CO)O |
452.5394 |
Slightly reactive (GSH) >> Methacrylates (MA) |
2,2-bis-[4-(3'-methacryloyloxy-2'-hydroxy)propoxyphenyl] propane |
bis-GMA |
O=C(OCC(O)COc1ccc(cc1)C(c2ccc(OCC(O)COC(=O)\C(=C)C)cc2)(C)C)\C(=C)C |
512.61 |
Slightly reactive (GSH) >> Methacrylates (MA) |
4,4'-Isopropylidenediphenol, oligomeric reaction products with 1-chloro-2,3-epoxy propane, reaction products with methacrylic acid |
Bis-GMA NLP (DSM/Akzo/+others) |
|
n.d |
Slightly reactive (GSH) >> Methacrylates (MA) |
Diethyleneglycol dimethacrylate |
DEGDMA |
CC(=C)C(=O)OCCOCCOC(=O)C(=C)C |
242.27 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Glycerol dimethacrylate |
GDMA |
O=C(OCC(O)COC(=O)\C(=C)C)\C(=C)C |
228.24 |
Slightly reactive (GSH) >> Methacrylates (MA) |
7,7,9-(resp. 7,9,9-)trimethyl-4,13-dioxo-3,14-dioxa-5,12-diazahexadecane-1,16-diol-dimethacrylate |
HEMATMDI |
O=C(OCCOC(=O)NCCC(C)CC(C)(C)CNC(=O)OCCOC(=O)\C(=C)C)\C(=C)C |
470,57 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Triethyleneglycol dimethacrylate |
TREGDMA |
O=C(OCCOCCOCCOC(=O)\C(=C)C)\C(=C)C |
286.32 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Tetraethyleneglycol dimethacrylate |
TTEGDMA/4EDMA |
CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(=C)C |
198.22 |
Slightly reactive (GSH) >> Methacrylates (MA) |
2-hydroxyethyl methacrylate phosphate |
HEMA phosphate |
CC(=C)C(=O)OCCOP(=O)(O)O |
228.14 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Methacrylic anhydride |
MAAH |
CC(=C)C(=O)OC(=O)C(=C)C |
154.16 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Hydroxyethyl ethylene urea methacrylate |
MEEUW |
O=C1NCCN1CCOC(=O)\C(=C)C |
129.16 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Tetrahydrofurfurylmethacrylat |
THFMA |
O=C(OCC1OCCC1)\C(=C)C |
170.21 |
Slightly reactive (GSH) >> Methacrylates (MA) |
2,2-dimethyl-1,3-dioxolan-4-ylmethyl methacrylate |
|
CC(=C)C(=O)OCC1COC(O1)(C)C |
200.23 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Polyethylengeglycol-200-dimethacrylate |
PEG200DMA |
for approximation see Tetraethyleneglycol dimathacrylate |
no data |
Slightly reactive (GSH) >> Methacrylates (MA) |
2,2,2-Trifluoroethyl methacrylate |
TFMEA 3FM |
CC(=C)C(=O)OCC(F)(F)F |
336 |
Slightly reactive (GSH) >> Methacrylates (MA) |
N-Trimethylammoniumpropyl methacrylamide-chloride |
MAPTAC |
CC(=C)C(=O)NCCC[N+](C)(C)C.[Cl-] |
220.74 |
Moderately reactive (GSH) >> 2-Vinyl carboxamides (MA) |
2-Trimethylammoniummethyl methacrylate-chloride |
TMAEMC |
CC(=C)C(=O)OCC[N+](C)(C)C.[Cl-] |
207.7 |
Slightly reactive (GSH) >> Methacrylates (MA) |
Applicant's summary and conclusion
- Conclusions:
- Interpretation of results (migrated information): other: low reactivity with GSH
A dataset with methacrylic acid derivatives has been assessed using the reactivity profiler in the OECD QSAR Toolbox. This profiler contains structural alerts derived from an analysis of experimental reactivity data as measured using glutathione (the Schultz assay). The profiler assigns chemicals to one of five potency classes (non-reactive, slightly reactive, moderately reactive, highly reactive and extremely reactive) based on the experimental results.
The majority of the chemicals, including HEMA, are slightly reactive. For methacrylates it is well known that the addition of an alkyl group on the alpha-carbon significantly reduces reactivity in the Michael addition reaction.
There are also a group of vinyl carboxamides (methacrylamide derivatives) that have been flagged as being moderately reactive. It should be noted, however, that in the underlying QSAR data in the TB there is no information regarding the effect of an alpha substituent for this class of chemical. In reality this means that no chemicals were tested with glutathione that contained an alpha alkyl substituent thus the prediction is being made based on the un-substituted parent (acrylamide; thus the over-cautious prediction). The investigator indicated that they are likely to be pretty unreactive in reality. - Executive summary:
A dataset with methacrylic acid derivatives has been assessed using the reactivity profiler in the OECD QSAR Toolbox. This profiler contains structural alerts derived from an analysis of experimental reactivity data as measured using glutathione (the Schultz assay). The profiler assigns chemicals to one of five potency classes (non-reactive, slightly reactive, moderately reactive, highly reactive and extremely reactive) based on the experimental results.
The majority of the chemicals, including HEMA, are slightly reactive. For methacrylates it is well known that the addition of an alkyl group on the alpha-carbon significantly reduces reactivity in the Michael addition reaction.
There are also a group of vinyl carboxamides (methacrylamide derivatives) that have been flagged as being moderately reactive. It should be noted, however, that inthe underlying QSAR data in the TB there is no information regarding the effect of an alpha substituent for this class of chemical. In reality this means that no chemicals were tested with glutathione that contained an alpha alkyl substituent thus the prediction is being made based on the un-substituted parent (acrylamide; thus the over-cautious prediction). The investigator indicated that they are likely to be pretty unreactive in reality.
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