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EC number: 696-026-0
CAS number: 1395383-69-3
Short description of key information on bioaccumulation potential result: In accordance with REACh Regulation (EC) No 1907/2006 Annex VIII section 8.8.1, a toxicokinetics study is not required as assessment of the toxicokinetic behaviour of the substance has been derived from the relevant available information. This assessment is located within the endpoint summary for toxicokinetics, metabolism and distribution.
studies specifically investigating the toxicokinetic properties ofbis(2,3-epoxypropyl)cyclohexane-1,2-dicarboxylatewere
available; thus, the physicochemical properties of the substance and the
results of toxicity studies were used to assess the toxicokinetics.
low molecular weight (i. e., <500 g/mol), viscous liquid state, moderate
log Pow value (i. e., between -1 and 4), and water solubility (i. e.,
around 14 g/L) of bis(2,3-epoxypropyl)cyclohexane-1,2-dicarboxylate
favour its absorption from the
gastrointestinal tract . The
absorption of bis(2,3-epoxypropyl)cyclohexane-1,2-dicarboxylate
following oral exposure is supported
by the systemic toxicity (i. e., clinical signs and mortality) observed
in rats and mice acute oral administration of 5000 mg epoxy resins/kg
body weight [2,3].
the available oral toxicity data suggest that bis(2,3-epoxypropyl)cyclohexane-1,2-dicarboxylate
is absorbed following oral exposure
and distributed to the organism. No
other relevant toxicokinetic information can be deduced from the results
of the available studies.
viscous liquid state, water solubility and log Pow value do not favour
dermal absorption, since these values indicate that bis(2,3-epoxypropyl)cyclohexane-1,2-dicarboxylate
may be too hydrophilic to cross the
stratum corneum. Although
dermal irritancy or corrosion may enhance dermal absorption by
compromising the integrity of the epidermal barrier, no corrosion or
systemic effects were observed in the acute dermal toxicity study
considering the physicochemical properties ofbis(2,3-epoxypropyl)cyclohexane-1,2-dicarboxylate,
and the lack of observed systemic effects following dermal exposure,
their absorption via the skin can be considered to be unsignificant.
regarding inhalation exposure to epoxy resins were available. Although the
low vapour pressure and as no boiling point could be determined < 200°C
, indicate that inhalation exposure is unlikely, whether the
substance would be absorbed following inhalation exposure cannot be
deduced from the available information. In
addition, no reproductive or developmental studies were available;
therefore, whether bis(2,3-epoxypropyl)cyclohexane-1,2-dicarboxylate
would be expected to cross the
placental barrier cannot be deduced.
may be first hydrolysed by the low pH during stomach passage. The half
live of bis(2,3-epoxypropyl)cyclohexane-1,2-dicarboxylate upon
hydrolysis in 0.1was determined to be 12.9 +/- 0.7 min..
bis(2,3-epoxypropyl)cyclohexane-1,2-dicarboxylate may be metabolized by
two different enzymatic routes: conjugation of the epoxide moiety with
the endogenous tripeptide glutathione (GSH) catalysed by glutathione
S-transferase (GST) or hydrolysis of the epoxide moiety catalysed by
epoxide hydrolase (EH), the second way being the most efficient way of
detoxification of epoxy compounds. The epoxide hydrolases are a class of
proteins that catalyze the hydration of chemically reactive epoxides to
their corresponding dihydrodiol products. Simple epoxides are hydrated
to their corresponding vicinal dihydrodiols, and arene oxides to
trans-dihydrodiols. In general, this hydration leads to more stable and
less reactive intermediates that can be readily conjugated and excreted.
In mammalian species, there are at least five epoxide hydrolase forms,
microsomal cholesterol 5,6-oxide hydrolase, hepoxilin A(3) hydrolase,
leukotriene A(4) hydrolase, soluble epoxide hydrolase, and microsomal
epoxide hydrolase. Although highly concentrated in the liver, epoxyde
hydrolases are also found in other organs like brain, adrenal gland
Investigation of epoxide
hydrolysis and alkylation potency of
bis(2,3-epoxypropyl)cyclohexane-1,2-dicarboxylate in vitro showed that
half life of the substance was 54.8 minutes in mouse liver homogenate
. Epoxide hydrolases in mammals are similar, and human is the species
with the highest epoxide hydrolase activity compared to rodents, dogs or
hamsters , Therefore it can be concluded that human can metabolize
epoxides even faster than laboratory animals.
The epoxide hydrolase
converts epoxides to trans-dihydrodiols, which can be conjugated and
excreted from the body.
during metabolization can be conjugated and excreted from the body in
the urine or feaces. As mentioned above cis-dihydrodiols can be
conjugated and excreted directly or further metabolized in
Cis-1,2-cyclohexanedicarboxylic acid and then excreted unchanged. The
study perfomed in mouse on the metabolites in urine and faeces following
a single dose of 14C-Diglycidylether of Bisphenol A  showed that
approximately 45% of the metabolites are excreted by feacal elimination
whereas 6% are excreted by urinary elimination. Considering the smaller
molecular weight of the metabolites of bis(2,3-epoxypropyl)cyclohexane-1,2-dicarboxylate
it can be supposed that this ratio is probably more
equilibrated in this case.
Scheme of the probable metabolism of bis(2,3-epoxypropyl)cyclohexane-1,2-dicarboxylate
is attached as document.
on the above mentioned data and taking into consideration the low
molecular weight and log Pow value, and water solubility, bis(2,3-epoxypropyl)cyclohexane-1,2-dicarboxylate
is not excpect to bioaccumalte.
Information on Registered Substances comes from registration dossiers which have been assigned a registration number. The assignment of a registration number does however not guarantee that the information in the dossier is correct or that the dossier is compliant with Regulation (EC) No 1907/2006 (the REACH Regulation). This information has not been reviewed or verified by the Agency or any other authority. The content is subject to change without prior notice.Reproduction or further distribution of this information may be subject to copyright protection. Use of the information without obtaining the permission from the owner(s) of the respective information might violate the rights of the owner.
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