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CAS NUMBER: 183658-27-7
EC NUMBER: 214-089-0
MOLECULAR FORMULA: C15H18Br4O2
MOLECULAR WEIGHT: 549.9
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is part of the group of Brominated and Chlorinated Flame Retardants.
2-Ethylhexyl 2,3,4,5-Tetrabromobenzoate is a new brominated flame retardant.
2-Ethylhexyl 2,3,4,5-Tetrabromobenzoate is a new brominated flame retardant in air.
2-Ethylhexyl 2,3,4,5-Tetrabromobenzoate is a flame retardant.
Due to the observed toxicity of mixtures containing 2-ethylhexyl-2,3,4,5-tetrabromobenzoate (TBB) and that of a closely related analog, the 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate has classified TBB as a moderate hazard for neurological, developmental, reproductive and repeated dose toxicities.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate has been used as a substitute ingredient for PBDEs in flexible polyurethane foam.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoates are typically found in consumer products such as upholstered furniture, auto cushions, and baby products, and persist in products containing recycled polyurethane foam.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate and TBPH make up about 50% of the widely-used flame retardant mixture Firemaster 550.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoates are also components of Firemaster 550.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is one of two primary components in the novel brominated flame retardant, Firemaster 550.
Widespread use of 2-Ethylhexyl-2,3,4,5-tetrabromobenzoates has lead to an increase in human exposure to this new family of chemicals and little research has been done on their chronic effects on human health.
While 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is not considered an endocrine disrupting chemical, its primary metabolite 2,3,4,5-tetrabromobenzoic acid (TBBA) has been shown to be anti-estrogenic (IC50 of 31.75 µM) and anti-adrogenic.
Unlike the other major component of Firemaster 550, 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate was shown to be metabolized without enzymatic catalysis into TBBA in human microsomes with a Km of 11.1 µM and a Vmax of 0.655 ± 0.144nmol/min * mg protein in human microsomes.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoates are the two brominated components of the commercial flame retardant composition Firemaster 550, which together account for about 50 Mass percent, with their mass ratio being 4:1.
Firemaster 550 is used as a flame retardant for plastics such as polyurethane.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is a brominated component of flame retardant mixtures used as substitutes for some PBDEs.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is added to various consumer products, including polyurethane foams, and has been detected in humans.
The present study characterized the fate of E2-Ethylhexyl-2,3,4,5-tetrabromobenzoate in rodents.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate was absorbed, metabolized, and eliminated via the urine and feces following single administrations of 0.1–100 µmol/kg (∼0.05–55 mg/kg) or repeated administration (0.1 µmol/kg/day × 5–10 days) by gavage to female Hsd:Sprague DawleySD (SD) rats.
Cumulative excretion via feces increased (39–60%) with dose (0.1–10 µmol/kg) with corresponding decreases in urinary excretion (54 to 37%) after 72 h.
Delayed excretion of [14C]-radioactivity in urine and feces of a 100 µmol/kg oral dose was noted.
Recovery was complete for all doses by 72 h.
IV-injected rats excreted more of the 0.1 µmol/kg dose in urine and less in feces than did gavaged rats, indicating partial biliary elimination of systemically available compound.
No tissue bioaccumulation was found for rats given 5 oral daily doses of EH-TBB.
Parent molecule was not detected in urine whereas 2 metabolites, tetrabromobenzoic acid (TBBA), a TBBA-sulfate conjugate, and a 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate-glycine conjugate were identified.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoates were identified in extracts from feces.
Data from gavaged male B6C3F1/Tac mice indicated minimal species differences are likely for the disposition of 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate.
Approximately 85% of a 0.1 µmol/kg dose was absorbed from the gut.
Overall absorption of 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is expected to be even greater at lower levels.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate has been described using a number of different abbreviations in the contemporary literature, eg, EH-TBB, EHTeBB, EHTBB, or TBB.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is a component in some commercial brominated flame retardant (BFR) mixtures (eg, Firemaster BZ-54 [BZ-54], Firemaster 550 [FM550], and Firemaster 600 [FM600]) introduced for use in polyurethane foams as a replacement for the commercial pentabrominated PBDE mixture.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate has been detected in furniture foam, baby products (mattresses and high-chair foam), house dust, outdoor dust and sediment, and wildlife.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate (EH-TBB) is lipophilic and may cross membranes, but little is known about the disposition of EH-TBB in vivo for humans or animals.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate by esterases present in porcine intestine preparations, human and rat liver cytosol and microsomal protein, and rat serum.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate (EH-TBB; MW 549.92 g/mol; CAS 183658-27-7) is a brominated component of flame retardant mixtures used as substitutes for some PBDEs.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is added to various consumer products, including polyurethane foams, and has been detected in humans.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is used as a flame retardant.
Biomonitoring for 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate exposures include the metabolite, 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate, in urine. We derived a Reference Dose (RfD) for TBB and a Biomonitoring Equivalent (BE) for TBBA in urine.
Three longer-term studies of oral gavage dosing of a commercial mixture BZ-54 (which includes 70% TBB) in rats were evaluated for deriving the RfD.
The 95% lower confidence limits on the BMD associated with a 1 SD change from the mean (BDMLSD) values ranged from 77 to 134 mg/kg-day.
The mean BMDLSD value of 91 mg/kg-day for maternal body weight changes was selected as the appropriate point of departure (POD), corresponding to a human equivalent dose (PODHEC) of 25 mg/kg-day. A total composite uncertainty factor (UF) of 300 yields an RfD of 0.08 mg/kg-day.
A urinary mass excretion fraction (Fue) of 0.6 for 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate following oral doses of 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate in rats was used to calculate BEs for 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate in urine of 2.5 mg/L and 2.5 mg/g cr.
Mean (5.3 × 10−6 mg/L) and maximum (340 × 10−6 mg/L) levels of 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate measured in urine from human volunteers reported in the literature indicates margins of safety (MOS) are approximately 450,000 and 7,000, respectively.
The chemical 2-ethylhexyl-2,3,4,5 tetrabromobenzoate is used as a brominated flame retardant.
Brominated flame retardants have received increased scrutiny, since the late 1990s, when polybrominated diphenyl ethers were found in samples of human blood.
Because biomonitoring brought about early detection of brominated flame retardants in these sample types, biomonitoring samples of today for brominated flame retardants is often included during exposure assessments.
As a result, there is a need for methods to interpret the biomonitoring levels reported for brominated flame retardants in a public health risk context.
This paper provides such an approach for interpreting biomonitoring data for 2-ethylhexyl-2,3,4,5 tetrabromobenzoate (TBB) and its metabolite tetrabromobenzoic acid.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is not known to exist as an environmental degradant of 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate.
As a result, 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is identified as a specific biomarker for 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate exposures.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate in blood is likewise specific to exposures to 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate, since 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is not known to be a metabolite of any currently known compound.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate in urine has the advantage of being collected with relatively non-invasive techniques, while 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate in blood is more invasive since blood must be collected via venipuncture.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate in blood are reasonable biomarkers for assessing exposures to TBB.
Since the mode of action for the toxicity of TBB is not clearly known, it is likewise unknown whether TBB and/or TBBA is actually a proximate toxicant.
Therefore, at this time, neither biomarker has an advantage with respect to these noted factors.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate has been used as a replacement in some commercial flame-retardant mixtures.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is widely used in industrial products, so the probability of human exposure to TBPH is high.
To this end, we investigated what effect oral exposure of Balb/c mice to TBPH at concentrations of 200 mg kg−1 had on hepatic damage.
Staining results showed liver injury in the mice exposed to TBPH. Oxidative stress markers and endoplasmic reticulum stress associated proteins were altered in the TBPH exposed mice, and these changes could be attenuated by administration of curcumin at 25 mg kg−1.
Overall, TBPH induces hepatic damage via increasing oxidative stress, and curcumin plays a protective role in alleviating the TBPH-mediated histopathological alterations in the liver.
2-Ethylhexyl 2,3,4,5-Tetrabromobenzoate is the labelled analogue of 2-Ethylhexyl 2,3,4,5-Tetrabromobenzoate, which is a flame retardant.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is an ingredient in common market replacements for PBDEs in flexible polyurethane foam.
Approximately 50% of the Firemaster® 550 mixture is 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate and TBPH at a ratio of 4:1 by mass.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate treated foams have been used in many everyday products such as couches, chairs, other upholstered furniture, children’s furniture, baby products, office furniture, foam used in gymnastic facilities, and automotive cushions.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate may also be present in products made from recycled foam such as carpet backings and pads
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate is extensively metabolized to TBBA within several hours in rats.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoateshowed antiglucocorticoid activity in a reporter gene assay (IC50 were 1.9 nM, 37.5 nM, respectively).
The glucocorticoid receptor plays key roles in the immune system, metabolism and fetal development.
Both the parent compound and 2-Ethylhexyl-2,3,4,5-tetrabromobenzoate were potent agonists of the pregane X receptor (PXR) and induced transcription of gene products (CYP3A4 mRNA) in vitro.
Activation of PXR helps detoxify xenobiotics but can also cause endocrine disruption through enhanced metabolism of endogenous hormones.
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate did not alter the activity of two enzymes that regulate intercellular thyroid hormone levels (thyroid hormone deiodinase and sulfotransferase) in human liver microsomal and cytosolic bioassays.
TECHNICAL INFORMATION:
-Physical State: Liquid
-Solubility: Soluble in DMSO, chloroform, and methanol.
-Storage: Store at 4° C
-Refractive Index: n20D 1.57 (Predicted)
PROPERTIES:
-Quality Level: 200
-isotopic purity: ≥99 atom % D
-assay: ≥99% (CP)
-form: powder
-autoignition temp.: 1061 °F
-bp: 249 °C (lit.)
-mp: 121-125 °C (lit.)
-mass shift: M+5
-SMILES string: [2H]c1c([2H])c([2H])c(c([2H])c1[2H])C(O)=O
-InChI: 1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)/i1D,2D,3D,4D,5D
SYNONYM:
Benzoic acid, 2,3,4,5-tetrabromo-, 2-ethylhexyl ester
2-Ethylhexyl-2,3,4,5-tetrabromobenzoate
2,3,4,5-Tetrabromobenzoic Acid 2-Ethylhexyl Ester
2-Ethylhexyltetrabromobenzoate
Firemaster 550 component
2-Ethylhexyl 2,3,4,5-Tetrabromobenzoate(TBB)
C15H18Br4O2
SCHEMBL2728830
DTXSID9052686
MFCD26960592
AKOS027323847
2-Ethylhexyl2,3,4,5-Tetrabromobenzoate
SY261702
CS-0449217
FT-0668285
Z1976
A929326
J-011768
Q20054520
Benzoic acid, 2,3,4,5-tetrabromo-, 2-ethylhexyl ester (TBB)
