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BIS(2-ETHYLHEXYL)-3,4,5,6- TETRARABROMOPHTHALATE

CAS NUMBER: 93951-87-2

MOLECULAR FORMULA: C24D4H34O4

MOLECULAR FORMULA: 394.58

 


Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate is used to investigate the influence of environmentally relevant dose of DEHP on adipogenesis in the human cell culture model SGBS. 
Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate is can be used to study the quantify indoor phthalate ester degradation through both biotic and abiotic mechanisms.

Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate is a ubiquitous environmental contaminant, but its toxicity is not fully understood.
Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate had biphasic elimination behavior where 94% of the body burden was depleted within the first 12 h of elimination and the remaining 6% eliminated very slowly thereafter (half-life of 15 days). 

There was little evidence for biotransformation of either chemical. 
This investigation confirms the extremely hydrophobic behavior of Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate and its impact on its bioavailability.

Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate has been used as a replacement in some commercial flame-retardant mixtures. 
Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate is widely used in industrial products, so the probability of human exposure to TBPH is high. 

Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate is known about how it is metabolized or its toxicity. 
To this end, we investigated what effect oral exposure to Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate at concentrations of 200 mg kg−1 had on hepatic damage. 

Staining results showed liver injury in the mice exposed to Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate. 
Oxidative stress markers and endoplasmic reticulum stress associated proteins were altered in the Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate exposed, and these changes could be attenuated by administration of curcumin at 25 mg kg−1. 

Overall, Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate induces hepatic damage via increasing oxidative stress, and curcumin plays a protective role in alleviating the Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate-mediated histopathological alterations in the liver.
Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalates are the two brominated components of the Firemaster 550 commercial flame retardant blend , which together account for approximately 50% by mass, with a 1:4 mass ratio. 

The remaining 50 percent by mass consists of an isopropylated triaryl phosphate and a triphenyl phosphate.
Firemaster 550 is used as a flame retardant in plastics such as polyurethane.

In a study conducted in 2011, an average concentration of 4  ppmfound, confirming the presence of EH-TBB in electronic devices.
Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate was included by the EU in 2015 in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of the substance evaluation in the Community Rolling Action Plan ( CoRAP ). 

Here, the effects of the substance on human health and the environment are reassessed and, if necessary, follow-up measures are initiated. 
The reasons for the inclusion of bis(2-ethylhexyl)tetrabromophthalate were concerns about environmental exposure , other hazard concerns and widespread use as well as the hazards arising from possible assignment to the group of PBT / vPvB substances and as a potentialendocrine disruptor.

Bis(2-ethylhexyl)tetrabromophthalate is a mixture of three isomeric organic chemical compounds with the empirical formula C 24 H 34 Br 4 O 4 , which is used as a flame retardant. 
Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate is the diester of tetrabromophthalic acid and 2-ethylhexanol.

Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate, a replacement for restricted flame retardants, has become ubiquitous in the environment. 
To reveal the neurotoxicity and underlying mechanism of TBPH, we first evaluated its penetrability through the blood-brain barrier (BBB) using hCMEC/D3 cells as in vitro model, and found TBPH had poor penetrability through BBB with a maximum Papp of 14.8 × 10−6 cm s−1. 

Further study using transgenetic zebrafish (Tg flk1: EGFP) as in vivo model confirmed that Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate could affect the BBB permeability, probably via affecting the transcription of genes encoding tight junction proteins. 
Finally, wild type zebrafish embryos/larvae were exposed to Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate to evaluate the neurotoxicity. 

The neurodevelopment, neurotransmitters and locomotor activity of zebrafish larvae did not changed, which may be because Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate can hardly cross the BBB to pose direct exposure to the central nervous system. 
However, the transcription of opsins genes and visual response to light stimulation in zebrafish larvae were inhibited, pointing to additional mechanism that may cause visual impairment indirectly. 

Above all, these results can help further understand the neurotoxicity and underlying mechanism by Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate, and also pointed out potential risk of this chemical to aquatic organisms.
Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate is classified by the EPA as a moderate hazard for developmental, reproductive, neurological and repeated-dose exposures based on toxicity in rodent studies to TBPHcontaining flame retardant mixtures and structural analogs.

Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate was added to work plan due to developmental, acute and chronic toxicity, and moderate environmental persistence and bioaccumulation potential. 
Altered thyroid function in pregnant rats fed a commercial mixture containing Bis(2-ethylhexyl)-3,4,5,6-tetrabromophthalate, and significantly increased weights in offspring. 
Also, early puberty in female pups and significantly increased left ventricular thickness and blood glucose levels in male pups was noted.

 

PROPERTIES:

Quality Level: 200

isotopic purity: 98 atom % D

assay: 99% (CP)

bp: 231 °C/5 mmHg (lit.)

mp: -50 °C (lit.)

density: 0.996 g/mL at 25 °C

mass shift: M+4

SMILES string: [2H]c1c([2H])c([2H])c(C(=O)OCC(CC)CCCC)c(c1[2H])C(=O)OCC(CC)CCCC

InChI: 1S/C24H38O4/c1-5-9-13-19(7-3)17-27-23(25)21-15-11-12-16-22(21)24(26)28-18-20(8-4)14-10-6-2/h11-12,15-16,19-20H,5-10,13-14,17-18H2,1-4H3/i11D,12D,15D,16D

InChI key: BJQHLKABXJIVAM-SAQXESPHSA-N

 

STORAGE:

20 °C

 

SYNONYM:

bis(2-ethylhexyl) 3,4,5,6-tetrabromophthalate
Bis(2-ethylhexyl) tetrabromophthalate
bis(2-ethylhexyl) 3,4,5,6-tetrabromobenzene-1,2-dicarboxylate
UNII-413M0N3V1G
1,2-Benzenedicarboxylic acid, 3,4,5,6-tetrabromo-, 1,2-bis(2-ethylhexyl) ester
413M0N3V1G
bis(2-ethylhexyl)tetrabromophthalate
Di-2-ethylhexyl tetrabromo phthalate
1,2-Benzenedicarboxylic acid, 3,4,5,6-tetrabromo-, bis(2-ethylhexyl) ester
Pyronil 45
C24H34Br4O4
HSDB 8216
di(2-ethylhexyl)tetrabromophthalate
EINECS 247-426-5
Bis(2-ethyhexyl) tetrabromophthalate
DSSTox_CID_7887
EC 247-426-5

 

 

 

 

 

 

 

 

 

 

 

 

 

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