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Mono-(2-ethyhexyl) tetrabromophthalate (TBMEHP)

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Catalog: ASIS-0003

Formal Name: Mono-(2-ethyhexyl) tetrabromophthalate (TBMEHP)

Produced By: AsisChem, Inc.

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pdfASIS-0003 Technical Product Information.pdf (535.18 KB )
pdfASIS-0003 SDS (92.87 KB )

Biological Description

TBMEHP is the primary metabolite of the novel brominated flame retardant TBPH (Roberts et al. 2012, Springer et al. 2012, Fic et al. 2014). While data does not support uncatalyzed conversion of TBPH to TBMEHP, studies have shown that exposure of TBPH to porcine hepatic carboxyesterase is sufficient to catalyze the conversion to its primary metabolite at a rate of 1.08pmol/min*mg protein (Roberts et al. 2012). Additionally, while TBPH is not thought to be an endocrine disrupting chemical, TBMEHP is associated with both anti-estrogenic (IC50 of 0.265 µM) and anti-androgenic (IC50 of 2.92 µM) (Fic et al. 2014). Exposure of pregnant female rats to TBMEHP, the primary metabolite, at a dose of 200 or 500 mg/kg lead to dose dependent increases in hypothyroidism, hepatotoxicity, and an increase in male fetus multinucleated germ cells associated with fetal testes toxicity (Springer et al. 2012).

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Additional Information

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Catalog ASIS-0003
Formal Name Mono-(2-ethyhexyl) tetrabromophthalate (TBMEHP)
CAS Number 61776-60-1
Molecular Weight 593.927734375
Formula C16 H18 Br4 O4
Lead Time 3
LogP 6.808000088
Purity 95
SMILES C1(C(Br)=C(C(=O)O)C(C(=O)OCC(CC)CCCC)=C(Br)C=1Br)Br
Solubility and Handling No
inchikey VPAAZTQOJLVWLA-UHFFFAOYSA-N
TPSA 63.59999847
HBD 1
HBA 4

Details

Fic, A., B. Zegura, D. Gramec and L. P. Masic (2014). "Estrogenic and androgenic activities of TBBA and TBMEPH, metabolites of novel brominated flame retardants, and selected bisphenols, using the XenoScreen XL YES/YAS assay." Chemosphere 112: 362-369. (http://www.ncbi.nlm.nih.gov/pubmed/25048928)(Abstract)

Roberts, S. C., L. J. Macaulay and H. M. Stapleton (2012). "In vitro metabolism of the brominated flame retardants 2-ethylhexyl-2,3,4,5-tetrabromobenzoate (TBB) and bis(2-ethylhexyl) 2,3,4,5-tetrabromophthalate (TBPH) in human and rat tissues." Chem Res Toxicol 25(7): 1435-1441. (http://www.ncbi.nlm.nih.gov/pubmed/22575079)(Abstract)

Springer, C., E. Dere, S. J. Hall, E. V. McDonnell, S. C. Roberts, C. M. Butt, H. M. Stapleton, D. J. Watkins, M. D. McClean, T. F. Webster, J. J. Schlezinger and K. Boekelheide (2012). "Rodent thyroid, liver, and fetal testis toxicity of the monoester metabolite of bis-(2-ethylhexyl) tetrabromophthalate (tbph), a novel brominated flame retardant present in indoor dust." Environ Health Perspect 120(12): 1711-1719. (http://www.ncbi.nlm.nih.gov/pubmed/23014847)(Abstract)

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Product Details

Additional Information

Quantities Please contact us for larger or different quantities
Catalog ASIS-0003
Formal Name Mono-(2-ethyhexyl) tetrabromophthalate (TBMEHP)
CAS Number 61776-60-1
Molecular Weight 593.927734375
Formula C16 H18 Br4 O4
Lead Time 3
LogP 6.808000088
Purity 95
SMILES C1(C(Br)=C(C(=O)O)C(C(=O)OCC(CC)CCCC)=C(Br)C=1Br)Br
Solubility and Handling No
inchikey VPAAZTQOJLVWLA-UHFFFAOYSA-N
TPSA 63.59999847
HBD 1
HBA 4
References

Details

Fic, A., B. Zegura, D. Gramec and L. P. Masic (2014). "Estrogenic and androgenic activities of TBBA and TBMEPH, metabolites of novel brominated flame retardants, and selected bisphenols, using the XenoScreen XL YES/YAS assay." Chemosphere 112: 362-369. (http://www.ncbi.nlm.nih.gov/pubmed/25048928)(Abstract)

Roberts, S. C., L. J. Macaulay and H. M. Stapleton (2012). "In vitro metabolism of the brominated flame retardants 2-ethylhexyl-2,3,4,5-tetrabromobenzoate (TBB) and bis(2-ethylhexyl) 2,3,4,5-tetrabromophthalate (TBPH) in human and rat tissues." Chem Res Toxicol 25(7): 1435-1441. (http://www.ncbi.nlm.nih.gov/pubmed/22575079)(Abstract)

Springer, C., E. Dere, S. J. Hall, E. V. McDonnell, S. C. Roberts, C. M. Butt, H. M. Stapleton, D. J. Watkins, M. D. McClean, T. F. Webster, J. J. Schlezinger and K. Boekelheide (2012). "Rodent thyroid, liver, and fetal testis toxicity of the monoester metabolite of bis-(2-ethylhexyl) tetrabromophthalate (tbph), a novel brominated flame retardant present in indoor dust." Environ Health Perspect 120(12): 1711-1719. (http://www.ncbi.nlm.nih.gov/pubmed/23014847)(Abstract)

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