TETRABROMOBISPHENOL A

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H12Br4O2
Molecular Weight	543.871
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C1=CC(Br)=C(O)C(Br)=C1)C2=CC(Br)=C(O)C(Br)=C2

InChI

InChIKey=VEORPZCZECFIRK-UHFFFAOYSA-N

InChI=1S/C15H12Br4O2/c1-15(2,7-3-9(16)13(20)10(17)4-7)8-5-11(18)14(21)12(19)6-8/h3-6,20-21H,1-2H3

HIDE SMILES / InChI

Molecular Formula	C15H12Br4O2
Molecular Weight	543.871
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Potent competitive interactions of some brominated flame retardants and related compounds with human transthyretin in vitro.	2000 Jul	10869457
Estrogen-like properties of brominated analogs of bisphenol A in the MCF-7 human breast cancer cell line.	2001	11693576
2,2',6,6'-Tetrachloro-4,4'-propane-2,2-diyldiphenol, 2,2',6-tribromo-4,4'-propane-2,2-diyldiphenol and 2,2',6,6'-tetrabromo-4,4'-propane-2,2-diyldiphenol.	2001 Nov	11706259
Effects of the environmental oestrogens bisphenol A, tetrachlorobisphenol A, tetrabromobisphenol A, 4-hydroxybiphenyl and 4,4'-dihydroxybiphenyl on oestrogen receptor binding, cell proliferation and regulation of oestrogen sensitive proteins in the human breast cancer cell line MCF-7.	2003 Apr	12753421
The flame retardants tetrabromobisphenol A and tetrabromobisphenol A-bisallylether suppress the induction of interleukin-2 receptor alpha chain (CD25) in murine splenocytes.	2003 Feb 14	12505372
Brominated dioxin-like compounds: in vitro assessment in comparison to classical dioxin-like compounds and other polyaromatic compounds.	2003 Sep	12850102
Effects of the brominated flame retardants hexabromocyclododecane (HBCDD), and tetrabromobisphenol A (TBBPA), on hepatic enzymes and other biomarkers in juvenile rainbow trout and feral eelpout.	2004 Aug 25	15276329
Inhibitory effects of environmental chemicals on protein disulfide isomerase in vitro.	2005 Dec	16617682
Effects of tetrabromobisphenol A, brominated flame retardant, in ICR mice after prenatal and postnatal exposure.	2006 Aug	16716481
In vitro profiling of the endocrine-disrupting potency of brominated flame retardants.	2006 Jul	16601080
Exposure to tetrabromobisphenol-A alters TH-associated gene expression and tadpole metamorphosis in the Pacific tree frog Pseudacris regilla.	2006 Jun 30	16678281
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Cytotoxicity of TBBPA and effects on proliferation, cell cycle and MAPK pathways in mammalian cells.	2007 Apr	17254629
In vitro toxicity of tetrabromobisphenol-A on cerebellar granule cells: cell death, free radical formation, calcium influx and extracellular glutamate.	2007 Apr	17205976
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008 Apr	18324785
Effects of tetrabromobisphenol A, a brominated flame retardant, on the immune response to respiratory syncytial virus infection in mice.	2010 Apr	20074668
Disruption of thyroid hormone-dependent hypothalamic set-points by environmental contaminants.	2010 Jul 29	20399831
Characterization of novel ligands of ERα, Erβ, and PPARγ: the case of halogenated bisphenol A and their conjugated metabolites.	2011 Aug	21622942
Molecular Mechanism of Tetrabromobisphenol A (TBBPA)-induced Target Organ Toxicity in Sprague-Dawley Male Rats.	2011 Jun	24278553
Disruption of the hypothalamic-pituitary-thyroid axis in zebrafish embryo-larvae following waterborne exposure to BDE-47, TBBPA and BPA.	2012 Feb	22100034
Tetrabromobisphenol-A disrupts thyroid hormone receptor alpha function in vitro: use of fluorescence polarization to assay corepressor and coactivator peptide binding.	2012 May	22277881
Modulation of human α4β2 nicotinic acetylcholine receptors by brominated and halogen-free flame retardants as a measure for in vitro neurotoxicity.	2012 Sep 3	22750351
Endocrine disruptors differentially target ATP-binding cassette transporters in the blood-testis barrier and affect Leydig cell testosterone secretion in vitro.	2013 Dec	24014645
Brominated flame retardants stimulate mouse immune cells in vitro.	2013 Dec	22972382
Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity.	2013 Jun	22954530
Similarities in the endocrine-disrupting potencies of indoor dust and flame retardants by using human osteosarcoma (U2OS) cell-based reporter gene assays.	2013 Mar 19	23398518
Mimicking of estradiol binding by flame retardants and their metabolites: a crystallographic analysis.	2013 Oct	23959441
In vitro study on the agonistic and antagonistic activities of bisphenol-S and other bisphenol-A congeners and derivatives via nuclear receptors.	2013 Oct 1	23714657
Comparative antioxidant status in freshwater fish Carassius auratus exposed to six current-use brominated flame retardants: a combined experimental and theoretical study.	2013 Sep 15	23880106
Ioxynil and tetrabromobisphenol A suppress thyroid-hormone-induced activation of transcriptional elongation mediated by histone modifications and RNA polymerase II phosphorylation.	2014 Apr	24449421
Structurally-diverse, PPARγ-activating environmental toxicants induce adipogenesis and suppress osteogenesis in bone marrow mesenchymal stromal cells.	2015 May 4	25777084

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:41:25 GMT 2023` Edited by `admin` on `Fri Dec 15 18:41:25 GMT 2023`
Record UNII	FQI02RFC3A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRABROMOBISPHENOL A

Systematic Name

English

TETRABROMOBISPHENOL A, 3,3',5,5'-

Common Name

English

TBBPA

Common Name

English

NSC-59775

Code

English

4,4'-(1-METHYLETHYLIDENE)BIS(2,6-DIBROMOPHENOL)

Systematic Name

English

2,2',6,6'-TETRABROMOBISPHENOL A [HSDB]

Common Name

English

2,2-BIS(3,5-DIBROMO-4-HYDROXYPHENYL)PROPANE

Systematic Name

English

TETRABROMOBISPHENOL A [IARC]

Common Name

English

CP-2000

Code

English

TETRABROMOBISPHENOL A [MI]

Common Name

English

4,4'-ISOPROPYLIDENEBIS(2,6-DIBROMOPHENOL)

Systematic Name

English

3,3',5,5'-TETRABROMOBISPHENOL A

Common Name

English

Code System Code Type Description

PUBCHEM

6618