A tetrabromobisphenol A degradation product and an environmental contaminant
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2,2',6-Tribromobisphenol A

Item No. 9004566

Technical Information
Formal Name
2,6-dibromo-4-[1-(3-bromo-4-hydroxyphenyl)-1-methylethyl]-phenol
CAS Number
6386-73-8
Synonyms
  • Tri-BBPA
  • Tribromobisphenol A
Molecular Formula
C15H13Br3O2
Formula Weight
Purity
≥98%
Formulation
A solid
DMSO: Soluble: ≥10 mg/mlEthanol: Soluble: ≥10 mg/ml
SMILES
CC(C1=CC=C(O)C(Br)=C1)(C2=CC(Br)=C(O)C(Br)=C2)C
InChi Code
InChI=1S/C15H13Br3O2/c1-15(2,8-3-4-13(19)10(16)5-8)9-6-11(17)14(20)12(18)7-9/h3-7,19-20H,1-2H3
InChi Key
WYBOEVJIVYIEJL-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    2,2',6-Tribromobisphenol A (Tri-BBPA) is a degradation product of the flame retardant tetrabromobisphenol A and an environmental contaminant.1 It is an inhibitor of 12-lipoxygenase (12-LO) and 15-LO (IC50s = 7 and 5 µM, respectively, for the human enzymes).2 Tri-BBPA (60 µM) induces apoptosis and cell cycle arrest at the G0/G1 phase in primary human embryonic stem cells (ESCs).3 It decreases serum levels of total protein, albumin, γ-glutamyl transpeptidase (GGT), lactate dehydrogenase (LDH), creatine kinase (CK), and urea, increases serum levels of acetylcholinesterase (AChE), and disrupts hepatic metabolism of tryptophan (Item No. 29600) in mice when administered at a dose of 200 mg/kg per day for 14 days.4 Tri-BBPA has been found in industrial soil samples and human breast milk.1,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Liu, A., Shi, J., Qu, G., et alIdentification of emerging brominated chemicals as the transformation products of tetrabromobisphenol A (TBBPA) derivatives in soil. Environ. Sci. Technol. 51(10), 5434-5444 (2017).

    2. Segraves, E.N., Shah, R.R., Segraves, N.L., et alProbing the activity differences of simple and complex brominated aryl compounds against 15-soybean, 15-human, and 12-human lipoxygenase. J. Med. Chem. 47(16), 4060-4065 (2004).

    3. Yang, Y., He, S., Qi, Z., et alProliferation toxicity and mechanism of novel mixed bromine/chlorine transformation products of tetrabromobisphenol A on human embryonic stem cell. J. Hazard. Mater. 449, 131050 (2023).

    4. Kuang, H.X., Dong, C.Y., Yan, L., et alExposure to synthesized tribromobisphenol A and critical effects: Metabolic pathways, disease signature, and benchmark dose derivation. Sci. Total Environ. 932, 173117 (2024).

    5. Nakao, T.A., Akiyama, E., Kakutani, H., et alLevels of tetrabromobisphenol A, tribromobisphenol A, dibromobisphenol A, monobromobisphenol A, and bisphenol a in Japanese breast milk. Chem. Res. Toxicol. 28(4), 722-728 (2015).