A metabolite of pentachlorophenol
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Tetrachlorohydroquinone

Item No. 23231

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3,5,6-tetrachloro-1,4-benzenediol
CAS Number
87-87-6
Synonyms
  • NSC 4858
  • NSC 100888
  • TCHQ
Molecular Formula
C6H2Cl4O2
Formula Weight
247.9
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
λmax
309 nm
SMILES
OC1=C(Cl)C(Cl)=C(O)C(Cl)=C1Cl
InChi Code
InChI=1S/C6H2Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11/h11-12H
InChi Key
STOSPPMGXZPHKP-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Tetrachlorohydroquinone (TCHQ) is a metabolite of the organochlorine biocide pentachlorophenol.1 It is cytotoxic to RTL-W1 rainbow trout liver cells (EC50 = 1.55 μM in a neutral red assay). TCHQ increases production of reactive oxygen species (ROS), inhibits apoptosis, and induces loss of the mitochondrial membrane potential and necrosis in splenocytes.2 In vivo, TCHQ induces glutathione (GSH) depletion in mouse liver.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pietsch, C., Hollender, J., Dorusch, F., et al. Cytotoxic effects of pentachlorophenol (PCP) and its metabolite tetrachlorohydroquinone (TCHQ) on liver cells are modulated by antioxidants. Cell Biol. Toxicol. 30(4), 233-252 (2014).

    2. Chen, H.-M., Zhu, B.-Z., Chen, R.-J., et al. The pentachlorophenol metabolite tetrachlorohydroquinone induces massive ROS and prolonged p-ERK expression in splenocytes, leading to inhibition of apoptosis and necrotic cell death. PLoS One 9(2), e89483 (2014).

    3. Wang, Y.-J., Ho, Y.-S., Chu, S.-W., et al. Induction of glutathione depletion, p53 protein accumulation and cellular transformation by tetrachlorohydroquinone, a toxic metabolite of pentachlorophenol. Chem. Biol. Interact. 105(1), 1-16 (1997).