Tetrachlorohydroquinone

Tetrachlorohydroquinone (TCHQ) is a metabolite of the organochlorine biocide pentachlorophenol. 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. In vivo, TCHQ induces glutathione (GSH) depletion in mouse liver.

LIGHT BEIGE CRYSTALLINE POWDER

Tetrachlorohydroquinone is a chlorinated hydroquinone compound used as an analytical standard.

ChEBI: A tetrachlorobenzene that is 1,2,4,5-tetrachlorobenzene in which the hydrogens at positions 3 and 6 are replaced by hydroxy groups.

Crystallise the quinone from EtOH or AcOH/EtOH. Sublime it at 77o/0.6x10-3mm. The dibenzoyl derivative has m 233o. [Conant & Fieser J Am Chem Soc 45 2207 1923, Rabideau et al. J Am Chem Soc 108 8130 1986, Beilstein 6 H 851, 6 I 417, 6 II 846, 6 III 4436, 6 IV 5775.]

[1] CONSTANZE PIETSCH. Cytotoxic effects of pentachlorophenol (PCP) and its metabolite tetrachlorohydroquinone (TCHQ) on liver cells are modulated by antioxidants.[J]. Cell Biology and Toxicology, 2014, 30 4: 233-252. DOI: 10.1007/s10565-014-9283-4
[2] HSIU-MIN CHEN. The pentachlorophenol metabolite tetrachlorohydroquinone induces massive ROS and prolonged p-ERK expression in splenocytes, leading to inhibition of apoptosis and necrotic cell death.[J]. PLoS ONE, 2014: e89483. DOI: 10.1371/journal.pone.0089483
[3] YING-JAN WANG . Induction of glutathione depletion, p53 protein accumulation and cellular transformation by tetrachlorohydroquinone, a toxic metabolite of pentachlorophenol[J]. Chemico-Biological Interactions, 1997, 105 1: Pages 1-16. DOI: 10.1016/s0009-2797(97)00023-9