Description
Tetrachlorohydroquinone (TCHQ) is a metabolite of the organochlorine biocide pentachlorophenol. It is cytotoxic to RTL-W1 rainbow trout liver cells (EC
50 = 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.
Chemical Properties
LIGHT BEIGE CRYSTALLINE POWDER
Uses
Tetrachlorohydroquinone is a chlorinated hydroquinone compound used as an analytical standard.
Definition
ChEBI: A tetrachlorobenzene that is 1,2,4,5-tetrachlorobenzene in which the hydrogens at positions 3 and 6 are replaced by hydroxy groups.
Purification Methods
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.]
