The pathway with the name Biodegradation Pathway Assignment: 2,4,6-trichlorophenol has the following structure: Result: C1=C(C(=C(C=C1O)Cl)O)Cl no rule associatedC1=C(C(=C(C=C1O)O)O)Cl C(=C/C(=O)O)/C(=O)CC(=O)O no rule associatedC(CC(=O)O)C(=O)CC(=O)O C1=C(C(=C(C=C1O)O)O)Cl no rule associatedC(=C(/C(=O)[O-])\Cl)/C(=O)CC(=O)[O-] C1=C(C(=C(C=C1Cl)Cl)O)Cl no rule associatedC1=C(C(=C(C=C1O)Cl)O)Cl C(=C(/C(=O)[O-])\Cl)/C(=O)CC(=O)[O-] no rule associatedC(=C/C(=O)O)/C(=O)CC(=O)O Description: 2,4,6-Trichlorophenol (2,4,6-TCP) is a chlorinated aromatic compound widely used as an antiseptic, glue, leather, and wood preservative, antimildew agent, water chlorinator, organic solvent, and in the synthesis of various agricultural chemicals. 2,4,6-TCP has been classified as an extremely toxic, mutagenic, and carcinogenic compound due to the C-Cl bond position relative to the -OH group. This makes it recalcitrant to biodegradation and leads to its interference in mitochondrial oxidative phosphorylation through the inhibition of cytochrome P450-dependent mixed-function oxidases.
This chemical enters the environment through several routes, like industrial waste, insecticides, or the degradation of complex chlorinated hydrocarbons. In the environment, 2,4,6-TCP has been quantified in groundwater with about 91.3 ppb, in surface waters in Canada with up to 30 ppb, and in drinking waters of the USA, Finland, and Canada with about 0.014-0.7 ppb. Its occurrence has also been extensively recorded. In China, 54.4% of the 600 sampled sites in seven major watersheds and three drainage areas showed contamination of 2,4,6-TCP. Mukherjee et al, 2022
Certain bacterial species, Cupriavidus necator JMP134, for example, have demonstrated the ability to degrade 2,4,6-TCP through enzymatic pathways. C. necator JMP134 is encoded by the tcp genes. These genes are located in a genetic context, tcpRXABCYD, which resembles a putative catabolic operon.

2,4,6-TCP monooxygenase preforms a hydroxylation of 2,4,6-TCP to form 2,6-dichlorohydroquinone. The monooxygenase further hydroxylates, leading to 6-chlorohydroxyquinol, making it ready for ring cleavage. A dioxygenase cleaves the aromatic ring structure, making 6-chlorohydroxyquinol convert to 2-chloromaleylacetate. Maleylacetate reductase converts 2-chloromaleylacetate to maleylacetate by dechlorination and reduction. The reductase also converts maleylacetate to 3-oxoadipic acid, which enters the central metabolic pathways. Sanchez et al, 2007

Author:
Eve Holl, Manchester University
4/18/2025 Your Options: Update the Pathway Information: POST with (required) pathwayName and (optional) pathwayDescription. Delete the Pathway: DELETE. Show nodes: GET on https://envipath.org/package/34a5d273-cf25-4228-b26f-1d72261fde94/pathway/0e452f02-b7d6-4abf-aaf3-62bb0330452d/node Show edges: GET on https://envipath.org/package/34a5d273-cf25-4228-b26f-1d72261fde94/pathway/0e452f02-b7d6-4abf-aaf3-62bb0330452d/edge