Compounds > 4-hydroxy-2',4',6'-trichlorobiphenyl
Page last updated: 2024-12-07

4-hydroxy-2',4',6'-trichlorobiphenyl

Description

4-hydroxy-2',4',6'-trichlorobiphenyl, also known as 4-OH-TCB, is a persistent organic pollutant (POP) that has been widely studied due to its environmental persistence and potential toxicity. It is a chlorinated biphenyl derivative, a group of compounds that have been associated with various health problems, including endocrine disruption, developmental effects, and cancer. The synthesis of 4-OH-TCB typically involves the chlorination of biphenyl followed by hydroxylation. It is a highly lipophilic compound, which contributes to its bioaccumulation in the food chain and persistence in the environment. Research on 4-OH-TCB is primarily focused on understanding its environmental fate, toxicity, and potential health risks. Studies have investigated its bioaccumulation in organisms, its degradation in the environment, and its potential to disrupt endocrine systems. The importance of this compound lies in its potential to pose significant risks to human health and the environment. Understanding its properties and behavior is crucial for developing strategies to mitigate its negative impacts.'

4-hydroxy-2',4',6'-trichlorobiphenyl: do not confuse with the tetrachlorinated compound, also known as 4-OH-TCB (see 4-OH-TCB (tetra)) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID105036
CHEMBL ID79850
CHEBI ID34235
SCHEMBL ID2767670
MeSH IDM0274520

Synonyms (26)

Synonym
BIDD:ER0051
chebi:34235 ,
CHEMBL79850
14962-28-8
2,4,6-trichloro-4'-biphenylol
4-hydroxy-2',4',6'-trichlorobiphenyl
C14189 ,
2',4',6'-trichloro-4-biphenylol
4-biphenylol, 2',4',6'-trichloro-
2',4',6'-trichloro-(1,1'-biphenyl)-4-ol
(1,1'-biphenyl)-4-ol, 2',4',6'-trichloro-
ccris 9183
oh-pcb-30
4-(2,4,6-trichlorophenyl)phenol
03kw6rt30c ,
unii-03kw6rt30c
phenol, 4-phenyl-2',4',6'-trichloro-
2',4',6'-trichloro(1,1'-biphenyl)-4-ol
2',4',6'-trichlorobiphenyl-4-ol
SCHEMBL2767670
LTQJFLVGNGVJCX-UHFFFAOYSA-N
2',4',6'-trichloro[1,1'-biphenyl]-4-ol #
DTXSID7074539
Q27115931
2',4',6'-trichloro-4-biphenylol (oh-pcb-30)
PD015516
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
biphenylsBenzenoid aromatic compounds containing two phenyl or substituted-phenyl groups which are joined together by a single bond.
trichlorobenzeneAny member of the class of chlorobenzenes carrying three chloro substituents at unspecified positions.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TransthyretinHomo sapiens (human)Concentration0.02000.01000.13800.6000AID161428
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
signal transductionTransthyretinHomo sapiens (human)
purine nucleobase metabolic processTransthyretinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
hormone activityTransthyretinHomo sapiens (human)
protein bindingTransthyretinHomo sapiens (human)
identical protein bindingTransthyretinHomo sapiens (human)
thyroid hormone bindingTransthyretinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
extracellular regionTransthyretinHomo sapiens (human)
extracellular spaceTransthyretinHomo sapiens (human)
azurophil granule lumenTransthyretinHomo sapiens (human)
extracellular exosomeTransthyretinHomo sapiens (human)
extracellular spaceTransthyretinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID230635KPCB/ K352 ratio of the compound1986Journal of medicinal chemistry, Dec, Volume: 29, Issue:12
A theoretical study of the binding of polychlorinated biphenyls (PCBs), dibenzodioxins, and dibenzofuran to human plasma prealbumin.
AID161431Thyroxine binding constant on human plasma prealbumin.1986Journal of medicinal chemistry, Dec, Volume: 29, Issue:12
A theoretical study of the binding of polychlorinated biphenyls (PCBs), dibenzodioxins, and dibenzofuran to human plasma prealbumin.
AID161427Relative binding affinity to prealbumin was determined from the competition binding assays and is expressed relative to L-T41986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Structurally specific binding of halogenated biphenyls to thyroxine transport protein.
AID161428Concentration at which 50% total binding against prealbumin protein occurs1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Structurally specific binding of halogenated biphenyls to thyroxine transport protein.
AID161430Displacement of [125I]thyroxin from human plasma prealbumin.1986Journal of medicinal chemistry, Dec, Volume: 29, Issue:12
A theoretical study of the binding of polychlorinated biphenyls (PCBs), dibenzodioxins, and dibenzofuran to human plasma prealbumin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (22.22)18.7374
1990's4 (44.44)18.2507
2000's2 (22.22)29.6817
2010's1 (11.11)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.16

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.16 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.16)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
thyroxine
[no description available]		1.96102-halophenol;
amino acid zwitterion;
iodophenol;
iodothyronine;
non-proteinogenic alpha-amino acid;
tyrosine derivative		mitogen
potassium chloride
Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.		1.9910inorganic chloride;
inorganic potassium salt;
potassium salt		fertilizer
tetraethylammonium
Tetraethylammonium: A potassium-selective ion channel blocker. (From J Gen Phys 1994;104(1):173-90)		1.9910quaternary ammonium ion
thyroxine
Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.		1.96102-halophenol;
iodophenol;
L-phenylalanine derivative;
non-proteinogenic L-alpha-amino acid;
thyroxine zwitterion;
thyroxine		antithyroid drug;
human metabolite;
mouse metabolite;
thyroid hormone
triiodothyronine
Triiodothyronine: A T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.. 3,3',5-triiodo-L-thyronine : An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.		1.96102-halophenol;
amino acid zwitterion;
iodophenol;
iodothyronine		human metabolite;
mouse metabolite;
thyroid hormone
bisphenol a
4,4'-isopropylidene diphenol: stimulates proliferative responses and cytokine productions of murine spleen cells and thymus cells in vitro. bisphenol : By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom.. bisphenol A : A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.		210bisphenolendocrine disruptor;
environmental contaminant;
xenobiotic;
xenoestrogen
diphenyl
diphenyl: RN given refers to unlabeled cpd; structure		2.3720aromatic fungicide;
benzenes;
biphenyls		antifungal agrochemical;
antimicrobial food preservative
heptanol
Heptanol: A colorless liquid with a fragrant odor. It is used as an intermediate, solvent and in cosmetics.. heptanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of seven carbon atoms.. heptan-1-ol : A primary alcohol that is heptane substituted by a hydroxy group at position 1. It has been isolated from Capillipedium parviflorum.		1.9910heptanol;
primary alcohol		flavouring agent;
fragrance;
gap junctional intercellular communication inhibitor;
plant metabolite
2,4,6-triiodophenol
[no description available]		1.9610
3,3',5'-triiodothyronine
[no description available]		1.9610iodothyroninehuman metabolite
2,2',6,6'-tetrachlorobiphenyl
2,2',6,6'-tetrachlorobiphenyl: structure in first source		2.3720
3,4,5,3',4',5'-hexachlorobiphenyl
[no description available]		2.3720hexachlorobiphenyl;
trichlorobenzene
kc 400
KC 400: mixture of polychlorinated biphenyls. 3,3',5,5'-tetrachlorobiphenyl : A tetrachlorobiphenyl that is biphenyl in which both phenyl groups are substituted by chlorines at positions 3 and 5.		1.9610dichlorobenzene;
tetrachlorobiphenyl
2,2-bis(4-hydroxyphenyl)-1,1,1-trichloroethane
2,2-bis(4-hydroxyphenyl)-1,1,1-trichloroethane: methoxychlor metabolite		210bisphenol
3,3',5,5'-tetrachlorobiphenyl-4,4'-diol
3,3',5,5'-tetrachlorobiphenyl-4,4'-diol : A member of the class of hydroxybiphenyls formed formally by chlorination of biphenyl-4,4'-diol at C-3, -3', -5 and -5'.		2.3720dichlorobenzene;
hydroxybiphenyls
fulvestrant
Fulvestrant: An estradiol derivative and estrogen receptor antagonist that is used for the treatment of estrogen receptor-positive, locally advanced or metastatic breast cancer.. fulvestrant : A 3-hydroxy steroid that is 17beta-estradiol in which the 7alpha hydrogen has been replaced by a nonyl group in which one of the hydrogens of the terminal methyl has been replaced by a (4,4,5,5,5-pentafluoropentyl)sulfinyl group. An estrogen receptor antagonist, it is used in the treatment of breast cancer.		2.412017beta-hydroxy steroid;
3-hydroxy steroid;
organofluorine compound;
sulfoxide		antineoplastic agent;
estrogen antagonist;
estrogen receptor antagonist
4-hydroxy-2',3',4'-5'-tetrachlorobiphenyl
4-hydroxy-2',3',4'-5'-tetrachlorobiphenyl: structure in first source		7.940biphenyls;
tetrachlorobenzene
oxytocin
Oxytocin: A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION.. oxytocin : A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour.		6.9910heterodetic cyclic peptide;
peptide hormone		oxytocic;
vasodilator agent
afimoxifene
afimoxifene : A tertiary amino compound that is tamoxifen in which the phenyl group which is in a Z- relationship to the ethyl substituent is hydroxylated at the para- position. It is the active metabolite of tamoxifen.		210phenols;
tertiary amino compound		antineoplastic agent;
estrogen receptor antagonist;
metabolite
tamoxifen
[no description available]		2.420stilbenoid;
tertiary amino compound		angiogenesis inhibitor;
antineoplastic agent;
bone density conservation agent;
EC 1.2.3.1 (aldehyde oxidase) inhibitor;
EC 2.7.11.13 (protein kinase C) inhibitor;
estrogen antagonist;
estrogen receptor antagonist;
estrogen receptor modulator
genistein
[no description available]		2107-hydroxyisoflavonesantineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
geroprotector;
human urinary metabolite;
phytoestrogen;
plant metabolite;
tyrosine kinase inhibitor
calcimycin
Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.		1.9910benzoxazole
phytoestrogens
Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.		210
ConditionIndicatedRelationship StrengthStudiesTrials
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.420
Sterility, Female
[description not available]		0210
Infertility, Female
Diminished or absent ability of a female to achieve conception.		0210
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