Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6Cl4O2 |
| Molecular Weight | 245.875 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O
InChI
InChIKey=UGNWTBMOAKPKBL-UHFFFAOYSA-N
InChI=1S/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11
| Molecular Formula | C6Cl4O2 |
| Molecular Weight | 245.875 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Chloranil is an oxidant, practically useful for dehydrogenation to aromatic and alpha,beta-desaturated carbonyl compounds. Chloranil was found to inhibit human carboxylesterases: carboxylesterase 1 and 2, acetylcholinesterase and butyrylcholinesterase. In 1950s chloranil ointment was used for the treatment of psoriasis and onychomycosis.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3180 |
57.4 nM [Ki] | ||
Target ID: CHEMBL2265 |
83.9 nM [Ki] | ||
Target ID: CHEMBL220 |
163.0 nM [Ki] | ||
Target ID: CHEMBL1914 |
268.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Spectroscopic and thermodynamic study of charge transfer interaction between vitamin B6 and p-chloranil in aqueous ethanol mixtures of varying composition. | 2008-07 |
|
| Synthesis and biological evaluation of a series of A,B-ring modified 16,17-secoandrostane derivatives. | 2008-06 |
|
| Oxidative amination of cuprated pyrimidine and purine derivatives. | 2008-05-01 |
|
| Complex polarization propagator calculations of magnetic circular dichroism spectra. | 2008-03-07 |
|
| Does bimolecular charge recombination in highly exergonic electron transfer afford the triplet excited state or the ground state of a photosensitizer? | 2008-01-31 |
|
| Utility of some pi-acceptors for spectrophotometric determination of gatifloxacin in pure form and in pharmaceutical preparations. | 2008-01 |
|
| Levels of polychlorinated dibenzo-p-dioxins and dibenzofurans in China and chemometric analysis of potential emission sources. | 2008-01 |
|
| Charge-sensitive vibrations in p-chloranil: the strange case of the C=C antisymmetric stretching. | 2007-11-08 |
|
| Spectroscopic investigation of the charge-transfer interactions between 1,4,7-trimethyl-1,4,7-triazacyclononane and the acceptors iodine, TCNE, TCNQ and chloranil. | 2007-11 |
|
| Hydrogen-bond interaction in organic conductors: redox activation, molecular recognition, structural regulation, and proton transfer in donor-acceptor charge-transfer complexes of TTF-imidazole. | 2007-09-05 |
|
| Application of a microbial toxicity assay for monitoring treatment effectiveness of pentachlorophenol in water using UV photolysis and TiO2 photocatalysis. | 2007-09-05 |
|
| The first structural study on a cyclic tricoordinate phosphorochloridite and a pentacoordinate phosphorane based on 1,2,3,5-protected myo-inositol--a new conformation of 1,3,2-dioxaphosphorinane ring. | 2007-07-02 |
|
| Oxidative dimer produced from a 2,3,4-trihydroxybenzoic ester. | 2007-07 |
|
| Spectroscopic studies of charge transfer complexes between colchicine and some pi acceptors. | 2007-07 |
|
| Nucleobase-dependent reactivity of a quinone metabolite of pentachlorophenol. | 2007-06 |
|
| Quinone-induced inhibition of urease: elucidation of its mechanisms by probing thiol groups of the enzyme. | 2007-06 |
|
| Mechanistic aspects of the formation of aldehydes and nitriles in photosensitized reactions of aldoxime ethers. | 2007-05-25 |
|
| Charge-transfer complex formation between p-chloranil and 1,n-dicarbazolylalkanes. | 2007-04 |
|
| One-electron oxidation of alcohols by the 1,3,5-trimethoxybenzene radical cation in the excited state during two-color two-laser flash photolysis. | 2007-03-15 |
|
| Microwave assisted synthesis of triazoloquinazolinones and benzimidazoquinazolinones. | 2007-03-05 |
|
| Chemical, pulse radiolysis and density functional studies of a new, labile 5,6-indolequinone and its semiquinone. | 2007-03-02 |
|
| Enyne metathesis-oxidation sequence for the synthesis of 2-phosphono pyrroles: proof of the "yne-then-ene" pathway. | 2007 |
|
| Competitive consecutive electron transfer in determination of ionization potentials: ketene derivatives. | 2006-12-28 |
|
| An efficient synthesis and biological activity of substituted p-benzoquinones. | 2006-12-15 |
|
| Toroidal hopping of a single hole through the circularly-arrayed naphthyl groups in hexanaphthylbenzene cation radical. | 2006-12-07 |
|
| Charge transfer complex studies between some non-steroidal anti-inflammatory drugs and pi-electron acceptors. | 2006-12 |
|
| Inhibition of jack bean urease by tetrachloro-o-benzoquinone and tetrachloro-p-benzoquinone. | 2006-10 |
|
| Effect of structure in benzaldehyde oximes on the formation of aldehydes and nitriles under photoinduced electron-transfer conditions. | 2006-09-29 |
|
| Spectrophotometric determination of rifampicin through chelate formation and charge transfer complexation in pharmaceutical preparation and biological fluids. | 2006-08 |
|
| Synthesis of some new testosterone derivatives fused with substituted pyrazoline ring as promising 5alpha-reductase inhibitors. | 2006-06 |
|
| Charge transfer complex formation between p-chloranil and 1,n-di(9-anthryl)alkanes. | 2006-06 |
|
| Chemical modification at subunit 1 of rat kidney Alpha class glutathione transferase with 2,3,5,6-tetrachloro-1,4-benzoquinone: close structural connectivity between glutathione conjugation activity and non-substrate ligand binding. | 2006-05-28 |
|
| Synthesis and cofacial pi-stacked packing arrangement of 6,13-bis(alkylthio)pentacene. | 2006-05-25 |
|
| Kinetic substituent and solvent effects in 1,3-dipolar cycloaddition of diphenyldiazomethanes with fullerenes C60 and C70: a comparison with the addition to TCNE, DDQ, and chloranil. | 2006-04-14 |
|
| Evaluation of the effect of terpenoid quinones on Trichophyton mentagrophytes by solution and vapor contact. | 2006-04 |
|
| Catalytic, enantioselective [4 + 2]-cycloadditions of ketene enolates and o-quinones: efficient entry to chiral, alpha-oxygenated carboxylic acid derivatives. | 2006-02-15 |
|
| Time-resolved EPR study of the photophysics and photochemistry of 1-(3-(methoxycarbonyl)propyl)-1-phenyl[6.6]C61. | 2005-12-29 |
|
| Characterization of a deoxyguanosine adduct of tetrachlorobenzoquinone: dichlorobenzoquinone-1,N2-etheno-2'-deoxyguanosine. | 2005-11 |
|
| Spectrophotometric and electrical studies of charge transfer complexes of 2-amino-1,3,4-thiadiazole with pi-acceptors. | 2005-11 |
|
| Nanosecond time-resolved infrared studies of visnagin and khellin triplets and radical ions. | 2005-10-20 |
|
| Divergent oxidative rearrangements in solution and in a zeolite: distal vs proximal bond cleavage of methylenecyclopropanes. | 2005-10-19 |
|
| Synthesis of 1,3,4-thiadiazole, 1,3,4-thiadiazine, 1,3,6-thiadiazepane and quinoxaline derivatives from symmetrical dithiobiureas and thioureidoethylthiourea derivatives. | 2005-08-31 |
|
| Photoreactions of p-quinones with dimethyl sulfide and dimethyl sulfoxide in aqueous acetonitrile. goerner@mpi-muelheim.mpg.de. | 2005-08-04 |
|
| Distribution patterns of PCDD/Fs in chlorinated chemicals. | 2005-08 |
|
| Quinone-sensitized steady-state photolysis of acetophenone oximes under aerobic conditions: kinetics and product studies. | 2005-07-26 |
|
| Spectroscopic and thermodynamic study of charge transfer complexes of cloxacillin sodium in aqueous ethanol medium. | 2005-07 |
|
| Development and validation of spectrophotometric methods for determination of fluoxetine, sertraline, and paroxetine in pharmaceutical dosage forms. | 2005-03-12 |
|
| [Ultraviolet spectral characteristics of charge-transfer reaction complex in micellar system and its application]. | 2005-02 |
|
| Molecular switch based on a biologically important redox reaction. | 2005-01-13 |
|
| [Study on fluorescence characteristics of pefloxacin based on charge transfer reaction]. | 2004-05 |
Sample Use Guides
For the treatment of psoriasis, chloranil was used as a 10% ointment.
Route of Administration:
Topical
Carboxylesterase (CE) inhibition was determined using a spectrophotometric multiwell plate assay with 3mM o-nitrophenyl acetate (o-NPA) as a substrate. Briefly, the test compound (100 uM) and substrate were aliquoted into wells and the enzyme was added using a multiwell pipettor. The rate of change in absorbance at 420 nm was measured at 15 s intervals for 5 min and compared to wells containing no inhibitor. Compounds that demonstrated 50% reduction in CE activity were subsequently evaluated in detail.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:51:34 GMT 2025
by
admin
on
Mon Mar 31 17:51:34 GMT 2025
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| Record UNII |
01W5X7N5XV
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| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
79301
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204-274-4
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8432
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chloranil
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D002703
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m3348
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PRIMARY | Merck Index | ||
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8371
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01W5X7N5XV
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36703
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CHLORANIL
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DTXSID2020266
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1533
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118-75-2
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