Dicofol (CHEM000134)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (74)XML
Record Information
Version1.0
Creation Date2009-03-06 18:58:09 UTC
Update Date2026-03-26 22:50:18 UTC
Accession NumberCHEM000134
Identification
Common NameDicofol
ClassSmall Molecule
DescriptionDicofol is an organochlorine pesticide that is chemically related to DDT. Specifically, it is used as a miticide against the red spider mite. Though difocol is not extremely toxic, its use is controverial because one of the intermediates used in its production is DDT. It also may accumulate in the environment and its use is restricted in many areas. (5)
Contaminant Sources
  • Clean Air Act Chemicals
  • EPA Endocrine Screening
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,1-Bis(4-chlorophenyl)-2,2,2-trichloroethanolChEBI
1,1-Bis(p-chlorophenyl)-2,2,2-trichloroethanolChEBI
2,2,2-Trichloro-1,1-bis(p-chlorophenyl)ethanolChEBI
4,4'-Dichloro-alpha-(trichloromethyl)benzhydrolChEBI
4-Chloro-alpha-(4-chlorophenyl)-alpha-(trichloromethyl)benzenemethanolChEBI
AcarinChEBI
Di-(p-chlorophenyl)trichloromethylcarbinolChEBI
DTMCChEBI
KelthaneChEBI
MitiganChEBI
p,p-DicofolChEBI
4,4'-Dichloro-a-(trichloromethyl)benzhydrolGenerator
4,4'-Dichloro-α-(trichloromethyl)benzhydrolGenerator
4-Chloro-a-(4-chlorophenyl)-a-(trichloromethyl)benzenemethanolGenerator
4-Chloro-α-(4-chlorophenyl)-α-(trichloromethyl)benzenemethanolGenerator
KeltaneMeSH
Chemical FormulaC14H9Cl5O
Average Molecular Mass370.486 g/mol
Monoisotopic Mass367.910 g/mol
CAS Registry Number115-32-2
IUPAC Name2,2,2-trichloro-1,1-bis(4-chlorophenyl)ethan-1-ol
Traditional Namedicofol
SMILESOC(C1=CC=C(Cl)C=C1)(C1=CC=C(Cl)C=C1)C(Cl)(Cl)Cl
InChI IdentifierInChI=1S/C14H9Cl5O/c15-11-5-1-9(2-6-11)13(20,14(17,18)19)10-3-7-12(16)8-4-10/h1-8,20H
InChI KeyUOAMTSKGCBMZTC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Tertiary alcohol
  • Halohydrin
  • Chlorohydrin
  • Organochloride
  • Organohalogen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alkyl chloride
  • Alcohol
  • Alkyl halide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point77.5°C
Boiling PointNot Available
Solubility0.0008 mg/mL at 25 °C [TOMLIN,C (1997)]
Predicted Properties
PropertyValueSource
Water Solubility0.0001 g/LALOGPS
logP5.59ALOGPS
logP5.56ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)11.03ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity86.81 m³·mol⁻¹ChemAxon
Polarizability33.08 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-6980000000-1194141018f6ebab2656Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-c280b963638b7e0e5a0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0019000000-fc7eb9a2ea97f037b072Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0490000000-f51f126c68d9d6426283Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-a0b7c6ac1f1ab734fe45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-0915000000-1da7cfbf512196658fdeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-0982000000-757981834cf4e899f9aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-7a5daea377bb0304cb41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0009000000-7a5daea377bb0304cb41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1439000000-3eeec9d362e5b14ac7a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-cf1e107d16eb7c9fa93eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0219000000-49d35f215ffc3df27cf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0149000000-abcde91e107317ee4fb1Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udr-2950000000-3f1491713e95b5a6218dSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral(5) ; inhalation (5) ; dermal (5).
Mechanism of ToxicityLike other organochloride pesticides, dicofol is believed to act by at least four mechanisms, possibly all functioning simultaneously. It may reduce potassium transport across the membrane. Dicofol also alters the porous channels through which sodium ions pass. These channels activate (open) normally but are inactivated (closed) slowly, thus interfering with the active transport of sodium out of the nerve axon during repolarization. Dicofol inhibits neuronal adenosine triphosphatases (ATPases), particularly Na+K+-ATPase, and Ca2+-ATPase which play vital roles in neuronal repolarization. Dicofol also inhibits the ability of calmodulin, a calcium mediator in nerves, to transport calcium ions that are essential for the release of neurotransmitters. All these inhibited functions reduce the rate of depolarization and increase the sensitivity of neurons to small stimuli that would not elicit a response in a fully depolarized neuron. Difocol is also an endocrine disruptor and binds both the androgen and estrogen receptor. In addition, it may alter sex hormone metabolism by directly inhibiting cytochrome P-450 19A1. Difocol is able to competitively bind transthyretin, which lowers plasma thyroid hormone levels. (7, 1, 2, 3)
MetabolismDicofol can be absorbed via oral, inhahation, and dermal routes. It is distributed primarily to the adipose tissue, as well as the adrenal glands, thyroid, and liver. Metabolism of dicofol produces the metabolites 4,4'-dichloro-benzophenone and 4,4'-dichlorodicofol. Dicofol and its metabolites are excreted mainly in the faeces. (5, 6)
Toxicity ValuesLD50: 595 mg/kg (Oral, Rat) (9) LD50: 2100 mg/kg (Percutaneous, Rabbit) (8)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (4)
Uses/SourcesDicofol is used as a pesticide on agricultural crops and ornamental plants, as well as for agricultural and domestic buildings for mite control. (5)
Minimum Risk LevelNot Available
Health EffectsDicofol poisoning affects the liver, kidneys and the central nervous system. Very severe cases may result in convulsions, coma, or death from respiratory failure. High doses may also cause reproductive damage. (5)
SymptomsSymptoms exposure include nausea, dizziness, weakness and vomiting. Dermal exposure may cause skin irritation or a rash, and eye contact may cause conjunctivitis. (7, 5)
TreatmentTreatment of dicofol poisoning is mainly symptomatic. Areas of contact should be washed with soap and water, and gastric lavage may be performed if ingested. (6)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0251207
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDicofol
Chemspider ID7970
ChEBI ID34692
PubChem Compound IDNot Available
Kegg Compound IDC14301
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available