Clofenotane (CHEM000010)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (64)XML
Record Information
Version1.0
Creation Date2009-03-06 18:57:55 UTC
Update Date2026-05-14 19:33:16 UTC
Accession NumberCHEM000010
Identification
Common NameClofenotane
ClassSmall Molecule
DescriptionInsecticide. Clofenotane is a major component of commercial DDT (other names *Gespan*, *Gesarol*, *Geverol*, *Chlorophenotane*). Use banned or discouraged in many countries Clofenotane belongs to the family of Diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups[1]. (Reference: [1] Diphenylmethane: http://en.wikipedia.org/wiki/Diphenylmethane).
Contaminant Sources
  • Clean Air Act Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2A
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Cigarette Toxin
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,1'-(2,2,2-Trichloroethylidene)bis[4-chlorobenzene]ChEBI
1,1,1-Trichloro-2,2-bis(4-chlorophenyl)ethaneChEBI
1,1,1-Trichloro-2,2-bis-(4'-chlorophenyl)ethaneChEBI
1,1-Bis(4-chlorophenyl)-2,2,2-trichloroethaneChEBI
4,4'-DDTChEBI
alpha,alpha-Bis(p-chlorophenyl)-beta,beta,beta-trichlorethaneChEBI
DichlorodiphenyltrichloroethaneChEBI
p,P'-DDTChEBI
p,P'-dichlorodiphenyltrichloroethaneChEBI
DichlorojiphinyltrichloroethaneKegg
DDTKegg
a,a-Bis(p-chlorophenyl)-b,b,b-trichlorethaneGenerator
Α,α-bis(p-chlorophenyl)-β,β,β-trichlorethaneGenerator
1,1'-(2,2,2-Trichloroethane-1,1-diyl)bis(4-chlorobenzene)HMDB
1,1'-(2,2,2-Trichloroethylidene)bis(4-chloro)-benzeneHMDB
1,1'-(2,2,2-Trichloroethylidene)bis(4-chlorobenzene), 9ciHMDB
1,1,1-trichloro-2,2-Bis(4,4'-dichlorodiphenyl)ethaneHMDB
1,1,1-trichloro-2,2-Bis(4-chlorophenyl)-ethaneHMDB
1,1,1-trichloro-2,2-Bis(P-chlorophenyl)-ethaneHMDB
1,1,1-trichloro-2,2-Bis(P-chlorophenyl)ethaneHMDB, MeSH
1,1,1-trichloro-2,2-Di(4-chlorophenyl)-ethaneHMDB
1,1,1-trichloro-2-2-Bis(4-chlorophenyl)ethaneHMDB
1,1,1-Trichlorobis(chlorophenyl)ethaneHMDB
1,1-Bis(P-chlorophenyl)-2,2,2-trichioroethaneHMDB
1,1-Bis-(P-chlorophenyl)-2,2,2-trichloroethaneHMDB
1-chloro-4-[2,2,2-trichloro-1-(4-Chlorophenyl)ethyl]benzeneHMDB
2,2,2-trichloro-1,1-Bis(4-chlorophenyl)ethaneHMDB
2,2,2-trichloro-1,1-Bis(P-chlorophenyl)-ethaneHMDB
2,2,2-Trichlorobis(4-chlorophenyl)ethaneHMDB
2,2-Bis(P-chlorophenyl)-1,1,1-trichloroethaneHMDB
Bis(P-chlorophenyl)-2,2,2-trichloroethaneHMDB
ChlofenotanHMDB
ChlorophenothaneHMDB, MeSH
ChlorphenotaneHMDB
Dicophane, banHMDB
DiphenyltrichloroethaneHMDB
P,P'-DDT, bsiHMDB
ZeidaneHMDB
ZerdaneHMDB
ZithiolHMDB
TbisC-ethaneMeSH, HMDB
BenzochlorylMeSH, HMDB
P',p'-DDTMeSH, HMDB
4,4' DichlorodiphenyltrichloroethaneMeSH, HMDB
4,4' DDTMeSH, HMDB
4,4'-DichlorodiphenyltrichloroethaneMeSH, HMDB
TbisC ethaneMeSH, HMDB
ClofenotaneChEBI
Chemical FormulaC14H9Cl5
Average Molecular Mass354.486 g/mol
Monoisotopic Mass351.915 g/mol
CAS Registry Number50-29-3
IUPAC Name1-chloro-4-[2,2,2-trichloro-1-(4-chlorophenyl)ethyl]benzene
Traditional Namedetox
SMILESClC1=CC=C(C=C1)C(C1=CC=C(Cl)C=C1)C(Cl)(Cl)Cl
InChI IdentifierInChI=1S/C14H9Cl5/c15-11-5-1-9(2-6-11)13(14(17,18)19)10-3-7-12(16)8-4-10/h1-8,13H
InChI KeyYVGGHNCTFXOJCH-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
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • 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
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point108.5 - 109°C
Boiling PointNot Available
Solubility5.5e-06 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility3.5e-06 g/LALOGPS
logP6.29ALOGPS
logP6.46ChemAxon
logS-8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity85.32 m³·mol⁻¹ChemAxon
Polarizability32.28 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-3390000000-676266969a9e4afcfeb3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4590000000-8e90af62825794d4ed32Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0390000000-a23b93b08974f28c17eaSpectrum
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-000i-2690000000-56d8c5298b5593a66540Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-3390000000-676266969a9e4afcfeb3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4590000000-8e90af62825794d4ed32Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0390000000-a23b93b08974f28c17eaSpectrum
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-000i-2690000000-56d8c5298b5593a66540Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2391000000-465776e134f2d14e4200Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-e4d354c1abce5df3562fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-5eec9abfcedc700c1772Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0019000000-c51586281a4bc626b427Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-9ede63c6934bd954c6faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-1339aaa8050c984b8945Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0009000000-80a4d52beed84a9206f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-dd77118949b674041bd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-dd77118949b674041bd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0092000000-b7ea5b5c363c85b85916Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-17d9b4a570d431baa8a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-17d9b4a570d431baa8a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0009000000-17d9b4a570d431baa8a9Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-2590000000-25fc1b81a71c7822ba39Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (2)
Mechanism of ToxicityDDT toxicity occurs via at least four mechanisms, possibly all functioning simultaneously. DDT reduces potassium transport across the membrane. DDT inhibits the inactivation of voltaged-gated sodium channels. The channels activate (open) normally but are inactivated (closed) slowly, thus interfering with the active transport of sodium out of the nerve axon during repolarization and resulting in a state of hyperexcitability. DDT inhibits neuronal adenosine triphosphatases (ATPases), particularly Na+K+-ATPase, and Ca2+-ATPase which play vital roles in neuronal repolarization. DDT 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. DDT is also believed to adversely affect the reproductive system by mimicking endogenous hormones and binding to the estrogen and adrogen receptors. (8, 2)
MetabolismDDT is absorbed in the stomach and intestine, after which it enters the lymphatic system and is carried throughout the body and incorporated into fatty tissues. Metabolism of DDT occurs mainly via cytochrome P-450 enzymes in the liver and kidney, where it undergoes reductive dechlorination to DDD (dichlorodiphenyldichloroethane) and DDE (dichlorodiphenyldichloroethylene). These compounds are further degraded into additional metabolites, mainly DDA (bis(p-chlorophenyl) acetic acid), which are excreted in the urine. (2)
Toxicity ValuesLD50: 87 mg/kg (Oral, Rat) (6) LD50: 1931 mg/kg (Dermal, Rat) (6) LD50: 1500 mg/kg (Subcutaneous, Rat) (6)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)DDT is possibly carcinogenic to humans (Group 2B). (7)
Uses/SourcesDDT is used as a pesticide and in disease vector control. (1)
Minimum Risk LevelAcute Oral: 0.0005 mg/kg/day (3) Intermediate Oral: 0.0005 mg/kg/day (3)
Health EffectsExposure to DDT causes loss of weight and anorexia. DDT poisoning affects CNS function in humans, but pathologic changes are observed in the liver and reproductive organs. Hypertrophy of hepatocytes and subcellular organelles such as mitochondria, proliferation of smooth endoplasmic reticulum, centrolobular necrosis after exposure to high concentrations, and an increase in the incidence of hepatic tumors have been noted. (8)
SymptomsAcute signs of DDT poisoning include paresthesia after oral ingestion. Studies have shown that a mammal poisoned with DDT-type agents displays periodic persistent tremoring and/or convulsive seizures that are suggestive of repetitive discharges in neurons. These repetitive tremors and seizures can be initiated by tactile and auditory stimuli. (8)
TreatmentTreatment of DDT exposure should be primarily directed towards decontamination and supportive care, as there is no specific antidote. The use of gastric lavage and activated charcoal for large ingestions may be effective. (5)
Concentrations
Not Available
DrugBank IDDB13424
HMDB IDHMDB0032127
FooDB IDFDB008850
Phenol Explorer IDNot Available
KNApSAcK IDC00040097
BiGG IDNot Available
BioCyc IDCPD-43
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDDT
Chemspider ID2928
ChEBI ID16130
PubChem Compound ID3036
Kegg Compound IDC04623
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17949680
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24328540
3. Sharma HR, Kaushik A, Kaushik CP: Pesticide residues in bovine milk from a predominantly agricultural state of Haryana, India. Environ Monit Assess. 2007 Jun;129(1-3):349-57. doi: 10.1007/s10661-006-9368-5. Epub 2006 Dec 16.
4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.