You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-09-13 11:51:21 UTC
Update Date2016-02-11 03:55:39 UTC
HMDB IDHMDB41980
Secondary Accession NumbersNone
Metabolite Identification
Common NamePerchloroethylene
DescriptionAnimal studies and a study of 99 twins by Dr. Samuel Goldman and researchers at the Parkinson's Institute in Sunnyvale, California determined there is a 'lot of circumstantial evidence' that exposure to tetrachloroethene increases the risk of developing Parkinson's disease ninefold. Larger population studies are planned. Tetrachloroethene is a common soil contaminant. With a specific gravity greater than 1, tetrachloroethylene will be present as a dense nonaqueous phase liquid if sufficient quantities of liquid are spilled in the environment. Because of its mobility in groundwater, its toxicity at low levels, and its density (which causes it to sink below the water table), cleanup activities are more difficult than for oil spills. Recent research has focused on the in place remediation of soil and ground water pollution by tetrachloroethylene. Instead of excavation or extraction for above-ground treatment or disposal, tetrachloroethylene contamination has been successfully remediated by chemical treatment or bioremediation. Bioremediation has been successful under anaerobic conditions by reductive dechlorination by Dehalococcoides sp. and under aerobic conditions by cometabolism by Pseudomonas sp. Partial degradation daughter products include trichloroethylene, cis-1,2-dichloroethene and vinyl chloride; full degradation converts tetrachloroethylene to ethene and hydrogen chloride dissolved in water. Tetrachloroethylene is an excellent solvent for organic materials. Otherwise it is volatile, highly stable, and nonflammable. For these reasons, it is widely used in dry cleaning. Usually as a mixture with other chlorocarbons, it is also used to degrease metal parts in the automotive and other metalworking industries. It appears in a few consumer products including paint strippers and spot removers. Tetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene ('perc'), and many other names, is a chlorocarbon with the formula Cl2C=CCl2. It is a colorless liquid widely used for dry cleaning of fabrics, hence it is sometimes called 'dry-cleaning fluid.' It has a sweet odor detectable by most people at a concentration of 1 part per million (1 ppm). Worldwide production was about one million metric tons in 1985. The International Agency for Research on Cancer has classified tetrachloroethene as a Group 2A carcinogen, which means that it is probably carcinogenic to humans. Like many chlorinated hydrocarbons, tetrachloroethene is a central nervous system depressant and can enter the body through respiratory or dermal exposure. Tetrachloroethene dissolves fats from the skin, potentially resulting in skin irritation. This reaction can be catalyzed by a mixture of potassium chloride and aluminium chloride or by activated carbon. Trichloroethylene is a major byproduct, which is separated by distillation.
Structure
Thumb
Synonyms
ValueSource
1,1,2,2-TetrachloroethyleneChEBI
Ethylene tetrachlorideChEBI
PCEChEBI
PERCChEBI
PerchloroethyleneChEBI
PERKChEBI
TetrachloraethenChEBI
TetrachlorethyleneChEBI
TetrachloroethyleneChEBI
1,1,2, 2-TetrachloroethyleneHMDB
1,1,2,2-TetrachloroetheneHMDB
1,1,2,2-Tetrachloroethylene (acd/name 4.0)HMDB
AnkilostinHMDB
Antisal 1HMDB
Antisol 1HMDB
Carbon bichlorideHMDB
Carbon dichlorideHMDB
CzterochloroetylenHMDB
DidakeneHMDB
Dow-perHMDB
Fedal-unHMDB
NemaHMDB
Nema, veterinaryHMDB
PerawinHMDB
Perchloorethyleen, perHMDB
PerchlorHMDB
Perchloraethylen, perHMDB
PerchlorethyleneHMDB
Perchlorethylene, perHMDB
PerchloroetheneHMDB
PercleneHMDB
Perclene DHMDB
Perclene TGHMDB
PercloroetileneHMDB
PercosolveHMDB
PerkloneHMDB
PerSecHMDB
RCRA waste number u210HMDB
TetlenHMDB
TetracapHMDB
TetrachlooretheenHMDB
TetrachlorathenHMDB
tetrachloro-EtheneHMDB
tetrachloro-EthyleneHMDB
TetracloroeteneHMDB
TetraguerHMDB
TetralenoHMDB
TetralexHMDB
TetravecHMDB
TetroguerHMDB
TetropilHMDB
Chemical FormulaC2Cl4
Average Molecular Weight165.833
Monoisotopic Molecular Weight163.875410828
IUPAC Nametetrachloroethene
Traditional Nameperchloroethylene
CAS Registry Number127-18-4
SMILES
ClC(Cl)=C(Cl)Cl
InChI Identifier
InChI=1S/C2Cl4/c3-1(4)2(5)6
InChI KeyInChIKey=CYTYCFOTNPOANT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassVinyl halides
Sub ClassVinyl chlorides
Direct ParentVinyl chlorides
Alternative Parents
Substituents
  • Chloroalkene
  • Haloalkene
  • Vinyl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Toxin/Pollutant
Biofunction
  • Nutrient
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-22.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.206 mg/mL at 25 °CNot Available
LogP3.40Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.33 mg/mLALOGPS
logP3.13ALOGPS
logP2.62ChemAxon
logS-2.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.77 m3·mol-1ChemAxon
Polarizability11.6 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-02u0-2900000000-b8b0d0d4e84c9a237c39View in MoNA
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000302 (0.000241-0.000362) uMAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID13837281
KEGG Compound IDC06789
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Linkperchloroethylene
NuGOwiki LinkHMDB41980
Metagene LinkHMDB41980
METLIN IDNot Available
PubChem Compound31373
PDB IDNot Available
ChEBI ID17300
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. GRANDJEAN E, WANNER HU, RHINER A: [INVESTIGATIONS OF TETRACHLOROETHYLENE VAPORS IN 2 TYPES OF OPEN METAL CLEANING APPLIANCES]. Int Arch Gewerbepathol Gewerbehyg. 1964 Nov 3;21:69-79. [14340446 ]
  2. Braeckevelt M, Seeger EM, Paschke H, Kuschk P, Kaestner M: Adaptation of a constructed wetland to simultaneous treatment of monochlorobenzene and perchloroethene. Int J Phytoremediation. 2011 Nov-Dec;13(10):998-1013. [21972567 ]
  3. Tseng WJ, Guo SF: Synthesis of nanoporous Al2O3 membranes from polybutyl methacrylate functionalized SiO2 particles as a sacrificial template. J Nanosci Nanotechnol. 2012 Oct;12(10):7909-14. [23421155 ]
  4. Tsuruta H: Skin absorption of organic solvent vapors in nude mice in vivo. Ind Health. 1989;27(2):37-47. [2745160 ]
  5. Wroblewska K, Rogaczewska T: [Evaluation of occupational exposure to tetrachloroethylene (PER) in a dry cleaning business]. Med Pr. 1987;38(2):96-101. [3626854 ]