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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:20 UTC
Update Date2018-03-12 21:54:39 UTC
HMDB IDHMDB0029593
Secondary Accession Numbers
  • HMDB29593
Metabolite Identification
Common NameTrichloroethylene
DescriptionTrichloroethylene is a solvent and extractive in the manufacture of foods. One recent review of the epidemiology of kidney cancer rated cigarette smoking and obesity as more important risk factors for kidney cancer than exposure to solvents such as trichloroethylene. In contrast, the most recent overall assessment of human health risks associated with trichloroethylene states, "[t]here is concordance between animal and human studies, which supports the conclusion that trichloroethylene is a potential kidney carcinogen". The evidence appears to be less certain at this time regarding the relationship between humans and liver cancer observed in mice, with the NAS suggesting that low-level exposure might not represent a significant liver cancer risk in the general population. The chemical compound trichloroethylene is a chlorinated hydrocarbon commonly used as an industrial solvent. It is a clear non-flammable liquid with a sweet smell. The first known report of TCE in groundwater was given in 1949 by two English public chemists who described two separate instances of well contamination by industrial releases of TCE. Based on available federal and state surveys, between 9% to 34% of the drinking water supply sources tested in the U.S. may have some TCE contamination, though EPA has reported that most water supplies are in compliance with the Maximum Contaminant Level (MCL) of 5 ppb. In addition, a growing concern in recent years at sites with TCE contamination in soil or groundwater has been vapor intrusion in buildings, which has resulted in indoor air exposures, such is in a recent case in the McCook Field Neighborhood of Dayton, Ohio. Trichloroethylene has been detected in 852 Superfund sites across the United States, according to the Agency for Toxic Substances and Disease Registry (ATSDR). Under the Safe Drinking Water Act of 1974, and as amended annual water quality testing is required for all public drinking water distributors. The EPA'S current guidelines for TCE can be found here. It should be noted that the EPA's table of "TCE Releases to Ground" is dated 1987 to 1993, thereby omitting one of the largest Superfund Cleanup sites in the nation, the NIBW in Scottsdale, Arizona. The TCE "released" here occurred prior to its appearance in the municipal drinking wells in 1982. This reaction can be catalyzed by a variety of substances. The most commonly used catalyst is a mixture of potassium chloride and aluminum chloride. However, various forms of porous carbon can also be used. This reaction produces tetrachloroethylene as a byproduct, and depending on the amount of chlorine fed to the reaction, tetrachloroethylene can even be the major product. Typically, trichloroethylene and tetrachloroethylene are collected together and then separated by distillation.Trichloroethylene: Parkinsonism and complex 1 mitochondrial neurotoxicity). Trichloroethylene is an effective solvent for a variety of organic materials
Structure
Thumb
Synonyms
ValueSource
1,1-dichloro-2-ChloroethyleneChEBI
Acetylene trichlorideChEBI
Ethinyl trichlorideChEBI
Ethylene trichlorideChEBI
NarcogenChEBI
TCEChEBI
TrichlorChEBI
Trichloraethylenum pro narcosiChEBI
TrichloraethenChEBI
TrichloraethylenChEBI
TrichlorethyleneChEBI
TrichloroethylenumChEBI
TricieneChEBI
1,1,1-TrichloroethyleneHMDB
1,1,2-trichloro-EtheneHMDB
1,1,2-TrichloroetheneHMDB
1,1,2-TrichloroethyleneHMDB
1,2,2-TrichloroethyleneHMDB
1-chloro-2,2-DichloroethyleneHMDB
AlgylenHMDB
Altene DGHMDB
AnamenthHMDB
BenzinolHMDB
BlacosolvHMDB
BlancosolvHMDB
C2HCL3HMDB
CecoleneHMDB
ChlorilenHMDB
ChloryleaHMDB
ChlorylenHMDB
ChorylenHMDB
CircosolvHMDB
CrawhaspolHMDB
Densi nfluatHMDB
DensinfluatHMDB
Disparit bHMDB
Distillex DS2HMDB
Dow-triHMDB
DukeronHMDB
Fleck-flipHMDB
Flock flipHMDB
FluateHMDB
GemalgeneHMDB
GermalgeneHMDB
LanadinHMDB
LethurinHMDB
NarkogenHMDB
NarkosoidHMDB
NialkHMDB
Perm-a-chlorHMDB
Perm-a-clorHMDB
PetzinolHMDB
PhilexHMDB
R 1120HMDB
Tce (chlorohydrocarbon)HMDB
ThrethylenHMDB
ThrethyleneHMDB
TrethyleneHMDB
TRIHMDB
Tri-cleneHMDB
Tri-plusHMDB
Tri-plus mHMDB
TrialHMDB
TriasolHMDB
Tric hloroetheneHMDB
TrichlooretheenHMDB
Trichloorethyleen, triHMDB
Trichloraethylen, triHMDB
TrichloraethylenumHMDB
TrichloranHMDB
TrichlorathaneHMDB
TrichlorenHMDB
TrichloretheneHMDB
Trichlorethylene, triHMDB
TrichlorethylenumHMDB
Trichloride, ethinylHMDB
trichloro-EtheneHMDB
trichloro-EthyleneHMDB
TrichloroetheneHMDB
Trichloroethene, 9ciHMDB
Trichloroethylene (iupac)HMDB
Trichloroethylene (tce)HMDB
Trichloroethylene (with epichlorohydrin)HMDB
Trichloroethylene (without epichlorohydrin)HMDB
TrichlorotheneHMDB
TricloreteneHMDB
TricloroetileneHMDB
TricloroetilenoHMDB
TrieleneHMDB
TrielinHMDB
TrielinaHMDB
TrielineHMDB
Trik loneHMDB
TrikloneHMDB
Triklone NHMDB
TrilenHMDB
TrileneHMDB
Trilene te-141HMDB
TrilineHMDB
TrimarHMDB
TriolHMDB
VestrolHMDB
VitranHMDB
WestrosolHMDB
Chemical FormulaC2HCl3
Average Molecular Weight131.388
Monoisotopic Molecular Weight129.914383153
IUPAC Name1,1,2-trichloroethene
Traditional Nametrichloroethylene
CAS Registry Number79-01-6
SMILES
ClC=C(Cl)Cl
InChI Identifier
InChI=1S/C2HCl3/c3-1-2(4)5/h1H
InChI KeyXSTXAVWGXDQKEL-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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-84.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.28 mg/mL at 25 °CNot Available
LogP2.42Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.96 g/LALOGPS
logP2.45ALOGPS
logP2.18ChemAxon
logS-1.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.18 m³·mol⁻¹ChemAxon
Polarizability9.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001j-9600000000-35bd416ad747042a0c53View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001j-9800000000-152d0336467c74545ec4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03ea-9200000000-655b220bf877474e22b4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001j-9600000000-35bd416ad747042a0c53View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001j-9800000000-152d0336467c74545ec4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03ea-9200000000-655b220bf877474e22b4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003v-7900000000-401c79c003cea991b031View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-1c5d55a90bcf42fd6a79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-54723e87d2cf07e437d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-2160348c43ed061e6433View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-ddeffc3538dadd85ccfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-ddeffc3538dadd85ccfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-ddeffc3538dadd85ccfdView in MoNA
MSMass Spectrum (Electron Ionization)splash10-001j-9600000000-1c547ee123cf751604dcView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000752
KNApSAcK IDNot Available
Chemspider ID13837280
KEGG Compound IDC06790
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrichloroethylene
METLIN IDNot Available
PubChem Compound6575
PDB IDNot Available
ChEBI ID16602
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. SCANSETTI G, RUBINO GF, TROMPEO G: [Study on chronic trieline poisoning. Note 3. Metabolism of trichloroethylene]. Med Lav. 1959 Dec;50:743-54. [PubMed:14442215 ]
  2. Formica M, Vallero A, Forneris G, Cesano G, Pozzato M, Borca M, Iadarola GM, Quarello F: [Organohalogen contamination of a dialysis-water treatment plant]. G Ital Nefrol. 2002 Jul-Aug;19(4):479-82. [PubMed:12369053 ]
  3. Cichocka D, Imfeld G, Richnow HH, Nijenhuis I: Variability in microbial carbon isotope fractionation of tetra- and trichloroethene upon reductive dechlorination. Chemosphere. 2008 Mar;71(4):639-48. Epub 2007 Dec 21. [PubMed:18155126 ]
  4. Pistelli A, Masini E, Caramelli L, Botti P, Peruzzi S, Zorn AM, Mannaioni PF: [Acute toxicity of trichloroethylene. Description of a case series at the Autonomous Service of Toxicology of Florence during the 1977-1988 period]. Clin Ter. 1990 Nov 15;135(3):173-80. [PubMed:2150018 ]
  5. BOKAY J, GOSZLETH T, GERGELY P: [Anesthesia with narcogen (trichloroethylene) in obstetrics]. Magy Noorv Lapja. 1955 Jan;18(1):30-43. [PubMed:14382738 ]
  6. Ray K, Sahana CC, Chaudhuri SB, De GC, Chatterjee K: Effects of trichloroethylene anaesthesia on salivary paracetamol elimination. Indian J Physiol Pharmacol. 1993 Jan;37(1):79-81. [PubMed:8449552 ]
  7. RUBINO GF, SCANSETTI G, TROMPEO G, GAIDO PC: [Study on chronic trieline poisoning. Note 4. Catabolism of derivatives of trichloroethylene]. Med Lav. 1959 Dec;50:755-65. [PubMed:14439909 ]
  8. Guehl D, Bezard E, Dovero S, Boraud T, Bioulac B, Gross C: Trichloroethylene and parkinsonism: a human and experimental observation. Eur J Neurol. 1999 Sep;6(5):609-11. [PubMed:10457397 ]
  9. Kostrzewski P, Jakubowski M, Kolacinski Z: Kinetics of trichloroethylene elimination from venous blood after acute inhalation poisoning. J Toxicol Clin Toxicol. 1993;31(2):353-63. [PubMed:8492349 ]
  10. Eckerbom B, Lindholm CE: Performance evaluation of six heat and moisture exchangers according to the Draft International Standard (ISO/DIS 9360). Acta Anaesthesiol Scand. 1990 Jul;34(5):404-9. [PubMed:2389657 ]
  11. Nystrom PO, Broome A, Hojer H, Ling L: A controlled trial of a plastic wound ring drape to prevent contamination and infection in colorectal surgery. Dis Colon Rectum. 1984 Jul;27(7):451-3. [PubMed:6378555 ]
  12. VAN VLIET AG: [A case of toxic psychosis caused by trichloroethylene addiction]. Ned Tijdschr Geneeskd. 1959 Jan 10;103(2):75-8. [PubMed:13622851 ]
  13. RUBINO GF, SCANSETTI G, TROMPEO G: [Study on chronic trieline poisoning. Note 2. Absorption of trichloroethylene]. Med Lav. 1959 Dec;50:733-42. [PubMed:14439910 ]
  14. HEDGE HM: Occupational dermatitis of the nails and paronychia following use of permachlor diluted with methyl alcohol. Arch Derm Syphilol. 1948 Mar;57(3 Pt. 2):428. [PubMed:18100972 ]
  15. HOLTORFF J: [Temporary report on our experiences in the use of the trichloroethylene compound chlorylene for inhalation analgesia in obstetrics]. Dtsch Gesundheitsw. 1952 Aug 14;7(33):1038-43. [PubMed:13020452 ]
  16. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Only showing the first 10 proteins. There are 19 proteins in total.

Enzymes

General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTM2
Uniprot ID:
P28161
Molecular weight:
25744.395
Reactions
Trichloroethylene + Glutathione → S-(1,2-Dichlorovinyl)glutathione + Hydrochloric aciddetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTM1
Uniprot ID:
P09488
Molecular weight:
25711.555
Reactions
Trichloroethylene + Glutathione → S-(1,2-Dichlorovinyl)glutathione + Hydrochloric aciddetails
General function:
Involved in protein disulfide oxidoreductase activity
Specific function:
Significant glutathione conjugating activity is found only with the model substrate, 1-chloro-2,4-dinitrobenzene (CDNB).
Gene Name:
GSTK1
Uniprot ID:
Q9Y2Q3
Molecular weight:
31565.605
Reactions
Trichloroethylene + Glutathione → S-(1,2-Dichlorovinyl)glutathione + Hydrochloric aciddetails
General function:
Involved in glutathione transferase activity
Specific function:
Also functions as a glutathione peroxidase.
Gene Name:
MGST3
Uniprot ID:
O14880
Molecular weight:
16516.185
Reactions
Trichloroethylene + Glutathione → S-(1,2-Dichlorovinyl)glutathione + Hydrochloric aciddetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. May govern uptake and detoxification of both endogenous compounds and xenobiotics at the testis and brain blood barriers.
Gene Name:
GSTM3
Uniprot ID:
P21266
Molecular weight:
26559.32
Reactions
Trichloroethylene + Glutathione → S-(1,2-Dichlorovinyl)glutathione + Hydrochloric aciddetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTA1
Uniprot ID:
P08263
Molecular weight:
25630.785
Reactions
Trichloroethylene + Glutathione → S-(1,2-Dichlorovinyl)glutathione + Hydrochloric aciddetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Has a wide substrate specificity.
Gene Name:
MGST1
Uniprot ID:
P10620
Molecular weight:
17598.45
Reactions
Trichloroethylene + Glutathione → S-(1,2-Dichlorovinyl)glutathione + Hydrochloric aciddetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Active on 1-chloro-2,4-dinitrobenzene.
Gene Name:
GSTM4
Uniprot ID:
Q03013
Molecular weight:
25561.095
Reactions
Trichloroethylene + Glutathione → S-(1,2-Dichlorovinyl)glutathione + Hydrochloric aciddetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTM5
Uniprot ID:
P46439
Molecular weight:
25674.455
Reactions
Trichloroethylene + Glutathione → S-(1,2-Dichlorovinyl)glutathione + Hydrochloric aciddetails
General function:
Involved in enzyme activator activity
Specific function:
Can catalyze the production of LTC4 from LTA4 and reduced glutathione. Can catalyze the conjugation of 1-chloro-2,4-dinitrobenzene with reduced glutathione.
Gene Name:
MGST2
Uniprot ID:
Q99735
Molecular weight:
16620.4
Reactions
Trichloroethylene + Glutathione → S-(1,2-Dichlorovinyl)glutathione + Hydrochloric aciddetails

Only showing the first 10 proteins. There are 19 proteins in total.