trans-1,2-Dichloroethene (T3D0173)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (4)XML
Targets (4)
Record Information
Version2.0
Creation Date2009-03-06 18:58:13 UTC
Update Date2014-12-24 20:21:16 UTC
Accession NumberT3D0173
Identification
Common Nametrans-1,2-Dichloroethene
ClassSmall Molecule
DescriptionTrans-1,2-dichloroethene (1,2-DCE) is one of two isomers of 1,2-dichloroethene. It is a highly flammable, colorless liquid with a sharp, harsh odor. 1,2-DCE is used as a solvent for waxes, resins, acetylcellulose, perfumes, dyes, lacquers, thermoplastics, fats, and phenols. It is also used as an intermediate in the preparation of other chlorinated solvents. (3, 4)
Compound Type
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organochloride
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
(E)-1,2-Dichloroethene
(E)-1,2-Dichloroethylene
1,2-Dichloro Ethylene
1,2-Dichloroethene
1,2-Dichloroethylene
1,2-Dichloroethylene (trans)
1,2-trans-Dichloroethene
1,2-trans-Dichloroethylene
1,trans-2-Dichloroethene
Acetylene dichloride
cis or trans 1,2-Dichloroethene
cis-1,2-Dichloroethylene
Dichloroethylene-trans
Dioform
Ethene,1,2-dichloro
SYM-dichloroethylene
Trans-1, 2-Dichloroethene
Trans-1,2-Dichloroethylene
Trans-acetylene dichloride
Trans-Di-1, 2-chloroethylene
Trans-Di-1,2-Chloroethylene
Trans-dichloroethene
Trans-dichloroethylene
Chemical FormulaC2H2Cl2
Average Molecular Mass96.943 g/mol
Monoisotopic Mass95.953 g/mol
CAS Registry Number156-60-5
IUPAC Name(E)-1,2-dichloroethene
Traditional Nametrans-1,2-dichloroethylene
SMILESCl\C=C\Cl
InChI IdentifierInChI=1S/C2H2Cl2/c3-1-2-4/h1-2H/b2-1+
InChI KeyInChIKey=KFUSEUYYWQURPO-OWOJBTEDSA-N
Chemical Taxonomy
Description 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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-49.8°C
Boiling Point47.2 °C at 745 mm Hg 48.0 - 48.5 °C at 760 mm Hg
Solubility6.41 mg/mL at 25 °C [HORVATH,AL et al. (1999)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.43 g/LALOGPS
logP1.85ALOGPS
logP1.74ChemAxon
logS-1.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity19.58 m³·mol⁻¹ChemAxon
Polarizability7.65 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-c9fdfc15f1ccbff5ce7d2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-54422779dce25776f3b42016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-04c61d11ae47815e6b362016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-aa0004925bd4f501180b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-e71490525ce3118551652016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-28fe12f941e45c2f67762016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03dj-9000000000-018777a851597b716bf72014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, TMS, experimental)Not Available2014-09-20View Spectrum
Toxicity Profile
Route of ExposureInhalation (3) ; oral (3) ; dermal (3) ; eye contact (3)
Mechanism of ToxicityTrans-1,2-dichloroethene is a volatile, lipophilic molecule that easily moves through the respiratory and gastrointestinal systems. It has a high affinity for lipids and blood, but little accumulation in tissues. 1,2-Dichloroethene isomers inhibit liver enzymes involved in metabolism and may increase the “toxic” response to other chemicals. Reactive metabolites of trans-1,2-dichloroethene modify the heme moiety of hepatic microsomal cytochrome P-450, resulting in a loss of both cytochrome P-450 and heme. Trans-1,2-dichloroethene can also mixed-function oxidase activities. Metabolism of trans-1,2-dichloroethene can lead to dose-related decrease in the levels of serum glutamicoxaloacetic transaminase (SGOT) and serum glutamic-pyruvic transaminase (SGPT). (3)
MetabolismMetabolism of trans-1,2-dichloroethene is initially catalyzed by hepatic microsomal cytochrome P-450. This metabolism is believed to involve epoxidation of the ethylene double bond, forming dichlorinated epoxides. Dichlorinated epoxides, in turn, can undergo a non-enzymatic rearrangement. Studies on the metabolism of 1,2-dichloroethene by hepatic microsomes and hepatocytes provide evidence to suggest that dichloroacetaldehyde is the predominant metabolite of microsomal cytochrome P-450 and that it, in turn, is extensively converted to dichloroethanol and dichloroacetate by cytosolic and/or mitochondrial aldehyde and alcohol dehydrogenases present in hepatocytes. (3)
Toxicity ValuesLD50: 1 300-10 000 mg/kg/day (Inhalation, Rat) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (2)
Uses/SourcesTrans-1,2-DCE is used as a solvent for waxes, resins, acetylcellulose, perfumes, dyes, lacquers, thermoplastics, fats, and phenols. It is also used as an intermediate in the preparation of other chlorinated solvents. One may be exposed by breathing contaminated air, eating, or drinking the substance, or by skin contact (3, 4).
Minimum Risk LevelAcute Inhalation: 0.2 ppm (Rat) (3) Acute Oral: 1 mg/kg/day (Rat) (3) Intermediate Oral: 0.3 mg/kg/day (3)
Health EffectsBreathing trans-1,2-DCE can cause sever liver and kidney damages, pulmonary capillary hyperemia, as well as alveolar septal distention; depression of the central nervous sustem can occur; moderate iritis and conjunctivitis can follow eye exposure; dermatitis and irritation of mucous membranes can follow dermal exposure. Symptoms associated with lethal oral doses included decreased activity, ataxia, suppressed or total loss of righting reflex, and depressed respiration. (3)
SymptomsSymptoms of trans-1,2-DCE exposure include nausea, dowiness, and tiredness. Mild or moderate erythema may follow dermal exposure, and skin or eye irritation can follow dermal/eye contact. (3)
TreatmentFollowing inhalation exposure, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of seizures, administer a benzodiazepine IV. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes in case of eye exposure. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. (1)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID638186
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDC06791
UniProt IDNot Available
OMIM ID
ChEBI ID29027
BioCyc ID11-DCE
CTD IDNot Available
Stitch ID1,2-Dichloroethene, trans-
PDB IDNot Available
ACToR ID3719
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0173.pdf
General References
  1. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  2. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  3. ATSDR - Agency for Toxic Substances and Disease Registry (1996). Toxicological profile for trans-1,2-dichloroethene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. Wikipedia. 1,2-Dichloroethene. Last Updated 7 July 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Estrogen receptor
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
  2. Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
Target Details
2. Estrogen receptor beta
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular Weight:
59215.765 Da
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
  2. Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
Target Details
3. Cytochrome P450 2E1
General Function:
Steroid hydroxylase activity
Specific Function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
References
  1. Mathews JM, Raymer JH, Etheridge AS, Velez GR, Bucher JR: Do endogenous volatile organic chemicals measured in breath reflect and maintain CYP2E1 levels in vivo? Toxicol Appl Pharmacol. 1997 Oct;146(2):255-60. [9344893 ]
Target Details
4. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]