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Record Information
Creation Date2009-06-24 15:20:01 UTC
Update Date2014-12-24 20:24:52 UTC
Accession NumberT3D1907
Common Nametrans-1,3-Dichloropropene
ClassSmall Molecule
DescriptionTrans-1,3-Dichloropropene, also known as trans-Telone or simply trans-1,3-D, is a colorless liquid with a sweet smell. It is one of 2 isomers of 1,3-D. Trans-1,3-Dichloropropene is widely used as a preplanting soil fumigant for the control of nematodes, and it has been available for agricultural use in many formulations (7).
Compound Type
  • Chloropropene
  • Food Toxin
  • Lachrymator
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
1,3-dichloro-1-propene, (E)-isomer
1,3-dichloro-1-propene, (Z)-isomer
1,3-Dichloropropene (mixed isomers)
1,3-Dichloropropene (mixed)
1,3-Dichloropropene (technical grade)
3-Chloroallyl chloride
3-Chloropropenyl chloride
Alpha-chloroallyl chloride
Chloroallyl c hloride
Chloroallyl chloride
Chloropropenyl chloride
Di-trapex CP
Dichloropropene, 1,3- (Telone II)
Dorlone II
Gamma-chloroallyl chloride
Propylene, 1,3-dichloro-, (trans)
Telone c
Telone C17
Telone ec
Telone II
Telone II soil fumigant
Telone II, technical
Telone II, technical grade
Telone II-b
Telone IIr
trans-3-Chloroallyl chloride
Vorlex 201
Chemical FormulaC3H4Cl2
Average Molecular Mass110.970 g/mol
Monoisotopic Mass109.969 g/mol
CAS Registry Number10061-02-6
IUPAC Name(1Z)-1,3-dichloroprop-1-ene
Traditional Nametelone II
InChI IdentifierInChI=1S/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1-
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
  • Chloroalkene
  • Haloalkene
  • Vinyl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
AppearanceColourless liquid (7).
Experimental Properties
Melting PointNot Available
Boiling Point112°C
Solubility2.8 mg/mL at 25°C [VERSCHUEREN,K (2001)]
LogPNot Available
Predicted Properties
Water Solubility2.3 g/LALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity25.28 m³·mol⁻¹ChemAxon
Polarizability9.62 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-f9c91d446ea07605419aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-977e355dc25f96907d7eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01t9-9000000000-7fbebdd73428e6aa1542JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-efde9484329b87cac536JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4900000000-efd53f52cce22e3ba76dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-2d9a0decfdc0fb59dd41JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-004r-9100000000-647503adccf7181af269JSpectraViewer | MoNA
Toxicity Profile
Route of ExposureInhalation (7) ; oral (7) ; dermal (7) ; eye contact (7).
Mechanism of ToxicityThe primary toxic effects of trans-1,3-dichloropropene are portal-of-entry effects resulting from the chemical reactivity of the compound and its physicochemical properties. Repeated irritation results in a hyperplastic response in the target tissues. The mutagenicity of trans-1,3-dichloropropene is attributed to its biotransformation by cytochrome P-450 to stereospecific epoxides and the hydrolysis product, 3-chloro-2-hydroxypropanal. It is likely that depletion of glutathione would block the major detoxification pathway for trans-1,3dichloropropene, resulting in increased toxicity of organs such as the liver and kidney because of binding of reactive intermediates to macromolecules in cells. There is some evidence that cytotoxicity of hepatic cells exposed to trans-1,3-dichloropropene is preceded by increased levels of phospholipid hydroperoxides (7).
MetabolismThe major metabolic pathway is rapid conjugation with glutathione, resulting in the formation of a mercapturic acid metabolite that is excreted in the urine. Trans-1,3-Dichoropropene may also undergo hydrolysis and dechlorination to form 1-chloroallyl alcohol, an intermediate that reacts with alcohol dehydrogenase to form 1-chloroacrolein. Another minor pathway involves reaction with cytochrome P450 to form mutagenic cis and trans epoxides that convert to the mutagen 3-chloro2- hydroxy-propanal. Conjugation with glutathione can occur in the nasal tissue, kidney, and liver. The glutathione conjugate of cis-1,3-dichloropropene is then converted to the mercapturic acid and acetylated for excretion as the N-acetyl-cysteine metabolite. Alternative metabolic pathways for trans-1,3-dichloropropenes have also been proposed. reaction with cytochrome P-450 resulted in the formation of trans-1,3-dichloropropene epoxides. The trans-1,3-dichloropropene epoxides undergo hydrolysis, possibly catalyzed by epoxide hydrolase, to 3-chloro-2-hydroxypropanal (7).
Toxicity ValuesLD50: 304 mg/kg (Oral, Rat) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (6)
Uses/SourcesBreathing in contaminated air; drinking contaminated water; eating contaminated food; dermal and eye exposure (7).
Minimum Risk LevelIntermediate Inhalation: 0.008 ppm (Rabbit) (7) Chronic Inhalation: 0.007 ppm (Rabbit) (7)
Health EffectsIngestion of trans-1,3-D can lead to developed gastrointestinal distress, adult respiratory distress syndrome, hematological and hepatorenal functional impairment, acute gastrointestinal distress with pulmonary congestion and edema, central nervous depression, perhaps even in the absence of impaired oxygen uptake. Moreover, this can lead to death. Coma may occur rapidly after inhalation. Inhalation of trans-1,3-D at low concentration can cause central nervous depression and moderate irritation of respiratory system; headache is frequent. After inhalation exposures, malaise, headache, chest and abdominal discomfort and irritability have been reported to persist for several weeks, and perhaps for several years. Severe skin irritation with marked inflammatory response of epidermis can underlying tissues can follow dermal exposure. By any route, possible late injuries to liver, kidneys and heart (4).
SymptomsSymptoms occuring after inhalation include gasping, refusal to breathe, coughing, substernal pain; lacrimation and headache are prominant. After inhalation exposures, malaise, headache, chest and abdominal discomfort and irritability can persist during weeks or years. Moreover, Irritation of eyes and upper respiratory mucosa appears promptly after exposure to concentrated vapors. Ingestion can cause cough, sore throat, headache, dizziness, nausea, vomiting, unconsciousness, and laboured breathing (4, 7).
TreatmentFollowing oral exposure, administer charcoal as a slurry. Monitor liver and kidney function; elevations may not be seen for several days. Following eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Following inhalation, move patient to fresh air, even though initial symptoms and signs are mild; keep the victim quiet, in a semi-reclining position. Minimum physical activity limits the likehood of pulmonary edema. If victim is not breathing, clear the airway of secretions and resuscitate with positive pressure oxygen apparatus. If this is not available, use chest compression to sustain respiration. (3, 2)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID24726
ChEMBL IDNot Available
ChemSpider IDNot Available
UniProt IDNot Available
ChEBI ID18624
CTD IDNot Available
Stitch ID1,3-Dichloropropene, trans
PDB IDNot Available
ACToR ID8203
Wikipedia LinkNot Available
Synthesis ReferenceNot Available
General References
  1. Ghia M, Robbiano L, Allavena A, Martelli A, Brambilla G: Genotoxic activity of 1,3-dichloropropene in a battery of in vivo short-term tests. Toxicol Appl Pharmacol. 1993 May;120(1):120-5. [8511773 ]
  2. Dalfo D, Marques N, Albalat R: Analysis of the NADH-dependent retinaldehyde reductase activity of amphioxus retinol dehydrogenase enzymes enhances our understanding of the evolution of the retinol dehydrogenase family. FEBS J. 2007 Jul;274(14):3739-52. Epub 2007 Jul 2. [17608724 ]
  3. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  4. Gosselin RE, Smith RP, and Hodge HC (1984). Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins.
  5. Sullivan JB Jr. and Krieger GR (eds) (1999). Hazardous Materials Toxicology-Clinical Principles of Environmental Health. Baltimore, MD: Williams and Wilkins.
  6. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  7. ATSDR - Agency for Toxic Substances and Disease Registry (2008). Toxicological profile for dichloropropenes. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available


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:
Uniprot ID:
Molecular Weight:
66215.45 Da
  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.
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:
Uniprot ID:
Molecular Weight:
59215.765 Da
  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.
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:
Uniprot ID:
Molecular Weight:
127499.88 Da
  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 ]