| Record Information |
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| Version | 2.0 |
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| Creation Date | 2009-06-24 15:20:01 UTC |
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| Update Date | 2014-12-24 20:24:52 UTC |
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| Accession Number | T3D1906 |
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| Identification |
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| Common Name | cis-1,3-Dichloropropene |
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| Class | Small Molecule |
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| Description | Cis-1,3-Dichloropropene, also known as cis-Telone or simply cis-1,3-D, is a colorless liquid with a sweet smell. It is one of 2 isomers of 1,3-D. cis- 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). |
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| Compound Type | - Chloropropene
- Food Toxin
- Lachrymator
- Organic Compound
- Organochloride
- Pesticide
- Pollutant
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Synonym | | (1Z)-1,3-Dichloro-1-propene | | (1Z)-1,3-dichloroprop-1-ene | | (Z)-1,3-Dichloro-1-propene | | (Z)-1,3-Dichloropropene | | .alpha.,.gamma.-dichloropropylene | | .alpha.-chloroallyl chloride | | .gamma.-chloroallyl chloride | | 1,3-Dichloro-1-propene | | 1,3-Dichloro-1-propene (Z) | | 1,3-Dichloro-2-propene | | 1,3-Dichloropropene | | 1,3-Dichloropropene (cis+trans) | | 1,3-DICHLOROPROPENE, HIGH BOILING, PRACT | | 1,3-Dichloropropene-1 | | 1,3-DICHLOROPROPENE-1,LOW BOILING | | 1,3-Dichloropropylene | | 1-Propene, 1,3-dichloro-, (Z)- (9CI) | | 3-Chloropropenyl chloride | | cis-1,3-Dichloro-1-Propene | | cis-1,3-Dichloropropylene | | Cis-DCP | | D-d mixture | | Dichloropropene | | Nemex | | Telone | | Telone c | | Telone II | | Vidden d |
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| Chemical Formula | C3H4Cl2 |
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| Average Molecular Mass | 110.970 g/mol |
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| Monoisotopic Mass | 109.969 g/mol |
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| CAS Registry Number | 10061-01-5 |
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| IUPAC Name | 1,3-dichloroprop-1-ene |
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| Traditional Name | dichloropropene |
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| SMILES | ClCC=CCl |
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| InChI Identifier | InChI=1S/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2 |
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| InChI Key | InChIKey=UOORRWUZONOOLO-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organohalogen compounds |
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| Class | Vinyl halides |
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| Sub Class | Vinyl chlorides |
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| Direct Parent | Vinyl chlorides |
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| Alternative Parents | |
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| Substituents | - Chloroalkene
- Haloalkene
- Vinyl chloride
- Hydrocarbon derivative
- Organochloride
- Alkyl halide
- Alkyl chloride
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | - Cytoplasm
- Extracellular
- Microsome
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Liquid |
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| Appearance | Colourless liquid (7). |
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| Experimental Properties | | Property | Value |
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| Melting Point | -50°C | | Boiling Point | Not Available | | Solubility | 2.18 mg/mL at 20°C [TOMLIN,C (1997)] | | LogP | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-9200000000-c598c9b2927ffe6d4020 | 2021-09-24 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0900000000-f9c91d446ea07605419a | 2016-06-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-0900000000-977e355dc25f96907d7e | 2016-06-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01t9-9000000000-7fbebdd73428e6aa1542 | 2016-06-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-1900000000-efde9484329b87cac536 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-4900000000-efd53f52cce22e3ba76d | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9000000000-2d9a0decfdc0fb59dd41 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03k9-5900000000-6420b995013910ad0d39 | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03k9-9500000000-1e881a15990580321767 | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0229-9000000000-70d2500b930c153a7161 | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-d36f52e33fcad27ed733 | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-9000000000-c2fa753da65a4bac80a1 | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-9000000000-c2fa753da65a4bac80a1 | 2021-10-12 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Inhalation (7) ; oral (7) ; dermal (7) ; eye contact (7). |
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| Mechanism of Toxicity | The primary toxic effects of cis-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 cis-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 cis-1,3- dichloropropene, 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 cis-1,3-dichloropropene is preceded by increased levels of phospholipid hydroperoxides (7). |
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| Metabolism | The major metabolic pathway is rapid conjugation with glutathione, resulting in the
formation of a mercapturic acid metabolite that is excreted in the urine. Cis-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 cis-1,3-dichloropropenes have also been proposed. reaction with cytochrome P-450 resulted in the formation of cis-1,3-dichloropropene epoxides. The cis-1,3-dichloropropene epoxides undergo hydrolysis, possibly catalyzed by epoxide hydrolase, to 3-chloro-2-hydroxypropanal (7). |
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| Toxicity Values | LD50: 121 mg/kg (Oral, Rat) (7) |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | 3, not classifiable as to its carcinogenicity to humans. (6) |
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| Uses/Sources | Breathing in contaminated air; drinking contaminated water; eating contaminated food; dermal and eye exposure (7). |
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| Minimum Risk Level | Intermediate Inhalation: 0.008 ppm (Rabbit) (7)
Chronic Inhalation: 0.007 ppm (Rabbit) (7) |
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| Health Effects | Ingestion of cis-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 cis-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). |
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| Symptoms | Symptoms 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). |
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| Treatment | Following 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) |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| PubChem Compound ID | 5280970 |
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| ChEMBL ID | Not Available |
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| ChemSpider ID | 23264 |
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| KEGG ID | C06610 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 18809 |
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| BioCyc ID | PROPENE |
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| CTD ID | Not Available |
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| Stitch ID | 1,3-Dichloropropene, cis |
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| PDB ID | Not Available |
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| ACToR ID | Not Available |
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| Wikipedia Link | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | T3D1906.pdf |
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| General References | - 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 ]
- 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 ]
- Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
- Gosselin RE, Smith RP, and Hodge HC (1984). Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins.
- Sullivan JB Jr. and Krieger GR (eds) (1999). Hazardous Materials Toxicology-Clinical Principles of Environmental Health. Baltimore, MD: Williams and Wilkins.
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
- 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]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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