Introduction：Basic information about CAS 5598-15-2|Chlorpyrifos Oxon, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Chlorpyrifos Oxon |
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| CAS Number | 5598-15-2 | Molecular Weight | 334.52100 |
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| Density | 1.461g/cm3 | Boiling Point | 357.8ºC at 760mmHg |
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| Molecular Formula | C9H11Cl3NO4P | Melting Point | / |
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| MSDS | / | Flash Point | 170.2ºC |
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Names
| Name | Chlorpyrifos-oxon |
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| Synonym | More Synonyms |
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Chlorpyrifos Oxon BiologicalActivity
| Description | Chlorpyrifos-oxon, an active metabolite of Chlorpyrifos, is a potent phosphorylating agent that potently inhibits AChE. Chlorpyrifos-oxon can induce cross-linking between subunits of tubulin and disrupt microtubule function[1][2][3][4]. |
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| Related Catalog | Research Areas >>Neurological DiseaseSignaling Pathways >>Neuronal Signaling >>AChE |
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| In Vitro | Treatment of tubulin with 1.5 mM Chlorpyrifos-oxon (CPO) leads to protein aggregation. However, even at 1.5 μM Chlorpyrifos-oxon cross-linked trimers are apparent. Chlorpyrifos-oxon promotes isopeptide bond cross-linking of tubulin monomers to make multimers[2]. In PC12 cells in culture, 24 hours of exposure to Chlorpyrifos at a concentration 10-fold below the concentration that inhibits AChE activity (3.0 μM) impaired neurite outgrowth while Chlorpyrifos-oxon inhibits neurite outgrowth at 1.0 nM[3]. |
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| In Vivo | Chlorpyrifos-oxon (CPO) is rapidly detoxified by human liver microsomes via CYP-dependent deethylation and dearylation, and by glutathione-S-transferase. In addition, reactions with A-esterases such as paraoxonase 1 (PON 1) or B-esterases such as carboxylesterase and butyrylcholinesterase (BChE) in the liver may rapidly degrade or scavenge Chlorpyrifos-oxon[1]. Chlorpyrifos-oxon (3 mg/kg, ip; once; wild-type mice) treatment shows the dimensions of microtubules from Chlorpyrifos-oxon-treated mice are about 60% of those from control mice. The microtubules from mice exposed to Chlorpyrifos-oxon have covalently modified amino acids and abnormal structure, suggesting disruption of microtubule function[4]. |
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| References | [1]. Florian Eyer, et al. Extreme variability in the formation of chlorpyrifos oxon (CPO) in patients poisoned by chlorpyrifos (CPF). Biochem Pharmacol. 2009 Sep 1;78(5):531-7. [2]. Lawrence M Schopfer, et al. Chlorpyrifos oxon promotes tubulin aggregation via isopeptide cross-linking between diethoxyphospho-Lys and Glu or Asp: Implications for neurotoxicity. J Biol Chem. 2018 Aug 31;293(35):13566-13577. [3]. Jie Gao, et al. Chlorpyrifos and chlorpyrifos oxon impair the transport of membrane bound organelles in rat cortical axons. Neurotoxicology. 2017 Sep;62:111-123. [4]. Wei Jiang, et al. Mice treated with chlorpyrifos or chlorpyrifos oxon have organophosphorylated tubulin in the brain and disrupted microtubule structures, suggesting a role for tubulin in neurotoxicity associated with exposure to organophosphorus agents. Toxicol Sci. 2010 May;115(1):183-93. |
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Chemical & Physical Properties
| Density | 1.461g/cm3 |
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| Boiling Point | 357.8ºC at 760mmHg |
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| Molecular Formula | C9H11Cl3NO4P |
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| Molecular Weight | 334.52100 |
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| Flash Point | 170.2ºC |
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| Exact Mass | 332.94900 |
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| PSA | 67.46000 |
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| LogP | 4.60170 |
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| Index of Refraction | 1.523 |
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| InChIKey | OTMOUPHCTWPNSL-UHFFFAOYSA-N |
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| SMILES | CCOP(=O)(OCC)Oc1nc(Cl)c(Cl)cc1Cl |
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| Storage condition | 0-6°C |
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Toxicological Information
CHEMICAL IDENTIFICATION - RTECS NUMBER :
- TC2370100
- CHEMICAL NAME :
- Phosphoric acid, diethyl 3,5,6-trichloro-2-pyridyl ester
- CAS REGISTRY NUMBER :
- 5598-15-2
- LAST UPDATED :
- 199612
- DATA ITEMS CITED :
- 1
- MOLECULAR FORMULA :
- C9-H11-Cl3-N-O4-P
- MOLECULAR WEIGHT :
- 334.53
HEALTH HAZARD DATAACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 135 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB85-143766
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Safety Information
| Hazard Codes | T+ |
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| RIDADR | UN 2783 |
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| Packaging Group | III |
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| Hazard Class | 6.1(b) |
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Synonyms
