Basic information
- CAS
53494-70-5- Standard SMILES
O=C1C2CC3C1C1(Cl)C(Cl)C4(Cl)C2C3C1(Cl)C4(Cl)Cl- InChIKey
IZHZFAQWVKBTSL-UHFFFAOYSA-N- Molecular formula
- C12H8Cl6O
- Average molar mass
- 380.9 g/mol
- Monoisotopic mass
- 377.870631
Overview
Endrin ketone is the chemical produced when endrin is exposed to light. Endrin is a chlorinated hydrocarbon used as an insecticide on cotton, maize, and rice. It also acts as an avicide and rodenticide. Due to its toxicity and tendency to bioaccumulate, its use is now banned in most parts of the world. (L111)
Names & identifiers
- Preferred name
- Endrin ketone
- IUPAC
- 1,2,2,3,10,11-hexachloropentacyclo[5.4.1.03,10.04,12.05,9]dodecan-8-one
- English name
- ENDRIN KETONE
- Molecular formula
- C12H8Cl6O
- Molecular weight
- 380.91
Names & synonyms
Endrin ketone53494-70-5delta-Ketoendrindelta-Keto 153SD 2614.delta.-Ketoendrin1,2,2,3,10,11-hexachloropentacyclo[5.4.1.03,10.04,12.05,9]dodecan-8-one.delta.-Keto 1532,5,7-Metheno-3H-cyclopenta(a)pentalen-3-one, 3b,4,5,6,6,6a-hexachlorodecahydro-, (2-alpha,3a-beta,3b-beta,4-beta,5-beta,6a-beta,7-alpha,7a-beta,8R*)-2,5,7-Metheno-3H-cyclopenta(a)pentalen-3-one, 3b,4,5,6,6,6a-hexachlorodecahydro-, (2R,3aR,3bS,4R,5R,6aS,7S,7aR,8R)-rel-DTXSID00872845deltaKetoendrin
Show more names
sd2614KETOENDRINKETOENDERINδ-Ketoendrindelta-keto153Endrin Ketone 99%Endrin ketone (95-98%)ENDRIN KETONE STANDARD
1,2,2,3,10,11-hexachloropentacyclo(5.4.1.03,10.04,12.05,9)dodecan-8-onedeltaKeto 153RefChem:136814DTXCID208204042,5,7Metheno3Hcyclopenta(a)pentalen3one, 3b,4,5,6,6,6ahexachlorodecahydro, (2alpha,3abeta,3bbeta,4beta,5beta,6abeta,7alpha,7abeta,8R*)2,5,7Metheno3Hcyclopenta(a)pentalen3one, 3b,4,5,6,6,6ahexachlorodecahydro, (2R,3aR,3bS,4R,5R,6aS,7S,7aR,8R)relIZHZFAQWVKBTSL-UHFFFAOYSA-N7378-10-1
Properties
Computed structural properties
- XLogP
- 3.2
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 564
Experimental & physicochemical properties
PesticidesPesticides -> Organochlorine Pesticides
Physical DescriptionWhite solid; [Cerilliant MSDS]
Physicochemical properties
- Boiling point
- 496.11 °C · 496.11°C (rough estimate)
- Density
- 1.5674 · 1.5674 (rough estimate)
- refractive index
- 1.555 · 1.5550 (estimate)
- Flash point
- 2 °C · 2 °C
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly, Sonicated), Ethyl Acetate (Slightly)
- Major Application
- agriculture
- InChI
- 1S/C12H8Cl6O/c13-8-9(14)6-2-1-3(7(6)19)4-5(2)11(9,16)12(17,18)10(4,8)15/h2-6,8H,1H2/t2-,3+,4+,5-,6+,8+,9-,10+,11-/m1/s1
- InChIKey
- IZHZFAQWVKBTSL-YTMKBKNTSA-N
- SMILES
- Cl[C@@H]1[C@@]2(Cl)[C@H]3[C@@H]4C[C@@H]5[C@H]3[C@](Cl)(C2(Cl)Cl)[C@@]1(Cl)[C@@H]5C4=O
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 2.4% (1 of 42) of reports.
Danger
H300 (97.6%): Fatal if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Hazards SummaryHighly toxic by ingestion; [Cerilliant MSDS] See Endrin.
Hazard Classes and CategoriesAcute Tox. 2 (97.6%)
Toxicology
TreatmentTreatment is symptomatic, aimed at controlling convulsions, coma, and respiratory depression. If ingested, gastric lavage may be performed, followed by administering activated charcoal powder. (L150)
Health EffectsEndrin poisoning affects primarily the nerve system. Exposure causes various harmful effects including hyperexcitability, severe central nervous system damage, and death. Endrin is also believed to cause birth defects. (T10, L112)
Adverse EffectsOther Poison - Organochlorine
Exposure RoutesOral (L111)
Toxicity Summary
Endrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. Endrin also inhibits Na+ K+ ATPase and Ca2+ and Mg2+ ATPase which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. Endrin also causes increased lipid peroxidation, decreased membrane fluidity, and DNA damage in hepatocytes, but the exact mechanism is unknown. (T10, L112)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Endrin is absorbed orally and distributed primarily to the fat and skin. The major biotransformation product is anti-l 2-hydroxyendrin and the corresponding sulfate, as well as glucuronide metabolites. Anti- and syn-12-hydroxyendrin and 12-ketoendrin are the main toxic metabolites of endrin. Endrin and its metabolites are excreted in urine and feces. (L112)
Uses & manufacturing
UsesEndrin is used as a pesticide. (L111)
Applications
Uses-Ketoendrin is an isomerization product of Endrin (E555530), a chlorinated hydrocarbon insecticide that produces hepatic and neurologic toxicity. Endrin is also known to produce hyperexcitability of the human central nervous system that could result in convulsions. -Ketoendrin is an endocrine disrupting compound that has been found in human fetal and newborn tissues.
Suppliers30 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
江苏智芯廷科技有限公司18221391031 · [email protected]
广州佳途科技股份有限公司81960175-877 18933936954 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
Related reactions
0 records
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Compound notes
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