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Dieldrin

Catalog Number: BT-264488

CAS Number: 60-57-1

Molecular Formula: C12H8Cl6O

Molecular Weight: 380.9 g/mol

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

Dieldrin is a highly toxic organochlorine compound that was widely used as an insecticide in the 1950s and 1960s. It is a persistent organic pollutant that can remain in the environment for decades and has been linked to various health and environmental problems. This paper aims to provide a comprehensive review of dieldrin, including its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges.

Properties

CAS Number

60-57-1

Product Name

Dieldrin

IUPAC Name

(1R,2R,3R,6S,7S,8S,9R,11S)-3,4,5,6,13,13-hexachloro-10-oxapentacyclo[6.3.1.13,6.02,7.09,11]tridec-4-ene

Molecular Formula

C12H8Cl6O

Molecular Weight

380.9 g/mol

InChI

InChI=1S/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15)12(11,17)18/h2-7H,1H2/t2-,3+,4-,5+,6+,7-,10-,11+

InChI Key

DFBKLUNHFCTMDC-UHFFFAOYSA-N

SMILES

C1C2C3C(C1C4C2O4)C5(C(=C(C3(C5(Cl)Cl)Cl)Cl)Cl)Cl

Solubility

less than 1 mg/mL at 75° F (NTP, 1992)
5.80e-07 M
SLIGHTLY SOL IN MINERAL OILS, MODERATELY SOL IN ACETONE
Soluble in aromatic solvents; moderately soluble in acetone
Insol in methanol, aliphatic hydrocarbons; soluble in benzene
48 g/100 ml ethylene dichloride at 20 °C
In acetone 220, ethanol 40, dichloromethane 480, benzene 400, toluene 410, carbon tetrachloride 380, methanol 10 (all in g/l at 20 °C)
In water, 0.195 mg/l @ 25 °C
Solubility in water: none
0.02%

Synonyms

Alvit 55
Alvit-55
Alvit55
Dieldrin

Canonical SMILES

C1C2C3C(C1C4C2O4)C5(C(=C(C3(C5(Cl)Cl)Cl)Cl)Cl)Cl

Isomeric SMILES

C1[C@@H]2[C@@H]3[C@H]([C@H]1[C@@H]4[C@H]2O4)[C@@]5(C(=C([C@]3(C5(Cl)Cl)Cl)Cl)Cl)Cl

Method of Synthesis or Extraction

Dieldrin is synthesized by the reaction of hexachlorocyclopentadiene with norbornadiene in the presence of a catalyst. The yield of this method is around 50%, and the process is highly efficient. However, the synthesis of dieldrin is not commonly used due to its toxicity and environmental concerns. Dieldrin can also be extracted from technical-grade aldrin, which is a mixture of isomers that can be converted to dieldrin by heating. The yield of this method is around 80%, and it is less toxic and more environmentally friendly than the synthesis method.

Chemical Structure and Biological Activity

Dieldrin is a cyclic compound with six chlorine atoms attached to a six-membered ring. It is highly lipophilic and can accumulate in fatty tissues. Dieldrin acts as a neurotoxin by binding to the gamma-aminobutyric acid (GABA) receptor in the central nervous system, leading to hyperexcitability and convulsions. It also inhibits the sodium-potassium ATPase pump, which is essential for maintaining the ion balance in cells. Dieldrin has been shown to have potent insecticidal activity, with a lethal dose of 0.1-1 mg/kg in insects.

Biological Effects

Dieldrin has been shown to have various biological effects on cell function and signal transduction. It can induce oxidative stress, DNA damage, and apoptosis in cells. Dieldrin has also been linked to various health problems, including Parkinson's disease, cancer, and reproductive disorders. However, dieldrin has also been found to have potential therapeutic effects, such as its ability to inhibit cancer cell growth and induce apoptosis in cancer cells.

Applications

Dieldrin has been used in medical research, particularly in drug development. It has been shown to have potential as an anticancer agent and has been used in clinical trials for the treatment of various cancers. However, its toxicity and environmental concerns have limited its use in medical research. In environmental research, dieldrin has been found to have significant effects on ecosystems, particularly on aquatic organisms. It has been linked to the decline of fish populations and the disruption of food chains. Dieldrin has also been used in pollution management, particularly in the remediation of contaminated soils. In industrial research, dieldrin has been used in manufacturing processes, particularly in the production of plastics and rubber. However, its toxicity and environmental concerns have led to its replacement by safer alternatives.

Future Perspectives and Challenges

The use and study of dieldrin face various limitations, particularly its toxicity and environmental concerns. Possible solutions and improvements include the development of safer and more environmentally friendly alternatives to dieldrin, the implementation of stricter regulations on its use and disposal, and the development of more effective methods for its remediation. Future trends and prospects in the application of dieldrin in scientific research include its potential as an anticancer agent and its use in the development of new drugs. However, further research is needed to fully understand its biological effects and potential therapeutic applications.
Conclusion:
Dieldrin is a highly toxic organochlorine compound that has been widely used as an insecticide. It has significant environmental and health concerns and has been linked to various health problems and environmental issues. The use and study of dieldrin face various limitations, and further research is needed to fully understand its biological effects and potential therapeutic applications. The development of safer and more environmentally friendly alternatives to dieldrin is essential to mitigate its adverse effects on human health and the environment.

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