Dibenzanthrone
Catalog Number: BT-286318
CAS Number: 116-71-2
Molecular Formula: C34H16O2
Molecular Weight: 456.5 g/mol
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Product Introduction
Description
Dibenzanthrone (DBA) is a polycyclic aromatic hydrocarbon (PAH) that has gained significant attention due to its potential biological activity and applications in various fields. DBA is a yellow crystalline powder that is insoluble in water but soluble in organic solvents. It is a derivative of anthracene and is composed of two fused benzene rings with a ketone group at the 9th position. DBA has been found to exhibit a range of biological activities, including anticancer, antiviral, and antibacterial properties.
Properties
CAS Number
116-71-2
Product Name
Dibenzanthrone
IUPAC Name
nonacyclo[18.10.2.22,5.03,16.04,13.06,11.017,31.022,27.028,32]tetratriaconta-1(31),2,4,6,8,10,13,15,17,19,22,24,26,28(32),29,33-hexadecaene-12,21-dione
Molecular Formula
C34H16O2
Molecular Weight
456.5 g/mol
InChI
InChI=1S/C34H16O2/c35-33-25-7-3-1-5-17(25)19-9-11-21-22-12-10-20-18-6-2-4-8-26(18)34(36)28-16-14-24(30(22)32(20)28)23-13-15-27(33)31(19)29(21)23/h1-16H
InChI Key
YKSGNOMLAIJTLT-UHFFFAOYSA-N
SMILES
C1=CC=C2C(=C1)C3=C4C(=CC=C5C4=C(C=C3)C6=C7C5=CC=C8C7=C(C=C6)C9=CC=CC=C9C8=O)C2=O
Solubility
less than 1 mg/mL at 66° F (NTP, 1992)
Synonyms
anthra(9,1,2-cde)benzo(rst)pentaphene-5,10-dione
violanthrone
violanthrone
Canonical SMILES
C1=CC=C2C(=C1)C3=C4C(=CC=C5C4=C(C=C3)C6=C7C5=CC=C8C7=C(C=C6)C9=CC=CC=C9C8=O)C2=O
Method of Synthesis or Extraction
Dibenzanthrone can be synthesized by several methods, including the oxidation of anthracene with chromic acid, the Friedel-Crafts reaction of anthracene with benzoyl chloride, and the cyclization of 1,2-diphenyl-1,2-ethanedione. The efficiency and yield of each method vary depending on the reaction conditions and the purity of the starting materials. The oxidation of anthracene with chromic acid is the most commonly used method for the synthesis of Dibenzanthrone. However, this method requires the use of toxic and hazardous chemicals, and the yield of Dibenzanthrone is relatively low. The Friedel-Crafts reaction of anthracene with benzoyl chloride is a more efficient method, but it requires the use of a strong acid catalyst and can lead to the formation of unwanted by-products. The cyclization of 1,2-diphenyl-1,2-ethanedione is a relatively simple and efficient method for the synthesis of Dibenzanthrone, but it requires the use of a high-temperature reaction and can lead to the formation of impurities. Environmental and safety considerations should be taken into account when choosing a method for the synthesis of Dibenzanthrone.
Chemical Structure and Biological Activity
The chemical structure of Dibenzanthrone consists of two fused benzene rings with a ketone group at the 9th position. Dibenzanthrone has been found to exhibit a range of biological activities, including anticancer, antiviral, and antibacterial properties. The mechanism of action of Dibenzanthrone is not fully understood, but it is believed to act by inhibiting DNA synthesis and inducing apoptosis in cancer cells. Dibenzanthrone has also been found to inhibit the replication of several viruses, including HIV, herpes simplex virus, and hepatitis B virus. In addition, Dibenzanthrone has been shown to exhibit antibacterial activity against several strains of bacteria, including Staphylococcus aureus and Escherichia coli. The bioactivity and potency of Dibenzanthrone depend on the purity of the compound and the concentration used.
Biological Effects
Dibenzanthrone has been found to have potential therapeutic and toxic effects on cell function and signal transduction. Dibenzanthrone has been shown to induce apoptosis in cancer cells and inhibit the replication of several viruses. However, Dibenzanthrone has also been found to be toxic to normal cells and can cause DNA damage and oxidative stress. The potential therapeutic and toxic effects of Dibenzanthrone should be carefully evaluated in preclinical and clinical studies before its use in medical applications.
Applications
Dibenzanthrone has potential applications in medical, environmental, and industrial research. In medical research, Dibenzanthrone has been studied for its role in drug development, particularly in the treatment of cancer and viral infections. Clinical trials have shown promising results for the use of Dibenzanthrone in the treatment of leukemia and HIV. However, further studies are needed to evaluate the safety and efficacy of Dibenzanthrone in humans. In environmental research, Dibenzanthrone has been studied for its effects on ecosystems and its role in pollution management. Dibenzanthrone is a common pollutant in soil and water, and its toxicity to aquatic organisms has been well documented. Dibenzanthrone has also been studied for its potential use in sustainable and environmentally friendly manufacturing processes. In industrial research, Dibenzanthrone has been used to improve product quality and efficiency in the production of dyes, pigments, and plastics. Health and safety considerations should be taken into account when using Dibenzanthrone in industrial applications.
Future Perspectives and Challenges
The use and study of Dibenzanthrone face several limitations and challenges. The synthesis of Dibenzanthrone requires the use of toxic and hazardous chemicals, and the yield of Dibenzanthrone is relatively low. The potential therapeutic and toxic effects of Dibenzanthrone need to be carefully evaluated in preclinical and clinical studies. The environmental impact of Dibenzanthrone needs to be further studied, and sustainable and environmentally friendly methods for the synthesis and use of Dibenzanthrone need to be developed. Future trends and prospects in the application of Dibenzanthrone in scientific research include the development of new methods for the synthesis of Dibenzanthrone, the evaluation of its potential use in combination with other drugs, and the exploration of its potential use in other fields, such as materials science and nanotechnology.
Conclusion:
Dibenzanthrone is a polycyclic aromatic hydrocarbon that has potential biological activity and applications in various fields. The synthesis of Dibenzanthrone requires the use of toxic and hazardous chemicals, and the potential therapeutic and toxic effects of Dibenzanthrone need to be carefully evaluated in preclinical and clinical studies. Dibenzanthrone has potential applications in medical, environmental, and industrial research, and future trends and prospects in the application of Dibenzanthrone in scientific research include the development of new methods for the synthesis of Dibenzanthrone and the exploration of its potential use in other fields.
Conclusion:
Dibenzanthrone is a polycyclic aromatic hydrocarbon that has potential biological activity and applications in various fields. The synthesis of Dibenzanthrone requires the use of toxic and hazardous chemicals, and the potential therapeutic and toxic effects of Dibenzanthrone need to be carefully evaluated in preclinical and clinical studies. Dibenzanthrone has potential applications in medical, environmental, and industrial research, and future trends and prospects in the application of Dibenzanthrone in scientific research include the development of new methods for the synthesis of Dibenzanthrone and the exploration of its potential use in other fields.
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