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Usage

Uses

Given the highly carcinogenic and mutagenic nature of Dibenzo[c,mno]chrysene, it does not have direct applications in any industry due to its harmful effects. However, it is a subject of study and research in various fields for the following reasons:
Used in Environmental Research:
Dibenzo[c,mno]chrysene is utilized as a subject of study in environmental research to understand its behavior in ecosystems, its persistence in the environment, and its impact on wildlife and human health. This research aids in developing strategies for monitoring and reducing its presence in the environment.
Used in Toxicology and Carcinogenesis Studies:
In toxicology and carcinogenesis studies, Dibenzo[c,mno]chrysene serves as a model compound to investigate the mechanisms of PAH-induced carcinogenesis and to assess the potential risks associated with exposure to similar compounds. These studies contribute to the development of preventive measures and regulations to protect public health.
Used in Analytical Chemistry:
Dibenzo[c,mno]chrysene is employed as a reference compound in the development and validation of analytical methods for detecting and quantifying PAHs in environmental and biological samples. Accurate measurement of these compounds is crucial for assessing exposure levels and implementing effective pollution control strategies.
While Dibenzo[c,mno]chrysene itself is not used in a positive application due to its harmful nature, understanding its properties and effects is vital for the development of strategies to mitigate its presence and impact on the environment and human health.

InChI:InChI=1/C24H14/c1-2-7-20-15(4-1)8-10-18-14-19-11-9-16-5-3-6-17-12-13-21(23(18)20)24(19)22(16)17/h1-14H

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Relevant academic research and scientific papers

Triflic acid promoted synthesis of polycyclic aromatic compounds

The triflic acid (CF3SO3H) promoted cyclizations of 2-styrylbiaryls are found to be useful for the synthesis of polycyclic aromatic compounds, including functionalized derivatives of polycyclic aromatic compounds and heterocyclic sys

Synthesis, in vitro metabolism, cell transformation, mutagenicity, and DNA adduction of dibenzo[c,mno] chrysene

Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous environmental pollutants. Due to its structural similarity with the potent carcinogen dibenzo [a,l] pyrene (DB [a,l]P) and because of its environmental presence, dibenzo[c,mno]chrysene (naphtho[1,2-a]pyrene, N[1,2-a]P) is of considerable research interest. We therefore developed an efficient synthesis of N[1,2-a]P, and examined its in vitro metabolism by male Sprague Dawley rat liver S9 fraction. Its mutagenic activity in S. typhimurium TA 100 and its morphological cell transforming ability in mouse embryo fibroblasts were evaluated. On the basis of spectral analyses, the in vitro major metabolites were identified as the fjord region dihydrodiol trans-9,10-dihydroxy-9,10- dihydro-N[1,2-a]P (N[1,2-a]P-9,10-dihydrodiol), the K-region diols N[1,2-a]P-4,5-dihydrodiol and N[1,2-a]P-7,8-dihydrodiol, and also the 1-, 3-, and 10-hydroxy-N[1,2-a]P; the structure of N[1,2-a]P-9,10-dihydrodiol was also confirmed by independent synthesis. In assays with S. typhimurium TA 100, N[1,2-a]P-9,10-dihydrodiol was half as mutagenic as (±)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene (B[a]P-7,8-dihydrodiol) at ≥ nmol/plate. N[1,2-a]P-9,- 10-dihydrodiol was much more mutagenic than N[1,2-a]P at all dose levels, suggesting that the N[1,2-a]P-9,10-dihydrodiol is the likely proximate mutagen of N[1,2-a]P. Evaluation of morphological cell transformation in C3H10T1/2C18 mouse embryo fibroblasts revealed that N[1,2-a]P was comparable to B[a]P. We further examined the pattern of in vitro adduct formation between calf thymus DNA and (±)-anti-9,10-dihydroxy-9,10-dihydro-11,12-epoxy- 9,10,11,12-tetrahydro-N[1,2-a]P (N[1,2-a]PDE) and found that dG-adduct formation is 2.9-fold greater than dA-adduct formation. On the basis of our results and those reported in the literature, our working hypothesis is that N[1,2-a]P may be added to the list of potent carcinogens that includes DB [a,l]P. This hypothesis is currently being tested in our laboratory.

A convenient and general synthesis of cata- and peri-condensed polycyclic aromatic hydrocarbons with a Fjord-region

Cata- and peri-condensed polycyclic aromatic hydrocarbons (PAHs) 10a-d and 11 have been conveniently synthesized by the application of Suzuki cross-coupling reaction. In three to four steps, these PAHs having fjord-region were obtained in an overall yield of 35-51% from commercially or easily accessible aryl boronic acids and aryl bromides.