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Chrysene
Chrysene
Chrysene
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Chrysene[1]
Skeletal structure
Skeletal structure
Ball-and-stick model of the chrysene molecule
Names
Preferred IUPAC name
Chrysene[2]
Other names
1,2-Benzophenanthrene; 1,2-Benzphenanthrene; Benzo[a]phenanthrene; NSC 6175; [4]Phenacene
Identifiers
3D model (JSmol)
1909297
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.386 Edit this at Wikidata
EC Number
  • 205-923-4
262600
KEGG
RTECS number
  • GC0700000
UNII
  • InChI=1S/C18H12/c1-3-7-15-13(5-1)9-11-18-16-8-4-2-6-14(16)10-12-17(15)18/h1-12H checkY
    Key: WDECIBYCCFPHNR-UHFFFAOYSA-N checkY
  • InChI=1/C18H12/c1-3-7-15-13(5-1)9-11-18-16-8-4-2-6-14(16)10-12-17(15)18/h1-12H
    Key: WDECIBYCCFPHNR-UHFFFAOYAK
  • c1ccc2c(c1)ccc3c2ccc4c3cccc4
Properties
C18H12
Molar mass 228.294 g·mol−1
Appearance white solid
Density 1.274 g/cm3
Melting point 254 °C (489 °F; 527 K)
Boiling point 448 °C (838 °F; 721 K)
Insoluble
Solubility in ethanol 1 g/1300 mL[3]
−166.67·10−6 cm3/mol
Related compounds
Related PAHs
 Pyrene, Tetracene, Triphenylene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Chrysene is a polycyclic aromatic hydrocarbon (PAH) with the molecular formula C
18H
12[4] that consists of four fused benzene rings. It is a natural constituent of coal tar, from which it was first isolated and characterized. It is also found in creosote at levels of 0.5–6 mg/kg.[5]

The name "chrysene" originates from Greek Χρύσoς (chrysos), meaning "gold", and is due to the golden-yellow color of the crystals of the hydrocarbon, thought to be the proper color of the compound at the time of its isolation and characterization. However, high purity chrysene is colorless, the yellow hue being due to the traces of its yellow-orange isomer tetracene, which cannot be separated easily.

Occurrence

[edit]

Chrysene is a constituent of tobacco smoke.[6]

Safety

[edit]

As with other PAHs, chrysene is suspected to be a human carcinogen. Some evidence suggests that it causes cancer in laboratory animals,[7] but chrysene is often contaminated with more strongly carcinogenic compounds. Chrysene is estimated to have about 1% of the toxicity of benzo(a)pyrene.[8]

Derivatives

[edit]

Derivatives of chrysene include tetrahydrochrysene and 2,8-dihydroxyhexahydrochrysene, which are estrogenic compounds. The experimental cancer drug crisnatol is a derivative of chrysene.

See also

[edit]

References

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Chrysene

View on Grokipedia
from Grokipedia
Chrysene is a (PAH) with the molecular formula C₁₈H₁₂, consisting of four angularly fused rings. It appears as a white to light yellow crystalline solid with a molecular weight of 228.29 g/mol and CAS number 218-01-9. First isolated from in the and named after the Greek word for due to impurities in early samples, chrysene exhibits strong under light. Physically, chrysene has a melting point of 252–256 °C and a boiling point of 448 °C, with a density of 1.274 g/cm³ at 20 °C. It is highly lipophilic and insoluble in water (solubility <0.0001 g/L), but readily dissolves in organic solvents such as and . Chemically stable and combustible, it is incompatible with strong oxidizing agents. Chrysene occurs naturally and anthropogenically as a product of incomplete of , found in environmental sources including , cigarette smoke, automobile exhaust, wood smoke, grilled meats, and petroleum products. It persists in and sediments due to slow ( 77–387 days) and low volatility (vapor pressure 6.23 × 10⁻⁹ mmHg at 25 °C). In the environment, it bioaccumulates and is very toxic to aquatic life with long-lasting effects. Uses of chrysene are limited primarily to research and organic synthesis, including applications in organic light-emitting diodes (OLEDs); it is not widely used commercially due to health concerns. In the European Union, its concentration is restricted to 0.00005% in tattoo inks. From a health perspective, chrysene is classified as a probable human carcinogen (EPA Group B2) and suspected of causing genetic defects, with evidence of liver tumors in animal studies and potential for mutagenicity, reproductive toxicity, and immunotoxicity. It is also a persistent, bioaccumulative, and toxic (PBT) substance under EU regulations and included on the Candidate List of Substances of Very High Concern (SVHC). Human exposure occurs via inhalation, ingestion, or skin contact from contaminated air, water, soil, food, or occupational settings like coal processing.

Structure and Properties

Molecular Structure

Chrysene has the molecular formula C18_{18}H12_{12} and a molecular weight of 228.29 g/mol. As a (PAH), chrysene features four rings fused in a linear yet angular arrangement, forming a rigid, planar structure classified under the phenanthrene series. Its IUPAC name is benzophenanthrene, reflecting the fusion of a benzene ring at the a-position of phenanthrene. The systematic numbering of carbon positions adheres to IUPAC conventions for ortho-fused systems: positions 1–14 designate the peripheral carbon atoms bearing hydrogen atoms across the four rings, while positions 15–18 correspond to the quaternary carbon atoms at the ring fusions (specifically, 4a, 4b, 10a, and 14a in standard notation). This numbering ensures consistent identification of substitution sites and facilitates comparison with related PAHs. X-ray crystallographic studies reveal that chrysene's molecular structure is nearly planar, with C–C bond lengths varying between 1.36 Å and 1.44 Å, indicative of partial double-bond character due to π-delocalization across the conjugated system. Bond angles are approximately 120°, consistent with sp² hybridization at each carbon atom, though slight deviations occur at fusion points to accommodate the angular geometry. For instance, the central bond in the phenanthrene-like moiety measures about 1.365 Å, shorter than peripheral bonds approaching single-bond lengths. These dimensions underscore the aromatic stability of the fused rings, with no significant distortions from planarity. The is commonly depicted using Kekulé representations, which illustrate alternating single and double bonds to highlight localized π-electrons, though delocalizes the electrons over the entire , yielding equivalent bond orders. Multiple structures (five primary Kekulé forms) contribute to this delocalization, stabilizing the system and influencing its electronic properties. In for clarity, a simplified linear fusion pattern can be conceptualized as:

Ring A Ring B Ring C Ring D /\/\/\ /\/\/\ /\/\/\ /\/\/\ (angular bend between B and C)

Ring A Ring B Ring C Ring D /\/\/\ /\/\/\ /\/\/\ /\/\/\ (angular bend between B and C)

For precise visualization, structural diagrams show the rings fused such that rings A and D are terminal, with B and C forming the angular core. Compared to related PAHs, chrysene's ring fusion pattern is angular, akin to (three rings with a bay region), but extended by an additional linearly fused ring, enhancing its planarity and conjugation length. In contrast, exhibits a more compact, rectangular arrangement of four rings without the extended linear chain, resulting in different electronic and steric properties. This angular configuration in chrysene distinguishes it from linear acenes like , promoting greater stability against photo-oxidation.

Physical Properties

Chrysene appears as a crystalline with a monoclinic ( C2/c). It has a of 1.274 g/cm³ at 20 °C, making it denser than . The compound exhibits a of 254–255 °C and a boiling point of 448 °C at 760 mmHg. Chrysene displays low volatility, with a on the order of 10^{-8} mmHg at , and it undergoes sublimation at elevated temperatures above its . Chrysene is practically insoluble in water, with a solubility of approximately 0.002 mg/L (2 μg/L) at 25 °C, attributable to its nonpolar, polycyclic aromatic structure. It shows greater solubility in organic solvents, such as 1 g per 1300 mL in at 25 °C and moderate solubility in . In terms of spectroscopic properties, chrysene displays UV absorption maxima in alcohol at approximately 268 nm (strongest band) and around 320–353 nm, with characteristic in the 300–370 nm region. It is fluorescent, with an excitation maximum near 344 nm and emission peak at 380 nm.

Chemical Properties

Chrysene demonstrates high thermal stability owing to its extended aromatic conjugation, which confers resistance to thermal degradation up to temperatures exceeding 500°C, as evidenced by thermogravimetric analyses showing minimal below this threshold. This stability arises from the delocalized π-electron system across its four fused rings, contributing to its persistence in high-temperature environments like combustion processes. In reactions, chrysene preferentially undergoes attack at positions 3 and 6 due to their higher in the resonance-stabilized intermediate. For instance, yields primarily 6-nitrochrysene and 3-nitrochrysene. Similarly, sulfonation predominantly forms chrysene-6-sulfonic acid, further underscoring the reactivity at position 6. Chrysene shows resistance to standard chemical oxidation under ambient conditions, reflecting the stability of its fully aromatic , but it is susceptible to photo-oxidation in the presence of and oxygen, leading to the formation of quinone derivatives such as chrysene-5,6-dione and chrysene-9,10-dione. These photo-oxidation products result from addition and subsequent rearrangement, enhancing its environmental transformation pathways. Aromaticity metrics for chrysene indicate strong delocalization, with the Harmonic Oscillator Model of Aromaticity (HOMA) index averaging approximately 0.86 across its rings, signifying near-ideal bond length alternation consistent with high aromatic character. Resonance energy calculations, estimated at around 83 kcal/mol via heat-of-formation methods, further quantify the stabilization from π-delocalization relative to localized benzene-like structures. In , chrysene exhibits a prominent molecular at m/z 228 (100% relative intensity) under , reflecting its intact polycyclic framework. Characteristic fragmentation includes loss of H₂ to yield m/z 226 (21%) and minor peaks at m/z 229 (isotopic) and m/z 114 (possible ring cleavage), providing diagnostic patterns for identification in complex mixtures. This stability of the molecular underscores chrysene's resistance to extensive fragmentation, aiding its detection in environmental analyses. The chemical stability of chrysene contributes to its environmental persistence, where it resists rapid degradation but undergoes slow photo-oxidative transformations.

History and Synthesis

Discovery and Isolation

Chrysene was first discovered in 1837 by French chemist Auguste Laurent during his systematic studies of , a complex mixture obtained from the of , which marked an important early advancement in . Laurent's initial isolation of the compound involved of to isolate higher-boiling fractions, followed by purification through fractional from pitch using solvents such as or alcohol to yield the crystalline . The name chrysene derives from the Greek word chrysos, meaning "," reflecting the golden-yellow hue of the impure observed in early preparations, though purified samples are colorless. The molecular formula of chrysene (C₁₈H₁₂) was established through in the late . Structural elucidation occurred in the early via oxidative degradation studies, which produced identifiable products such as , combined with comparisons to partially synthetic analogs to confirm the four-fused-ring arrangement. crystallographic studies in the 1930s definitively confirmed the molecular structure and D₂h symmetry of chrysene. A key milestone came in 1910 when Robert Pschorr achieved the first total synthesis of chrysene through an intramolecular arylation reaction, adapting his earlier phenanthrene method involving diazotization of a naphthyl-substituted cinnamic acid derivative, thereby verifying the proposed structure.

Synthetic Methods

Chrysene is primarily produced industrially as a byproduct during the distillation of coal tar, where it constitutes a minor fraction of the high-boiling residues. The process involves fractional distillation of crude coal tar obtained from coke production, followed by extraction and purification steps such as solvent extraction, chromatography, or zone melting to isolate chrysene from other polycyclic aromatic hydrocarbons. Yields from coal tar extraction are typically low, less than 1% by weight of the tar, due to its dilute presence at concentrations around 0.065% in bulk coal tar. A classical synthesis of chrysene employs the Pschorr reaction, involving diazotization of a naphthyl-substituted derivative followed by copper-mediated intramolecular arylation to form the tetracyclic framework. This method, developed in the early , provides a route to verify the structure and offers moderate efficiency for constructing the angularly fused rings characteristic of chrysene. Modern syntheses favor oxidative cyclodehydrogenation of appropriate biaryl precursors using oxidants like chloranil in refluxing or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in . These conditions promote dehydrogenative to chrysene, achieving yields of 70-90% after purification by or recrystallization. This approach is preferred for its high efficiency and adaptability to substituted derivatives. Alternative routes include photocyclization of stilbene derivatives, where oxidative irradiation in the presence of iodine or air yields chrysene through sequential double-bond closure and dehydrogenation, with reported yields of 60-83%. Another method utilizes metal-catalyzed coupling, exemplified by PtCl₂-mediated 6-endo-dig cyclization of ethynylnaphthalenes under reflux in toluene, providing substituted chrysenes in moderate to good yields (typically 50-80%) with high regioselectivity. These techniques highlight the versatility of catalytic and photochemical strategies for targeted chrysene production.

Occurrence

Natural Sources

Chrysene forms naturally through the geological transformation of during and catagenesis, embedding it within fossil fuels such as and . In , it appears at higher concentrations relative to many other polycyclic aromatic hydrocarbons (PAHs), often comprising a notable portion of the PAH fraction derived from ancient plant and algal remains. In , chrysene arises similarly from the maturation of sedimentary organic , with concentrations in crude oils varying by source, typically 0.02–0.2 mg/kg (e.g., 0.018 mg/kg in Scotia Light crude and 0.2 mg/kg in Cold Lake Blend diluted ). It is also detected in natural gas condensates, where PAHs including chrysene occur at trace levels as byproducts of hydrocarbon maturation in rocks. Traces of chrysene appear in sediments through the degradation of algal and , as well as natural incomplete processes like wildfires, contributing to low-level PAH distributions in depositional environments. In source rock extracts, chrysene and its methylated derivatives are common, reflecting biological precursors transformed under geological conditions. Chrysene has been identified in , including carbonaceous chondrites and interplanetary dust particles, suggesting its presence as a primitive PAH in interstellar and meteorites formed through cosmic processes. Concentrations in such samples are typically low, on the order of , but confirm its role in pre-solar . As a geochemical marker, chrysene aids in oil-source rock correlations due to its stable distribution patterns and carbon isotope ratios, which preserve signatures of original organic inputs and maturation stages; for instance, δ¹³C values of individual aromatic hydrocarbons like chrysene distinguish depositional environments in basins such as those in .

Environmental and Anthropogenic Sources

Chrysene is released into the environment primarily through anthropogenic activities involving incomplete processes. Emissions from tobacco smoke represent a significant personal exposure source, with mainstream containing 10–50 ng of chrysene per across various commercial brands. exhaust contributes substantially to urban PAH pollution, with chrysene detected in particulate matter from and diesel engines at levels around 2 mg/kg in particulate matter. Residential wood burning also emits chrysene, particularly during incomplete in wood stoves and open fires, accounting for a major portion of atmospheric PAHs in areas with high domestic heating reliance. Industrial processes are key contributors to chrysene releases. Coal tar creosote, used as a wood preservative, contains chrysene at concentrations ranging from 19 to 620 mg/kg across commercial samples. Asphalt production and paving operations release chrysene through volatilization and particulate emissions during heating and mixing of bitumen. Aluminum smelting generates chrysene via the use of coal tar pitch as a binder in electrodes, leading to emissions during high-temperature reduction processes. In the environment, chrysene exhibits and mobility, facilitating its widespread distribution. It bioaccumulates in sediments due to its low water solubility and high affinity for , with factors in aquatic organisms ranging from 10 to 10,000; its in sediments exceeds 371 days under aerobic conditions. Atmospheric transport occurs mainly bound to fine particulates, enabling long-range dispersion and deposition via wet and dry processes, with urban air concentrations typically ranging from 1 to 10 ng/m³ in particle-bound form. Regulatory frameworks address chrysene as part of broader PAH monitoring efforts. It is included in the U.S. EPA's list of 129 priority pollutants under the Clean Water Act for tracking and control. In the , chrysene falls under REACH regulations for polycyclic aromatic hydrocarbons, requiring registration, evaluation, and risk management in chemical supply chains. Globally, chrysene levels are elevated in industrialized regions due to concentrated emissions. Contaminated soils near coking plants, a major source of PAH releases, show chrysene concentrations of 100–500 µg/kg, reflecting ongoing deposition from stack emissions and fugitive losses.

Applications

Industrial Uses

In metallurgical processes, chrysene is incorporated as a component of coal tar pitch, which acts as a binder in the production of carbon electrodes and refractories for steelmaking. Coal tar pitch, containing polycyclic aromatic hydrocarbons including chrysene, provides the necessary carbon matrix for these high-temperature applications, enhancing electrode conductivity and refractory durability during steel production. Historically, chrysene was utilized in formulations for , where it contributed to the protective properties against decay and in applications such as railroad ties and utility poles; however, its use has been phased out due to toxicity concerns.

Research and Pharmaceutical Applications

Chrysene is widely utilized as a model compound in studies of (PAH) metabolism, particularly to investigate the role of enzymes in processes. Researchers have employed chrysene to demonstrate the formation of hydroxylated metabolites through liver microsomal activity, providing insights into PAH pathways. Nitrated chrysene derivatives have also been examined for their capacity to induce 1A1 expression in human hepatoma HepG2 cells, highlighting chrysene's relevance in understanding enzyme induction mechanisms. These studies underscore chrysene's structural similarity to environmental PAHs, making it a valuable probe for metabolic . In , chrysene functions as a reference standard for determining quantum yields owing to its high purity availability and well-defined emission properties. Alongside , chrysene is recommended for in quantitative fluorescence measurements, enabling accurate assessment of photophysical efficiencies in complex molecular systems. Pharmaceutical applications of chrysene derivatives include crisnatol, a 6-substituted chrysene compound (2-(chrysen-6-ylmethylamino)-2-methylpropane-1,3-diol) evaluated as an antitumor agent. Crisnatol advanced to phase I clinical trials in the 1980s and 1990s, with dosing regimens tested intravenously every 28 days to assess safety and in cancer patients. These trials established maximum tolerated doses up to 900 mg/m², positioning crisnatol as a promising candidate for further anticancer development based on its chrysene core. In , chrysene acts as a key precursor for synthesizing discotic liquid crystals that form ordered columnar phases, beneficial for charge transport in electronic devices. Benzochrysene-based discotics, prepared via Suzuki-Miyaura coupling with pendant alkoxy chains, exhibit stable hexagonal columnar mesophases over broad temperature ranges. Chrysene derivatives also serve as emitters in organic light-emitting diodes (OLEDs), delivering pure blue with external quantum efficiencies exceeding 3% and Commission Internationale de l'Eclairage y-coordinates near 0.08. Post-2020 research has focused on nanostructured polycyclic aromatic hydrocarbons, including chrysene nanoparticles, for environmental sensing applications. These nanostructures facilitate the uptake and detection of atmospheric PAHs by mimicking aggregation behaviors in polluted environments, enabling sensitive molecular analysis through molecular beam experiments.

Toxicology and Safety

Health Effects

Chrysene is classified by the International Agency for Research on Cancer (IARC) as a Group 2B carcinogen, indicating it is possibly carcinogenic to humans, based on sufficient evidence of carcinogenicity in experimental animals. In animal studies, chrysene has induced skin tumors following topical application in mice, contributing to its classification. The carcinogenic mechanism of chrysene involves metabolic activation primarily by cytochrome P450 enzymes to form reactive diol-epoxide metabolites, such as the bay-region 1,2-dihydroxy-3,4-epoxy-chrysene, which covalently bind to DNA to form adducts. These DNA adducts can lead to mutations and initiate tumorigenesis. Acute toxicity of chrysene is low, with an oral LD50 exceeding 5 g/kg in rats, indicating minimal immediate systemic effects from ingestion. However, it acts as a skin and eye irritant, causing redness, inflammation, and discomfort upon direct contact. Chronic exposure to chrysene induces aryl hydrocarbon hydroxylase (AHH) activity, a marker of polycyclic aromatic hydrocarbon (PAH) metabolism, in human lymphocytes and animal tissues. Its carcinogenic potency is approximately 0.1-0.4% that of benzopyrene, with an EPA relative potency factor of 0.001-0.0044, as determined by relative potency factors used in risk assessments for PAH mixtures. Human exposure to chrysene occurs primarily through of contaminated air or , and dermal absorption from sources like , which can lead to skin deposition and uptake.

Environmental Impact

Chrysene exhibits significant persistence in environmental compartments such as and water, where it primarily undergoes microbial degradation to and other metabolites over weeks to months. In , biodegradation half-lives range from 371 to 387 days under natural conditions, reflecting its recalcitrance due to strong binding to and sediments. This slow degradation contributes to long-term in aquatic and terrestrial ecosystems, with limited abiotic processes like photolysis or playing minor roles. Due to its high hydrophobicity, chrysene bioaccumulates readily in aquatic organisms, particularly in fatty tissues. Its (log K_ow) of 5.81 indicates strong partitioning into lipids, leading to factors (BCFs) in and crustaceans ranging from 10 to 10,000. For instance, estimated BCF values in reach up to 6,465, facilitating transfer through food webs and elevating concentrations in higher trophic levels such as predatory . Chrysene poses notable ecotoxicity to aquatic life, with acute toxicity observed at low concentrations. The 2-hour LC50 for the invertebrate Daphnia magna is approximately 1.9 mg/L, though values as low as 0.7 μg/L have been reported under UV-enhanced conditions, indicating sensitivity to photoactivated effects. In mollusks, chrysene disrupts endocrine systems, altering reproductive processes and hormone regulation in species like the scallop Chlamys farreri, potentially leading to population-level declines in contaminated habitats. Remediation of chrysene-contaminated sites often employs bioremediation with polycyclic aromatic hydrocarbon (PAH)-degrading bacteria, such as species of Mycobacterium, which utilize chrysene as a carbon source and achieve substantial degradation rates in soil and water. Complementary chemical methods include oxidation using Fenton reagents (Fe²⁺/H₂O₂), which generate hydroxyl radicals to break down chrysene and other PAHs, with modified Fenton processes enhancing efficiency in heterogeneous soils by up to 95% removal in targeted applications. These approaches address the compound's persistence but require optimization for site-specific conditions like pH and oxidant dosing. Regulatory frameworks monitor chrysene due to its environmental risks, with the U.S. Environmental Protection Agency (EPA) including it in assessments at sites where PAHs exceed action levels. For , the (WHO) guideline for benzopyrene (a reference PAH) is 0.7 μg/L to protect ecosystems and indirect human exposure via water sources; no specific guideline exists for total PAHs including chrysene. National criteria, such as EPA's updated human health ambient criteria, further guide permissible levels in surface and to mitigate and .

Derivatives

Key Derivatives

Chrysene, with its extended aromatic system, readily undergoes derivatization through and , yielding several key compounds with applications in synthesis and . Tetrahydrochrysene, obtained via partial of chrysene, serves as a crucial intermediate in the hydrochrysene approach to total synthesis, where it provides a tetracyclic framework amenable to further ring modifications and functionalizations. A more extensively hydrogenated , 2,8-dihydroxyhexahydrochrysene, features hydroxyl groups at the 2- and 8-positions on the partially saturated chrysene core, creating a rigid cyclic analog of hexestrol with a specific substitution pattern that mimics aspects of steroidal estrogens. Crisnatol, or 2-[(chrysen-6-ylmethyl)amino]-2-methylpropane-1,3-diol, is a substituted chrysene bearing an aminopropanediol at the 6-position, designed and evaluated as an anthracene-like analog for chemotherapeutic applications against various tumors. Nitrochrysene isomers, including 6-nitrochrysene, arise as environmental metabolites when chrysene reacts in the atmosphere with hydroxyl radicals and oxides, forming nitro-substituted products during photochemical and oxidative processes. Electrophilic substitutions on chrysene, such as bromination and , predominantly target the electron-rich positions 3 and 6, facilitating the preparation of mono- and di-substituted chrysenes that serve as precursors for further derivatization in .

Biological Activity of Derivatives

Crisnatol, a chrysene featuring a chrysen-6-ylmethylamino , underwent phase II clinical trials in the 1980s for the treatment of due to its ability to inhibit topoisomerase II, leading to DNA intercalation and G2-phase arrest. However, development was abandoned following observations of significant , alongside other dose-dependent toxicities such as membrane perturbation and loss of cell viability at concentrations above 5 µM. Nitro derivatives of chrysene, particularly 6-nitrochrysene, exhibit markedly enhanced mutagenicity compared to the parent compound in the using Salmonella typhimurium strains TA98 and TA100 due to direct-acting nitroreduction pathways that form DNA adducts without requiring metabolic activation. These derivatives are implicated in the carcinogenicity of particles, where they arise from atmospheric of chrysene and contribute to genotoxic effects in exposed populations through formation of reactive metabolites like trans-1,2-dihydroxy-6-nitrochrysene. Hydroxy derivatives, such as 2-hydroxychrysene, demonstrate estrogenic activity by binding to the (ERα), with an IC50 of approximately 0.1 μM (10^{-7} M) in receptor binding assays, potentially acting as endocrine disruptors by mimicking and promoting hormone-dependent cellular responses. This activity is mediated through weak agonistic effects on ERα, leading to supra-maximal estrogenic responses in combination with other metabolites. Recent chrysene analogs incorporating motifs like fused chrysene structures have shown promise in for cancer, generating triplet states for production under light activation, with post-2020 studies highlighting their efficacy in heavy-atom-free photosensitizers that target tumor cells while minimizing dark toxicity. Overall, chrysene derivatives frequently display improved over the parent compound due to increased polarity and metabolic stability, yet this is often accompanied by heightened , as seen in elevated formation and mutagenic responses across nitro and hydroxy variants.

References

  1. https://www.sciencedirect.com/topics/pharmacology-toxicology-and-pharmaceutical-science/chrysene
  2. https://www.chemicalbook.com/ProductChemicalPropertiesCB9853344_EN.htm
  3. https://webbook.nist.gov/cgi/cbook.cgi?ID=C218019
  4. https://echa.europa.eu/substance-information/-/substanceinfo/100.005.386
  5. https://pubchem.ncbi.nlm.nih.gov/compound/Chrysene
  6. https://webbook.nist.gov/cgi/cbook.cgi?ID=C218019&Mask=40
  7. https://journals.iucr.org/q/issues/1956/03/00/a01674/a01674.pdf
  8. https://royalsocietypublishing.org/doi/10.1098/rspa.1960.0168
  9. https://www.chemeo.com/cid/60-666-6/Chrysene
  10. https://pubs.acs.org/doi/10.1021/acs.jpca.5c05216
  11. https://gost.tpsgc-pwgsc.gc.ca/Contfs.aspx?ID=37&lang=eng
  12. https://srdata.nist.gov/solubility/IUPAC/STD-CHRY-WAT-0001
  13. https://www.aatbio.com/absorbance-uv-visible-spectrum-graph-viewer/chrysene
  14. https://pubs.rsc.org/en/content/articlehtml/2015/tc/c4tc02669a
  15. https://pubs.rsc.org/en/content/articlehtml/1981/p2/p29810000675
  16. https://www.webqc.org/compound.php?compound=Chrysene
  17. https://www.tandfonline.com/doi/abs/10.1080/10406630601028221
  18. https://pmc.ncbi.nlm.nih.gov/articles/PMC3812938/
  19. https://pubs.aip.org/aip/jcp/article-pdf/doi/10.1063/1.1824895/10862569/014109_1_online.pdf
  20. https://s3.smu.edu/dedman/catco/publications/pdf/380.pdf
  21. https://www.agilent.com/cs/library/applications/SI-02276.pdf
  22. https://www.sciencedirect.com/science/article/abs/pii/S004313540000230X
  23. https://www.thefreelibrary.com/Auguste%2BLaurent%253A%2BA%2BRemarkable%2BNineteenth%2BCentury%2BFrench%2BChemist.-a065806719
  24. https://link.springer.com/content/pdf/10.1007/978-3-662-01665-7_21.pdf
  25. https://www.researchgate.net/publication/253215585_Purity_and_zone_refining_of_some_coal-tar_aromatic_hydrocarbons
  26. https://pmc.ncbi.nlm.nih.gov/articles/PMC7756344/
  27. https://www.mdpi.com/1420-3049/28/1/237
  28. https://www.sciencedirect.com/science/article/abs/pii/S0040403916316306
  29. https://www.sciencedirect.com/topics/medicine-and-dentistry/chrysene
  30. https://nap.nationalacademies.org/read/21834/chapter/4
  31. https://www.canada.ca/en/environment-climate-change/services/evaluating-existing-substances/screening-assessment-petroleum-sector-stream-approach-natural-gas-condensates.html
  32. https://www.sciencedirect.com/science/article/abs/pii/S0146638012001775
  33. https://www.sciencedirect.com/science/article/pii/S0016703722004604
  34. https://www.jstor.org/stable/1699601
  35. https://www.researchgate.net/publication/251511219_Stable_carbon_isotopic_compositions_of_individual_aromatic_hydrocarbons_as_source_and_age_indicators_in_oils_from_western_Australian_basins
  36. https://www.researchgate.net/publication/334250693_Occurrence_and_Distribution_of_Chrysene_and_its_Derivatives_in_Crude_Oils_and_Soure_Rock_Extracts_from_Niger_Delta_Nigeria
  37. https://pmc.ncbi.nlm.nih.gov/articles/PMC4540633/
  38. https://www.atsdr.cdc.gov/toxprofiles/tp69.pdf
  39. https://tsapps.nist.gov/srmext/certificates/1975.pdf
  40. https://www.mdpi.com/2076-3417/10/13/4632
  41. https://www.epa.gov/sites/default/files/2015-09/documents/priority-pollutant-list-epa.pdf
  42. https://pmc.ncbi.nlm.nih.gov/articles/PMC4673601/
  43. https://pmc.ncbi.nlm.nih.gov/articles/PMC6407006/
  44. https://www.ispatguru.com/coal-tar-pitch/
  45. https://www.agilent.com/cs/library/applications/SI-02279.pdf
  46. https://oehha.ca.gov/chemicals/chrysene
  47. https://www.inchem.org/documents/iarc/vol32/chrysene.html
  48. https://nj.gov/health/eoh/rtkweb/documents/fs/0441.pdf
  49. https://www.sciencedirect.com/science/article/pii/0304383587900462
  50. https://pubs.acs.org/doi/10.1021/tx970114x
  51. https://pubmed.ncbi.nlm.nih.gov/509410/
  52. https://www.epa.gov/sites/default/files/2015-11/documents/pah-rpfs.pdf
  53. https://stacks.cdc.gov/view/cdc/19412/cdc_19412_DS1.pdf
  54. https://www.atsdr.cdc.gov/toxprofiles/tp85.pdf
  55. https://www.echemi.com/sds/chrysene-pid_Seven13673.html
  56. https://www.rivm.nl/bibliotheek/rapporten/601357008.pdf
  57. https://pubmed.ncbi.nlm.nih.gov/27131750/
  58. https://www.intechopen.com/chapters/59150
  59. https://www.sciencedirect.com/science/article/abs/pii/S0048969711015191
  60. https://downloads.regulations.gov/EPA-HQ-OW-2014-0135-0184/content.pdf
  61. https://www.who.int/docs/default-source/wash-documents/wash-chemicals/polynuclear-aromatic-hydrocarbons-background-document.pdf
  62. https://www.epa.gov/superfund/superfund-regulations
  63. https://pubs.rsc.org/en/content/articlelanding/1980/p2/p29800001828
  64. https://pubs.acs.org/doi/10.1021/ja01605a023
  65. https://pubs.acs.org/doi/10.1021/jo50003a006
  66. https://pubmed.ncbi.nlm.nih.gov/1754731/
  67. https://pubs.acs.org/doi/10.1021/acs.est.9b03090
  68. https://pubmed.ncbi.nlm.nih.gov/1607248/
  69. https://www.researchgate.net/publication/21548981_An_efficient_multiple-exposure_analysis_of_the_toxicity_of_crisnatol_a_DNA_intercalator_in_phase_II_clinical_trials
  70. https://aacrjournals.org/cancerres/article/48/16/4706/493014/Phase-I-and-Clinical-Pharmacology-Trial-of
  71. https://www.ncbi.nlm.nih.gov/books/NBK531376/
  72. https://pubs.acs.org/doi/10.1021/jo01336a008
  73. https://ntp.niehs.nih.gov/sites/default/files/iccvam/docs/endo_docs/final1002/erbndbrd/erbd034504.pdf
  74. https://www.sciencedirect.com/science/article/abs/pii/S1382668904001279
  75. https://pmc.ncbi.nlm.nih.gov/articles/PMC12261949/
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