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1-Hydroxybenzo[a]pyrene

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Identification
Molecular formula
C20H12O
CAS number
13057-18-8
IUPAC name
benzo[a]pyren-1-ol
State
State

At room temperature, 1-Hydroxybenzo[a]pyrene exists as a solid. It is relatively stable and exhibits the characteristic properties of aromatic compounds.

Melting point (Celsius)
162.00
Melting point (Kelvin)
435.20
Boiling point (Celsius)
685.40
Boiling point (Kelvin)
958.50
General information
Molecular weight
268.31g/mol
Molar mass
268.3140g/mol
Density
1.3440g/cm3
Appearence

1-Hydroxybenzo[a]pyrene is typically a yellowish crystalline solid. It is a polycyclic aromatic hydrocarbon (PAH) compound with a notable luster and defined crystal structure.

Comment on solubility

Solubility of Benzo[a]pyren-1-ol

Benzo[a]pyren-1-ol, with its complex polycyclic structure, exhibits unique solubility characteristics. Here are some key points to consider:

  • Polar Nature: The presence of a hydroxyl group (-OH) in benzo[a]pyren-1-ol increases its polarity slightly compared to its parent compound, benzo[a]pyrene.
  • Solvent Interaction: It is generally more soluble in polar solvents such as methanol and ethanol compared to non-polar solvents like hexane.
  • Environmental Concerns: Because of its size and structure, benzo[a]pyren-1-ol can be relatively soluble in organic solvents yet may present low water solubility, raising concerns about its mobility in aquatic environments.
  • Hydrophobic Effects: While the hydroxyl group introduces some polarity, the overall hydrophobic characteristics of the polycyclic framework can hinder solubility in aqueous solutions.

To summarize, the solubility behavior of benzo[a]pyren-1-ol requires careful analysis of both its chemical structure and the solvent properties involved. Understanding these interactions is crucial for applications in environmental chemistry and toxicology.

Interesting facts

Interesting Facts about Benzo[a]pyren-1-ol

Benzo[a]pyren-1-ol is a fascinating compound that belongs to the family of polycyclic aromatic hydrocarbons (PAHs). It is particularly notable for its dual role as both an environmental pollutant and a key research focus due to its potential implications in human health. Here are some interesting aspects of this compound:

  • Source: Benzo[a]pyren-1-ol is primarily generated through the incomplete combustion of organic materials such as coal, oil, gas, and even tobacco. Its presence in urban environments is often linked to traffic emissions and industrial activities.
  • Health Concerns: Classified as a probable human carcinogen, its metabolites have been studied extensively for their ability to cause DNA damage, posing significant risks in relation to cancer development.
  • Environmental Impact: This compound is persistent in the environment, particularly in soil and sediment. Its stability makes it a concerning pollutant, as it can accumulate in ecological systems.
  • Biochemical Interactions: In biochemical studies, benzo[a]pyren-1-ol has been noted for its ability to form adducts with DNA, which can impair cellular function and lead to mutagenesis.
  • Research Significance: Scientists are interested in benzo[a]pyren-1-ol for its role as a model compound in the study of PAHs. Researchers often investigate its pathways of metabolism and detoxification mechanisms in various organisms.
  • Analytical Techniques: It is commonly analyzed using advanced techniques such as HPLC (High-Performance Liquid Chromatography) and GC-MS (Gas Chromatography-Mass Spectrometry) to monitor environmental levels and human exposure.

In conclusion, benzo[a]pyren-1-ol serves as a pertinent example of how organic compounds can operate at the intersection of chemistry, environmental science, and human health. The ongoing research into its properties and effects continues to be of great significance in understanding the broader impacts of polycyclic aromatic hydrocarbons.

Synonyms
1-Hydroxybenzo(a)pyrene
benzo[a]pyren-1-ol
13345-23-8
1-Hydroxybenzo[a]pyrene
CCRIS 1070
BENZO(a)PYREN-1-OL
BRN 2380732
DTXSID40158115
3-06-00-03808 (Beilstein Handbook Reference)
DTXCID6080606
hydroxybenzo[a]pyrene
Hydroxybenzo(a)pyrene, 1-
TG2AP6R64H
SCHEMBL3341439
CHEMBL1907999