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Dibenz(a,j)anthracene

Summary

Dibenz[a,j]anthracene or Benzo[m]tetraphene or 1,2:7,8-Dibenzanthracene is an organic compound with the chemical formula C22H14. It belongs to the class of polycyclic aromatic hydrocarbons (PAHs) and is formed whenever there is incomplete combustion of organic matter. The IARC (International Agency for Research on Cancer) has classified it as possibly carcinogenic to humans, grouped into IARC group 2B.

Dibenz[a,j]anthracene
Names
Preferred IUPAC name
Benzo[m]tetraphene
Other names
1,2:7,8-Dibenzanthracene[1]
Identifiers
  • 224-41-9
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:82438
ChEMBL
  • ChEMBL24775
ChemSpider
  • 8821
ECHA InfoCard 100.005.390 Edit this at Wikidata
EC Number
  • 90321
KEGG
  • C19389
  • 9176
UNII
  • M477C74UCX
  • DTXSID8074811 Edit this at Wikidata
  • InChI=1S/C22H14/c1-3-7-19-15(5-1)9-11-17-13-18-12-10-16-6-2-4-8-20(16)22(18)14-21(17)19/h1-14H
  • InChI=1/C22H14/c1-3-7-19-15(5-1)9-11-17-13-18-12-10-16-6-2-4-8-20(16)22(18)14-21(17)19/h1-14H
  • c35cc2ccc1ccccc1c2cc3c4ccccc4cc5
Properties
C22H14
Molar mass 278.3466
Appearance colorless crystals
Melting point 196 °C (385 °F; 469 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Description edit

Dibenz(a,j)anthracene is a polycyclic aromatic hydrocarbon with five benzene rings. It has low water solubility and low volatility and therefore occurs predominantly in solid form, bound to particulates in polluted air, soil, or sediment. [2]

Occurrence edit

Dibenz(a,j)anthracene is generated whenever organic matter or fuel is incompletely burnt or combusted. Examples include industrial emissions such as coke oven operations in the coal and steel industry, coal tar distillation, or within engine exhaust. On a personal level it is produced with high temperature cooking like frying, grilling, broiling, roasting and baking, but also when cigarette smoking or marijuana smoking.[3]

Health effects edit

As of 2010, the IARC (International Agency for Research on Cancer) has classified dibenz(a,j)anthracene as possibly carcinogenic to humans, grouped into IARC group 2B. No epidemiological studies on human exposure to dibenz(a,j)anthracene as an individual PAH exist, because PAHs always occur as components of complex chemical mixtures and never occur in isolation in the environment. PAHs all have a similar mechanism of causing cancer in both humans and experimental animals whereby they are metabolically converted to oxides and dihydrodiols, and then oxidized to diol epoxides, which react with DNA, inducing mutations.[2]

In space edit

In February 2014, NASA announced a database for tracking polycyclic aromatic hydrocarbons (PAHs), including dibenz[a,j]anthracene, in the universe.[4] According to scientists, more than 20% of the carbon in the universe may be associated with PAHs, possible starting materials for the formation of life. PAHs seem to have been formed shortly after the Big Bang, are widespread throughout the universe, and are associated with new stars and exoplanets.[5]

See also edit

References edit

  1. ^ National Institute of Standards and Technology (NIST) (nd). "Dibenz[a,j]anthracene". NIST Chemistry WebBook, SRD 69.
  2. ^ a b Charles William Jameson (2019). "7, Polycyclic aromatic hydrocarbons and associated occupational exposures". part 1. concordance between cancer in humans and in experimental animals (PDF). IARC.
  3. ^ California OEHHA. "Dibenz[a,j]anthracene". oehha.ca.gov. Retrieved 2024-02-01.
  4. ^ "NASA Ames PAH IR Spectroscopic Database". www.astrochemistry.org. nd. Retrieved 2024-02-01.
  5. ^ Hoover, Rachel (February 21, 2014). "Need to Track Organic Nano-Particles Across the Universe? NASA's Got an App for That". NASA. Archived from the original on May 10, 2020. Retrieved February 22, 2014.