Dibenz[a,h]anthracene
Names
Preferred IUPAC name
Benzo[k]tetraphene
Other names
1,2:5,6-Dibenzanthracene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.166 Edit this at Wikidata
EC Number
  • 200-181-8
KEGG
RTECS number
  • HN2625000
UNII
UN number 3077
  • InChI=1/C22H14/c1-3-7-19-15(5-1)9-11-17-14-22-18(13-21(17)19)12-10-16-6-2-4-8-20(16)22/h1-14H
  • c1ccc2c(c1)ccc3c2cc4ccc5ccccc5c4c3
Properties
C22H14
Molar mass 278.354 g·mol−1
Density 1.232 g/cm3
Melting point 262 °C (504 °F; 535 K)[1]
Hazards
GHS labelling:
GHS08: Health hazardGHS09: Environmental hazard
Danger
H350, H410
P201, P202, P273, P281, P308+P313, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dibenz[a,h]anthracene or Benzo[k]tetraphene or 1,2:5,6-Dibenzanthracene is an organic compound with the chemical formula C22H14. It is a polycyclic aromatic hydrocarbon (PAH) made of five fused benzene rings. It is a fused five-ringed PAH which is common as a pollutant of smoke and oils. It is stable and highly genotoxic in bacterial and mammalian cell systems, as it intercalates into DNA and causes mutations.

Description

Dibenz(a,h)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, white to light yellow crystalline, bound to particulates in polluted air, soil, or sediment. [2]It was first synthesized in 1918.[1]

Occurrence

Dibenz(a,h)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

As of 2010, dibenz(a,h)anthracene has been classified as probably carcinogenic to humans, grouped into IARC group 2A. No epidemiological studies on human exposure to dibenz(a,h)anthracene as an individual PAH exists, because PAHs always occur as components of complex chemical mixtures and never occur in isolation in the environment.[2]

See also

References

  1. ^ a b Weitzenbock, Richard; Klingler, Albert (1918). "Synthesis of the isomeric hydrocarbons 1,2,5,6-dibenzanthracene and 3,4,5,6-dibenzophenanthrene". Journal of the Chemical Society, Abstracts. 114(I): 494.
  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.
source: http://en.wikipedia.org/wiki/Dibenz(a,h)anthracene