1-Hydroxyphenanthrene

1-Hydroxyphenanthrene is a phenanthrol and a human metabolite of phenanthrene that can be detected in urine of persons exposed to PAHs.[1]

1-Hydroxyphenanthrene
Names
IUPAC name
phenanthren-1-ol
Other names
1-Phenanthrenol
1-Phenanthrol
1-hydroxy-phenanthrene
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • C1=CC=C2C(=C1)C=CC3=C2C=CC=C3O
Properties
C14H10O
Molar mass 194.23 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It can also be used as a marker for PAH pollution measured in marine fish bile.[2]

The model fungus Cunninghamella elegans produces, in the case of the biodegradation of phenanthrene, a glucoside conjugate of 1-hydroxyphenanthrene (phenanthrene 1-O-beta-glucose).[3]

Relationship with smoking

Highly significant differences and dose-response relationships with regard to cigarettes smoked per day were found for 2-, 3- and 4-hydroxyphenanthrene and 1-hydroxypyrene, but not for 1-hydroxyphenanthrene.[4]

References

  1. PAH metabolites (1-hydroxyphenanthrene, 4-hydroxyphenanthrene, 9-hydroxyphenanthrene, 1-hydroxypyrene). The MAK Collection for Occupational Health and Safety, Biomonitoring Methods, Vol. 6 (article)
  2. PAH Metabolites in Bile Fluids of Dab (Limanda limanda) and Flounder (Platichthys flesus): Spatial Distribution and Seasonal Changes. Ulrike Kammann, Environmental Science and Pollution Research - International, March 2007, Volume 14, Issue 2, pages 102-108, doi:10.1065/espr2006.05.308
  3. Cerniglia, C. E.; Campbell, W. L.; Freeman, J. P.; Evans, F. E. (1989). "Identification of a novel metabolite in phenanthrene metabolism by the fungus Cunninghamella elegans". Applied and Environmental Microbiology. 55 (9): 2275–2279. doi:10.1128/AEM.55.9.2275-2279.1989. PMC 203068. PMID 2802607.
  4. Urinary monohydroxylated phenanthrenes and hydroxypyrene – the effects of smoking habits and changes induced by smoking on monooxygenase-mediated metabolism. Heudorf U and Angerer J, International Archives of Occupational and Environmental Health, April 2001, Volume 74, Issue 3, pages 177-183, doi:10.1007/s004200000215
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