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1-Hydroxyphenanthrene

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1-Hydroxyphenanthrene
Chemical structure of 1-hydroxyphenanthrene
Names
Preferred IUPAC name Phenanthren-1-ol
Other names 1-Phenanthrenol
1-Phenanthrol
1-hydroxy-phenanthrene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • C1=CC=C2C(=C1)C=CC3=C2C=CC=C3O
Properties
Chemical formula C14H10O
Molar mass 194.233 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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

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).

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.

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. Bibcode:1989ApEnM..55.2275C. 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

External links

Phenanthrenoids and their glycosides (molecules with a C6-C2-C6 backbone)
Phenanthrols
polyhydroxylated phenanthrenes
9,10-dihydrophenanthrene derivatives
glycosides
Phenanthrene glycosides
9,10-dihydrophenanthrene glycoside
dimeric phenanthrenes
Cyclic bibenzyl-dihydrophenanthrene derivative
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