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1-Hydroxyphenanthrene
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| Names | |
|---|---|
| Preferred IUPAC name
Phenanthren-1-ol | |
| Other names
1-Phenanthrenol
1-Phenanthrol 1-hydroxy-phenanthrene | |
| Identifiers | |
3D model (JSmol)
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| 1869717 | |
| ChEBI | |
| ChemSpider | |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C14H10O | |
| Molar mass | 194.233 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1-Hydroxyphenanthrene is a phenanthrol and a human metabolite of phenanthrene that can be detected in urine of persons exposed to PAHs.[1]
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
[edit]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
[edit]- ^ PAH metabolites (1-hydroxyphenanthrene, 4-hydroxyphenanthrene, 9-hydroxyphenanthrene, 1-hydroxypyrene). The MAK Collection for Occupational Health and Safety, Biomonitoring Methods, Vol. 6 (article)
- ^ 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
- ^ 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.
- ^ 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