1-Hydroxyphenanthrene
{{Chembox
| ImageFile = 1-Hydroxyphenanthrene.svg
| ImageAlt = Chemical structure of 1-hydroxyphenanthrene
| PIN = Phenanthren-1-ol
| OtherNames = 1-Phenanthrenol
1-Phenanthrol
1-hydroxy-phenanthrene
|Section1={{Chembox Identifiers
| CASNo = 2433-56-9
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Y1FTF7MUY7
| ChemSpiderID = 88945
| PubChem = 98490
| SMILES = C1=CC=C2C(=C1)C=CC3=C2C=CC=C3O
}}
|Section2={{Chembox Properties
| C = 14 | H = 10 | O = 1
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|Section3={{Chembox Hazards
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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.PAH metabolites (1-hydroxyphenanthrene, 4-hydroxyphenanthrene, 9-hydroxyphenanthrene, 1-hydroxypyrene). The MAK Collection for Occupational Health and Safety, Biomonitoring Methods, Vol. 6 ([http://onlinelibrary.wiley.com/doi/10.1002/3527600418.bi0pahmete0006/pdf article])
It can also be used as a marker for PAH pollution measured in marine fish bile.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}}
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).{{Cite journal
| last1 = Cerniglia | first1 = C. E.
| last2 = Campbell | first2 = W. L.
| last3 = Freeman | first3 = J. P.
| last4 = Evans | first4 = F. E.
| title = Identification of a novel metabolite in phenanthrene metabolism by the fungus Cunninghamella elegans
| journal = Applied and Environmental Microbiology
| volume = 55
| issue = 9
| pages = 2275–2279
| year = 1989
| pmid = 2802607
| pmc = 203068
| doi = 10.1128/AEM.55.9.2275-2279.1989
| bibcode = 1989ApEnM..55.2275C
}}
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.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}}
References
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External links
- {{HMDB|59797}}
{{phenanthrenes}}
{{DEFAULTSORT:Hydroxyphenanthrene, 1-}}