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
3D model (JSmol)
1869717
ChEBI
ChemSpider
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E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
KEGG
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C14H10O/c15-14-7-3-6-12-11-5-2-1-4-10(11)8-9-13(12)14/h1-9,15H
    Key: GTBXZWADMKOZQJ-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C=CC3=C2C=CC=C3O
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).

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

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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

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  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, Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  3. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  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, Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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