1-Hydroxyphenanthrene

1-Hydroxyphenanthrene
Names
	Preferred IUPAC name Phenanthren-1-ol
	Other names 1-Phenanthrenol; 1-Phenanthrol; 1-hydroxy-phenanthrene
Identifiers
CAS Number	2433-56-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	88945;
PubChem CID	98490;
UNII	Y1FTF7MUY7 ;
CompTox Dashboard (EPA)	DTXSID90872758 ;
	SMILES C1=CC=C2C(=C1)C=CC3=C2C=CC=C3O;
Properties
Chemical formula	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). Infobox references

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

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

^ 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

External links

1-Hydroxyphenanthrene at the Human Metabolome Database

[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

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