1-Hydroxyphenanthrene

1-Hydroxyphenanthrene
Names

IUPAC name phenanthren-1-ol
Other names 1-Phenanthrenol 1-Phenanthrol 1-hydroxy-phenanthrene
Identifiers
CAS Number	2433-56-9
3D model (Jmol)	Interactive image
ChemSpider	88945
PubChem	98490
SMILES C1=CC=C2C(=C1)C=CC3=C2C=CC=C3O
Properties
Chemical formula	C₁₄H₁₀O
Molar mass	194.23 g/mol
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. 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

Phenanthrenoids and their glycosides (molecules with a C6-C2-C6 backbone)

Phenanthrols

1-Phenanthrol
2-Phenanthrol
3-Phenanthrol
4-Phenanthrol
9-Phenanthrol

polyhydroxylated phenanthrenes

coeloginanthrin
confusaridin
confusarin
dehydroeffusol
dehydrojuncusol
flavanthrinin
gymnopusin
Nudol
Perakensol
plicatol A
Plicatol B

2,3,4-trimethoxy-7,8-methylenedioxyphenanthrene
2,5-dihydroxy-3,4-dimethoxyphenanthrene
2,5-dihydroxy-3,4,9-trimethoxyphenanthrene
2,7-dihydroxy-3,4,6-trimethoxyphenanthrene
2,7-dihydroxy-3,4,9-trimethoxyphenanthrene
2,7-Dihydroxy-3,6-dimethoxyphenanthrene
3-hydroxy-2,4,-dimethoxy-7,8-methylenedioxyphenanthrene
2-hydroxy-3,5,7-trimethoxyphenanthrene
2-hydroxy-3,5,7-trimethoxy-9,10-dihydrophenanthrene
3,4,8-Trimethoxyphenanthrene-2,5-diol
4,6-dimethoxyphenanthrene-2,3,7-triol
4,9-dimethoxyphenanthrene-2,5-diol
7-Hydroxy-2,3,4,8-tetramethoxyphenanthrene

9,10-dihydrophenanthrene derivatives

coelogin
coeloginin
coeloginanthridin
coelonin
effusol
hircinol
juncusol
loroglossol
orchinol
Plicatol C
4-methoxy-9,10-dihydrophenanthrene-2,3,7-triol
4,6-dimethoxy-9,10-dihydrophenanthrene-2,3,7-triol
9,10-dihydro-2,7-dihydroxy-3,4-dimethoxyphenanthrene
9,10-dihydro-2,7-dihydroxy-3,4,6-trimethoxyphenanthrene
9,10-Dihydro-2,5-dimethoxyphenanthrene-1,7-diol
9,10-dihydro-2,5-dihydroxy-3,4-dimethoxyphenanthrene

glycosides

Phenanthrene glycosides	denneanoside A, B, C, D and E

9,10-dihydrophenanthrene glycoside	denneanoside F

dimeric phenanthrenes

cirrhopetalanthrin
flavanthrin
reptanthrin
isoreptanthrin
8,8'-bidehydrojuncusol

Cyclic bibenzyl-dihydrophenanthrene derivative

Cavicularin

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