1-Hydroxypyrene

1-Hydroxypyrene is a human metabolite. It can be found in urine of outdoor workers exposed to air pollution.[1]

1-Hydroxypyrene
Chemical structure of 1-hydroxypyrene
Names
Preferred IUPAC name
Pyren-1-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.152.834
KEGG
UNII
  • InChI=1S/C16H10O/c17-14-9-7-12-5-4-10-2-1-3-11-6-8-13(14)16(12)15(10)11/h1-9,17H
    Key: BIJNHUAPTJVVNQ-UHFFFAOYSA-N
  • InChI=1/C16H10O/c17-14-9-7-12-5-4-10-2-1-3-11-6-8-13(14)16(12)15(10)11/h1-9,17H
    Key: BIJNHUAPTJVVNQ-UHFFFAOYAT
  • C1=CC2=C3C(=C1)C=CC4=C(C=CC(=C43)C=C2)O
Properties
C16H10O
Molar mass 218.255 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

Biochemistry

Experiments in pig show that urinary 1-hydroxypyrene is a metabolite of pyrene, when given orally.[2]

A Mycobacterium sp. strain isolated from mangrove sediments produced 1-hydroxypyrene during the degradation of pyrene.[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
  1. Ciarrocca, Manuela; Rosati, Maria Valeria; Tomei, Francesco; Capozzella, Assuntina; Andreozzi, Giorgia; Tomei, Gianfranco; Bacaloni, Alessandro; Casale, Teodorico; Andrè, Jean Claude; Fioravanti, Mario; Cuartas, Maria Fernanda; Caciari, Tiziana (2013). "Is urinary 1-hydroxypyrene a valid biomarker for exposure to air pollution in outdoor workers? A meta-analysis". Journal of Exposure Science and Environmental Epidemiology. 24 (1): 17–26. doi:10.1038/jes.2012.111. PMID 23299300.
  2. Keimig, S. D; Kirby, K. W; Morgan, D. P; Keiser, J. E; Hubert, T. D (2009). "Identification of 1-hydroxypyrene as a major metabolite of pyrene in pig urine". Xenobiotica. 13 (7): 415–20. doi:10.3109/00498258309052279. PMID 6659544.
  3. Zhong, Y; Luan, T; Zhou, H; Lan, C; Tam, N. F (2006). "Metabolite production in degradation of pyrene alone or in a mixture with another polycyclic aromatic hydrocarbon by Mycobacterium sp". Environmental Toxicology and Chemistry. 25 (11): 2853–9. doi:10.1897/06-042R.1. PMID 17089707. S2CID 23874147.
  4. Heudorf, U; Angerer, J (2001). "Urinary monohydroxylated phenanthrenes and hydroxypyrene - the effects of smoking habits and changes induced by smoking on monooxygenase-mediated metabolism". International Archives of Occupational and Environmental Health. 74 (3): 177–83. doi:10.1007/s004200000215. PMID 11355291. S2CID 27836084.
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