Naphthalene trans-dihydrodiols
Master's thesis in Environmental Technology The currently used GC-MS method for analysis of PAH metabolites in fish bile only focus on phenols; 1-naphthol, 2-naphthol, 1-hydroxyphenanthrene, and alkylated derivatives. 1- Hydroxypyrene is also included, but not alkylated forms. However, since tr...
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University of Stavanger, Norway
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ftunivstavanger:oai:uis.brage.unit.no:11250/2580632 2023-06-11T04:10:07+02:00 Naphthalene trans-dihydrodiols Vaaland, Ingrid Caroline Sydnes, Magne Olav Pampanin, Daniela Maria 2018-09 application/pdf http://hdl.handle.net/11250/2580632 eng eng University of Stavanger, Norway Masteroppgave/UIS-TN-IKBM/2018; http://hdl.handle.net/11250/2580632 Laccase Trametes versicolor atlanterhavstorsk Gadus morhua organic synthesis biliary metabolites naphthalene trans-dihydrodiols teknisk miljøvern VDP::Teknologi: 500::Miljøteknologi: 610 Master thesis 2018 ftunivstavanger 2023-05-29T16:02:06Z Master's thesis in Environmental Technology The currently used GC-MS method for analysis of PAH metabolites in fish bile only focus on phenols; 1-naphthol, 2-naphthol, 1-hydroxyphenanthrene, and alkylated derivatives. 1- Hydroxypyrene is also included, but not alkylated forms. However, since trans-naphthalene dihydrodiol and methylated derivatives are formed in vivo and are known carcinogens, their presence in fish bile should be further investigated. Due to the absence of commercially available standards of trans-dihydro diols and their methylated derivatives, these compounds need to be synthesized. trans-1,2-Dihydronaphthalene-1,2-diol (13±), trans-6-methyl-1,2-dihydronaphthalene-1,2- diol (19±), trans-5,7-dimethyl-1,2-dihydronaphthalene-1,2-diol (20±) and trans-4,6,7- trimethyl-1,2-dihydronaphthalene-1,2-diol (21±) were synthesized from commercially available starting materials, and their overall yield were 40%, 59%, 28% and 3%, respectively. The compunds were prepared from 1,2-naphthoquinone, 6-methyl-1-tetralone, 5,7-dimethyl-1- tetralone, 1,2-dihydroxybenzene and 2,3-dimethyl-1,3-butadiene, and oxidation was performed by using 2-iodoxybenzoic acid (IBX) or Laccase-catalyzed Diels-Alder reaction, following reduction by sodium borohydride (NaBH4) to give the trans-naphthalene dihydrodiols. Fish bile samples obtained from Atlantic cod (Gadus morhua), exposed to dispersed crude oil, were prepared by de-conjugation, extraction and derivatisation, following standard procedure in order to prepare the samples for GC-MS analysis. Master Thesis atlanterhavstorsk atlantic cod Gadus morhua University of Stavanger: UiS Brage |
institution |
Open Polar |
collection |
University of Stavanger: UiS Brage |
op_collection_id |
ftunivstavanger |
language |
English |
topic |
Laccase Trametes versicolor atlanterhavstorsk Gadus morhua organic synthesis biliary metabolites naphthalene trans-dihydrodiols teknisk miljøvern VDP::Teknologi: 500::Miljøteknologi: 610 |
spellingShingle |
Laccase Trametes versicolor atlanterhavstorsk Gadus morhua organic synthesis biliary metabolites naphthalene trans-dihydrodiols teknisk miljøvern VDP::Teknologi: 500::Miljøteknologi: 610 Vaaland, Ingrid Caroline Naphthalene trans-dihydrodiols |
topic_facet |
Laccase Trametes versicolor atlanterhavstorsk Gadus morhua organic synthesis biliary metabolites naphthalene trans-dihydrodiols teknisk miljøvern VDP::Teknologi: 500::Miljøteknologi: 610 |
description |
Master's thesis in Environmental Technology The currently used GC-MS method for analysis of PAH metabolites in fish bile only focus on phenols; 1-naphthol, 2-naphthol, 1-hydroxyphenanthrene, and alkylated derivatives. 1- Hydroxypyrene is also included, but not alkylated forms. However, since trans-naphthalene dihydrodiol and methylated derivatives are formed in vivo and are known carcinogens, their presence in fish bile should be further investigated. Due to the absence of commercially available standards of trans-dihydro diols and their methylated derivatives, these compounds need to be synthesized. trans-1,2-Dihydronaphthalene-1,2-diol (13±), trans-6-methyl-1,2-dihydronaphthalene-1,2- diol (19±), trans-5,7-dimethyl-1,2-dihydronaphthalene-1,2-diol (20±) and trans-4,6,7- trimethyl-1,2-dihydronaphthalene-1,2-diol (21±) were synthesized from commercially available starting materials, and their overall yield were 40%, 59%, 28% and 3%, respectively. The compunds were prepared from 1,2-naphthoquinone, 6-methyl-1-tetralone, 5,7-dimethyl-1- tetralone, 1,2-dihydroxybenzene and 2,3-dimethyl-1,3-butadiene, and oxidation was performed by using 2-iodoxybenzoic acid (IBX) or Laccase-catalyzed Diels-Alder reaction, following reduction by sodium borohydride (NaBH4) to give the trans-naphthalene dihydrodiols. Fish bile samples obtained from Atlantic cod (Gadus morhua), exposed to dispersed crude oil, were prepared by de-conjugation, extraction and derivatisation, following standard procedure in order to prepare the samples for GC-MS analysis. |
author2 |
Sydnes, Magne Olav Pampanin, Daniela Maria |
format |
Master Thesis |
author |
Vaaland, Ingrid Caroline |
author_facet |
Vaaland, Ingrid Caroline |
author_sort |
Vaaland, Ingrid Caroline |
title |
Naphthalene trans-dihydrodiols |
title_short |
Naphthalene trans-dihydrodiols |
title_full |
Naphthalene trans-dihydrodiols |
title_fullStr |
Naphthalene trans-dihydrodiols |
title_full_unstemmed |
Naphthalene trans-dihydrodiols |
title_sort |
naphthalene trans-dihydrodiols |
publisher |
University of Stavanger, Norway |
publishDate |
2018 |
url |
http://hdl.handle.net/11250/2580632 |
genre |
atlanterhavstorsk atlantic cod Gadus morhua |
genre_facet |
atlanterhavstorsk atlantic cod Gadus morhua |
op_relation |
Masteroppgave/UIS-TN-IKBM/2018; http://hdl.handle.net/11250/2580632 |
_version_ |
1768384377734037504 |