Document Detail

Steroidal aromatic 'naphthenic acids' in oil sands process-affected water: structural comparisons with environmental estrogens.
MedLine Citation:
PMID:  22014158     Owner:  NLM     Status:  MEDLINE    
The large volumes, acute toxicity, estrogenicity, and antiandrogenicity of process-affected waters accruing in tailings ponds from the operations of the Alberta oil sands industries pose a significant task for environmental reclamation. Synchronous fluorescence spectra (SFS) suggest that oil sands process-affected water (OSPW) may contain aromatic carboxylic acids, which are among the potentially environmentally important toxicants, but no such acids have yet been identified, limiting interpretations of the results of estrogenicity and other assays. Here we show that multidimensional comprehensive gas chromatography-mass spectrometry (GCxGC-MS) of methyl esters of acids in an OSPW sample produces mass spectra consistent with their assignment as C(19) and C(20) C-ring monoaromatic hydroxy steroid acids, D-ring opened hydroxy and nonhydroxy polyhydrophenanthroic acids with one aromatic and two alicyclic rings and A-ring opened steroidal keto acids. High resolution MS data support the assignment of several of the so-called 'O3' species. When fractions of distilled, esterified, OSPW acid-extractable organics were examined, the putative aromatics were mainly present in a high boiling fraction; when examined by argentation thin layer chromatography, some were present in a fraction with a retardation factor between that of the methyl esters of synthetic monoalicyclic and monoaromatic acids. Ultraviolet absorption spectra of these fractions indicated the presence of benzenoid moieties. SFS of model octahydro- and tetrahydrophenanthroic acids produced emissions at the characteristic excitation wavelengths observed in some OSPW extracts, consistent with the postulations from ultraviolet spectroscopy and mass spectrometry data. We suggest the acids originate from extensive biodegradation of C-ring monoaromatic steroid hydrocarbons and offer a means of differentiating residues at different biodegradation stages in tailings ponds. Structural similarities with estrone and estradiol imply that such compounds may account for some of the environmental estrogenic activity reported in OSPW acid-extractable organics and naphthenic acids.
Steven J Rowland; Charles E West; David Jones; Alan G Scarlett; Richard A Frank; L Mark Hewitt
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Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, Non-U.S. Gov't     Date:  2011-10-20
Journal Detail:
Title:  Environmental science & technology     Volume:  45     ISSN:  1520-5851     ISO Abbreviation:  Environ. Sci. Technol.     Publication Date:  2011 Nov 
Date Detail:
Created Date:  2011-11-14     Completed Date:  2012-02-29     Revised Date:  2014-02-20    
Medline Journal Info:
Nlm Unique ID:  0213155     Medline TA:  Environ Sci Technol     Country:  United States    
Other Details:
Languages:  eng     Pagination:  9806-15     Citation Subset:  IM    
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MeSH Terms
Carboxylic Acids / analysis*,  chemistry
Environmental Pollutants / analysis*,  chemistry
Estrogens / chemistry*
Gas Chromatography-Mass Spectrometry
Petroleum / analysis*
Silicon Dioxide / chemistry*
Water / chemistry*
Grant Support
228149//European Research Council
Reg. No./Substance:
0/Carboxylic Acids; 0/Environmental Pollutants; 0/Estrogens; 0/Petroleum; 059QF0KO0R/Water; 1338-24-5/naphthenic acid; 7631-86-9/Silicon Dioxide
Erratum In:
Environ Sci Technol. 2012 Aug 21;46(16):9200

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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