Metabolism of n-butyl, n-hexyl, and n-octyl benzene in the bile of rainbow trout
Exposure of fish to petroleum can occur directly in the aquatic environment, via the water, or indirectly through the diet. In previous investigations of petroleum metabolites extracted from the bile of fish, the analysis indicated the presence of ..beta..-glucuronides enriched with unsaturated vs saturated carbons, when comparing the metabolites mixture to No. 2 fuel oil. The naphthenic carbons represented a significant fraction of the total carbons and were observed at different chemical shifts than in the petroleum oil, strongly indicating that metabolic oxidations took place on the aliphatic carbons. Mass spectra analysis of the hydrolyzed metabolites isolated from the bile of trout exposed to No. 2 fuel oil, using ..beta..-glucuronidase, enabled the identification of at least eight metabolites. These two- and three-ring aromatic alcohols had side chains of two to six carbons. In order to answer some of the questions raised from the above observations, the metabolism of n-butyl benzene, n-hexyl benzene and n-octyl benzene was considered. The present study was undertaken in order to answer three questions: (1) For a given ring system, does the number of carbons in the alkyl side chain influence the rate of hydrocarbon uptake. (2) For n-alkyl aromatic molecules, are primary, secondary or aromatic alcohols formed preferentially. (3) Are long alkyl side chains attached to aromatic rings degraded to a relatively shorter number of carbon atoms prior to excretion. To the authors knowledge, these questions had not been previously considered in the study of fish metabolites.
- Research Organization:
- Dept. of Fisheries and Oceans, St. John's, Newfoundland (Canada)
- OSTI ID:
- 5379275
- Journal Information:
- Bull. Environ. Contam. Toxicol.; (United States), Vol. 39:2
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
02 PETROLEUM
BENZENE
METABOLISM
PETROLEUM
TOXICITY
BILE
CHEMICAL PROPERTIES
DIET
ENZYMATIC HYDROLYSIS
GAS CHROMATOGRAPHY
MASS SPECTROSCOPY
TROUT
WATER POLLUTION
ANIMALS
AQUATIC ORGANISMS
AROMATICS
BIOLOGICAL MATERIALS
BODY FLUIDS
CHEMICAL REACTIONS
CHROMATOGRAPHY
DECOMPOSITION
ENERGY SOURCES
FISHES
FOSSIL FUELS
FUELS
HYDROCARBONS
HYDROLYSIS
LYSIS
MATERIALS
ORGANIC COMPOUNDS
POLLUTION
SEPARATION PROCESSES
SOLVOLYSIS
SPECTROSCOPY
VERTEBRATES
560300* - Chemicals Metabolism & Toxicology
020600 - Petroleum- Health & Safety