Environmental chemistry of PCB-replacement compounds - VI - composition and metabolism of Wemcol ®, an isopropylbiphenyl formulation

Wemcol is a technical isopropylbiphenyl formulation that is used as a substitute for polychlorobiphenyl. According to the producer Wemcol is 4-isopropylbiphenyl, but we found our sample to consist of 60.3% 3-isopropylbiphenyl, 38.6% 4-isopropylbiphenyl and 3,5-, 3,3′-, 3,4′- and 4,4′-diisopropylbiphenyl in amounts of 0.3%, 0.4%, 0.2% and 0.1% respectively. The two major components of the mixture are metabolized in the rat by two routes : oxidation of the isopropyl group and hydroxylation of the aromatic nuclei. Rats fed the technical mixture retained 3- and 4-isopropylbiphenyl in a ratio 4.3 : 1 in their abdominal fat, whilst the ratio in the mixture is 1.6 : 1. One week after the simultaneous feeding of equal amounts of Wemcol, 4,4′-dichlorobiphenyl, 2,4′,5-trichlorobiphenyl and 2,2′,5,5′-tetrachlorobiphenyl, the isopropylbiphenyls, in contrast to the chlorobiphenyls, could no longer be detected in the abdominal fat of rats.     

Transformation of hydroxylated derivatives of 2,5-dichlorobiphenyl and 2,4,6-trichlorobiphenyl by Burkholderia xenovorans LB400

The polychlorinated biphenyl (PCB)-degrading bacterium, Burkholderia xenovorans LB400, was capable of transforming three hydroxylated derivatives of 2,5-dichlorobiphenyl (2,5-DCB) (2′-hydroxy- (2′-OH-), 3′-OH-, and 4′-OH-2,5-DCB) when biphenyl was used as the carbon source (i.e., biphenyl pathway-inducing condition), although only 2′-OH-2,5-DCB was transformed when the bacterium was growing on succinate (i.e., condition non-inductive of the biphenyl pathway). On the contrary, hydroyxlated derivatives of 2,4,6-trichlorobiphenyl (2,4,6-TCB) (2′-OH-, 3′-OH-, and 4′-OH-2,4,6-TCB) were not significantly transformed by B. xenovorans LB400, regardless of the carbon source used. Gene expression analyses showed a clear correlation between the transformation of OH-2,5-DCBs and expression of genes of the biphenyl pathway. The PCB metabolite, 2,5-dichlorobenzoic acid (2,5-DCBA), was produced following the transformation of OH-2,5-DCBs. 2,5-DCBA was not further transformed by B. xenovorans LB400. The present study is significant because it provides evidence that PCB-degrading bacteria are capable of transforming hydroxylated derivatives of PCBs, which are increasingly considered as a new class of environmental contaminants.     

The bacterial metabolism of 4,4′-dichlorobiphenyl,and its suppression by alternative carbon sources

The metabolism of 4,4′-dichlorobiphenyl by mixed cultures of bacteria, isolated from activated sludge, was studied in shake cultures and in soil, both in presence and absence of alternative carbon sources. When 4,4′-dichlorobiphenyl was used as sole carbon source, 4-chlorobenzoic acid and 4,4′-dichloro-2,3-biphenyldiol could be isolated from the culture medium. Polar metabolites however, could not be detected in soil and in media in which alternative carbon sources such as glucose, glycerol, peptone, yeast-extract, humic acid or activated sludge were present. No hydroxylated or carboxylic acid derivatives could be isolated when 2,4′, 5-tri-, 2,2′,5,5′,-textra-, 2,2′,3,4,5′-penta-, 2,2′,3,4,5,5′-hexa- and decachlorobiphenyl were used as the sole carbon sources for incubation with bacteria in shake culture.     

Gas-phase ozonolysis of the monoterpenoids (S)-(+)-carvone, (R)-(−)-carvone, (−)-carveol, geraniol and citral

Biogenic emissions of volatile organic compounds (VOCs) play a fundamental role in atmospheric chemistry. Vegetation is the most abundant natural source of VOCs, while terpenoids, as limonene, α and β pinene and mircene, top the plants emission list. Much interest has been demonstrated in oxidation and photooxidation reactions of VOCs, particularly of monoterpenoids, owing to their diversity and to uncertainties regarding their mechanism of reaction. Quantification of primary carbonylic compounds, as well as of biradical reaction components, is highly relevant to the understanding of the major reactions. In this context, taking into account both structural factors and the fact that these compounds are found in the essential oils of plants typically found in Brazil and that they may be present in the atmosphere from emission by the plants, the monoterpenoids (S)-(+)-carvone, (R)-(−)-carvone, (−)-carveol, geraniol and citral (a mixture of the isomers geranial and neral) were selected for this study.The ozonolysis reactions of the monoterpenoids were carried out under dark conditions for all experiments, due to their photochemical reactivity. The analysis of the results lets us propose a mechanism by which these reactions occur. The observed results of the ozonolysis of S and R carvone suggest that the stereochemistry of asymmetric carbon does not affect either in the yields of both formaldehyde and of OH radicals produced in the reaction, or in the reactivity of these compounds, for which the rate constants were in the scale of 10⁻⁶ s⁻¹.We found that, in the (−)-carveol's cis and trans mixture, even though the hydroxyl in the axial position—in the case of trans-(C) and cis-(D′) isomers—favors the attack by the ozone molecule on the external double bond, thus increasing the mixture's reactivity , it affects the average production of formaldehyde. The presence of geraniol and citral led to the production of formaldehyde, propanone, glyoxal, methyl–glyoxal and cyclohexanone (OH radicals) as reaction products. The influence of an electron attractor group bonded to the carbon of the double bond, on the reactivity of the double bond, could not be observed in the case of citral, due to strong interference occurring in the instrument in all experiments with this monoterpenoid. For this reason, only the kinetics of geraniol was monitored .     

Detection of DDT and its metabolites in two estuaries of South China using a SPME-based device: First report of p,p′-DDMU in water column

A solid-phase microextration-based sampling method was employed to determine the concentrations of 1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane (DDT) and its metabolites, 1,1-dichloro-2,2-bis(p-chlorophenyl)ethane (DDD), 1,1-dichloro-2,2-bis(p-chlorophenyl)ethene (DDE) and 1-chloro-2,2-bis(p-chlorophenyl)ethene (DDMU), in two estuarine bays, Daya Bay and Hailing Bay, of South China. Six DDT components including p,p′-DDT, o,p′-DDD, p,p′-DDD, o,p′-DDE, p,p′-DDE, and p,p′-DDMU were detected in Hailing Bay, while only p,p′-DDD was found in Daya Bay. p,p′-DDD was the most abundant DDT component in both bays, sharply different from the previous finding in the water column of the Palos Verdes Shelf, California, USA that p,p′-DDE was prevalent. In addition, the occurrence of p,p′-DDMU (with a range of 0.047-0.21 ng/L in Hailing Bay) has not been reported around the globe, and its presence in our study region appeared to stem from dehydrochlorination of p,p′-DDD, favored under aerobic conditions, but further investigations are clearly needed to confirm the mechanism for generation of DDMU in estuarine environments.     

Chlorination of p-cymene by chlorine in carbon tetrachloride: Model compounds for environmental analyses

p-Cymene was chlorinated by chlorine in CCl₄. The products of the chlorination were separated by distillation and purified by preparative gas chromatography. The structures of chlorocompounds were confirmed by means of their NMR and mass spectra. The distillation gave as the main compounds: (2) 2-chloro-, (4) 2,3-dichloro-, (5) 2,5-dichloro-, (6) 2,3,6-trichloro-, (7) 2,3,5,6-tetrachloro-p-cymenes and as by-products: (8) 2,5,7-trichloro-p-cymene, (9) 2,6-dichloro-1-methyl-4-(1-methylethenyl)benzene (cymenene), and (10) 2,3,6-trichloro-1-methyl-4-(1-methylethenyl)benzene (cymenene).     

Atmospheric degradation of alkylfurans with chlorine atoms: Product and mechanistic study

As part of a study on the oxidation mechanism of heterocyclic aromatic compounds, some aspects of the atmospheric chemistry of several alkyl derivatives of furan have been investigated. The aim of this work was to identify the products of the reactions of chlorine atoms with 2-methylfuran, 2-ethylfuran and 2,5-dimethylfuran. Experiments were performed in two different smog chambers at 296 ± 2 K and 1000 ± 20 mbar of synthetic air. The experimental investigation was carried out using in situ long-path FTIR absorption spectroscopy and both SPME-GC/FID-ECD and SPME-GC/MS as sampling and detection techniques. The major primary products from the addition reaction channel were 4-oxo-2-pentenoyl chloride and formaldehyde for the reactions of 2-methylfuran and 2,5-dimethylfuran; 4-oxo-2-hexenoyl chloride and acetaldehyde for the reaction of 2-ethylfuran and 5-chloro-2(5H)-furanone for the reactions of both 2-methylfuran and 2-ethylfuran. Other minor products were 4-oxo-2-pentenal, 4-oxo-2-hexenal and 3-hexene-2,5-dione for the 2-methylfuran, 2-ethylfuran and 2,5-dimethylfuran reactions, respectively. From the abstraction pathway, HCl, furfural, 2-acetylfuran, 5-methylfurfural, maleic anhydride and 5-hydroxy-2(5H)-furanone were detected. The formation of furfural, 2-acetylfuran and 5-methylfurfural confirmed the H-atom abstraction from the alkyl group of 2-methylfuran, 2-ethylfuran and 2,5-dimethylfuran, respectively. This mechanism was not observed in previous studies with OH and NO₃ radicals. A mechanism is proposed to explain the main reaction products observed. The observed products confirm that addition of Cl atoms to the double bond of the alkylfuran is the dominant reaction pathway.     

Destruction of halogen-containing pesticides by means of detonation combustion

Pesticides that contain a halogen functional group have been destructed by means of detonative combustion. The following compounds were examined: (1) atrazine—2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine—herbicide; (2) bromophos—O,4-bromo-2,5-dichlorophenyl O,O-dimethyl phosphorothioate—insecticide; (3) chloridazon—5-amino-4-chloro-2-phenylopyridazin-3(2H)-one—herbicide; (4) linuron—3-(3,4-dichlorophenyl)-1-metoxy-1-methylurea—herbicide; (5) metoxychlor—1,1,1-trichloro-2,2-bis(4-metoxyphenyl)ethane—insecticide and acaricide; and (6) trichlorfon—dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate—insecticide. Explosive material has been produced on the basis of ammonium nitrate, which served as an oxidizer while the pesticides were used as fuels. Composition of the explosive was adjusted in such a way as to respect thermodynamic parameters. Detonative decomposition of the mixtures has been carried out in shot-holes pre-drilled in soil. Efficiency of the pesticide decomposition has been examined with gas chromatography in order to determine pesticides residues in the environment. It was found that for some, the amount of pesticides in some compounds in the analyzed samples after decomposition was below the determination threshold of the applied method.     

Accumulation and elimination kinetics of di-, tri- and tetra chlorobiphenyls by goldfish after dietary and aqueous exposure

Bioaccumulation kinetics of five di-, tri- and tetrachlorobiphenyls from water and food were studied in laboratory experiments with goldfish (Carassius auratus). First order rate constants for uptake from water and clearance were determined after simultaneous administration of the five compounds in constant concentration, and were related to bioconcentration factors obtained in a static fish-water equilibration system. Biomagnification by retention of the PCB's from food was studied in a separate experiment.The difference in clearance rates for the chlorobiphenyls is the main reason for the different bioconcentration and biomagnification factors.Absorption efficiencies from water and food are higher than 40%. Clearance half lives vary from 10 days for 2,5-dichlorobiphenyl to 60 days for 2,3′,4′5-tetrachlorobiphenyl, which is correlalated with the decreasing aqueous solubilities of the compounds. Bioconcentration factors are between 0.4 × 10⁶ and 1.5 × 10⁶, biomagnification factors between 0.2 and 1.7, based on extractable lipids. Substitution of chlorine in the position para to the phenyl-phenyl bond influences hydrophobicity and bioaccumulation of the PCB's more strongly than substitution in ortho position.A kinetic model is developed which accounts for the influence of the lipid content of the fish on the clearance rate of a chemical. Reproducible determination of the bioconcentration potential of environmental chemicals is possible by use of an “internal bioaccumulation standard” in a kinetic test system. Food chain accumulation in fish is likely to be an important process only for persistent chemicals with extremely low water solubility.     

Chemical characterization of fatty acids,alkanes, n-diols and alkyl esters produced by a mixed culture of Trichoderma koningii and Penicillium janthinellum grown aerobically on undecanoic acid,potatoe dextrose and their mixture

Little is known about the mixed fungal synthesis of high-value aliphatics derived from the metabolism of simple and complex carbon substrates. Trichoderma koningii and Penicillium janthinellum were fed with undecanoic acid (UDA), potatoe dextrose broth (PDB), and their mixture. Pyrolysis Field Ionization Mass Spectrometry (Py-FIMS) together with ¹H and ¹³C Nuclear Magnetic Resonance (NMR) characterized CHCl₃ soluble aliphatics in the fungal cell culture. Data from NMR and Py-FIMS analysis were complementary to each other. On average, the mixed fungal species produced mostly fatty acids (28% of total ion intensity, TII) > alkanes (2% of TII) > n-diols (2% of TII) > and alkyl esters (0.8% of TII) when fed with UDA, PDB or UDA+PDB. The cell culture accumulated aliphatics extracellularly, although most of the identified compounds accumulated intracellularly. The mixed fungal culture produced high-value chemicals from the metabolic conversion of simple and complex carbon substrates.     

Pb remobilization by bacterially mediated dissolution of pyromorphite Pb5(PO4)3Cl in presence of phosphate-solubilizing Pseudomonas putida

Remediation of lead (Pb)-contaminated sites with phosphate amendments is one of the best studied and cost-effective methods for in situ immobilization. In this treatment, a very stable mineral, pyromorphite Pb₅(PO₄)₃Cl, is formed. Several studies propose to improve this treatment method with the addition of phosphate-solubilizing bacteria (PSB). The effect of bacteria on solubilization of pyromorphite is unknown. In this study, the effect of the soil microorganisms on the stability of pyromorphite Pb₅(PO₄)₃Cl has been investigated in a set of batch solution experiments. The mineral was reacted with Pseudomonas putida, a common soil microorganism. Dissolution of pyromorphite was enhanced by the presence of P. putida, resulting in an elevated Pb concentration in the solution. This occurred even when the bacteria were provided with an additional source of phosphate in the solution. Pyromorphite has been shown to be a potential source of nutrient phosphorus for common soil bacteria. Thus, the use of PSB in remediation treatments of Pb contaminated sites may have adverse long-term impacts on Pb immobilization. Conscious phosphate management is suggested for long-term sustainability of the in situ Pb immobilization by pyromorphite formation.     

Concentrations and sources of carbonaceous aerosol in the atmosphere of Summit,Greenland

High-volume PM_2.5 samples were collected at Summit, Greenland for approximately six months from late May through December of 2006. Filters were composited and analyzed for source tracer compounds. The individual organic compounds measured at Summit are orders of magnitude smaller than concentrations measured at other sites, including locations representative of remote oceanic, and remote and urban continental aerosol. The measured tracers were used to quantify the contribution of biomass burning (0.6–0.9 ng C m^?3), vegetative detritus (0.3–0.9 ng C m^?3), and fossil fuel combustion (0.1–0.8 ng C m^?3) sources, 4% of OC total, to atmospheric organic carbon concentrations at the remote location of Summit, Greenland. The unapportioned organic carbon (96%) during the early summer period correlates well with the fraction of water soluble organic carbon, indicating secondary organic aerosol as a large source of organic carbon, supported by the active photochemistry occurring at Summit. To the author's knowledge, this paper represents the first source apportionment results for the polar free troposphere.     

Measurements of biogenic VOC emissions: sampling,analysis and calibration

We describe an experimental system and techniques for sampling and analyzing biogenic emissions of volatile organic compounds (VOC). The system uses a Teflon chamber to enclose a single branch of a tree. Temperature, photosynthetic active radiation (PAR), relative humidity and carbon dioxide concentration are continuously monitored with a time resolution of five minutes. VOCs are sampled on tubes containing solid adsorbents (Tenax TA and Carbotrap) with a time resolution of 1 h. Composition and concentration of VOC emissions are measured with a gas chromatographic system equipped with a flame ionization detector (FID) for quantitative and a mass spectrometer (MS) for qualitative analysis. To calibrate the system, a diffusion source was built to produce standard mixtures of up to 36 different compounds with mixing ratios at low concentrations and high accuracy. The diffusion rates were monitored over 17 months and showed variations between 0.2 and 7.6% for monoterpenes (expect for α-phellandrene, α-terpinene and γ-terpinene) and between 10.6 and 22.6% for sesquiterpenes. FID response factors calculated from calibration measurements were corrected using correction factors based on the effective carbon number concept. The individual response factors of 23 compounds were combined to a mean response factor (RF_m) with a value of 23,100 μV s ng⁻¹ and a standard deviation of 9%. The system described here was used to measure VOC emission rates of Scots pine (Pinus sylvestris) in 1998 and 1999.     

Biodegradation of Methoxychlor and Its Metabolites by the White Rot Fungus Stereum hirsutum Related to the Inactivation of Estrogenic Activity

The white rot fungus Stereum hirsutum was used to degrade methoxychlor [2,2,2-trichloro-1,1-bis(4-methoxyphenyl)ethane] in culture and the degraded products were extensively determined. The estrogenic activity of the degraded products of methoxychlor was examined using cell proliferation and pS2 gene expression assays in MCF-7 cells. S. hirsutum showed high resistance to methoxychlor 100 ppm, and the mycelial growth was fully completed within 8 days of incubation at 30°C. Methoxychlor in liquid culture medium was gradually converted into 2,2-dichloro-1,1-bis(4-methoxyphenyl)ethane, 2,2-dichloro-1,1-bis(4-methoxyphenyl)ethylene, 2-chloro-1,1-bis(4-methoxyphenyl) ethane, 2-chloro-1,1-bis(4-methoxyphenyl) ethylene, and 1,1-bis(4-methoxyphenyl)ethylene, indicating that methoxychlor is dominantly degraded by dechlorination and dehydrogenation. MCF-7 cells were demonstrated to proliferate actively at the 10^?5 M concentration of methoxychlor. However, cell proliferation was significantly inhibited by the incubation with methoxychlor culture media containing S. hirsutum. In addition, the expression level of pS2 mRNA was increased at the concentration (10^?5 M) of methoxychlor. The reductive effect of S. hirsutum for methoxychlor was clear but not significant as in the proliferation assay.     

Primary source attribution and analysis of α-pinene photooxidation products in Duke Forest,North Carolina

Samples of fine particulate organic matter were collected outside Durham, NC in the Duke Research Forest as part of the CELTIC study in July 2003. Particulate samples were collected on quartz filters using high volume air sampling equipment, and samples were analyzed for polar and non-polar organic species. Among compounds analyzed, oxidation products of α-pinene, namely pinic acid and pinonic acid, were identified in all samples. Pinic acid, being a dicarboxylic acid, has a low vapor pressure of the order of 10⁻⁸ Torr and is expected to contribute significantly to secondary organic aerosol (SOA) formation from the oxidation of α-pinene. Source contribution estimates from primary organic aerosol emissions were computed using the organic species as molecular markers with the chemical mass balance (CMB) model. The unapportioned organic carbon (OC) was determined as the difference between measured OC and OC apportioned to primary sources. This unapportioned OC was then correlated with pinic and pinonic acid to get a better understanding of the role of monoterpene oxidation products to form SOA. A reasonably good fit between pinic acid concentrations and unapportioned OC levels is indicative of the contribution of α-pinene oxidation products to SOA formation in ambient atmosphere. The results are significant considering the role of monoterpene emissions to global atmospheric chemistry.     

Effects of heavy metals and nitroaromatic compounds on horseradish glutathione S-transferase and peroxidase

Glutathione S-transferase (GST) and peroxidase (POX) activities have a direct relation to the effect of stress on plant metabolism. Changes in the activities of the enzymes were therefore studied. Horseradish hairy roots were treated by selected bivalent ions of heavy metals (HMs) and nitroaromatic compounds (NACs). We have shown differences in GST activity when assayed with substrates 1-chloro-2,4-dinitrobenzene (CDNB) and 1,2-dichloro-4-nitrobenzene (DCNB). The conjugation of DCNB catalysed by GST was inhibited in all roots treated with HMs as compared to non-treated roots, whereas NACs caused induction of the activity in dependence on the exposition time and concentration of compounds. The conjugation of CDNB by GST was not affected to the same extent. The increase of GST activity was determined in cultures treated by nickel (0.1 mM) and diaminonitrotoluenes (DANTs, 0.1 mM) for 6 h, whereas the roots treated by 2,4,6-trinitrotoluene (TNT), 4-amino-2,6-dinitrotoluene (ADNT) and dinitrotoluene (DNT, 1.0 mM) needed 27 h treatment to induce the activity. The POX activity of cultures treated by HMs was inhibited to 17-35% in comparison to non-treated cultures. The POX activity of roots treated by TNT (0.1 and 1.0 mM) for 6 and 27 h and by ADNT (0.1 and 1.0 mM) for 6 h was inhibited. A partial increase of POX activity was measured in roots treated by all NACs for 27 h. The content of oxidized glutathione (GSSG) and reduced glutathione (GSH) in the roots differed significantly. It was followed as a symptom of the stress reaction of the plant metabolism to the effect of NACs and HMs.     

Bioaccumulation, maternal transfer and elimination of polybrominated diphenyl ethers in wild frogs

To investigate bioaccumulation, maternal transfer and elimination of polybrominated diphenyl ethers (PBDEs) in amphibians, we collected adult frogs (Rana limnocharis) from a rice field in an e-waste recycling site in China. We found that ∑PBDEs in the whole frogs and various tissues (brain, liver, testis and egg) ranged from 17.10 to 141.11 ng g⁻¹ wet weight. Various tissues exhibited a similar PBDE congener profile, which was characterized by intermediate brominated congeners (BDE-99 and BDE-153) as the largest contributors, with less lower brominated congeners (BDE-28 and BDE-47) and higher brominated congeners (BDE-209). The maternal transfer capacity of PBDEs declined with the increase in bromine numbers of PBDE congeners. We suggest that the bromine atom number (the molecular size, to some degree) might be a determining factor for the maternal transport of a PBDE congener rather than K_ow (Octanol-Water partition coefficient), which expresses a compound’s lipophilicity. ∑PBDEs concentrations in frogs decreased over time during a depuration period of 54 days when these wild frogs were brought to the lab from the e-waste recycling site. The half-life of ∑PBDEs was 35 days, with about 14 days for BDE-47, and 36 and 81 days for BDE-99 and BDE-153, respectively. The data shows that the elimination of PBDEs has no essential difference from aquatic and terrestrial species.     

Compositional Changes of Aromatic Steroid Hydrocarbons in Naturally Weathered Oil Residues in the Egyptian Western Desert

Naturally weathered oil residues from an arid dumpsite in Al-Alamein, Egypt were analyzed for monoaromatic and triaromatic steranes to demonstrate the utility of biomarker compounds in assessing the chemical composition changes during the degradation of the released oil residues in a terrestrial environment. The characterizations of individual aromatic compounds were based on gas chromatography/mass spectrometry (GC/MS) analyses. The results showed that triaromatic sterane distributions were similar in the oil residues of varying weathering degradation extents and correlated with a fresh crude oil sample of the Western Desert-sourced oil. Molecular ratios of triaromatic sterane compounds (ratios of C₂₈20R /C₂₈20S, C₂₇20R /C₂₈20R, and C₂₈20S /[C₂₆20R + C₂₇20S ]) were proved to be suitable for source identification. Major changes in chemical compositions during weathering of the oil residues were the depletion of short chain mono- and tri-aromatic steranes in samples that had undergone extensive degradation. The results of triaromatic sterane distribution are in good agreement with weathering classification based on the analyses of saturate and aromatic hydrocarbons and the ratios of n -alkanes, PAHs and saturate biomarker compounds.     

Identification of 2,6-diisopropylnaphthalene metabolites in carp part 1. In vivo experiment

The metabolism of diisopropylnaphthalene (DIPN) in fish was studied from an ecotoxicological viewpoint to clarify the environmental fate of DIPN, a solvent of carbonless paper which is widely used as a substitute for PCB. This study identified the following metabolites in carp by in vivo experiment; 2-(1-hydroxy-1-methyl) ethyl-6-isopropylnaphthalene, 2-(1-methyl-2-hydroxyethyl)-6-isopropyl-naphthalene, 2,6-(1-hydroxy-1-methyl) ethyl-naphthalene, 2-(1-hydroxy-1-hydroxymethyl) ethyl-6-isopropylnaphthalene and α-[2-(6-isopropylnaphthyl)] propionic acid. Identification was based on UV, IR, MS, and NMR analyses. The metabolism of 2,6-DIPN in carp was concluded to mainly through oxidation of the isopropyl chain.