Elsevier

Chemistry and Physics of Lipids

Volume 60, Issue 3, January–February 1992, Pages 263-271
Chemistry and Physics of Lipids

Some oxidation products of ethoxyquin including those found in autoxidising systems

https://doi.org/10.1016/0009-3084(92)90078-4Get rights and content

Abstract

2,4-Dimethyl-6-ethoxyquinoline (2), 1,2-dihydro-6-ethoxy-2,2,4-trimethylquinoline nitroxide (3), 2,6-dihydro-2,2,4-trimethyl-6-quinone imine N-oxide (4), 2,6-dihydro-2,2,4-trimethyl-6-quinone imine (5), 1,8′-di(1,2-dihydro-6-ethoxy-2,2,4-trimethylquinoline) (6) and 1,2-dihydro-6-hydroxy-2,2,4-trimethylquinoline (7) have been prepared from 1,2-dihydro-6-ethoxy-2,2,4-trimethylquinoline (1) (ethoxyquin) and their spectroscopic properties (UV, IR, mass and NMR) examined.

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      Therefore, their concentration along with this of the parent compound were determined in all studies as is described below and will be referred as ‘total residues of EQ’. In the absence of commercial analytical standards, the two EQ metabolites were synthesized according to the procedure described by Thorisson et al. (1992) and their structure was verified by NMR analysis (see Supplementary materials). Commercial formulations of the pesticides were used in all fortification experiments described below including TECTO® 50 SC (TBZ), FUNGAZIL® 50 EC (IMZ), FRUITGARD® 20 SL (OPP), NO SCALD® 31.8 EC (DPA) and XEDAQUINE® 50 EC (EQ).

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      Some of them may be not related to EQ at all. Metabolism of EQ is not completely described neither in mammalian or fish, most likely due to methodological limitations in identification and quantification (Skaare and Nafstad, 1979; Sanders et al., 1996; Burka et al., 1996; Kim, 1991; He and Ackman, 2000b) of metabolites (Skaare and Roald, 1977; Skaare, 1979; Skaare and Nafstad, 1979; Skaare and Solheim, 1979; Sanders et al., 1996) many of which are highly reactive (Taimr et al., 1991; Thorrisson et al., 1992). In the present study, 4 of 14 observed compounds (Bohne et al., 2007a) were identified as parent EQ; de-ethylated EQ, earlier identified as a rat major urine metabolite (Skaare and Solheim, 1979); quinone imine, suspected product of in vitro oxidation of de-ethylated EQ (Skaare and Solheim, 1979), also found in salmonids (He and Ackman, 2000b); and finally, EQDM found in salmonids (He and Ackman, 2000b).

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    Present address: Icelandic Fisheries Laboratory, Rekyavik, Iceland.

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